sailboat cruising florida keys

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Small Boat Cruising in the Florida Keys

• By Bianca Dumas
• July 12, 2022

We were tied to the fuel dock in Marathon, the midpoint of the Florida Keys, in the early part of 2022, when I realized our mistake. 

Other cruisers traveling the Great Loop were on the loop’s southern stretch of the route, while some bluewater cruisers were starting to stage for passage to the Bahamas and beyond. I asked the dockmaster if any slips were available, and learned that it’s perpetually high season in the Keys, including at that moment. Along with cruisers and sailors, fish migrations change throughout the year, calm summer conditions attract divers, and festivals bring in the party crowds.

“We’re always booked out,” he said, shaking his head. Then he paused, perhaps realizing that he’d just sold us a total of 6 gallons of diesel. “Wait, what size is your sailboat?”

We were on Jackalope , a Nor’Sea 27. He shifted into a smile. “Oh yeah, we can probably squeeze you in down there,” he said, pointing to the inner harbor. 

We were grateful for the offer, but in the end, we stuck with our plan to anchor out. We had stayed on a dock—at Bahia Honda State Park—only once during our monthlong Keys cruise. While a lot of people on bigger boats doing the loop preferred marinas, anchoring out seemed to fit with our small-boat cruising style. We were basically camping, which required few amenities and created a lot of options. We took bucket baths when we couldn’t go ashore for showers. We cooked from simple ingredients that didn’t have to be refrigerated: lentils, rice and pasta. We paddled our inflatable kayak to shore for an occasional restaurant meal. 

We laughed when we were once mistaken for homeless people on a resupply walk, but how could we argue? We don’t have the same look as those who can blow-dry their hair and pull clothes off a hanger. 

But our small boat makes for a big adventure. We crossed the Gulf of Mexico from Fort Myers Beach directly to Key West, and because the 90-mile crossing took us three days and two nights, we had the experience of a much bigger, more challenging passage than other boats would. Our sails go up quickly and easily, so we take advantage of every quarter-hour of good wind that we can find.

Moving slow and low, we don’t fear crab pots; they’re easy to see and steer around, even in the dark. And since a keel-hung rudder protects our small propeller, hitting a crab-pot float head-on doesn’t cause trouble. At our top motoring speed of 4 knots, we can see dolphins, turtles and manatees before they dive for cover. 

We can’t avoid getting tan because we steer from an open center cockpit. Nor can we avoid getting exercise because we have to paddle ashore rather than motor. ( Jackalope ’s canoe stern means we don’t have a motorized dinghy on davits.) 

Like the mythical Western creature that shares its name, Jackalope has a small stature. Just right for us.

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Florida Keys Boating Guide

A Florida Keys boating or sailing itinerary is the stuff of smiling all day long. From Key Largo at the top of the archipelago down to Key West at the end, the Florida Keys offer enchanting scenery, fun-filled activities and great year-round cruising.

Here’s a look at a loose Florida Keys cruising guide, highlighting some of the best islands, places to stay and activities in the Upper, Middle and Lower Keys.

Best Boating Locations in the Florida Keys:

• John Pennekamp Coral Reef State Park (Key Largo)
• Florida Keys National Marine Sanctuary (Key Largo)
• Bud ’n’ Mary’s (Islamorada)
• Seven Mile Bridge (between Knight's Key and Lower Duck Key)
• Long Key State Park (Long Key)
• Key West Bight Marina (Key West)

10 Best Boating Destinations in Florida

Key Largo (Upper Keys)

The upper portion of the Florida Keys starts to the south of Miami and continues around the bottom curve of the state of Florida. The most popular attraction in this section of the Keys is John Pennekamp Coral Reef State Park.

Key Largo is the northernmost island in the Florida Keys, the one that boaters will reach first when cruising north to south. There are resorts and rental homes here, along with multiple marinas that accept transient boaters. Some of the marinas, such as Kings Kamp and Blue Fin Rock Harbor , also double as RV parks, if you want to do a land cruise to Key Largo and then take the boat off the trailer to do a southbound water cruise.

Major tourist attractions on Key Largo include:

• John Pennekamp Coral Reef State Park where you can sign up for snorkeling or scuba tours, take a ride in a glass-bottom boat, or rent a kayak or paddleboard (if you don’t already have them on board).
• Another must-visit place on Key Largo is the Florida Keys National Marine Sanctuary which has an Eco-Discovery Center filled with interactive exhibits including a mock-up of Aquarius, the world's only underwater ocean laboratory.

Restaurants abound in Key Largo—you can go for:

• The raw bar at Jimmy Johnson’s Big Chill ;
• Or sample the award-winning coffee at the Key Largo Conch House ;
• And Snook’s Bayside Restaurant and Grand Tiki Bar is the place for fresh lobster, scallops, shrimp and fish.

Tavernier (Upper Keys)

Tavernier is the largest island in the Upper Keys. Hotels on Tavernier offer an option beyond the Key Largo borders, but still close to a lot of the action. If you want to spend a night or two off the boat, then consider the Island Bay Resort for cottages with a view, or the Coconut Palm Inn which has a marina for guest use.

