Name: Key West Sunset Dinner Cruise
Brand: TripShock
SKU: 2480
Price: 86 USD
Availability: InStock
Rating: 4.5882 (289 reviews)

Dinner Cruises

Sunset Cruises

Boat Tours

If you are looking to make memories on a glorious Key West sunset as you dine and enjoy drinks with your loved ones, then this is the perfect cruise for you. This Key West Sunset Dinner Cruise allows you to have it all. Experience a delectable dinner and drinks out at sea with a friendly crew and dine on tropical-inspired featured dishes like Roast Pork with heavenly Cuban Bread followed by fried plantains. Your meal is prepared fresh on board and your catamaran features a fully stocked bar and comfortable seating in a climate-controlled cabin. So, get out on the water and dine, drink, and dance away the day on this classic Key West Sunset Dinner Cruise. Reserve your spot today!

Key West Sunset Dinner Cruise

How to Redeem: Print this ticket or show the confirmation details from your mobile device to join this activity. Please have a valid ID with you to confirm your order if needed.
Parking: Metered city lot and street parking are available. 
Departure Details: The cruise departs from 201 William St, Key West, FL 33040. Please arrive and check in at the Sunset Watersports booth 45 minutes before departure. Cruise departs on time. For any issues, please contact your provider, Sunset Watersports at 305-296-2554.
Gratuities: Gratuities are not required but are appreciated and encouraged.

Sunset Watersports

289 Reviews of Key West Sunset Dinner Cruise - TripShock!

Key West Sunset Dinner Cruise

Customer must cancel 24 hours prior to the arrival date in order to receive a full refund. Cancellations received less than 24 hours prior to the arrival date will not be eligible for a refund. No shows will not be refunded.

Cancel or Reschedule 24 hours prior to arrival for FREE

If you are looking to make memories on a glorious Key West sunset as you dine and enjoy drinks with your loved ones,...

Good fun crew
Great captain
Food selection hood

Smooth cruisen

Great property, great staff, overall awesome experience. Appreciate the great hospitality on my first trip to Key West.

Super Dope!!!

It was a wonderful time and the staff was great and very welcoming

Great

Great experience, I would definitely recommend, over the top hospitality

Sunset dinner cruise

We felt like it was a rush for everything. Could be organized by having ppl sit and then dismiss tables one at a time

I am sorry but that food was HORRIBLE.  I think it came from a can.  Nothing was good.  The fish was SQUARE nuggets?  We were extremely disappointed in the food and beverage.  We served ourselves, wiped off our table to sit down, retrieved our own water, then cleared our plates and scraped the food into the trash.  Seems like we should have at least had service for $90 per person.

SUNSET CRUISE with DINNER

Rachel was exceptional and very outgoing...food was great and other staff were very helpful taking pictures for people and mixing drinks

Captain

Great food and great staff, we just got rained on

Rain

Service spectacular, captain friendly and very knowledgeable! Food was great, drinks were good and atmosphere awesome! Enjoyed and highly recommend

Excellent Sunset Cruise

The sunset dinner cruise with Sunset Watersports was everything we were looking for!  We had a great crew manning the boat who were all friendly and knowledgeable. The sunset was of course beautiful and the DJ on board not only played music but played steel pan along with it which made it 100x better! The food was good and even though I’m pregnant and couldn’t have alcohol, my husband says the drinks were good and they were even able to make me some virgin drinks that were great (something which seems to be not the easiest thing to do without making the drink a dessert it’s so sweet). All in all we would definitely book again!

Wonderful

Key West

Embark on an unforgettable sailing adventure through the crystal-clear waters of Key West with the Dolphin Watch Sunset Sail. Enjoy superbly crafted tapas like tuna poke and shrimp cocktail along with champagne, select premium wines including LaCrema, beer, and sangria as you journey to view majestic dolphins, landmark sights and the world famous Key West sunset. Get an authentic sailing experience as the captain and crew raise the sails on your luxurious catamaran and set out to find dolphins playing and frolicking in the surf and often near the boat! Book yours today!

