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

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!

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...

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

We had a wonderful time & treated special by the workers.

Sunset cruise combo

Sunset Watersports

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

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

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...

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

The sunset cruise was amazing! The boat was clean and crew was awesome. There were other boats and the captain did great job of keeping us where we could see the sunset and get pictures. The crew were friendly and helpful. It was a relaxing trip with an amazing view!

Sunset cruise

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 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...

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

Everything was perfect!  The crew, the weather, the water and sunset all made for a great experience.  Highly recommend!

Everything was perfect!

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...

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

The captain and first mate were so accommodating and very professional. Truly they are one reason we come back to Key West. We thank you.

Second time

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

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!

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

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.

Southernmost Sunset Sail with Bar and Hors d’Oeuvres

Southernmost Sunset Sail with Bar and Hors d’Oeuvres

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