If you’re cruising with some boat buddies, the Coconut Palm Inn also can help you arrange an event, such as a wedding, fishing tournament or yoga retreat. Family reunions are also common here, as are birthday bashes and corporate retreats.

Islamorada (Upper Keys)

Islamorada is where you’ll find Bud ’n’ Mary’s , a legendary marina that serves as home base for sportfishing of all kinds.

• There is transient dockage here, but it’s limited, so call ahead for reservations.
• Once you’re in, you can enjoy—with or without a local guide, or a charter boat—some of the world’s best fishing for tarpon, swordfish, mahi mahi, sharks and more.

When you’re done hooking fish for the day, head on over to the Lorelei Restaurant and Cabana Bar , which has a kids’ menu to keep the whole family happy. The raw tuna nachos are a delight that you’d be hard-pressed to find anywhere but on the waterfront, and the restaurant will cook up anything you bring in after catching it yourself (grilled, fried or blackened—your choice).

Long Key (Middle Keys)

The middle portion of the Florida Keys starts at Long Key and continues to the Seven Mile Bridge , which connects Knight’s Key (in the Middle Keys) to Little Duck Key (in the Lower Keys). This middle section of the Florida Keys is often a bit quieter than the hotspots of Key Largo and Key West, if you’re looking to explore at a slower pace.

Fiesta Key RV Resort & Marina is a 28-acre property located on Long Key with an on-site marina, RV spaces and a hotel. A restaurant and a beach bar are here, and the place is within spitting distance of Long Key State Park , which is a favorite for birdwatching and swimming. If you want to rough it for a little while off the boat, there are campsites at this park with waterfront views.

Duck Key (Middle Keys)

Duck Key is where you’ll find Hawks Cay Resort , which is so well known that people sometimes refer to the whole island as Hawks Key. The property has a half dozen on-site restaurants that specialize in everything from surf and turf to ceviche.

The Oasis Cay bar on this property is noteworthy because it’s an adults-only poolside setup, if you’re looking to have a little grownup time after you drop off the kids for other activities.

Sugarloaf Key (Lower Keys)

The lower portion of the Florida Keys runs from Big Pine Key to Key West, which is the last stop on the line. Key West is arguably the most popular island within the whole of the Florida Keys, with tourist attractions galore and boaters of all kinds meandering the local streets.

Sugarloaf Key (what a great name, right?) draws a lot of kayakers, who love to explore the backwaters and all their mangroves. Guides and rentals are available at spots such as Backcountry Boat Rentals and Sugarloaf Marina Sugarloaf Marina has a boat-launch ramp in addition to a kayak-launch ramp, so novice paddlers won’t get caught up in too much hullaballoo while getting in and out of the water.

Key West (Lower Keys)

The mecca of many a Florida Keys pilgrimage is Key West, the last stop on the line before you’re adrift in the water and heading for Cuba about 90 miles away. The place has long been a haven for colorful characters ranging from Tennessee Williams to Ernest Hemingway. Several presidents also vacationed here; Franklin D. Roosevelt was a particularly big fan.

Boaters often head ashore to take part in the Duval Crawl, a do-it-yourself bar crawl along Duval Street in the heart of town.

• Sloppy Joe’s Bar , which has been around since the 1930s, starts pouring drinks by 9 a.m. most days and then hosts live music many nights.
• The Bull and Whistle Bar is filled with murals that tell the story of the city, and sells coolies that you can use to keep your drinks cool back on the boat.
• Visitors to Key West will want to have a photo taken at the giant “buoy” on land that marks the Southernmost Point in the continental United States.
• Then, head over to the Ernest Hemingway Home and Museum , where the writer lived during the 1930s on Whitehead Street across from the lighthouse. The Hemingway property has been a museum since the 1960s (officials say this property is a more popular tourist attraction than the Duval Street bars, even). 

Marinas are plentiful on Key West for boats of most sizes:

• Try the Galleon Marina if you want a slip near a sunset tiki bar;
• Or the Key West Bight Marina , which takes online reservations and has online 360-degree tours of the facility.

Read Next: The Great Loop Cruising Guide

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Sailing the Florida Keys: 2 week Florida Keys Sailing itinerary

By: Author Reilly Mulligan

Posted on Published: August 5, 2023  - Last updated: October 9, 2023

Categories Florida Keys

Home » Florida Keys » Sailing the Florida Keys: 2 week Florida Keys Sailing itinerary

Looking for a guide to sailing the Florida Keys ? You have come to the right place! Here’s a full circumnavigation Route of the Florida Keys from an avid Florida sailor. 

The Keys are a magical place and the only place in the continental US where you will find water that is a classic crystal clear turquoise shade. You could spend months exploring the hundreds of reefs and keys. If you don’t have months to spend exploring, I have got you covered.

I’ve compiled a cohesive itinerary for your Florida Keys circumnavigation that can be done within a week, but you’ll want to have more time. I promise. I would recommend that you set aside at least two weeks for this trip, so you can stop and explore the places that stand out to you the most.

This sailing journey through the Keys begins in the Miami/ Key Biscayne area. If you don’t have your own sailboat, you can rent one from sailo.com . For this journey, a sailboat with a shoal keel or a catamaran would be the best fit, as the Florida Keys are surrounded by relatively shallow waters.

