Name: Day Sail Aboard Schooner America 2.0
Brand: TripShock
SKU: 2452
Price: 73 USD
Availability: InStock
Rating: 5 (17 reviews)

Sailing

Boat Tours

Explore the high seas in style on the Schooner America 2.0, the namesake of the first sailboat to win America's Cup in 1851. This stunning 105-foot sailboat features teak decks, mahogany trimmings, and ample seating for the whole family. The sights you’ll see along the way include a waterside view of Fort Zachary Taylor, the famed Sand Key Lighthouse, Mallory Square, and Sunset Pier. So sit back and feel the warm breeze dance across your skin as you watch the sights of the beautiful water around Key West. Book your spot today!

Day Sail Aboard Schooner 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: 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, 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

17 Reviews of Day Sail Aboard Schooner America 2.0 - TripShock!

Day Sail Aboard Schooner 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

Explore the high seas in style on the Schooner America 2.0, the namesake of the first sailboat to win America's Cup in...

The crew was wonderful and the boat fantastic!

Excellent

Excellent Captain and Crew.  Superb sailing with good winds and beautiful weather

We absolutely loved the boat and crew. It was perfect weather and we got to have a blast when the sails went up. They only thing is be you have to pay for beer and wine. They are NOT complimentary like stated on your Day Sail ticket. They also do not provide snacks as stated as well. This is only for the sunset sails.

Loved our day trip

My husband and I enjoyed the day trip.  It was an hour and a half, which was perfect.  Very calm waters and not a cloud in the sky.  We couldn’t have picked a better day and the captain even let us steer the boat.  We will definitely do this again on our next trip to Key West!

Wonderful Time

Had a great sail on America2.0 in Key West!! Captain and mates were great and very friendly. We had a beautiful warm sunny afternoon sail… very relaxing and  beautiful  trip ..

Afternoon  sail in Key West

Staff was great and accommodating.. The weather could not have been more perfect. Great way to spe d an afternoon on on Key west. Bring your sunscreen

America 2 schooner sail excursion

Absoutly fantastic sail.  The crew was phenomenal.  The schooner was in tip top condition.  We had a beautiful sail.  It was the high point of my Key West visit.

Schooner America

Crew was awesome! What a great afternoon on the water at key west. Would definitely book again. Flo & Steve Evans

Afternoon cruise

We are sailors from Michigan and it was a beautiful time sailing! The crew was excellent and took great care of us. If it's your first time sailing or you're experienced, just go!!! ⛵

Beautiful Sailing Experience!

We had a fabulous sail with our all female crew of Amber  Heather and Mary! Very fun and knowledgeable as well as excellent sailors! The boat was gorgeous! The allotted time went way too fast...We will certainly go out again on next trip to the Keys!

Excellent Sail!

Key West

Take an adventure into the depths to explore Florida's best reef on a snorkeling experience you will never forget! The Sandie Cat is Key West's newest and fastest snorkeling catamaran, which means less time wasted and more time for exploring the deep blue sea! Join the crew as they hoist the sail and get you and your family and friends out for a true Key West experience. Enjoy a complimentary breakfast, as well as unlimited mimosas (mango, strawberry & orange) & unlimited draft beer, in this all-inclusive snorkel experience. Reserve your spot today!

Rise & Reef Snorkeling Trip With Breakfast & Unlimited Mimosas

Take an adventure into the depths to explore Florida's best reef on a snorkeling experience you will never forget! The...

The crew was fantastic! Knowledgeable, personable and made sure everyone had a great time. This activity is great for everyone whether you enjoy snorkeling or not. So much fun and I would definitely do it again.

Great Experience

If you only do one thing in Key West, this is it.  It’s fun, relaxing, and always a great time.  The trip was beautiful and the staff was amazing!

Key West must!

The absolute best time to take a snorkeling trip in the Keys is Sunday morning.
 Our boat, which will often carry over a 100 people, had about 20 making this a phenomenal experience.
Great crew
 Very knowledgeable and engaging.

Best time to snorkel

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

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

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.

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!

