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 waters 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

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!

Sebago Key West

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

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

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

Morning Reef Snorkel and Sail in Key West

Begin the day in the lap of luxury on an expansive 69’ sailing catamaran with Sebago Watersports. First, you’ll sail...

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

The crew was fantastic.it was our first time snorkeling with an ocean swell and none if us felt comfortable. It was murky the day we went as well.

Snorkeling

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...

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

Great trip, crew was super nice and ready to answer any question you may have,. Drinks were 

Wonderful experience. The crew was very friendly and knowledgeable. Beautiful boat ride. Fun snorkeling experience! Would do again.

Great experience

Sunset Watersports

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!

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

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

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'll 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!

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!

Get out on the water and experience nature at her finest with Full Day Sail, Snorkel, and Kayak Excursion complete with sailing, kayaking, and snorkeling. You'll see an incredible array of birds, fish, and other regional wildlife while you explore Key West's backcountry and take in all the beauty around you. Live the island dream as you set sail on a 65-foot Schooner, then kayak through the mangrove forests. Snorkel the blue waters in search of tropical marine species. Book this Full Day Sail, Snorkel, and Kayak Excursion today. Let your adventure begin!

Full Day Sail, Snorkel and Kayak Excursion

Get out on the water and experience nature at her finest with Full Day Sail, Snorkel, and Kayak Excursion complete with...

Fantastic time, great weather and staff was amazing

Full day boating with kayak and snorkel

Great time!  Great experience!  The trip was ran very well and the crew was excellent!  We will be back!

Highly recommend

Relaxing and adventurous at the same time. Friendly crew!

Great Trip.

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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