Dolphin Watch Sunset Sail with Premium Wine and Tapas Pairings

Embark on an unforgettable sailing adventure through the crystal-clear waters of Key West with the Dolphin Watch Sunset...

We loved the dolphin sunset cruise! We were in the right spot and saw about 20 dolphins. It’s August so it was very hot when the cruise started. An hour in it was much more comfortable!

So many dolphins!

It was super fun. The sangria was fabulous, the staff was very nice. We saw a family of dolphins. The sunset was out of this world. I totally recommend it. It was definitely worth the money.

Excellent

The experience was wonderful! Saw so many dolfins! Food and drinks were good. And the sunset was amazing!!! Crew was great.  Friendly and ready with drinks. And the music was really good too. Would highly recommend!!!

Couldn't have gone better!

Sebago Key West

This triple combo tour gives you three amazing experiences in one package. Watch pods of local dolphins playing in their natural habitat, snorkel at a tropical reef, and last but not least witness the famous Key West sunset! This action-packed, three-for-one adventure is sure to yield magic and memories to last a lifetime. Book now!

Triple Combo Snorkeling, Dolphin, and Sunset Cruise

This triple combo tour gives you three amazing experiences in one package. Watch pods of local dolphins playing in their...

La capitaine à bord et toute son équipe sont très gentils, endroit facile à trouver pour s’enregistrer.  On a vu quelques dauphins, mais de loin et très peu. L’apnée  était un désastre l’eau trouble et aucun poisson observé… une chance que le coucher de soleil était fantastique le plus beau que j’ai vu de la vie!!

Coucher de soleil magnifique

Great crew!

So worth the money! Paige and Ellen are super helpful and kind and play good music. Good drinks, environment, and staff. Captain Owen stopped so we can look at the dolphins and admire the ocean, also a very smooth ride. Would definitely do it again

Amazing trip

Enjoy a night you’ll never forget on a Champagne Sunset Catamaran Cruise in Key West. Watch the masterfully painted sunset fade into dark as the stars give an encore unlike any other. Stretch out and enjoy a pampering of complimentary drinks with family or a special someone. Come feel the ocean breeze blow through your hair and dance across your skin as the sun sets over Key West, book your Champagne Sunset Sail today!

Champagne Sunset Catamaran Cruise

Enjoy a night you’ll never forget on a Champagne Sunset Catamaran Cruise in Key West. Watch the masterfully painted...

Out on the water

We loved this relaxing experience. Bring sunglasses for before the sun sets. Fantastic staff.

Beautiful!

No issues, super easy and crew easy going and professional, very safe

Excellent cruise

Entice yourself with the starburst blaze of colors that is the Key West sunset on a luxurious sunset sail. See local landmarks and sail past Sunset Key and historic Fort Zachary Taylor as you dine on a tasty selection of varied hors d'oeuvres. Watch the sunset with your favorite drink in your hand and your loved ones by your side. Enjoy live music from local musicians! These are moments you’ll savor long after you leave town! Don't miss the boat. Book your spot today!

Southernmost Sunset Sail with Bar and Hors d’Oeuvres

Entice yourself with the starburst blaze of colors that is the Key West sunset on a luxurious sunset sail. See local...

Well organized, on time, fun cruise! The crew, the boat, and the music were terrific. We thoroughly enjoyed it!

Great sunset cruise

Sunset sail

Nice sail out of harbor, staff very nice and helpful.  More variety on premium beers would be nice.  Toilet wouldn't flush and smelled aweful!

Nice evening

Sail away with an ocean breeze for a night of music, drinks, and dancing on this Live Music Sunset Cruise in Key West, Florida. Experience some of Key West’s best musicians as you dance to the backdrop of a gorgeous, tropical sunset. Eat, drink, and be merry aboard a spacious and comfortable catamaran and take in all of the stunning sights and sounds. For an evening you'll want to last forever, set sail on this Live Music Sunset Cruise! Book your experience today!

