Name: Key West Sunset Sail on America 2.0
Brand: TripShock
SKU: 2455
Price: 127 USD
Availability: InStock
Rating: 4.9556 (45 reviews)

Sunset Cruises

Sailing

Boat Tours

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

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: Paid parking can be found in the municipal lot on Caroline Street, at the corner of Caroline Street and Margaret Street, very close to the ticket booth where you check in! Parking around the Historic Key West Bight is very limited. Finding a parking spot may take longer than expected. Please plan your arrival accordingly.
Departure Details: The ticket booth is located at Schooner Wharf Bar, 202 William Street, Key West, Florida 33040. Please arrive at least 30 minutes before the scheduled departure time to check in, receive your boarding passes, and get the assigned seating details. Boarding will begin 10-15 minutes before departure. The boat will depart on time. For any issues, please contact your provider, Classic Harbor Line Key West, at 305-293-7245. 
*Gratuities:** Although not required, gratuities are always appreciated and encouraged.

Classic Harbor Line Key West

45 Reviews of Key West Sunset Sail on America 2.0 - TripShock!

Key West Sunset Sail on America 2.0

Customer must cancel 72 hours prior to the arrival date in order to receive a full refund. Cancellations received less than 72 hours prior to the arrival date will not be eligible for a refund. No shows will not be refunded.

Cancel or Reschedule 72 hours prior to arrival for FREE

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

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

Everything was perfect!

Had a wonderful time! Great crew took good care of us and gave my husband a turn at the wheel

Sunset Sail

Superb activity and totally recommended.
Not a party boat but great fun and real sailing.

Schoonerful

This was the highlight of my trip.  What a fantastic sail. Crew members were very nice and knowledgeable. Captain was a lot  of fun. The sunset was beautiful!

Fantastic Experience

Totally perfect evening. The boat the crew the booze and the sunset did not disappoint

Smooth sailing sunset

Fabulous energetic hard working and friendly crew on a beautiful schooner.  Great snacks, too!  We highly recommend it!

Great Experience!

The staff was friendly but professional and we loved everything about this trip! If you love the water and romantic sunsets, this is a must when you visit Key West!

Wonderful evening cruise!

Key West

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

Sebago Key West

Enjoy a memorable evening on the water with the Key West Sunset Dinner Cruise. Savor a fresh, tropical-inspired dinner, including roast pork with Cuban bread and fried plantains, all prepared onboard. Relax with drinks from the fully stocked bar and take in the stunning sunset views. The friendly crew ensures a comfortable experience, with indoor seating in a climate-controlled cabin. This is the perfect way to dine, drink, and dance while making unforgettable memories. Reserve your spot today for an unforgettable Key West sunset experience!

Key West Sunset Dinner Cruise

Enjoy a memorable evening on the water with the Key West Sunset Dinner Cruise. Savor a fresh, tropical-inspired dinner,...

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

Sunset Watersports

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

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...

Excellent

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

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. Book your Sunset Sail today!

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

Spend a romantic evening aboard an authentic wooden schooner on this Windjammer Schooner Sunset Sail in Key West, Florida. 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 cruise. Book today!

Windjammer Champagne Sunset Sail

Spend a romantic evening aboard an authentic wooden schooner on this Windjammer Schooner Sunset Sail in Key West,...

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

Schooner Appledore

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

Enjoy a sunset cruise on the best value bar boat in Key West. Cruise the gorgeous water on this Rum Runner Bar Boat and give a cheer for every gorgeous sight. Perfect for you and up to 15 of your crew to kick back and chill or snorkel and swim at the stop at Wisteria Beach. See Sunset Key, Wisteria Island, a 100-year-old shipwreck, and more. You can BYOB or grab drinks at the beach bar at a discounted rate, this trip is a perfect way to end your day. Book your Rum Runner Sunset Downtown Tour now!

Rum Runner Sunset Downtown Tour

Enjoy a sunset cruise on the best value bar boat in Key West. Cruise the gorgeous water on this Rum Runner Bar Boat and...

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...

End your day soaking in the sights and sounds of the emerald waves on this Sunset Sail on the Schooner Jolly II Rover. Witness the beauty of Key West, Florida as you admire the sunset from the decks of a schooner. Watch for Florida wildlife, dolphins, turtles, flying fish, pelicans, and more as you coast through the ocean. Help raise the sails, fire the cannons, and take your turn at the wheel for an authentic sailing experience. Enjoy an exciting sailing experience and take in the amazing views. Book your tickets today!

Key West Sunset Sail on Schooner Jolly II Rover

End your day soaking in the sights and sounds of the emerald waves on this Sunset Sail on the Schooner Jolly II Rover....

Key West Sunset Sail on America 2.0

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Key West Sunset Sail on America 2.0

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