Private & Shared Sailing Charters
Sunset sail key west.
Have the sea to yourself with Sunset Sail Key West—chartered sailing trips led by us, tailored to you.
Get inspired with our most popular trips!
Private sunset sail.
Chillout Lilypad Sail
Key West Daysail
Sunset Sail on When & If
Privates Charters
Discover your perfect private charter.
Set out on a snorkeling, stargazing, or sunset sail, or build your own custom trip. Romance, relax or unwind from the privacy of your own chartered sailboat.
Shared Trips
Come together on a shared charter.
Rise above the crush of the crowds and set sail on a unique shared sunset charter, with a few friends you haven’t met yet. A personable local crew and captain will treat you to a stunning sunset view from the deck of an unforgettable vessel– General Patton’s elegant, private schooner When and If.
Three Classic Boats
View our fleet.
We sail a fleet of three vintage sailboats, each with their own unique charm and appeal. A custom sloop, a classic ketch, and a historic schooner are waiting to make memories with you on the crystal clear waters of Key West. Each boat is suited to different types of outings, so take a moment to get acquainted with our vessels.
Real. Fun. Sailing.
When And If is back at beautiful Stock Island Marina!
Check Out Our Ship's Store!
Wreckers' Race Season Is Back!
Hello, Sailor! Don’t miss out on the latest Sunset Sail news & offers.
Friends of SSKW
Legal & safety.
Key West & Marathon, Florida
We specialize in private luxury yacht & sailing charters at affordable prices. we offer day charters as well as multi-day charters., why blue ocean yacht charters.
Blue Ocean Yacht Charters, located in Key West, Florida, makes yacht rentals affordable and life-changing. We offer private multi-day bareboat charters to amazing destinations like The Dry Tortugas and the Florida Keys. Just looking for a day charter? Look no further. We offer four hour, eight hour, and 24 hour charters as well multi-day charters.
All our yachts come fully equipped to make your private boat charter experience what you’re looking for. We offer motor and sailing yachts that provide the best boat rental experience.
- Chesapeake Bay Itineraries
- Key West Itineraries
- Chesapeake Bay
- Virgin Islands
- St. Vincent & The Grenadines
- Browse our Fleet
- Meet Your Captains
- Charter Management
- Sailing Lessons
Key West Sailing Charters
Experience the beauty and wonder of an unspoiled tropical paradise without ever leaving the Continental United States. Our Key West sailing charter destination is located minutes from all the downtown Key West attractions and Duval Street night life, yet a short sail away from pristine reefs, underwater nature preserves, and uninhabited island locations such as the stunning and secluded Marquesas. Kayak, paddle board, and snorkeling excursions will open to you the offshore beauty offered only in the Florida Keys. Our native Floridian staff knows how to find the best activities on land or at sea, to guide you as you plan a unique and customized getaway.
Our Key West Sailing Charter Fleet
Sailing cats.
Southern Cross
Fountain Pajot Elba 45
Dream Reach
Sugar Magnolia
Seawind 1260
Second sight.
Stay Glassy
Nautitech 40 open.
Ever Summer
Fountaine pajot my44, key west attractions.
Historic Duval Street
One of the most popular destinations on the island of Key West is Duval Street. Visit the Ernest Hemingway Home and Museum where you can take in some history about the writer and meet a legendary six toed cat. If you feel like taking in some nature, visit the Key West Butterfly and Nature Conservatory where there are 50 - 60 different species of live butterflies from around the world. On Duval Street, you can simply take a stroll and hear live music, see art galleries, enjoy coffee shops and great restaurants, or find unique souvenirs at one of the many boutiques.
Romantic Sunsets
Beautiful sunsets are what Key West is all about. Enjoy the soothing ocean breeze, a glass of wine, and relax to the backdrop of the setting sun on your own private catamaran cruise. Watching the sunset has become an integral part of everyday life in paradise. This is one tradition you don’t want to miss!