The sailboat / yacht rentals out of the Miami/ Key Biscayne area are currently ranging from $450-$2000+ a day. I would recommend doing as much provisioning as possible while in this area, as you will have a wider variety of options and a better deal on gas and diesel.

After you get your boat stocked up and ready for your trip, you can anchor or moor off of Dinner Key for the night before starting your journey.

Florida Keys Sailing Guide: A 2 week itinerary

1. sailing from dinner key to rodriguez key.

49 Nautical Miles // 8 hours of sailing

If you decide to spend the first night of your journey at Dinner Key, the city has moorings available for $29.16 a night for vessels under 40 feet.

If you opt to spend the money for the mooring ball, you will also have access to pump-out facilities, laundry, exceptionally clean bathrooms and showers, and a dinghy dock (although it is quite a distance from the mooring field). There is also a shuttle service that runs to the mooring field from 8 am-5 pm; however, it doesn’t run if there are high winds and can result in having you stuck on shore without a ride back to your home.

This spot off Dinner Key offers very little protection and is open to all directions except the east.

Once you have weighed anchor and are ready to start heading to your next destination, head southwest towards the Biscayne flats, south of Key Biscayne.

If you want to stop for the night or need to duck away from an oncoming storm, you can anchor in No Name Harbor or along the edges of the Cape Florida Channel. After passing through the Biscayne flats, keep heading east towards the Atlantic Ocean. Once you’ve bypassed all of the channel markers, turn south and start heading through the waters of the Biscayne National Park.

Keep heading south down Hawk Channel, you will soon come to an area known as Mosquito Bank. Once you are sailing through the Mosquito Bank, you will see Rodriguez Key to your southwest. There are crab pots virtually everywhere, even within the channel. Be sure to be on the lookout, if you plan on getting in after dark it is crucial that you have a reliable bright spotlight.

I recommend anchoring on the northwest side of the island, in order to get the most protection possible. You might have a little bit of trouble trying to get your anchor to set, as the bottom consists of seagrass, rock, and coral.

Keep in mind that it is illegal to anchor on coral, so be sure to find a patch of sand or seagrass to drop the hook in. For southbound travelers, this is their first taste of the crystal clear water that the Keys are known for.

On days with better visibility, you can sometimes see your anchor in 7-10 feet of water. After getting your anchor set, be sure to go to shore and do some exploring on this beautiful, untouched mangrove island.

2. Sailing from Rodriguez Key to Little Crawl Key

37.9 Nautical Miles // 6 hours of sailing

Be cautious of crab pots along this route as they are littered everywhere. You should have no issues as you’re heading south down Hawk Channel, it is a relatively well-marked channel.

Once the channel starts bearing more west, you will find yourself coming up to the south side of Tavernier Key. You can also stop here and anchor for the night on both the north and south sides of the island and it has a decent sandy bottom that provides good holding. Little Crawl Key is home to Curry Hammock State Park.

Curry Hammock State Park is the largest piece of untouched land between Key Largo and Big Pine Key. If you visit during the fall you may be lucky enough to witness the huge migration of peregrine hawks that stop on the island on their pilgrimage south. Little Crawl Key is just south of Crawl Key.

They’ve been given their names due to the large number of turtle nesting that occurs on the island, with tons of tiny hatchlings crawling to the sea every year.

There are mangrove paddling trails that you can traverse on a kayak, dinghy, or paddleboard to get an up-close and personal view of the mangroves and all of the life inside of them. There are also hiking and biking trails on land if you would like to spend some time with solid ground under your feet. 

3. Cruising from Little Crawl Key to Newfound Harbor Key

28.8 Nautical Miles // 4.5 Hours of Sailing

Before heading west out of Hawk Channel, be sure to stop at Looe Key Reef to do some amazing snorkeling and diving. There are tons of mooring balls surrounding the island on a first come first serve basis, be sure not to drop the hook on any reef or coral, as it is illegal.

If the mooring balls are all taken and you must anchor, be sure to find a nice patch of sand to drop the hook in.  You will find some of the best snorkeling and diving in the Florida Keys at the reef off Looe Key. While swimming around the reef you may come across some goliath groupers, spotted eagle rays, barracudas, or even a black-tip reef shark.

If you have extremely placid weather, you may be able to spend the whole night at Looe Key Reef. However, if you have any type of wind or swell, I would recommend heading a bit further inland for the night. Leaving the reef, head west-northwest towards Big Pine Key.

There is a slightly shallow area just north of Munison Key where you should keep an eye on your depth finder. You will find a ½ square mile of reef just off the coast of Palm Island that hosts an amazing diversity of coral, including fan coral, brain coral, boulder coral, and star coral.

Diving, while there is a northwest wind blowing, will provide you with the best conditions for good visibility.

4. Cruising from Looe Key to Key West

25.3 Nautical Miles // 4 Hours of Sailing

As you are approaching Key West ; your senses may start to overwhelm you. It is one of the best places to go sailing in the Florida Keys.

