Key West, FL > Sailing Charters
04/14/2021 ~ 04/19/2021
Talk to us
We are currently closed.
Please call us during normal business hours or book online 24/7.

We are open 7am - 7pm
CST Monday-Sunday

Key West Sailing Charters

Southernmost Sunset Sail with Full Bar and Hors d’Oeuvres

Southernmost Sunset Sail with Full Bar and Hors d’Oeuvres

91 ratings
Duration2 Hrs.
Entice yourself with the starburst blaze of colors that is the Key West sunset on a luxurious sunset sail. See local...
Everything from check in to the wonderful crew and the view of the sunset was excellent!!! I would highly recommend!
Great value for all they do for you. Lot’s of food and all the drinks you can handle!
Absolutely a blast! Wonderful service!
from $70
$69
Champagne Sunset Catamaran Cruise

Champagne Sunset Catamaran Cruise

53 ratings
Duration1.5 Hrs.
Enjoy a night you’ll never forget on a Champagne Sunset Catamaran Cruise in Key West. Watch the masterfully painted...
The staff was nice,the one even took pictures of us. The sunset was beautiful. Of course free alcohol is nice. The only thing was that the ad said margaritas, but there wasn't any.
Nice sunset tour. We had a lot of fun. Music was great. Con . Better organization at the boarding process. It's was a cluster F***
Nice time with a nice crew and good music.
from $50
$48
Day Sail Aboard Schooner America 2.0

Day Sail Aboard Schooner America 2.0

11 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...
Staff was great and accommodating.. The weather could not have been more perfect. Great way to spe d an afternoon on on Key west. Bring your sunscreen
Absoutly fantastic sail. The crew was phenomenal. The schooner was in tip top condition. We had a beautiful sail. It was the high point of my Key West visit.
Crew was awesome! What a great afternoon on the water at key west. Would definitely book again. Flo & Steve Evans
from
$56
Sunset Sip and Sail with Open Bar and Live Music

Sunset Sip and Sail with Open Bar and Live Music

28 ratings
Duration2 Hrs.
Have you ever seen Key West at dusk on the open ocean? Just sit back and immerse yourself in the ambiance of this...
Our sailing trip was great we had a great time enjoyed Pete with the music and rest of staff were awesome. When we come back we will definitely do this again Thank You
Was a great sun set cruise with great entertainment and drinks
This was the highlight of our visit to Key West. Crew was great and very fun to be around. Unbelievable view and very comfortable trip. Highly recommend it and will be back in the future for another voyage.
from
$49
Wind and Wine Sunset Sail

Wind and Wine Sunset Sail

41 ratings
Duration2 Hrs.
Sail into an unforgettable Key West sunset while sampling beer, delicious hors d'oeuvres, and 8 fine wines from around...
Loved this excursion!
I booked this for myself and 5 friends. It was most of the group's favorite activity. We have such a great time and the staff was wonderful.
We had a wonderful time in the wind and wine sunset sail! The crew was AWSOME and the weather was perfect. Will definitely do it again next trip to the Keys!
from
$85
Key West Sunset Sail on America 2.0

Key West Sunset Sail on America 2.0

26 ratings
Duration2 Hrs.
Embark on a spectacular sunset sailing adventure off the coast of Key West in search of the famed "Green Flash"....
The WHOLE CREW was great. What a awesome experience. Totally enjoyed every moment. Wished it would have never ended. You should think about charging for the ride up to NewYork City when they run the schooner up to the other port.
The sunset was gorgeous. The crew was amazingly attentive. The best looking captain on the seas!
We had such a great time! Captain Eric made the experience even more memorable when he let our daughter steer the boat! The crew was beyond friendly! Can’t wait to go out with you guys again!
from
$96
Live Music Sunset Cruise with Cocktails Included

Live Music Sunset Cruise with Cocktails Included

26 ratings
Duration2 Hrs.
Sail away with an ocean breeze for a night of music, drinks, and dancing on this Live Music Sunset Cruise. Experience...
The band was great and the sunset was amazing!
We had a great time, weather, staff, and music was great
The people working the cruise were very friendly. The food served was delicious, and the live music was awesome! Add a beautiful sunset to that, and you have a perfect evening.
from
$65
Sunset Snorkel Sail with Open Bar & Live Music

Sunset Snorkel Sail with Open Bar & Live Music

37 ratings
Duration3 Hrs.
Treat yourself to an evening of incredible snorkeling, delicious drinks, and groovy melodies on 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!
from
$59
Morning Reef Snorkel and Sail in Key West

Morning Reef Snorkel and Sail in Key West

14 ratings
Duration3 Hrs.
Begin the day in the lap of luxury on an expansive 69’ sailing catamaran with Sebago Watersports. First, you’ll sail...
This was a fabulous value and wonderful time on the boat with the very helpful and friendly staff. I only wish we would have seen more while snorkeling...
Great boat ride and snorkeling excursion - couldn’t be happier!
One of the best experiences you can get. Book and enjoy. Thanks to the crew, you guys are awesome.
from $50
$42
Sunset Snorkel & Sail with Rum & Reggae Included

Sunset Snorkel & Sail with Rum & Reggae Included

3 ratings
Duration3 Hrs.
Leave the land behind for an evening of snorkeling and Reggae music on this Sunset Snorkel & Sail with Rum & Reggae...
Medium boat but a bit congested for covid era. Helpful staff.
Captain Ron and his crew were great. The reef snorkel was fantastic. The sunset was very memorable. I would highly recommend this excursion for others.
Snorkeling had a lot to see. Very pretty sunset and staff including Allie were very knowledgeable. Would book again.
from
$55
Private Harbor Day Sail Aboard the High Tide
Cruise the scenic waters of America's southernmost city on a private day sail adventure with the professionals at Sunset...
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 you'll find on the Straits if Flofida Keys by snorkeling this gorgeous coral reef. Climb...
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!...
Key West Sailing, Kayak, & Dolphin Watching with Breakfast and Lunch
This fun-filled Key West tour combines three awesome adventures into one package. Enjoy a day of sailing, dolphin...
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 some morning snorkeling in the sparkling waters of the Florida Keys on this Morning Coral Reef Snorkel...
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...