Key West, FL > Sailing Charters
02/26/2020 ~ 03/03/2020

Key West Sailing Charters

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

Champagne Sunset Sail

10 reviews
Duration2 Hrs.
Enjoy a night you’ll never forget on a Champagne Sunset Sail in Key West. Watch the masterfully painted sunset fade...
The Captain and crew were great and the evening was fun and beautiful.
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.
from $50
$42
Southernmost Sunset Sail with Full Bar and Hors d’Oeuvres

Southernmost Sunset Sail with Full Bar and Hors d’Oeuvres

10 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...
Wonderful sunset cruise, great apps, plenty of "beverages", cheerful staff! Highly recommend!!
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.
from $70
$64
Windjammer Schooner Sunset Sail

Windjammer Schooner Sunset Sail

23 reviews
Duration2 Hours
Spend a romantic evening aboard an authentic wooden schooner on the Windjammer Schooner Sunset Sail. This sailing vessel...
Went on a sunset sail tonight. Crew was great! Appetizers were delicious! Quite the variety. Drinks if you like alcohol you are all set BUT it would have...
Joe, Gus and especially DREW!!! Thank you for providing my husband and I with a Fabulous sunset cruise! We went for our first time- we've been visiting...
Anyone visiting Key West should most definitely make time to schedule a sunset cruise aboard this ship.My wife booked us on this delightful excursion and...
from
$64
Wind and Wine Sunset Sail

Wind and Wine Sunset Sail

18 reviews
Duration2 Hrs.
Sail into the Key West sunset while sampling 8 fine wines from around the world, beer, and delicious hors d'oeuvres....
Great crew that took care of us! The sunset alluded is that evening but we saw a spectacular moonrise and watched a man propose to his girlfriend. Very impressed that crew member Joe had memorized everyone’s names in about 30 minutes. I would definitely recommend.
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!
from
$85
Windjammer Schooner Day Sail

Windjammer Schooner Day Sail

23 reviews
Duration2 Hours
Catch the wind on a historic, dual-masted sailing vessel for a pleasure cruise through beautiful Key West. Journey the...
Went on a sunset sail tonight. Crew was great! Appetizers were delicious! Quite the variety. Drinks if you like alcohol you are all set BUT it would have...
Joe, Gus and especially DREW!!! Thank you for providing my husband and I with a Fabulous sunset cruise! We went for our first time- we've been visiting...
Anyone visiting Key West should most definitely make time to schedule a sunset cruise aboard this ship.My wife booked us on this delightful excursion and...
from
$37
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.
from
$49
Morning Reef Snorkel and Sail in Key West
Begin the day in the lap of luxury on an expansive 69’ sailing catamaran with Sebago Watersports. First, you’ll sail...
Full Day Watersports Adventure with Breakfast & Lunch
This all-inclusive trip includes sailing, jet skis, parasailing, banana boat rides, snorkeling, kayaking, and more!...
Private Snorkel and Sunset Sail Excursion
Climb aboard and set out on a private snorkel and sunset sail. You'll get the best of both worlds as you glide across...
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 BYOB Sunset Sailing Excursions
Cruise the picturesque waters of Key West at sunset aboard the 33' yacht of Sunset Sail Key West. Among the most popular...
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...
Schooner Champagne Sunset Sail
Come along on this Champagne Sunset Sail and step into the lap of luxury. Sip, relax, and unwind aboard a gorgeous...
Bloody Mary Schooner Sail
Set sail around the coast of Key West on an authentic wooden schooner. Take a cruise that boasts some gorgeous sights...
Captain's Choice Sunset Sail with Wine and Tapas Pairings
Embark on an unforgettable sailing adventure through the crystal-clear waters of Key West with the Captain's Choice...
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...