Crystal Clear Snorkeling
Key West offers many beaches and reefs where you can experience snorkeling in warm crystal-clear water. At Cottrell Key, see the unique sponge garden and large coral reefs. It is also an excellent place to see dolphins, sharks, stingrays, and Goliath groupers. Fort Zachary Taylor is considered one of the best offshore snorkeling spots in Key West where there are a variety of tropical fish species and living coral to see. A favorite among snorkeling enthusiasts is Sand Key Lighthouse Reef. With a remote location and strict no-take policy, the Sand Key Lighthouse Reef is one of the healthiest coral gardens in Florida.
Pristine Sandy Beaches
Craving a drink in your hand and your toes in the sand? Check out the turquoise waters at Smathers Beach. Rental shops are available with beach chairs, shade umbrellas, kayaks, jet skis and much more. Try South Beach for calm, shallow waters that are excellent for swimming and great for families. Higgs Beach is unique for its historical significance. Take a wander around, and you'll find monuments dedicated to the 19th-century slave cemetery located on the site. There is also a pier at Higgs Beach, where visitors can often spot stingrays and other marine species.
Find the best Key West boat rentals
- Boat Rentals
- • Florida Boat Rentals
- How much is it to rent a boat in Key West?
- How old do you have to be to rent a boat in Key West?
- Can you rent a yacht in Key West for the day?
- Experiences
- Top locations
Key West Sailing Adventure
Private sailing charters, 305.304.4911, [email protected], private sailing charters from key west for up to 6 passengers with various popular charter package choices., experience & explore the american caribbean aboard a sailboat., see our boats.
St. Vitus Dance
Sunset Sailing Charter More info
Half Day Sail More info
Full Day Sail More info
Weddings At Sea More info
Premium Charter Package More info
Key West Sampler Package More info
24hr At Sea Sailing Excursions More info
Stay-Sail Charter Package More info
Choose from three sailboats located downtown in Key West’s Historic Seaport just two blocks from Duval Street. The town is at your feet. There are famous bars and restaurants, beautiful parks, and dozens of attractions to enjoy. The sailboats are docked down the pier just far enough for quiet and privacy.
Sailing and snorkeling is the best fun Key West has to offer. Choose a sailboat to truly enjoy the Key West experience.
Our captains will sail you to the barrier reef to snorkel, take in a sunset, dive a wreck, fishing is an option, visit the dolphin playground. See the beauty this paradise has to offer. One of the favorite charters is the 24 hour Excursion or make it for a several day sailing adventure anchoring out at night. Charter the boat as if you own it selecting a sailing activity with your captain.
Sailing is not just the best vacation activity, it's also the most fun, visit our Key West Sailing YouTube Channel to see all the fun you could be having.
See how you can have the most fun on a sailboat visit our private sailing charters page.
Whether you want a pleasant sail with snorkeling to the barrier reef, an overnight sailing package, or a sailing excursion to the Bahamas. We are ready to unlock your dream vacation. All of our charter options are merely suggestions based on popularity. We can fully customize any charter to meet your wishes. It's your boat, your vacation, we just make it happen.
Some of our guests have expressed interest in learning more about sailing, we're creating new pages just for them. Visit our list of sailing and nautical terms , to know what the pirates are saying. Additional topics will follow soon.
- Explore boats
- Text (910) 447-2456 Call (910) 447-2456
Key West, FL Sailboat
Set sail in the florida keys & enjoy a perfect day on the water, custom 33' sloop (1975), description.
A sail on this custom sloop offers a great way to see Key West from the water! Experience the joy of setting sail and shutting off the engine as we sail you through the colorful waters that surround our beautiful Island. Sail through the internationally renowned live- aboard anchorage, past Mallory square and the old Customs House and out toward Fort Zachary Taylor. Sail around Sunset Key and take a look at Key West's most fantastic National wildlife preserve. You will always have a chance to see dolphins, turtles and countless variety of sea birds. Sit back and relax or take a turn at sailing the boat. This truly is your trip!
With over 15 years experience sailing and living in the Keys, our captains and crew provide you with the local knowledge of marine life, surrounding islands as well as stories of Key West's rich and colorful history. Come sail with us in comfort and style.
Trip Includes: soft drinks, bottled water and coolers stocked with ice. You are welcome to bring any adult beverages of your choice.
