Key West, FL > Sailing Charters
12/09/2019 ~ 12/15/2019

Key West Sailing Charters

Getting the best experiences for you...
Champagne Sunset Sail

Champagne Sunset Sail

9 reviews
Duration2 Hrs.
Enjoy a night you’ll never forget on a Champagne Sunset Sail in Key West. Watch the masterfully painted sunset fade...
We took my best friend on a sunset sail as part of her bachelorette trip and it was AMAZING. Eric and his crew were awesome and we had the best time celebrating! Highly recommend - can’t beat the price and experience!
Great evening, Wonderful boat, great crew, and the drinks weren't bad either.
Perfect sunset cruise with a great crew and nice drinks ! Can’t wait to come back to Key West and do it again !
from $50
Land's End Sunset Sail with Full Bar and Hors d’Oeuvres

Land's End Sunset Sail with Full Bar and Hors d’Oeuvres

8 reviews
Duration2 Hrs.
Excite yourself with the starburst blaze of colors that is the Key West sunset on a luxurious sunset sail. See the local...
This was a fantastic sunset cruise. We enjoyed the open bar and light appetizers. The crew was attentive and the music added to the experience. Highly recommend!
It was cloudy and rainy, but a very pleasant evening overall. Fortunately, the cloud front moved to the east, so we were able to see a fantastic sunset.
Perfect amount of time,crew was friendly and did was just the right touch
from $70
Wind and Wine Sunset Sail

Wind and Wine Sunset Sail

15 reviews
Duration2 Hrs.
Sail into the Key West sunset while sampling 8 fine wines from around the world, beer, and delicious hors d'oeuvres....
All female crew and they rocked it. The wines were good. The crew didn't make us adhere to a strict tasting (i.e. they let us skip around the sampling and have refills on the wines we liked). All three of the crew members were accommodating, friendly, and fun. The food was good. The sunset ending up being blocked by clouds, but the crew worked hard to get to the best vantage point. All in all it was a great trip. We look forward to doing it again.
Great trip. Crew with Brianna was the best! Thanks!
Nice selection of wine, need more sweet selection. Crew was great, boat was in nice shape, hors d’ouvers were tasty!
Sunset Snorkel Sail with Open Bar and Live Music

Sunset Snorkel Sail with Open Bar and Live Music

23 reviews
Duration3 Hrs.
Treat yourself to an evening of incredible snorkeling, delicious drinks, and groovy melodies on the the Sandie Cat...
Trip was fantastic. Crew (Captain Steve, IO and Dakota) were awesome. Our entire group had a great time celebrating my daughter's 21st birthday. This was a great value for the price.
We booked this trip last minute to get in some more snorkeling. We had snorkeled during the day the day before and this time the snorkeling was just as good if not better. The ship had a lot of people on it but it didn’t matter and made it extra fun. The crew was great as well. On the way back we had live entertainment and it was really fun. Watched the sunset, had a cocktail and even the kids really enjoyed the atmosphere. Coming into the harbor was extra fun with everyone singing along and dancing both on the boat and on the dock.
Had an amazing time snorkeling around the coral reef! Excellent explanation of rules and safety from crew members.
Key West Full Day Power Adventure

Key West Full Day Power Adventure

404 reviews
Duration6 Hrs.
The All Day Power Adventure is 6 hours of Key West awesome. This all-inclusive package includes everything you need to...
Best service I never had before.So enjoyful!!!Beautiful ocean and also free beer.After snorkeling get the beer just perfect.
A fantastic deal, and a fantastic crew!We did the All-day Watersports package: It was 6 hours that gets you a ride on a catamaran, snorkeling,...
I booked the Key West Back country Schooner Eco Tour with Trip Advisor which was $219 for two people. I will say this, look all all the fine print....
from $160
Private Snorkel and Sunset Sail for up to Six Guests

Private Snorkel and Sunset Sail for up to Six Guests

33 reviews
Duration4 Hrs.
Climb aboard and set out on a private snorkel and sunset sail. You'll get the best of both worlds as you glide across...
This was an amazing experience, Captain Dylan was awesome at giving us a beautiful sunset cruise tour, he explained the history of this amazing sail boat...
The highlight of our trip to Key West. Amazing Ship, once owned by General Patton!! Fantastic crew. It made for a wonderful night!!! I can't wait to...
Absolutely an amazing experience. I was just hanging out with some buddies and we saw this classic ship with a sunset tour. We asked if it was accessible...
Private Harbor Day Sail Aboard the High Tide
Cruise the scenic waters of America's southernmost city on a day sail adventure with the professionals at Sunset Sail...
Private Chill Out Lily-Pad Sail - Up to Six Guests
Live the Key West lifestyle as you set sail over calm blue waters then drop anchor and chill out on a giant floating...
Sunset Sip and Sail with Open Bar and Live Music
Have you ever seen Key West at dusk on the open ocean? Just sit back and immerse yourself in the ambiance of this...
Private Sunset Sail Aboard the High Tide
Cruise the picturesque waters of Key West at sunset aboard the 33' High Tide yacht of Sunset Sail Key West. Among the...
Morning Reef Snorkel Tour
Experience AM snorkeling in the sparkling waters of the Florida Keys on a Morning Reef Snorkel Tour. Climb on board a...
Afternoon Reef Snorkel and Sail
Immerse yourself in the tropical waters of Key West when you set out on a snorkel and sailing adventure. Watch swarms of...
Sunset Sail Aboard the Historic When and If
Set sail on Key West’s most elegant historic schooner, the When And If. Built in 1939 for General George Patton’s...
Key West Sunset Sail on America 2.0
Embark on a spectacular sunset sailing adventure off the coast of Key West in search of the famed "Green Flash"....
Day Sail Aboard Schooner America 2.0
Explore the high seas in style on the Schooner America 2.0, namesake of the first sailboat to win the America's Cup in...
Mimosa Day Sail Aboard Schooner America 2.0
Take the helm and experience the majesty of sailing for yourself as you sit back and relax with a mimosa on a scenic day...
Ultimate Adventure Key West
Embark on an all-day water excursion that includes breakfast, lunch, and unlimited water sports for you and your whole...