Get out early and experience nature at its finest with a half-day island adventure complete with sailing, kayaking, and snorkeling all in one. You will see an incredible array of birds, fish, and other regional wildlife while you explore Key West's backcountry and take in all the natural beauty around you. Live the island dream as you set sail in a 65-foot schooner, then kayak through the mangrove forests and snorkel the blue waters. Book today and let your adventure begin!

Morning Half Day Sail, Snorkel, and Kayak Excursion

Get out early and experience nature at its finest with a half-day island adventure complete with sailing, kayaking, and...

What a great way to spend the morning in paradise! The crew was fantastic, blending history, ecology, and fun in a 55 foot sailboat adventure. Loved going through the mangrove hideout in a kayak!

Danger Charters Sail, Snorkel, Kayak Tour

The crew was super friendly, the boat accommodated the tourists nicely and the gear was clean and well cared for.  We both like to learn about the area in which we are traveling and Dan, Maryann and Bronit(sp?) we’re exemplary!  Great service all day- from info, cold drinks flowing, appetizers and getting everyone in their equipment.  Absolutely recommend this his!

Great day on the water!

My family and I had an absolute wonderful time! The only regret was it was only a 1/2 day trip instead of a full day. The crew (Braza, Brad and Gannon) were so professional and knowledgeable and made an extra effort to make sure everyone was comfortable, safe and having an awesome time with each activity. The boat was in ship shape order, as were the kayaks and other equipment. One of the highlights of our trip to Key West! Hope to get back down to the Conch Republic and Danger Charters again sooner than later!

Danger Charters was great!

Danger Charters

Imagine yourself swimming in warm tropical waters with swarms of vibrant colorful fish all around you as you begin the day in the lap of luxury on an expansive 69’ sailing catamaran with Sebago Watersports. Sail seven miles off Key West’s majestic coast to the shallow Caribbean water of the Florida Keys Reef. Set off on this adventure and book your Morning Reef Snorkel with Sebago Watersports today.

Morning Reef Snorkel and Sail in Key West with Picnic and Unlimited Mimosas

Imagine yourself swimming in warm tropical waters with swarms of vibrant colorful fish all around you as you begin the...

Great trip, staff was friendly, snorkeling was amazing, food & drinks were good.

Key West snorkeling

My husband and I really enjoyed this little snorkeling jaunt! It was so fun and relaxing!

Even Old People Like Us Enjoyed It!

Captain Brett and his crew were great - is was a fun trip.

Great Trip

Take an afternoon and plunge into the depths of Florida's coral reef for an amazing snorkeling experience. The Sandie Cat is Key West's newest snorkeling catamaran, which allows you to get to the reef with speed, comfort, and some serious style. Join the captain and crew, round up your group, and hit the waves for an unforgettable Key West experience packed with fun, sun, and tasty spirits. This all-inclusive trip boasts an open well bar including unlimited mimosas (mango, strawberry & orange) & a variety of soft drinks! Book your spot today!

Dip and Sip Afternoon Snorkel with Open Bar

Take an afternoon and plunge into the depths of Florida's coral reef for an amazing snorkeling experience. The Sandie...

Snorkel Adventure

We had a great time! I’d never snorkeled before- turns out I’m not a huge fan but that didn’t stop us from enjoying the trip, the drinks and the great conversation of fellow passengers. It’s always fun to meet new people. 
I think Captain Jade and her crew are the best! 
Thanks for making our trip to KW memorable
Kurt & Mel

Fun trip

We saw many beautiful, colorful fish at a coral reef near Key West. The boat captain and crew were friendly, professional, and safety-focused. My original trip was rained out, but they rebooked me for the next day, no problem. This is a large group experience — probably 100 guests on my trip — but it’s a large boat, everyone was very nice, and I now have a lovely memory of reef snorkeling.

Friendly, Professional and Fun

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

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

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

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

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

Florida

Featured Key West Activities

- Activity: Day Sail Aboard Schooner America 2.0
- Hometown: Port Huron, MI
- Adults: Two
- Children: None


Day Sail Aboard Schooner America 2.0

Day Sail Aboard Schooner America 2.0

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