Key West Sailing

Key West has long been a top American destination for sailors. The generally pleasant and mild weather, a good selection of marinas and anchorages, and plenty of things to see and do both on- and off-shore make it an ideal destination or way point for cruising yachtsmen. Even in mid-winter, December through February, the temperature ranges from the mid-60s to the mid-70s, with sunshine nearly everyday. More importantly, there is also a 10-15 knot breeze just about every day, and the water stays warm enough for swimming and snorkeling on the many protected patch reefs around the island.

If you have ever dreamed of enjoying the cruising life, or simply wondered what it is like to spend some time on a sailboat crossing the water on wind power alone, a Key West visit is very likely to stir your desire to get out and fulfill some longings. With perfect weather, blue water in view from so many vantage points on the island, and the sight of boats of all types at anchor and underway very common throughout the day, this island can bring out the sailor in anyone. So how is a visitor in town going to get out there on the waves and get a taste of life before the mast? It’s simple really – Attractions Key West offers a number of good options that will have you out and under sail in no time.

For pure relaxation, there is nothing like a sunset wind and wine cruise. Get out on the water on a beautiful wooden sloop-rigged sailing vessel carrying a small 20-person party. Enjoy the peace and quiet of moving smoothly along under wind power as the sky colors with the famous Key West sunset. A selection of fine wines, high-quality beers, and non-alcoholic beverages, complemented by delicious snacks, makes for a nice on-board happy hour. A cruise like this is the perfect way to end an active day and begin a great Key West evening. It will give you some idea what lucky yachties experience day after day, and just might have you shopping for boats after you get back home!

If you are in the mood for a longer trip, and a more active sort of offshore adventure, consider the sailing Backcountry Safari. This 6.5-hour trip is a great full-day activity that will take you on an exploration of the natural world in the waters around Key West. Start out with the fun of sea kayaking as an expert guide takes you into the unique and mysterious mangrove island eco-system. Stable and easy-to-maneuver kayaks let even first-time beginners wind their way smoothly through the leafy tunnels between the mangrove thickets to encounter tropical birds, rays, sharks, sport fish, and many other creatures of land and water.

Follow up the kayaking with snorkeling over some of the pristine patch reefs found within the boundaries of the Florida Keys National Marine Sanctuary. The calm and protected waters of the Keys backcountry make for great visibility and easy access that will let you swim among an amazing variety of corals, dramatic marine life, tropical fish, and sponge gardens. Have no fear if you have never snorkeled before because one-on-one instruction will have you comfortable in no time at all. All equipment is provided at no extra charge, and wetsuits make it possible to enjoy the water year round. And the best thing about the backcountry sailing safari is that you finish up the day with a scenic sail back to port.

So, here are two nice options if you would like to experience a bit of time under sail in the pleasant waters and charming anchorages of Key West. Don’t let the opportunity pass you by – get on board and underway with an Attractions Key West sailing trip.

Read More
Key West Sail, Snorkel, Kayak with Sunset Option
Likely to Sell Out
Top10Top 10 Tour Ranked using exclusive Attractions Key West data that may include activity quality, traveler reviews, overall popularity, and availability.
Likely to Sell Out

Enjoy an unforgettable morning or afternoon of sailing, kayaking and snorkeling in the pristine marine wilderness of the Key West National Wildlife Refuge....

4.5 or 6.5 hours (approx.)Free Cancellation
4.5 or 6.5 hours (approx.)Free Cancellation
4.5 or 6.5 hours (approx.) • Free Cancellation
4.9 (2,703)
Best Rate
$105
Key West Backcountry Safari
Likely to Sell Out
Top10Top 10 Tour Ranked using exclusive Attractions Key West data that may include activity quality, traveler reviews, overall popularity, and availability.
Likely to Sell Out

Spend an unforgettable day sailing emerald waters, kayaking mangrove-shaded channels and snorkeling coral gardens in an unspoiled marine wilderness....

4.5 or 6.5 hours (approx.)Free Cancellation
4.5 or 6.5 hours (approx.)Free Cancellation
4.5 or 6.5 hours (approx.) • Free Cancellation
4.9 (2,703)
Best Rate
$105
Key West 6 Seater Gas Powered Golf Cart Rental
Likely to Sell Out
Likely to Sell Out

Need a Key West golf cart rental that can get a group of six around the island in fun style? A 6-seater gas-engine EZGO Express...

