Under sail · SAILING TOURS WITH DRINKS IN KEY WEST

9 Sailing Tours with Drinks in Key West to Book

9 sailing trips  ·  seats from $59 each

The good sailing tours with drinks in Key West fill their decks early in the season. Here are the 9 to book first, what each includes and how they differ.

Key West Sunset Sail with Open Bar, Live Music and Hors D'oeuvres - Finding the boat at 205 Elizabeth Street
Key West Sailing Tours, Party and Music Sailing Cruises, Sailing Tours, Sailing Tours with Drinks, Sailing Tours with Drinks in Key West, Sailing Tours with Drinks in the USA, Sunset Sailing Cruises, Sunset Sailing Cruises in Key West, Sunset Sailing Cruises in the USA, Tour Reviews, USA Sailing Tours

Key West Sunset Sail with Open Bar, Live Music and Hors D’oeuvres

1.Key West Sunset Sail with Open Bar, Live Music and Hors D’oeuvres

★★★★★★★★★★4.5 · 3,559 reviews · 2 hours (approx.) · from $79Top of the fleet

Spend about two hours sailing from Key West with an open liquor bar, champagne, sangria, wine, premium beer, soft drinks, and chef-prepared hors d’oeuvres. A local musician provides live entertainment while you pass Mallory Square, Fort Zachary Taylor, Sunset Key, and the Key West harbor. Arrive 30 minutes early and bring a sweater.

“Wonderful experience, drinks food and music all terrific and the sunset was breathtaking. Bring a sweater”

Check sailing dates →Read the whole sail review

Key West Afternoon Snorkel Sail with Unlimited Cocktails! - The hour-long run to the Florida Reef
Key West Sailing Tours, Sailing and Snorkeling Trips, Sailing and Snorkeling Trips in Key West, Sailing and Snorkeling Trips in the USA, Sailing Tours, Sailing Tours with Drinks, Sailing Tours with Drinks in Key West, Sailing Tours with Drinks in the USA, Tour Reviews, USA Sailing Tours

Key West Afternoon Snorkel Sail with Unlimited Cocktails!

2.Key West Afternoon Snorkel Sail with Unlimited Cocktails!

★★★★★★★★★★4.5 · 1,572 reviews · 3 hours (approx.) · from $59Lowest fare aboard

Sail from Key West’s historic seaport aboard the 69-foot Marquesa to the Florida Reef, about 7.5 miles offshore. The crew provides gear, safety instruction, and time to snorkel in shallow reef water. After swimming, enjoy included beer, wine, soft drinks, and cocktails on the return trip. The boat has restrooms and a freshwater rinse.

“The boat was great as well as the captain and mates! I didn't see a lot of fish that was a bit disappointing. Other than that it was fun!”

Check sailing dates →Read the whole sail review

Key West Small-Group Sunset Sail with Wine and Hors d'oeuvres - Setting sail with a small group
Key West Sailing Tours, Sailing Tours, Sailing Tours with Drinks, Sailing Tours with Drinks in Key West, Sailing Tours with Drinks in the USA, Sunset Sailing Cruises, Sunset Sailing Cruises in Key West, Sunset Sailing Cruises in the USA, Tour Reviews, USA Sailing Tours

Key West Small-Group Sunset Sail with Wine and Hors d’oeuvres

3.Key West Small-Group Sunset Sail with Wine and Hors d’oeuvres

★★★★★★★★★★5.0 · 1,366 reviews · 2 hours (approx.) · from $125Best loved

Join Danger Charters at 255 Front Street for a two-hour sunset sail with up to eight wines, five beers, soft drinks, and wine-paired hors d’oeuvres. Crews including Mary, James, Connor, and Molly are known for warm service, stories, blankets on cool evenings, and a relaxed small-boat setting.

“Great crew, excellent wine, delicious hors d’oeuvres, beautiful sunset ~ perfect evening! Plus, the limited number of guests was definitely preferred.”

