Key West, FL > Sailing Charters
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11/29/2020 ~ 12/04/2020
November 2020

Key West Sailing Charters

Southernmost Sunset Sail with Full Bar and Hors d’Oeuvres

Southernmost Sunset Sail with Full Bar and Hors d’Oeuvres

33 ratings
Duration2 Hrs.
Excite yourself with the starburst blaze of colors that is the Key West sunset on a luxurious sunset sail. See the local...
Had a great time. Met some great people and saw an awesome sunset.
Excellent excursion I highly recommend.
My friends and I had a lovely evening. The staff was super friendly and courteous and they went out of their way to make sure we had a great evening. Open bar was great, music was delightful and the apps were delicious. We even saw a rainbow and dolphins, talk about a perfect evening.
from $70
Wind and Wine Sunset Sail

Wind and Wine Sunset Sail

30 ratings
Duration2 Hrs.
Sail into the Key West sunset while sampling 8 fine wines from around the world, beer, and delicious hors d'oeuvres....
The crew was wonderful! Meg & other stew were great! Tony was a good skipper
A fun crew, beautiful ship, Wine and cheese were yummy, breathtaking sunset! Only thing that could have made it a better evening would have been seats or stadium pads :0) it’s a sail boat so your sitting on the deck...which after and hour or so is a bit uncomfortable.
This was a first-class outing from the captain and crew to the wine and food to the beautiful Key West Sunset. We even had an on-board wedding to make us all feel a little more romantic. If you're visiting the Keys, don't miss this trip!
Sunset Snorkel Sail with Open Bar and Live Music

Sunset Snorkel Sail with Open Bar and Live Music

35 ratings
Duration3 Hrs.
Treat yourself to an evening of incredible snorkeling, delicious drinks, and groovy melodies on the the Sandie Cat...
The sunset snorkeling cruise was the highlight of our trip. I’d give it 10 stars if I could. The crew was awesome and I felt quite safe even though it was my first time snorkeling. Had a fantastic time, got some great photos and ended my key west trip with a bang!
I really enjoyed the trip. Food was good and the ride to and from was so enjoyable. Made some new friends and will do it again next time we go to the keys.
This was definitely worth every penny!!! The staff was super kind, the music was great and the vibe was just right!
Day Sail Aboard Schooner America 2.0

Day Sail Aboard Schooner America 2.0

5 ratings
Duration1.5 Hrs.
Explore the high seas in style on the Schooner America 2.0, namesake of the first sailboat to win the America's Cup in...
We had a fabulous sail with our all female crew of Amber Heather and Mary! Very fun and knowledgeable as well as excellent sailors! The boat was gorgeous! The allotted time went way too fast...We will certainly go out again on next trip to the Keys!
Wonderful experience sailing with this all female crew under the guidance of Captain Amber...cheerful, knowledgeable and welcoming ... they taught us safety and all about the coral reef!
Highly recommend! The crew was professional and just a lot of fun. The boat is spotlessly clean. I have never sailed. This was a great introduction. I enjoyed every minute. I wish I could remember the names of the crew who worked with Captain Ron. They deserve a shout out!!! Smart women, passionate about their work. And did I say fun????
Private Harbor Day Sail Aboard the High Tide

Private Harbor Day Sail Aboard the High Tide

36 ratings
Duration1.5 Hrs.
Cruise the scenic waters of America's southernmost city on a private day sail adventure with the professionals at Sunset...
Absolutely loved the entire experience . They had by far the best hospitality and customer service I have EVER experienced in my entire life. They...
What an interesting ship! We brought our own beverages and chose from a high variety of nut, fruit, and cheese tray (way better than cheap included...
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 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...
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...
Coral Reef Snorkeling Catamaran Trip with Margaritas Included
Experience the best afternoon on the Straights of the Florida Keys by snorkeling it's gorgeous coral reef. Climb aboard...
Ultimate Water Sport Combo Package with Breakfast & Lunch Buffet
Embark on an all-day water excursion that includes breakfast, lunch, and unlimited water sports for you and your whole...
Full Day Watersports Adventure with Breakfast & Lunch
This all-inclusive trip includes sailing, jet skis, parasailing, banana boat rides, snorkeling, kayaking, and more!...
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 Coral Reef Snorkel Adventure & Catamaran Cruise
Experience AM snorkeling in the sparkling waters of the Florida Keys on a morning snorkel adventure. 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...
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...
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"....