Live Music Sunset Cruise with Cocktails Included

Sail away with an ocean breeze for a night of music, drinks, and dancing on this Live Music Sunset Cruise in Key West,...

My daughters and I had a really good time! Mathew and his crew were excellent! Thank you!

Sunset cruise 8/4/23

Both my wife and I had an amazing experience with your crew and cruise, food , and drinks were amazing!!!     Music was great , will definitely be seeing you again!!!

Cruise with cocktails

We had a fantastic time. The crew was great , thoroughly enjoyed the band. Would definitely recommend this cruise  to friends.

Commotion cruise

Fury Water Adventures

Embark on a spectacular sunset sailing adventure off the coast of Key West, Florida in search of the famed "Green Flash." Experience the magic and romance of sailing at dusk as you sip champagne and watch for dolphins and other marine wildlife in the surf. Your friendly captain and crew will teach you the basics of sailing and even let you take the wheel. So, take a turn at the helm of one of the fastest schooners in the United States, book today!

Key West Sunset Sail on America 2.0

Embark on a spectacular sunset sailing adventure off the coast of Key West, Florida in search of the famed "Green...

There's no better way to experience the gorgeous sunsets of Key West... it's how we celebrated our 20th wedding anniversary. The America 2.0 was beautiful and the captain and staff were impressive. We absolutely loved it!

Amazing experience!

The staff was outstanding.  They took excellent care of us all night.  The ship was just the right size for this adventure.

Sunset cruise to remember

The crew was extremely knowledgeable, very professional, personable great fun!!

Amazing Experience

Classic Harbor Line Key West

Escape the hustle and bustle and experience a breathtaking Key West sunset with a Seabreeze Sunset Harbor Cruise. Your journey takes you away from commonly charted boat paths to unobstructed views and miles of turquoise waters, while snacking on delicious sushi and snacks. Travel to where the Gulf meets the Atlantic and on to the Southernmost Point of the United States. For an intimate and romantic evening that is sure to help you unwind, book a Sunset Harbor Cruise and toast to life!

Seabreeze Sunset Harbor Cruise with Wine and Beer

Escape the hustle and bustle and experience a breathtaking Key West sunset with a Seabreeze Sunset Harbor Cruise. Your...

Very nice staff, really enjoyed the cruise.

Cruise

Our sunset cruise far exceeded our expectations!  The food was better than described. The Sushi was made at restaurant next door and the Prosecco did not disappoint but the real highlight of this trip was the outstanding service delivered by Marta!  Not only was she attentive to us but she anticipated everyone’s needs.  She and the captain were fun and committed to making it a memorable experience!  Do not miss this trip!

Amazing Night!

The sunset cruise was beautiful! Lots of fun! The food and drinks were great too!

Beautiful

Barefoot Billy's

Sail into an unforgettable Key West sunset while sampling beer, delicious hors d'oeuvres, and 8 fine wines from around the world. Rated one of the top two sunset tours in all of North America by Coastal Living Magazine, this luxurious Wind and Wine Sunset Sail on a historic Schooner will not disappoint. Make some new friends, enjoy tropical music, and delight your palate as you watch the sun melt into the water. Book your spot today!

Wind and Wine Sunset Sail

Sail into an unforgettable Key West sunset while sampling beer, delicious hors d'oeuvres, and 8 fine wines from around...

A wind and sail

A perfect 2 hour smooth sunset sail on a beautiful boat with experienced captain and crew! Plenty of a variety of wines to go around paired with tasty hors d’oeuvres. Would highly recommend!

Wind and Wine Sunset Cruise

Danger Charters

Have you ever seen Key West at dusk on the open ocean? Just sit back and immerse yourself in the ambiance of this nightlife experience. You can dance the night away to live music while you sail the calm waters. Enjoy the best seat in the house with all of the good time essentials like draft beer, live music, open well bar, and appetizers. Book your spot now!