Check sailing dates →Read the whole sail review

Key West Sunset Sail with Live Music, Drinks and Appetizers - Finding your place on the catamaran
Key West Sailing Tours, Party and Music Sailing Cruises, Sailing Tours, Sailing Tours with Drinks, Sailing Tours with Drinks in Key West, Sailing Tours with Drinks in the USA, Sunset Sailing Cruises, Sunset Sailing Cruises in Key West, Sunset Sailing Cruises in the USA, Tour Reviews, USA Sailing Tours

Key West Sunset Sail with Live Music, Drinks and Appetizers

4.Key West Sunset Sail with Live Music, Drinks and Appetizers

★★★★★★★★★★4.5 · 952 reviews · 2 hours (approx.) · from $79

Spend about two hours aboard Fury’s 65-foot catamaran as local musicians play popular cover songs, crew serve unlimited margaritas, beer, wine, champagne, soda, and seasonal appetizers. You can dance, sit in the shade, or watch the sunset near Mallory Square and Fort Zachary Taylor. Arrive early for a better seat.

“Great fun! Drinks flowed freely, great apps, but mostly awesome band & dancing under the beauty of Gods Key West sunset!!!”

Check sailing dates →Read the whole sail review

Key West Sunset Sail: Dolphin Watching, Wine, and Tapas - Passing Mallory Square and Key West landmarks
Key West Sailing Tours, Sailing Tours, Sailing Tours with Drinks, Sailing Tours with Drinks in Key West, Sailing Tours with Drinks in the USA, Sailing Tours with Lunch, Sunset Sailing Cruises, Sunset Sailing Cruises in Key West, Sunset Sailing Cruises in the USA, Tour Reviews, USA Sailing Tours, Whale and Dolphin Watching Sails, Whale and Dolphin Watching Sails in the USA

Key West Sunset Sail: Dolphin Watching, Wine, and Tapas

5.Key West Sunset Sail: Dolphin Watching, Wine, and Tapas

★★★★★★★★★★4.5 · 699 reviews · 2 hours 30 minutes (approx.) · from $89

Set out from Key West’s Historic Seaport for a 2.5-hour catamaran cruise past Mallory Square, Fort Zachary Taylor, and Sunset Key. The crew, including captains such as Daniel and hosts such as Jordan or Gracie, serves wine, champagne, beer, soda, and small bites. Dolphins are possible, not promised.

“Wonderful experience, excellent hors d’oevres, drinks, beautiful sunset, well worth the price - would have liked to be under sail instead of engine for the trip”

Check sailing dates →Read the whole sail review

Key West: Schooner Sunset Sail with Food & Drinks - The route along Key Wests western shore
Food, Key West Sailing Tours, Sailing Tours, Sailing Tours with Drinks, Sailing Tours with Drinks in Key West, Sailing Tours with Drinks in the USA, Sunset Sailing Cruises, Sunset Sailing Cruises in Key West, Sunset Sailing Cruises in the USA, Tall Ship and Schooner Sailing, Tall Ship Sailing in Key West, Tall Ship Sailing in the USA, Tour Reviews, USA Sailing Tours

Key West: Schooner Sunset Sail with Food & Drinks

6.Key West: Schooner Sunset Sail with Food & Drinks

★★★★★★★★★★4.9 · 318 reviews · 2 hours · from $122

Sail from Key West aboard the wooden schooner America 2.0 for a two-hour sunset outing. The crew serves alcoholic and non-alcoholic drinks plus a personal hors d'oeuvres plate as you pass Fort Zachary Taylor, Sand Key Reef, Mallory Square, and Sunset Pier. Keep watch for dolphins, turtles, water birds, and the Green Flash.

“Amazing cruise. The crew were fantastic, the cruise very relaxing, and the setting sun beautiful to see. Many thanks, a perfect evening.”

