Name: Southernmost Sunset Sail with Bar and Hors d’Oeuvres
Brand: TripShock
SKU: 2445
Price: 80 USD
Availability: InStock
Rating: 4.7299 (211 reviews)

Sunset Cruises

Sailing

Boat Tours

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

How to Redeem: Print this ticket or show the confirmation details from your mobile device for entry. Please have a valid ID with you to confirm your order if needed. 
Parking: Key West Bight Municipal Parking Lot, located at the corner of Margaret and Caroline Streets. The cost is $3/hour or $20/day.
Departure Details: Check-in is 30 minutes prior to departure. All participants must be present at check-in at 205 Elizabeth Street, Unit 1, Key West, FL 33040. For any issues, please reach out to your provider, Sebago Key West, at 305-294-5687.
Gratuities: A gratuity of 15-20% is recommended for your guide.

Sebago Watersports

211 Reviews of Southernmost Sunset Sail with Bar and Hors d’Oeuvres - TripShock!

Southernmost Sunset Sail with Bar and Hors d’Oeuvres

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

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

Captain and crew made the sunset cruise seamless. Plenty of room to move around and enjoy the views. Bartenders did a great job with the cocktails!  We would do this cruise again.

Excellent service, relaxing ride, amazing sunset

Fantastic!  Great crew and drinks and food.  My wife and I had a very romantic time even with lots of other guests on board.  Highly recommend this one!

Sunset Cruise out of Key West FL

Everything was fantastic except we saw no need for the music and the experience would 
 have been so much better without it it is hard to talk over it

Sun set sail

Enjoyed the Sunset Cruise very much!  We were able to get away from the storm clouds and saw a beautiful rainbow with a glimpse of it's double!!  Company, drinks,food and music were great!  And felt on safe hands with the captain.  

Beyond expectations!!  ⭐⭐⭐⭐⭐

It was a nice time. Not too crowded. Hordourves could have come a little sooner and the captain could have positioned us to see the green flash of the sunset but otherwise it was great

Nice time

The Sebago sunset cruise was so much fun!  My cousin and I were impressed from the start.  We had plenty of room to spread out and be comfortable on the boat.  The staff was super friendly and stopped to talk to us and offered to take a picture of us at sunset.  The singer/musician on board had a great voice and played great music.  The food (appetizers, mini key pies, etc.) was delicious and there was beer, wine, mixed drinks, sodas, or water for passengers to enjoy.   Oh, and the captain's sweet dog was aboard the ship and was a huge hit for dog lovers.  He was so chill.  
     The sunset was absolutely amazing and the photo opportunities were endless.  We met some really great people including a couple from Texas and a couple from Australia.  In fact, the gentleman from Australia proposed to his girlfriend right at sunset.  It was so sweet and she said "Yes!"  What a fabulous ending to the perfect night!

A Fantastic Excursion--Even Better than We Expected

I was looking forward to a sunset cruise on vacation and this one was perfect! Small hors d’oeuvres and the best key lime dessert bite. The crew was great-helpful, friendly and always willing to take a photo for you. The views and overall trip exceeded my expectations! It was a perfect romantic night with my boyfriend- definitely recommend.

Beautiful evening on vacation

Sebago Key West

Key West

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

Sunset Watersports

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!

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

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

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

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

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

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

Set sail on Key West’s most elegant historic schooner, the When and If. Built in 1939 for General George Patton’s dream of sailing around the world “When and If” he was able, is available to the public for the first time in the yacht's lifetime. Sit back and experience the beautiful Key West sunset in style as the wooden schooner glides through the water driven by wind power alone. Meet the crew as they serve up a beautiful array of gourmet cheeses and share their stories of old Key West and the sea.

Sunset Sail Aboard the Historic When and If

Set sail on Key West’s most elegant historic schooner, the When and If. Built in 1939 for General George Patton’s...

Great Sailing experience.  The crew was friendly and engaging and provided a full sail ship experience.  All of the guests were friendly and made the whole experience even that much better!  Will definitely do it again!

Great Sunset Sail

Fantastic trip

Loved getting a taste of real sailing on this amazing schooner. Captain and crew were skilled and attentive. A perfect way to enjoy the wind and sunset while in Key West. Would love to take a long trip on the When and If!

Sunset Sail Key West

Hit the water around tropical Key West with this carefree Barebones Sandbar Boat Charter. Experience the sights and sounds of a beautiful area as you enjoy ample and comfortable seating, expert navigation, and so much more! The sky's the limit with this boat rental unlike any other, but be sure to book early so you don't miss out!

Key West Sandbar Boat Charter

Hit the water around tropical Key West with this carefree Barebones Sandbar Boat Charter. Experience the sights and...

Lagerheads Watersports

Spend a romantic evening aboard an authentic wooden schooner on this Windjammer Schooner Sunset Sail. This sailing vessel is fit for royalty, with its wide decks and ample seating and includes an open bar. Journey in comfort to landmark sites like the Navy Mole, Fort Zachary Taylor, Sunset Key, and more as the sails are hoisted and the tropical breeze whisks your cares away. Witness the beauty of a Key West Sunset and behold the grandeur of the star-filled Southern sky on this 2 hour pleasure cruise.

Windjammer Champagne Sunset Sail

Spend a romantic evening aboard an authentic wooden schooner on this Windjammer Schooner Sunset Sail. This sailing...

With sunset sails being very prominent in Key West, we were pleasantly surprised to find this a very personal experience.  The live aboard crew members were very approachable, took time to talk to anyone who asked questions and shared their love of the water.  The Hors d'oeuvres were very classy and the  alcoholic beverages were well done.  This sail exceeded our expectations and we would highly recommend the Appledore II Schooner to anyone considering doing a Key West Sunset Sail.

Authentic Schooner Sunset Sail

There's no better way to spend your day than with this Private Sandbar Experience. Travel the crystal clear water of Key West with family and friends to the backcountry sandbars. Feel the sun and the salty breeze on your skin. Take in the moment and admire the natural beauty this part of Florida has to offer. Your captain knows the best spots to make your experience one to remember. Once at the sandbar, get out in the water to splash and play! Swim, relax on floats, or dive down under the water and snorkel. Make lifelong memories, book now!

Private Sandbar Experience

There's no better way to spend your day than with this Private Sandbar Experience. Travel the crystal clear water of Key...

Southernmost Sunset Sail with Bar and Hors d’Oeuvres

Southernmost Sunset Sail with Bar and Hors d’Oeuvres

Buy a gift card, choose a date later

Don't take our word for it

Plan Ahead & Save Up to 20% with Exclusive Savings From TripShock