You will be able to hear the music and people laughing from the downtown area, smell the burgers cooking on the grill, smell the deckhands cleaning fish on the docks while joking with their crewmates, and hear an almost constant buzzing of motors and jetskis all around the island.

You can anchor in the northwest inlet of Fleming Key, and dinghy into downtown from there. You will still have a little bit of traffic buzzing around you, which is virtually impossible to avoid in such close proximity to Key West. You can also anchor on the Northeast side of Wisteria Island, which is a good option as well.

However, a few people have reported that there is a sizable amount of derelict boats off of Wisteria Island that tend to drag if there is any weather at all. It is also a considerable distance from the dinghy docks on Key West. If you decide to leave your tender at the dinghy dock, it costs $8 a day. I would still recommend locking up your belongings to make sure that everything is where you left it when you return.

Once you get onshore in Key West, the activities available are essentially endless. There is something to do for the whole family. If you are a literary lover, you can stop at the Hemingway Home and Museum and meet the six-toed cats that live on the grounds.

You can also get a tour and see where Hemingway spent his nights writing his multiple masterpieces. The pool on the premises was constructed in 1938, and is gargantuan in size, especially for this era. It was the only pool within 500 miles of Key West when it was constructed. Entrance to the Hemingway Home costs $18/day for adults, $7 for children between 6-12 years old, or free for children 5 and under. Entrance into the home also gives you access to a 20-30 minute guided tour.

If you would like to get a little more in-depth view of the life of Ernest Hemingway, you can grab dinner and a drink at Sloppy Joe’s Bar, one of Hemingway’s favorite hang-outs.

If you would like to see a more colorful side of Key West, you can visit Nancy Forrester’s Secret Garden. Nancy Forrester’s Secret Garden is a parrot sanctuary that homes multiple endangered species of macaws and parrots.

Entrance to the sanctuary costs $10 for adults and $5 for children between the ages of 5 and 11 years old.

A visit to Key West is not complete until you’ve got a photo taken in front of the Southernmost Point in the Continental US, a classic must-see stop that is free to visit. From this point, it is only 90 miles to Cuba.

Duval Street runs right through the middle of Key West, oriented to run north and south. There are tons of little shops and cafes to stop and poke in and grab refreshments when necessary. If you find yourself on the north side of Duval Street, you will come across Mallory Square.

Mallory Square is known for its magnificent view of the sunset, and the countless buskers and street performers earning their living everywhere that you look. If you have a hankering for something sweet, be sure to stop at Kermit’s Key West Key Lime Shoppe for a frozen dark chocolate-covered piece of Key Lime Pie .

If you want to be blown away by the impressive size of the marine wildlife that Key West has to offer, take a trip over to Stock Island and visit Robbie’s of Key West Marina. There is a $2.50 entrance fee to go out on the dock and $4 more for a bucket full of fish to feed the tarpon. You will be able to see your hand and wrist get completely swallowed by a tarpon before it takes its treats and releases your appendages.

5. Key West to Dry Tortugas

64 Nautical Miles // 10 Hours of Sailing

Dry Tortugas National Park is a 100-square-mile park. It is a bird watcher’s paradise. It is one of the only places in the continental US where you can find endangered sooty terns nesting.

It is also home to one of the only known nesting colonies of frigate birds. There have been over 300 species of birds identified within its grounds. Fort Jefferson, an octagonal fort, proudly dominates Garden Key. The construction for it began in 1845. It was meant to be a military installment for US ships to patrol the Gulf of Mexico Construction was never completed and the fort was never armed, but it still sits on Garden Key, the second largest key in all of the Dry Tortugas.

Garden Key is also home to the visitors center, parks headquarters, and campgrounds. Entrance to the park costs $15 a person, excluding people under the age of 16, and is paid through a self-service fee area on the main dock at Garden Key.

here are no trash receptacles on the island so you need to “pack in and pack out” everything that you bring. Be sure to respect your neighbors and mother nature, and remember that littering is illegal. There are also no lifeguards on duty so swimming is at your own risk. It is encouraged to always use the buddy system while swimming or snorkeling

Keep in mind that it is illegal to molest, stand or sit on coral, as it does a considerable amount of damage to the ecosystem.

Anchoring on the southeast side of Fort Jefferson typically allows you the best protection. Once you get the hook set, you will find yourself in a remote tropical paradise. The Dry Tortugas National Park is only accessible by seaplane, ferry, or private boat.

The Dry Tortugas has some of the best fishing that you will ever have the pleasure of experiencing. People with their own boats are required to get a boating permit for each vessel in order to be allowed to fish. These permits are free and can be picked up at the Garden Key Dock House.

You will need to get a boating permit for any type of vessel including kayaks, paddle boards, or dinghies. You will also need your Florida saltwater fishing license . Lobstering and spearfishing are both prohibited within the park. “J” hooks are not permitted to be used within the park, but “circle” hooks are acceptable.

If you’re lucky, you’ll be able to catch some of the amazing gamefish that call the Dry Tortugas their home such as amberjacks, bluefin tunas, blackfin tunas, wahoos, kingfish, black grouper, red grouper, swordfish, sailfish, and permits. The species of fish that you pull up will be dependent on the time of year that you go.

