Top Key West Dinner Cruises

from $93

Key West Schooner Sunset Sail with Bar & Hors d'oeuvres

(862)

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

from $123

4.5

(352)

Eat your way around Key West on a food tour of “mom and pop” eateries in the Old Town historic district. Taste seafood, Cuban cuisine, and delicious key lime pie. The walking tour route takes you off typical touristy streets so you can see Key West like a local, listening to insights about the city's food, architecture, and history along the way. Tastings are enough for a hearty lunch.

from $72

Southernmost Food & Cultural Walking Tour by Key West Food Tours

(1,830)

3 hoursFree Cancellation

from $90

4.7

(3,650)

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

Escape to the still waters off the coast of Key West on this adults-only sunset champagne cruise. Enjoy the peaceful calm of a late afternoon sail on a comfortable catamaran limited to just 14 passengers. Enjoy house champagne, red or white wine, ice-cold beer, a soft drink or bottled spring water, and a gourmet cheese buffet. Then watch as the sun glistens and gently settles into the water, a perfect ending to a perfect cruise.

from $79

Small Group Key West Adult Sunset & Moët Sail & Amazing Cheeses

(969)

2 hours

from $109

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

(1,415)

The whole family can learn more about sharks and other marine wildlife on this boat tour from Key West. Travel on board an eco-friendly, 34-foot catamaran just a few miles off the coast to try your luck spotting dolphins, stingrays, turtles, and birds while you learn more about Key West’s waters than you ever would sailing along. Then watch as the pilot drops bait to draw a variety of sharks right to the edge of the boat.

from $135

Likely to Sell Out

Shark and Wildlife Viewing Adventure in Key West

5.0

(3,124)

Jam to crowd favorite beats by live musicians, eat, drink, and watch the sunset on this classic party cruise from Key West. Dance the evening away or relax on the sundeck or in shaded areas as you sip on a margarita, beer, or other beverages. Unlimited drinks and light appetizers are included so you don’t need to pay extra. A great standalone evening activity or the start of a night out.

from $99

Key West Sunset Sail with Live Music, Drinks and Appetizers

4.6

(986)

from $80

Sunset Sail in Key West with Beverages Included

(937)

1 hour 30 minutesFree Cancellation

from $79

4.5

(609)

Key West Reef Morning Snorkeling with Breakfast and Mimosas

3 hoursFree Cancellation

from $35

Get ready for fun in the sun—and check off two top experiences in just one trip—on this dolphin-watching and snorkeling tour off the coast of Key West. Departing Key West, look out for dolphins swimming alongside the boat, then jump in for a shallow-water snorkel at the Key West National Wildlife Refuge with many different species of marine life. Relax, feel the warm sea breezes, and select from a variety of refreshing beverages on board the boat.

Key West Dolphin Watch and Snorkel Tour - Eco Adventure

4.7

(1,178)

3 hoursFree Cancellation

from $80

4.6

(725)

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

2 hours 30 minutesFree Cancellation

from $89

Likely to Sell Out

4.7

(591)

Key West Champagne Sunset Catamaran Cruise

1 hour 30 minutesFree Cancellation

from $59

4.8

(173)

Key West Cocktail Cruise Adults Only Sunset Cruise with Open Bar

2 hours

from $65

Top Attractions in Key West

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Attractions

What are people saying about Key West

Southernmost Food & Cultural Walking Tour by Key West Food Tours

Cat_M, Mar 2026

Loved this tour!

Gogo was a charismatic and vibrant tour guide. We visited 5 restaurants, some on duval st and some off the beaten path. We made a few new tour friends and tried a lot of good food. Do this tour your first day on the island so you know where to circle back to during your trip. Loved the history around the Cuban and Caribbean communities within the island.

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

Claire_B, Mar 2026

Chill cruise in the sunset. Family run business.

The cruise was well organized. There were three boats departing that day. Ours had to leave a little later due to a couple arriving late. Since the couple had called thy were able to stall the departure 5 min, that said, w got stuck by returning cruises and jet skis. Once we were on our way we didn’t really sail at sea but along the coast of Key west We were offered 8 wines and 3 sets of hors d’oeuvres and chocolates at the end. The sic was appropriate for the occasion and i can’t say that there was more than 18/20 people on the boat. We really enjoyed the cruise and the whether was amazing so that helped a lot! The captain and his 2 staff were friendly and liked to chat with the guests, they knew a lot about the area and other boats around.

Small Group Key West Adult Sunset & Moët Sail & Amazing Cheeses

Ann_P, Mar 2026

Great experience on sunset wine tasting cruise!

Highly recommend this trip. I appreciated being on a smaller boat with less people, instead of a large party barge. The captain plus staff were very friendly and kept us in calmer water, while still allowing us to have great views of the sunset. It was a perfect night for sailing! I also chose this trip because I have Celiac disease, and the wine tasting, gourmet cheeses, plus fruit were all things I could consume safely and enjoy!

Key West Schooner Sunset Sail with Bar & Hors d'oeuvres

Tina_G, Mar 2026

A Sunset Sail You’ll Want to Repeat

Highly recommend. This is our second time to sail with them and both times were fantastic. The crew is friendly and we felt very safe and comfortable both times. It feels like you are traveling with family. The Captain Janet and her crew are very professional and handle the boat with such ease. We enjoyed an incredible sunset cruise and enjoyed the drinks and appetizers. The schooner is large enough that you can't even feel the movement of the ocean which I was very grateful. Will sail with them again if we return to Key West with family.