Check sailing dates →Read the whole sail review

Key West Signature Sunset Sail with Live Music, Open Bar & Food - Drinks are the main value calculation
Food, Key West Sailing Tours, Party and Music Sailing Cruises, Sailing Tours, Sailing Tours with Drinks, Sailing Tours with Drinks in Key West, Sailing Tours with Drinks in the USA, Sunset Sailing Cruises, Sunset Sailing Cruises in Key West, Sunset Sailing Cruises in the USA, Tour Reviews, USA Sailing Tours

Key West Signature Sunset Sail with Live Music, Open Bar & Food

7.Key West Signature Sunset Sail with Live Music, Open Bar & Food

★★★★★★★★★★4.5 · 314 reviews · 2 hours (approx.) · from $72

Sail from 201 William St. aboard the three-deck Sandie Cat for a two-hour Key West sunset cruise with live music, unlimited well drinks, beer, wine, champagne, and light appetizers. The mood can range from relaxed to lively, with open space for sunset views and a return to the same dock.

“We really enjoyed being on the water during sunset. The boat had plenty of seating for all the guests and plenty of room to move around to the best areas for views. The live violin duet was a great accompiment to the views. The free pinot grigio and food were what would be expected on this type of tour, acceptable. Great value for the price.”

Check sailing dates →Read the whole sail review

Key West: Sunset Sailing Trip with Open Bar, Food and Music - What the Sandie Cat offers on three decks
Food, Key West Sailing Tours, Party and Music Sailing Cruises, Sailing Tours, Sailing Tours with Drinks, Sailing Tours with Drinks in Key West, Sailing Tours with Drinks in the USA, Sunset Sailing Cruises, Sunset Sailing Cruises in Key West, Sunset Sailing Cruises in the USA, Tour Reviews, USA Sailing Tours

Key West: Sunset Sailing Trip with Open Bar, Food and Music

8.Key West: Sunset Sailing Trip with Open Bar, Food and Music

★★★★★★★★★★4.5 · 310 reviews · from $80

Sail from Key West’s historic seaport aboard the three-deck Sandie Cat for a two-hour sunset cruise. You’ll get open-bar drinks, light appetizers, live music, and room to move between decks. You may also help raise the sails or take a photo at the wheel.

“So much fun! Enjoyed some great music and tasty snacks! Sunset was priceless- my photo was even featured on our local weather newscast!!”

Check sailing dates →Read the whole sail review

Classic Key West Schooner Sunset Sail with Full Open Bar - Leaving from the Key West Historic Seaport
Key West Sailing Tours, Sailing Tours, Sailing Tours with Drinks, Sailing Tours with Drinks in Key West, Sailing Tours with Drinks in the USA, Sunset Sailing Cruises, Sunset Sailing Cruises in Key West, Sunset Sailing Cruises in the USA, Tall Ship and Schooner Sailing, Tall Ship Sailing in Key West, Tall Ship Sailing in the USA, Tour Reviews, USA Sailing Tours

Classic Key West Schooner Sunset Sail with Full Open Bar

9.Classic Key West Schooner Sunset Sail with Full Open Bar

★★★★★★★★★★5.0 · 213 reviews · 2 hours (approx.)

Set sail from Key West’s Historic Seaport aboard a schooner limited to 22 passengers. Captain Joe, Captain Josh, Cristina, Michael, Molly, or another crew team may handle the trip. Expect a gentle cruise, cocktails, wine, beer, champagne, snacks, and views of Mallory Square, Sunset Key, Fort Zachary Taylor, and the setting sun.

“Very nice professional staff. Fun ride and really liked that only a limited number of people can be on the boat. Did not feel crowded.”

Check sailing dates →Read the whole sail review

Other ways to get on the water

Sunset Sailing CruisesCatamaran Sailing TripsSailing and Snorkeling TripsPrivate Sailing ChartersIsland Hopping Sailing TripsTall Ship and Schooner Sailing
Scroll to Top

Explore sailing

Pick a boat, a coast or a time of day.

Kinds of sail

Catamaran tripsTall shipsYacht chartersPrivate chartersLessons

Time of day

Golden-hour sailsDinner sailsParty sailsTwo-hour sailsFull-day sails

On board

Drinks on boardLunch at anchorSwim stopsSnorkel sails

Out at sea

Island hoppingWhales and dolphinsNile feluccasEvery sailing trip