Top Key West Dinner Cruises

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

4.3

(1,908)

from $93

2 hours 30 minutesFree Cancellation

4.6

(758)

from $89

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

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

4.5

(394)

from $77

Key West Cocktail Cruise Adults Only Sunset Cruise with Open Bar

4.7

(3,811)

from $79

2 hours

Key West Reef Morning Snorkeling with Breakfast and Mimosas

(182)

from $65

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

(714)

from $54

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

(1,017)

from $73

1 hour 45 minutes to 2 hoursFree Cancellation

3.9

(611)

from $64

Southernmost Food & Cultural Walking Tour by Key West Food Tours

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.

Southernmost Food & Cultural Walking Tour by Key West Food Tours

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.

(1,919)

from $90

Key West Dolphin Watch and Snorkel Tour - Eco Adventure

Key West Dolphin Watch and Snorkel Tour - Eco Adventure

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.

4.7

(1,217)

from $73

Key West Afternoon Snorkel Sail with Unlimited Cocktails!

Key West Afternoon Snorkel Sail with Unlimited Cocktails!

Sunset Sail in Key West with Beverages Included

4.4

(1,611)

from $59

1 hour 30 minutesFree Cancellation

Key West Champagne Sunset Catamaran Cruise

(978)

from $79

1 hour 30 minutesFree Cancellation

4.7

(595)

from $59

Key West Small-Group Sunset Sail with Wine 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.

(1,470)

from $135

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

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

Southernmost Food & Cultural Walking Tour by Key West Food Tours

4.4

(388)

from $57

Top Attractions in Key West

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What are people saying about Key West

Jamie_R, Jul 2026

Great time

Our group was small but mighty! Azona did an awesome job of explaining what we were eating and how it was made. All the food choices were amazing! She was very conscious of the heat as she gave us history on the walk. I would definitely recommend this tour.

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

JASON_R, Jul 2026

Very chill not over...

Very chill not over crowded and fun crew made this trip enjoyable. Reef was teeming with life and so many fish varieties. I usually have a hard time with the mask but theirs fit well and didn't fog up or leak like others I've used. The 3 hours is about 50 minutes out, 50 minutes snorkeling which was plenty for us, and the rest just having a good time on the way back. Crew was excellent so tip them well!

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.

Sunset Sail in Key West with Beverages Included

Dean_R, May 2026

Fantastic sunset cruise!

We booked this sunset cruise as it appeared to be smaller and less crowded than others and the reviews were great. Well it did not disappoint! Only 8 guests aboard so it felt like a private charter! Liz and the crew were awesome and very attentive. The sunset itself was spectacular-no surprise for Key West. It was also my wife’s birthday which made it extra special. She had a blast! I would highly recommend this cruise for anyone not looking for the party boat experience. Quiet, low key and just awesome!

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

Mike_Y, Apr 2026

April 2026 Sunset Sail with Danger Charters

Fantastic experience. Sailing on the boat was excellent, the crew was very friendly and fun to chat with, the wines & hors d'oeuvres were tasty, and the views were spectacular! Highly recommend for anyone that is looking for a relaxed and fun sunset cruise!

Key West Afternoon Snorkel Sail with Unlimited Cocktails!

Melissa_C, Apr 2026

Great experience!

Fun day! We enjoyed the 45 minute ride to the reef, boat was clean and comfortable, crew was friendly, and there was a bathroom on board and plenty of water available. Snorkeling was great…beautiful reef, saw lots of fish, safety information and guidance from the crew was super helpful. Note…snorkeling was off the boat in open ocean, so maybe a bit intimidating for first timers or young kids? That said, the crew did a great job of providing help, ideas and modifications to accommodate various swimming levels and snorkeling experiences. Music and fruity adult drinks were also a fun touch! Would definitely recommend!

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.