Two hour sails reflect sunrise and sunset sails.
Price calendar and Availability
- Manufacturer Custom
- Model 33' Sloop
- Guest Capacity 6
- Single Beds 0
- Double Beds 1
- Bathrooms 1
- Number of engines 1
- Horsepower per engine 12
- Chart plotter
- Cocktail parties
Navigation & Safety
- Depth finder
- Life jackets
- Fire extinguisher
- First aid kit
- Cockpit table
Sports equipment
View all photos
Member since October 2015
I am a professional sailor, and a knowledgeable guide of Key West. I will work hard to make sure that you have an excellent day with us on the water.
Inquire about Seth's Custom
Almost done, but let's create an account first so you can receive a response from the boat owner
Congratulations your message was sent..
Your message was sent. We expect boat owners to answer your inquiry within a few hours. In the meantime note that it's always recommended that you contact multiple boat owners to increase your chances of finding the right boat.
You can always see your messages by clicking on the Messages link in the top bar. You can also click on the button below to view the message you just sent.
Location and Destination Guide
Key west attractions by boat, destination guide.
Usually this boat operates around Key West, FL .
Florida Keys is the boating paradise waiting to be discovered on board of Sailo’s top Key West sailing charters. From the many Key West attractions by boat, our favorites are snorkeling the reefs and mysterious shipwrecks, or Dry Tortugas fishing in crystal clear, turquoise waters. At the end of a long day on your yacht rental in Key West , Florida treat yourself with the perfect sunset cruise and take away memories for a lifetime.
Customer Questions & Answers
Congratulations! Your question has been submitted and it should be answered soon.
If you have an urgent question related to a confirmed booking, please contact the boat owner directly or send us an email at [email protected] .
Have a question about this boat? Ask it here.
Typical questions:
- How long can you take out the boat?
- Can you pick me up?
- How many life-jackets do you have?
Congratulations Your answer has been submitted and will be published soon pending staff review.
Delete confirmation
Are you sure you want to delete this answer?
What type of yacht should I charter?
What should i bring, how long does a rental last, experience sailing in south florida on a custom 33.0 boat rental in key west.
Welcome to one of the most famous year-round boating destinations in the world! Hop aboard your yacht charter in Key West, FL and enjoy this amazing floating playground for both beginners and experienced sailors. The boat rental in Key West, FL you have selected is a Custom Sail boat - a popular choice to explore the natural beauty of Florida’s coast. Sailing on a FL, Key West yacht charter is an experience you should not miss if you decide to visit the boating capital of the world. Picture yourself on romantic sunset cruise on this FL, Key West boat rental, or having fun with your family or friends on a sightseeing tour along the coast. For more ideas about things to do on your boat rental or yacht charter in Key West, FL, make sure to check our destination guide for Sailing in South Florida !
We invite you to browse through hundreds of Sailo boats perfect for sailing in Florida, and choose the dream Sail boat rental or yacht charter for your nautical adventure. Whether you are looking to spend a relaxed afternoon on a classy motorboat or sailboat, or have a fun on a sporty catamaran, our team here to make sure you will be making the best out of your time on the water. For details about this Custom 33.0 boat rental in Key West, FL, or to make special arrangements for your trip, please click on the “Message Owner “ blue button to send a direct message to the boat representative.
Explore options
- Los Angeles
- Great Abaco
- The British Virgin Islands
- FAQ and Policies
- Accessibility Statement
- Boat Rentals
- Boat Calculator
- Discover Boating
- Community questions
- Referral Program
- Vivre: Furniture & home decor
- British Virgin Islands
- La Paz, Mexico
- Cabo San Lucas, Mexico
- Key Largo, FL
- St. Vincent and Grenadines
Introducing Vivo Per Lei 58 Leopard Catamaran flagship model Learn More
Creating unforgettable journeys on custom designed luxury catamarans learn more, luxury catamaran sailing charters tailored in every way to suit your needs learn more, key west and key largo locations sailing the beautiful florida keys, bahamas and beyond learn more, catamaran sailing charters half day, full day & overnight learn more, welcome to calypso sailing.
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
- Iris -->