Sunset Sip and Sail with Open Bar and Live Music

Have you ever seen Key West at dusk on the open ocean? Just sit back and immerse yourself in the ambiance of this...

Everything was awesome! We were able to book the Sunset Sip n Sail the day of the event and the weather was sublime! Yummy rum bunch and plenty of it greeted us along with a variety of hors d’ouvres. I would have preferred more mellow, romantic  music -Caribbean or Sinatra-at that hour but one gal enjoyed the humpety hump quite a bit! Overall-5 stars!!

Sunset Sip n Sail

Tiffany was amazing.  Scheduling was a breeze with her.  Definitely recommend using her

Key West Sunset

Tiffany was a huge help in booking our dinner cruise for us in Key West!! We had a great time with wonderful food and entertainment! Highly recommend.

Dinner cruise in Key West

Treat yourself to an evening of incredible snorkeling, delicious drinks, and groovy melodies on the Miss Valyn Catamaran. A twilight experience unlike any other, this is your opportunity to enjoy the nightlife while having the option to plunge into the depths by Florida's best reef! Take in the fleeting Key West sunset while indulging in an ambiance that only the cat delivers. Enjoy reef snorkeling, draft beer & wine on this snorkeling experience. Book your spot today!

Key West Sunset Snorkel Cruise

Treat yourself to an evening of incredible snorkeling, delicious drinks, and groovy melodies on the Miss Valyn...

The price was good and the crew was professional and fun.

Scuba

Great time ! Great crew!

Come along on this Champagne Sunset Sail and step into luxury. Sip, relax, and unwind aboard a gorgeous wooden schooner. Enjoy your authentic sailing experience as you cruise the crystalline waters to landmark sites while sampling a wide variety of complimentary drinks. Come toast to an idyllic Key West sunset on the schooner cruise that is sure to become your favorite new Key West tradition. Book yours today!

Schooner Champagne Sunset Sail

Come along on this Champagne Sunset Sail and step into luxury. Sip, relax, and unwind aboard a gorgeous wooden schooner....

From the point of booking through to the end of the trip everything that was in was within the control of the crew was very nice  
Jamie, Bradley & Capt Mario were excellent.

everything was exceptional and all the crew were very accommodating

sunset cruise

If you're looking for one of the best sunset cruise experiences in Key West, this is it. My wife and I booked this cruise without knowing much about it, but we knew that we wanted to be on a boat that had fewer people than the big boats, and a more intimate experience. That's exactly what we got. The crew consisting of Russ the Captain, Isaac the First Mate, and Laura (her second day on the job) were the absolute best. They were fun, funny, willing to answer our silly questions, and went above and beyond to serve us first class snacks and excellent, top shelf drinks. They played music that added to the ambience. We made great friends on the boat and enjoyed the sail. The evening was perfect, the sea was calm, the sunset was spectacular, and there was a full moon that rose immediately after the sunset. This cruise was worth every penny we paid for it. We would do it again in a heartbeat. Don't miss it!

An Amazing Experience

Schooner Appledore

Live the Key West lifestyle as you set sail over calm blue waters then drop anchor and chill out on a giant floating lily pad. Enjoy this unique private adventure with family and friends, away from the crowds. Be sure to take in all of Key West's beauty while relaxing and soaking up the sun from the water. Book today and set out on a private sailing adventure.

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

Live the Key West lifestyle as you set sail over calm blue waters then drop anchor and chill out on a giant floating...

Great time

We took this tour and so far, it was the best tour we took in Key West. The captain and deckhand were so friendly, informative, and very kind. They had hummus, chips, huge fruit bowl and plenty of ice/water. We lounged on the lily pad, had adult beverages, learned more about sailing and absolutely loved this tour.

Loved this tour - beautiful ocean

Sunset Sail Key West

Florida

Featured Key West Activities

- Activity: Sunset Dinner Cruise by Sunset Watersports
- Hometown: Las Vegas, NV 
- Adults: Two
- Children: None

Key West Sunset Dinner Cruise

Key West Sunset Dinner Cruise

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