There are also at least five turtle species present in the park including Loggerheads, Green Turtles, Kemp’s Ridley, Hawksbill, and Leatherbacks. President Franklin D. Roosevelt designated the fort a national monument. Now, you cannot remove any seashells, sand, rocks, coral, or glass from the national park.

If you don’t feel up to making the entire 64-mile trip, you can stop about halfway in between Key West and the Dry Tortugas at the Marquesas Keys, turning the voyage into a slightly more manageable two-day trip.

The Marquesas Keys, not to be confused with the Marquesas Islands found in French Polynesia, are located about twenty miles west of Key West. It is sometimes referred to as “Button Island” due to its round shape. It was known to have been used for military target practice as recently as the 1980s.

The Marquesas are four miles in diameter, and the lagoon located in the center is known as Mooney Harbor. After leaving Marquesas Keys, it is a 36-mile distance to the Dry Tortugas.

The next section of this sailing route through the Keys is through the Inner Passage, on the northwest side of the Keys in the Florida Bay, rather than the Atlantic Ocean side.

his region in the Florida Keys is rather shallow, and I wouldn’t recommend attempting the journey without a functioning transducer on board. Also, if your boat draws more than five feet, you may want to reconsider and complete the trip through Hawk Channel, on the Atlantic Ocean side.

6. Dry Tortugas to Snipe Point

64.2 Nautical Miles // 10 Hours of Sailing

After visiting Key West and the Dry Tortugas, you may want to get away from the tourists a bit and hang out where the locals like to hang out. I would recommend going to Snipe Point on a weekday because the sandbar can become one giant party on the weekend.

Snipe Point is within the Great White Heron National Wildlife Refuge, which was established in 1938 as a refuge for migratory birds, great white herons, and other tropical wildlife.

This area is commonly referred to as “the backcountry” by locals. Tons of turtles use this beach as a nesting area, so be sure to keep a lookout for nesting spots, and keep your lights to a minimum at night. Great White Heron National Wildlife Reserve consists of 1,000’s acres of untouched shallow, crystal clear waters and mangrove islands.

There are no pets permitted on shore. Be sure to keep your eye out for crab pots as they are littered everywhere around the island and channel.

7. Snipe Point to Fat Deer Key

41 Nautical Miles  // 6.5 Hours of Sailing

Fat Deer Key is located just north of Marathon and south of Long Point Key. It is another of our favorite places for Sailing in the Florida Keys.  On the Atlantic side of the island, you will find Coco Plum Beach, with its pristine white powdery sand. This is a great place to hang out if you wish to spend the day cooling down a little bit.

Curry Hammock State Park is located on Fat Deer Key, and within this park you will find the Curry Hammock State Park Nature Trail. Once entering the park, travel west for one mile to find the mouth of the hiking trail. You can find parking on either side of the road.

The hammock that shadows over you gives you a little bit of relief from the hot Florida sun. This state park is home to the largest thicket of Florida thatch palms in the continental US.

Fat Deer Key is just north of Marathon. Marathon is a well established city, and you will find everything you need to reprovision and top off your gas and/or diesel tanks.

Once on shore, there are a multitude of marina and dive shops that you can check out. Some of them include: Captain Hooks Marina and Dive Center and Driftwood Marina and Storage. If you are hungry for some delicious, fresh seafood be sure to stop in at SS Wreck and Galley Grill or the Island Fish Company. You can also check out Florida Keys Aquarium Encounters while exploring Marathon.

8. Fat Deer Key to Butternut Key

45.5 Nautical Miles // 7 Hours of Sailing the Keys

Butternut Key is located in Florida Bay, the body of water between the Florida Keys and the southern tip of Florida, east of the Gulf of Mexico.

Butternut Key is off the southwest coast of Key Largo. Technically, it is considered to be a part of the Everglades National Park . The maximum stay that is permitted is 14 days. There is a poll and troll zone within 300 feet of the islands, meaning that motors are not permitted.

It is easiest to approach the island from the southwest, off of the Intracoastal Waterway. You will have a 6-7 foot depth at low tide. Just like every other anchorage on the west side of the Keys, be sure to keep an eye on your depth sounder. The bottom is fine sand and soft mud and provides excellent holding. The anchorage is the most comfortable if it is blowing out of the North or East.

You’ll have a fantastic view of the sunset, as this spot is completely open to the West. This untouched, serene, remote tropical paradise inspires everyone who has the pleasure of laying eyes on it, including legendary artist Clyde Butcher. He traveled to Butternut Key in 1997 to preserve her beauty in a photograph forever.

9. Butternut Key to Dinner Key

49 Nautical Miles // 7 Hours and 45 Minutes of Sailing

When you depart from Butternut Key, head southeast toward the Atlantic Ocean, and then start heading up north once you reach Key Largo. Heading west you are first going to sail north through Baker’s Cut and enter into Buttonwood Sound.

Keep heading northeast through Buttonwood Sound, until you reach Grouper Creek. Again, keep your eyes on your depth sounder to make sure you don’t run aground. Also, keep a diligent eye out for crab pots that cover the waterways through here. After passing through Grouper Creek, you will spit out to the east into Tarpon Basin. As you continue heading north up the Intracoastal Waterway, you will soon enter Dusenbury Creek.

