Key West, FL > Sailing Charters
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Key West Sailing Charters

Getting the best experiences for you...
Champagne Sunset Catamaran Cruise

Champagne Sunset Catamaran Cruise

24 ratings
Duration2 Hrs.
Enjoy a night you’ll never forget on a Champagne Sunset Catamaran Cruise in Key West. Watch the masterfully painted...
The 3 of us had a great time. We really enjoyed ourselves. Thank you!
Relaxing cruise. Don’t expect name brand alcohol for the price you paid, in other words you’ll have a headache. They charge an additional $10 each of you like for hard liquor. It was nice to do once. Before you know it the cruise was over.
Everyone was very polite
from $50
$42
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!
from
$49
Wind and Wine Sunset Sail

Wind and Wine Sunset Sail

27 ratings
Duration2 Hrs.
Sail into the Key West sunset while sampling 8 fine wines from around the world, beer, and delicious hors d'oeuvres....
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!
Had a great time , will visit again
from
$85
Live Music Sunset Cruise with Cocktails Included

Live Music Sunset Cruise with Cocktails Included

6 ratings
Duration2 Hrs.
Sail away with an ocean breeze for a night of music, drinks, and dancing on this Live Music Sunset Cruise. Experience...
Excellent crew and staff. The boat was beautiful, music was great and the scenery was perfect! Definitely a five star trip.
The actual cruise was really nice. Snacks were better than most, drinks kept flowing, staff were very accommodating and friendly.
The company went way above and beyond to make sure our night was very happy!! Thank you so much for making my husband Birthday that he'll never forget!!
from
$60
Private Harbor Day Sail Aboard the High Tide

Private Harbor Day Sail Aboard the High Tide

35 ratings
Duration1.5 Hrs.
PERFECT FOR GROUPS UP TO 6!
Cruise the scenic waters of America's southernmost city on a private day sail adventure with the professionals at Sunset...
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...
We can't recommend this Sunset sail enough! The captain and crew were fabulous, the service is on point. And what can I say about sailing on a classic...
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...
from
$295
Morning Reef Snorkel and Sail in Key West

Morning Reef Snorkel and Sail in Key West

6 ratings
Duration3 Hrs.
Begin the day in the lap of luxury on an expansive 69’ sailing catamaran with Sebago Watersports. First, you’ll sail...
We arrived just in time to set out for our adventure. Our 3 man crew took excellent care of us. Saw so much! Swam with a turtle and so many colorful fish. I will be back!
I had a warm and inviting experience on the boat for the snorkeling.
We had a great time! We took our 2 kids along with our 2 nieces which had never went snorkeling before and they had a blast! Will definitely go again. The captain and his crew was awesome!
from $50
$42
Private Chill Out Lily-Pad Sail - Up to Six Guests

Private Chill Out Lily-Pad Sail - Up to Six Guests

35 ratings
Duration3 Hrs.
Live the Key West lifestyle as you set sail over calm blue waters then drop anchor and chill out on a giant floating...
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...
We can't recommend this Sunset sail enough! The captain and crew were fabulous, the service is on point. And what can I say about sailing on a classic...
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...
from
$495
Private Snorkel and Sunset Sail Excursion

Private Snorkel and Sunset Sail Excursion

35 ratings
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...
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...
We can't recommend this Sunset sail enough! The captain and crew were fabulous, the service is on point. And what can I say about sailing on a classic...
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...
from
$695
Sunset Snorkel & Sail with Rum & Reggae Included
Leave land behind for an evening of snorkeling and Reggae music on this caribbean sunset sailing cruise. The rhythmic...
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...
Private 3 Hour Key West Coral Reef Snorkel & Sail - 18 Passengers
You never know what's in store when you set out for a day on the water in Key West. Join this 3 Hour Key West Coral Reef...
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...
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"....
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...