Name: Sunset Sail Aboard the Historic When and If
Brand: TripShock
SKU: 2505
Price: 117 USD
Availability: InStock
Rating: 4.95 (20 reviews)

Sunset Cruises

Sailing

Boat Tours

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

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: Parking is available for free.
Departure Details: Experience departs from 7009 Shrimp Rd Key West, FL 33040. Please arrive 15 minutes before scheduled departure time to check in. Boat departs on time. For any issues, please contact your provider, Sunset Sail Key West, at 305-587-4488.
Gratuities: Although not required, it is always appreciated and encouraged to tip.

Sunset Sail Key West

20 Reviews of Sunset Sail Aboard the Historic When and If - TripShock!

Sunset Sail Aboard the Historic When and If

Customer must cancel 48 hours prior to the arrival date in order to receive a full refund. Cancellations received less than 48 hours prior to the arrival date will not be eligible for a refund. No shows will not be refunded.

Cancel or Reschedule 48 hours prior to arrival for FREE

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

Loved the boat and the crew. Great experience.

Beautiful Key West Sunset

Wonderful time chatting with Captain Jack and enjoying the magical atmosphere of a sunset off the coast of Key West.

Sunset on When and If

Excellent experience with Chelsea and her crew! Would recommend this to anyone looking for a great time!!

We loved our 2 hour sunset sail with Kayla as our captain! She is so knowledgeable and has had fascinating tales to tell about her sailing life. Highly recommended!

Great sail- super friendly crew!

This was an incredible experience!! We had the BEST time! The crew was amazing. I would highly recommend this to everyone. PLEASE go on this cruise.

EXCELLENT!!!!!

Schooner was beautiful. The staff was friendly and the sunset was amazing. Seas were a bit rough on our trip, but the crew was attentive offering warm towels and blankets after we got splashed by a few waves.

Awesome Sunset

The captain and crew very knowledgeable and personable. The schooner is beautiful and well maintained.  The cheese and nut tray was perfect. The captain made sure that all onboard had a wonderful view of the sunset. A truly enjoyable evening.

Fabulous

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

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

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

Embark on an unforgettable sailing adventure through the crystal-clear water 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 water 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!

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...

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

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 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

Come along on this Champagne Sunset Sail and step into luxury in Key West, Florida. Sip, relax, and unwind aboard a gorgeous wooden schooner. Enjoy your authentic sailing experience as you cruise the crystalline water 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 in Key West, Florida. Sip, relax, and unwind aboard a...

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

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

Florida

Featured Key West Activities

Duval Street

- Activity: Sunset Sail Aboard the Historic When and If
- Hometown: Harrisburg, NC
- Adults: Four
- Children: None

Sunset Sail Aboard the Historic When and If

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Sunset Sail Aboard the Historic When and If

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