For this portion of the sailing route, it is crucial that you have a functioning engine onboard, as these voyages are nearly impossible without one. After exiting Dusenbury Creek, you will find yourself in a large bay, known as Blackwater Sound.

Continue heading northeast until you come to the mouth of Jewfish Creek. Jewfish Creek will bring you to Barnes Sound, then Card Sound, and then finally Biscayne Bay, inside of the Biscayne National Park. You will be able to anchor back at Dinner Key or find a slip in a marina to treat yourself after your jam-packed voyage.

Final Thoughts Before you set sail on your Yacht

If you plan to use our guide to Sailing the Florida Keys, we would love to hear from you so leave us a comment below.

Want more great Florida sailing routes? be sure to check out the Best Places to go Sailing in Florida !

Author: Reilly Mulligan is a sailing enthusiast from Florida who has spent her life sailing and exploring the Sunshine State.

Reilly is a sailing enthusiast from Florida who has spent her life sailing and exploring the Sunshine State. A native Floridian born who raised in St. Petersburg, Florida, Reilly has spent her whole life going on interesting, off-the-beaten-path trips around the state of Florida and has a plethora of information and experiences to share! While she is not sailing her boat around the Sunshine State she is sharing her experience traveling around the State with the readers of Florida Vacationers!

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Get Away to Key West and Explore the Florida Keys by Sailboat

Did you know there's an international airport perched out in the Gulf of Mexico at Key West? Serviced by all major US airlines and with frequent flights from main airports in the East and South, Key West is so easy to get to. That's where you'll find our boat charter operators, who have a range of sail and motor boats for you to explore this unique corner of the USA.  

Along the Florida Keys the holidaymaking options are numerous. Enjoy the aquatic environment with countless opportunities to snorkel, swim, kayak, paddleboard and more, while totally relaxing on board, or ashore on one of the Keys' beautiful beaches. Enjoy an evening meal in one of the upmarket restaurants that dot the Keys, shop and enjoy the nightlife in the major centers of population, and get close to nature at one of several locations designated State Parks. 

While pandemic concerns are limiting travel options, consider Key West as your next boat charter vacation destination. Local ordinances reflect the need to keep everyone protected and make this a safe destination. The communities are welcoming and open for business. 

Some of the highlights to experience on a Florida Keys Sailing Charter Vacation 

Your Florida Keys adventure likely begins and ends at Key West, which is closer to Cuba than Miami yet connected to the US mainland by the 90-mile long Overseas Highway that's an experience in itself. Most sailing charter visitors arrive by air and take the short transfer to one of the charter bases located on the island. Famous for its coral reefs, local architecture, historic sites and nightlife, charming Key West is well worth some time before or after your charter.  

Like most charterers however, you will probably be keen to go sailing and start exploring the chain of cays that make up this most southerly part of the Continental USA. Two great things about sailing here are that distances between attractions can be as short as you'd like them to be, and anchorages are plentiful, if shallow in places. A seven-day charter Key West to Key Largo and return is easily achievable. 

Travelling out of the Stock island marina, it's less than 30 nautical miles to Baihia Honda Key, a popular stopover. In the vicinity there's a variety of stunning beaches, some say the best in the world. Looe Key has some of the best snorkelling you'll experience on your vacation. 

A similar distance to that travelled above will take you from Bahia Honda Key to Long Key, via Marathon, a major sport fishing town of 10,000 people surrounded by the bountiful sea. Stop a while and enjoy a seafood lunch, or you may prefer to do Marathon on the return. At Long Key enjoy the natural surroundings, the greenery and the birdlife. 

Perhaps after two days of sailing that have taken you from Key West more than half way to the mainland, you're ready to take it a bit easier. Less than ten nautical miles onward you'll come to Indian Key Historic State Park at Islamorada. Nearby is the San Pedro Underwater Archeological Preserve, another one of the numerous state parks along the Keys. The San Pedro was a Dutch ship sunk during a hurricane in 1733. What remains lies in 18 feet of water 1.25nm south of Indian Key, easily accessible to good swimmers. 

From Indian Key, it's a further 20nm sailing distance to Key Largo. Apart from the shops, bars and restaurants, most of the attractions are aquatic-based as they are all along the Keys. A visit to the Florida Keys Wild Bird Rehabilitation Center can be rewarding, a reminder of the fragility of nature in this delicate place. 

If you enjoy walking while on vacation, the Florida Keys Overseas Heritage Trail is accessible to many points along your sailing route. 

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READY. SET. SAIL THE FLORIDA KEYS

At the end of a 110-mile-long chain of islands, stretched like a string of pearls across a Caribbean blue sea lies charmed Key West, it is here you will find Florida Yachts Charters. We are a boutique yacht charter company that specializes in Crewed and Bareboat Charter, ASA Sailing Instruction and Yacht Management. Experience the best of sailing the Florida Keys with a well maintained fleet of yachts, local knowledge and expertise, a warm island welcome and the personal touches of a luxury yacht charter.

