Top Key West Dinner Cruises

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

4.3

(1,917)

from $93

2 hours 30 minutesFree Cancellation

4.6

(760)

from $89

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

Snorkel North America’s only living coral reef, then catch an unforgettable Key West sunset, all in one trip. Jump into clear waters with provided gear and spot colorful marine life under the surface. Back on board and after you’re dried off, enjoy rum punch or other beverages on deck as reggae music sets the vibe. A perfect mix of adventure and relaxation, ideal for couples or friends.

4.7

(3,829)

from $79

Key West Rum and Reggae: Reef Snorkel Adventure and Sunset Sail

Key West Rum and Reggae: Reef Snorkel Adventure and Sunset Sail

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

4.4

(392)

from $57

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.

4.5

(400)

from $77

Key West Sunset Sail with Live Music, Drinks and Appetizers

Key West Sunset Sail with Live Music, Drinks and Appetizers

Key West Glass-Bottom Boat Tour with Sunset Option

4.6

(1,019)

from $73

1 hour 45 minutes to 2 hoursFree Cancellation

3.9

(611)

from $64

Key West Champagne Sunset Catamaran Cruise

1 hour 30 minutesFree Cancellation

4.7

(596)

from $59

Key West Reef Morning Snorkeling with Breakfast and Mimosas

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.

4.5

(724)

from $54

Key West Dolphin Watch and Snorkel Tour - Eco Adventure

Key West Dolphin Watch and Snorkel Tour - Eco Adventure

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.

4.7

(1,229)

from $73

Southernmost Food & Cultural Walking Tour by Key West Food Tours

Southernmost Food & Cultural Walking Tour by Key West Food Tours

Sunset Sail in Key West with Beverages Included

4.9

(1,926)

from $94

1 hour 30 minutesFree Cancellation

4.9

(983)

from $79

Key West Hop-On Hop-Off Trolley Tour

1 hour 30 minutesFree Cancellation

4.5

(1,759)

from $56

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

Discover a side of Key West some visitors miss, and immerse yourself in its beautiful scenery, on a half-day sailing tour. Board your catamaran and head to North America's only living coral barrier reef. Pass some of Key West’s top attractions on the way, then dive in to see hundreds of species of colorful fish, coral, and other sea life. This cruise includes snorkeling gear, plus beer, wine, and soft drinks.

4.9

(1,475)

from $135

Key West Afternoon Snorkel Sail with Unlimited Cocktails!

Key West Afternoon Snorkel Sail with Unlimited Cocktails!

Key West Rum and Reggae: Reef Snorkel Adventure and Sunset Sail

4.4

(1,615)

from $59

Top Attractions in Key West

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What are people saying about Key West

linda_k, Aug 2026

Super Experience for all ages

We had an awesome time on this excursion. There were 21 of us total which is a LOT. Ages ranging from 2 years old to 65 years old. The crew was super helpful and the water was beautiful. The only odd thing is the captain approached our group a number of times telling us we needed to tip the crew because we were such a large group. We ALWAYS tip the crew and certainly do not need numerous reminders. It was uncomfortable how pushy he was. We tipped over $300 as a group so the crew was well taken care of. It was just odd.

Southernmost Food & Cultural Walking Tour by Key West Food Tours

Prissy_G, Jul 2026

Eating with Scott!

This was an amazing way to see the low key and off the beaten path of Key West. The food a tasty mix from the cultures that make Key West unique. Our guide, Scott, was great! He had so much knowledge of the history and culture of the Keys. His insight and personality made the tour special. Definitely would request Scott!

Sunset Sail in Key West with Beverages Included

Christopher_D, Jun 2026

Magical. Unforgettable.

Magical experience for everyone. Our son’s girlfriend said she had ‘never seen a more beautiful sunset’ (and she is very well travelled)! To top it off, everything was heightened by two great captains, Eric and Ransom, who were kind, attentive, and professional. It was a truly lovely evening, which we will not forget any time soon. Thank you for a fantastic time!

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

Chuck_R, May 2026

Dolphins, Tapas & Sunset...Oh, My!

We went on the catamaran Tera Lani 2 operated by Sebago Water Sports in Key West. The group is limited to 50 people so it was not crowded. The crew was very helpful, the tapas were excellent and the beer wine & prosecco were good brands. The cruise is about an hour longer than most because we searched for dolphins on our way out. We were fortunate to see a few and even captured a photo. The sunset was fabulous that evening and not obstructed by any islands or clouds. It was a fantastic journey & we highly recommend this particular sunset cruise.

Key West Cocktail Cruise Adults Only Sunset Cruise with Open Bar

Lora_B, Feb 2026

Amazing crew, amazing sunset!

The boat was freshly cleaned and well-stocked. Our captain Steve was friendly and had a bunch of interesting information about the island. He played great music and was always up for suggestions. We had an intimate party of great guests. Sky, the bartender made excellent drinks and had great suggestions. They had about 9 different beers available and a full liquor bar, as well as wine. Both Sky and Steve went out of their way to make sure we were having a great time and had a beautiful view of a beautiful sunset on the water, we even got to see a couple pods of dolphins that they tracked down for a closer view. We enjoyed our experience so much, but what really made it special was the hospitality of Sky and Steve. They made the trip extraordinary, even pointing out different beaches and houses along the way to our sunset view and back. Overall, the trip was about 2.5 hours or so and we will definitely be back the next time we are in Key West to jump aboard “The Good Times”! If you booked through Viator, the details were limited but this is run through Snuba of Key West with a departure time of 5/515pm.