3 hours and upFree Cancellation
3 hours and upFree Cancellation
3 hours and up • Free Cancellation
4.9 (1,356)
Best Rate
$180
Key West 4-Seater Gas Powered Golf Cart Rental
Likely to Sell Out
Likely to Sell Out

Considering a golf cart rental in Key West? Four adults can zip around the island in style on a 4-seater gas-powered EZGO golf cart, and...

3 hours and upFree Cancellation
3 hours and upFree Cancellation
3 hours and up • Free Cancellation
4.9 (1,356)
$100
$99
Key West 8-Seater Gas Powered Golf Cart Rental
Likely to Sell Out
Likely to Sell Out

In Key West for a wedding or other family event? Got a large group of cruise ship friends who want to see all of the...

3 hours and upFree Cancellation
3 hours and upFree Cancellation
3 hours and up • Free Cancellation
4.9 (1,356)
Best Rate
$210
Key West Split Fishing Charter
Likely to Sell Out
Top10Top 10 Tour Ranked using exclusive Attractions Key West data that may include activity quality, traveler reviews, overall popularity, and availability.
Likely to Sell Out

On a Key West Split Fishing Charter, you save by dividing the charter cost between several people. Book your Key West split-charter fishing trip now...

4 or 6 hours (approx.)Free Cancellation
4 or 6 hours (approx.)Free Cancellation
4 or 6 hours (approx.) • Free Cancellation
4.8 (502)
$350
$200
Key West Snuba® (No Dive Certification Required)

Go Beyond Snorkeling is the closest you can get to scuba diving without being Dive Certified! Go Beyond Snorkeling into new depths for greater durations where you...

3 hours 30 minutes
3 hours 30 minutes
3 hours 30 minutes
5.0 (494)
from
$160
Key West Deep Sea Fishing Charter
Likely to Sell Out
Top10Top 10 Tour Ranked using exclusive Attractions Key West data that may include activity quality, traveler reviews, overall popularity, and availability.
Likely to Sell Out

Experience the thrill of a Key West deep sea fishing adventure on a hunt for trophy game fish with your own Key West fishing charter...

4, 6 or 8 hours (approx.)Free Cancellation
4, 6 or 8 hours (approx.)Free Cancellation
4, 6 or 8 hours (approx.) • Free Cancellation
4.9 (268)
$1,000
$900
Key West Dolphin Watch & Snorkel
Top10Top 10 Tour Ranked using exclusive Attractions Key West data that may include activity quality, traveler reviews, overall popularity, and availability.

Board the Dolphin Watch & Snorkel Cruise Key West for a journey to observe the beauty of Key West dolphins....

3 hours 30 minutes (approx.)Hotel pickup offeredFree Cancellation
3 hours 30 minutes (approx.)Hotel pickup offeredFree Cancellation
3 hours 30 minutes (approx.) • Hotel pickup offered • Free Cancellation
4.9 (25)
Best Rate
$99
Miami to Key West Day Trip with Snorkeling
Likely to Sell Out
Top10Top 10 Tour Ranked using exclusive Attractions Key West data that may include activity quality, traveler reviews, overall popularity, and availability.
Likely to Sell Out

Take a luxury coach tour from Miami to Key West then cruise out on the emerald waters to enjoy a Key West snorkeling trip on...

6 hours in Key West (approx.)Hotel pickup offeredFree Cancellation
6 hours in Key West (approx.)Hotel pickup offeredFree Cancellation
6 hours in Key West (approx.) • Hotel pickup offered • Free Cancellation
4.6 (3,231)
$169
$119
Key West Party Boat Fishing Charter

Our Key West Party Boat Fishing Charter is great for an affordable day on the water with friends and family enjoying the best Key West...

6 hours (approx.)Free Cancellation
6 hours (approx.)Free Cancellation
6 hours (approx.) • Free Cancellation
4.7 (147)
Best Rate
$69.69
Language
Currency

Site Settings

Activity name

Currency

Activity name

Sorting, ranking, and search results

Activity name

Attractions Key West wants to make your searches as relevant as possible. That's why we offer many ways to help you find the right experiences for you.

On some pages, you can select how to sort the results we display and also use filter options to see only those search results that meet your chosen preferences. You'll see explanations of what those sort options mean when you select them.

If you see a Badge of Excellence label, the award is based on average review ratings, share of bookings with a review, and number of bookings through Attractions Key West over a 12-month period.

The importance of any one factor over any other in a sort order varies, and the balance is constantly being reviewed and adjusted. We're always updating our systems and testing new ways to refine and improve your results to make them as relevant as possible to meet your needs.