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Sit back, relax, and let the professionals do all the work. Charter the yacht of your choice and connect with one of our experienced crew for your carefree sailing vacation in the Florida Keys. Want a full-service chef, we can help with that too!

Learn to Sail

Let us show you the ropes. Do you dream of owning or bareboat chartering your own sailing yacht one day? We are an accredited ASA Sailing School offering fully private courses for high quality one on one time with your instructor. Customize your itinerary and turn your Florida Keys sailing vacation into a great educational opportunity for you and your family.

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Raise the sails. With a bareboat charter i f you have the experience, then enjoy the freedom of captaining your own yacht on your own Florida Keys adventure. Explore our fleet of sailing monohulls and catamarans.

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How to Spend 3 Days Sailing in the Florida Keys

Lara Mega - Head of Content

Published: August 1, 2023

Hey there! I'm Lara, a passionate traveler who has spent several incredible days sailing in the beautiful Florida Keys. In this article, I'll share my top recommendations for making the most of your sailing adventure and ensuring an unforgettable experience in this tropical paradise.

If you've got some vacation time from work and either have your own boat or fancy chartering one, why not sail down to the stunning Florida Keys?

With its many coves and beaches, the Florida Keys is a great place to explore or simply hang out on your vessel and soak up the sun.

Whatever your plan may be, creating a robust itinerary is vital to make the most of your time. This guide will give you a head start on planning the perfect sailing trip!

From Biscayne Bay all the way down to Key West, it's time to prepare your itinerary and sail off into the sunset.

Day 1: Stop In Key Largo For Some Snorkeling And Seafood

Beginning in the Upper Keys, it is worth making a stop in Key Largo. As the name suggests, this is the longest section of the Keys.

Key Largo is well known for its glorious scenery and crystal clear waters, so you should take advantage of these conditions and get your snorkeling gear on.

You will find a wide array of exciting and exotic creatures , fish, and coral reefs below the surface. If you are feeling more adventurous, you can even take scuba lessons from any of the numerous PADI-certified instructors in the area and try a dive.

Then, top it all off by heading ashore and sampling the famous Key Largo seafood! Just try to resist the wine if you intend to sail on before you anchor for the night.

While Key Largo makes a great overnight stay, there's nothing more romantic than spending the night in Marathon, just a bit further south, and watching the sunset. Your island-hopping experience starts now!

Plus, the many sights and activities nearby will enhance this experience if you choose to explore in the morning.

Day 2: A Day of Relaxing On A Private Beach

Now that you have sailed to the middle keys, you can pass some time fishing, sailing and most importantly, relaxing. Explore Duck Key island and try swimming in the bluest water you've ever seen.

The Keys are full of secret beaches and coves just waiting to be discovered by adventurous sailors! You might even find an empty beach on one of the islands where you can while away a day in peace.

Whether you are fishing or just lounging in the shallow areas of the turquoise waters, see how many fish and birds you can spot, and let the beauty of the beaches soak in.

Or, for a more active adventure, hop onboard and sail your boat into the ocean to discover the incredible life further off-shore. The coral reef that mirrors the Florida Keys is the only living coral barrier reef in the continental US.

Day 3: Sail Around the Lower Keys and Visit Key West

South of the Middle Keys, you can cruise by Big Pine Key and Sugarloaf Key, Fl. Enjoy this time cruising and taking in the views. Then, arrive in the stunning Key West.

No Florida Keys sailing trip would be complete without at least a quick stop in Key West. This is the most popular Key island and it's not hard to see why!

At this southern tip of the US, you feel at the edge of the world. Drop anchor and soak in the stunning Lower Keys. If time permits, take this chance to discover the most western point of the Keys, Dry Tortugas.

Dry Tortugas is a national park located about 68 miles west of Key West in the Gulf of Mexico . Here, you will find Fort Jefferson and seven small islands. This is a hidden gem in the ocean and well worth the journey.

Then, when you're ready, let the wind take you home and cruise back to your everyday life.

Hopefully, this suggested sailing itinerary has inspired you to get some sailing instruction and start planning the perfect vacation!

Most Recommended Thing to Do

John Pennekamp Coral Reef State Park

Top Choice Hotel

Playa Largo Resort & Spa

Our Top Choice Restaurant

The Fish House Encore

Our Top Choice Bar for Nightlife

Mariners Club Key Largo

Best Time to Visit

Warm weather, clear skies, and beautiful sunsets prevail.

Average Temperature

The average temperature in Key Largo, USA is warm.

Transportation Options

Car rentals, taxis, shuttles, bicycles for transportation in Key Largo.

Average Cost ($, $$, $$$)

My Top Recommendation

Key Largo, located in the United States of America, is a tropical paradise that offers a multitude of exciting adventures for every traveler. From pristine beaches to vibrant coral reefs, this city promises an unforgettable escape from the mundane.

Indulge in the sparkling turquoise waters and immerse yourself in the captivating underwater world by embarking on a snorkeling excursion to the magnificent John Pennekamp Coral Reef State Park. Alternatively, bask in the sun on the soft sands of Cannon Beach, feeling the warm embrace of the gentle ocean breeze. With breathtaking natural wonders, Key Largo is the perfect destination for those seeking tranquility and adventure all in one place.

What You'll Need to Bring

• Valid passport or identification
• Comfortable walking shoes
• Swimwear and beach accessories
• Sunscreen and hat
• Camera or smartphone for capturing memories
• Personal toiletries and medications
• Cash or credit cards for purchases and emergencies
• Lightweight and breathable clothing for warm weather
• Snorkeling gear, if interested in exploring underwater beauty
• Travel guidebook or map for navigation purposes.

What Not to Miss

Key largo fisheries backyard cafe, florida keys wild bird rehabilitation center.

• Dagny Johnson Key Largo Hammock Botanical State Park

African Queen Canal Cruise

What to avoid.

• Crowded tourist spots
• Overpriced souvenir shops
• Subpar seafood restaurants
• Rush hour traffic
• Expensive parking fees
• Tourist traps
• Public transportation during peak hours
• Unsafe neighborhoods
• Overbooked hotels
• Limited dining options for vegetarians/vegans

Table of Contents

Get Your Vessel Ready For The Trip

A three-day trip might not sound like a lot, but without the proper preparation, you could find yourself spending more time messing around with your ship than actually enjoying yourself!

If you live outside of Florida but cannot transport it yourself, you can transport your yacht with Cross Chartering , which can move it from one location to another hassle-free. This will save you time and hassle.

Then, there are a few things you need to do to ensure smooth sailing:

Pack adequate clothing:

It will likely be hot and humid regardless of when you set sail (most of all from June to November). So, pack suitable clothing to make your trip comfortable. This includes correct footwear for the boat, hats, light clothing, and a few dressier outfits for when you eat out.

Stock up on essential supplies

Food, water, and fuel are the three main essentials. Ensure you have plenty of all three, so you don't get caught short.

Bring some additional entertainment

Although you will be occupied for most of the journey, you should pack your Kindle or tablet for those times you want to unwind.

Pack a well-stocked first-aid kit:

Accidents can and will happen when cruising on a ship, so keep a well-stocked kit on hand for emergencies.

Ensure your radios and safety devices are working:

Before you push off, you need to be sure your radios work and all the appropriate safety gear is aboard and in good condition.

Things To Add To Your Florida Keys Itinerary

Now you have your boat stoked and ready, it's time to plan what you will do.

Before planning a multiday Florida Keys sailing trip, decide what you want to achieve. If you are going for pure relaxation, you can spend most of your time aboard your ship.

Conversely, if you plan to take in the sights of the main islands, you should plan ahead to book space at a jetty.

Regardless of what you intend to do, you must ensure your ship is in tip-top shape and has everything you need for the adventure.

Now, let's work through a hypothetical 3-day itinerary for the Florida Keys sailing.

Frequently Asked Questions Relating to Sailing in the Florida Keys

Let's take a look at the most frequently asked questions relating to sailing in the Florida Keys.

What are the main national parks in Key Largo?

When sailing to Key Largo, it is worth stopping at the National Marine Sanctuary National Park. John Pennekamp Coral Reef State Park is also located in Key Largo, and Everglades National Park is just a short drive away.

How do you spend a day in Key West?

Key West is the most popular of the Florida Keys. While in Key West, you can visit the southernmost point of the continental US, enjoy the crystal clear water, visit Ernest Hemingway's house across from the lighthouse, and bar crawl along Duval Street.

Is Key Biscayne one of the Florida Keys?

Although it has "Key" in its name, Key Biscayne is not geographically part of the Florida Keys. Rather, it is a barrier island located in Biscayne Bay, north of the Keys. If you stop here on your way to the Keys, jump on land and check out Coconut Grove and Miami.

Should you take sailing classes before you charter a boat?

It is not actually a legal requirement to have a license or complete any sailing courses in Florida. However, it is advisable to take sailing classes at a reputable sailing school before you embark on a sailing vacation in the Florida Keys. Having prior sailing experience will make the experience safer and more fun.

Summing Up: How to Spend 3 Days in the Florida Keys

So, if you're sailing to sunny Florida, why stop at Fort Lauderdale or Miami Beach when you can head on down to the picturesque Florida Keys?

It is undeniable that the Florida Keys is one of the most beautiful spots in the continental United States. From Key Largo, past Duck Key, and all the way down to Key West, Fl, this part of the world is truly spectacular.

So, charter a boat, head over to the sailing school to develop your skills, and hit the ocean! While sailing classes are not mandatory, they will provide tips to keep you safe and well.

Then, it's time to start cruising the Keys. Have a great time in Florida and sail safe!

Dolphin Research Center

Florida keys overseas heritage trail, related articles, featured in.

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Calypso Sailing was established in 1988 in the beautiful Florida Keys. With locations in both Key Largo and Key West we specialize in luxury sailing vacations on a range of Leopard Catamarans, both bareboat and Captained. Our monohull sailing charters can take groups of 6 to 38 on day, sunset and overnight trips whilst not forgetting the iconic African Queen steamboat from the 1951 movie starring Humphrey Bogart and Katharine Hepburn which operates daily in Key Largo. 

Our aim is taking care of all your cruising needs 

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