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    The perfect itinerary for 3 days in Key West

  • Explore Key West
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  • Outside Key West

Duval Street

Ernest Hemingway Home and Museum

Bagatelle Key West

Mallory Square

Key West Butterfly & Nature Conservatory

Southernmost Point Buoy

Key West Lighthouse

Blue Heaven

Key West Aquarium

Key West Shipwreck Museum

Smathers Beach

Tiki House

Island tours

Day trips

Museums & exhibitions

Nearby sights

Duck KeyAttraction in Florida Keys, United States

Dolphin ConnectionAttraction in Duck Key, United States

  • Top experiences
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Sailing trips & boat tours

Snorkeling

Dolphin & whale watching

Boat parties

Canoe & kayak tours

Parasailing

Dinner & lunch cruises

Pub crawls & bar tours

Speed & jet boat tours

Jet Skis

Swim with dolphins

City cards

Explore more things to do in Key West

Nature & adventure

Sightseeing

Food & drinks

Culture & history

Nightlife & bars

Music activities

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Explore more things to do in Key West

Activities for couples

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Explore more things to do in Key West

  • Articles

The perfect itinerary for 3 days in Key West

Key West: Schooner Sunset Sail with Food & Drinks

Top rated
4.9210525 out of 5 stars
4.9
4.9210525 out of 5 stars
304 reviews
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Key West: Schooner Sunset Sail with Food & Drinks
Top rated
4.9210525 out of 5 stars
4.9
4.9210525 out of 5 stars
304 reviews

Watch the sunset over Key West from the deck of the elegant 105-foot schooner America 2.0 and sit back, relax, and see some of the top sights of the area.

About this activity

Free cancellation
Cancel up to 24 hours in advance for a full refund
Duration 2 hours
Check availability to see starting times

Highlighted reviews from other travelers

A
Alison – United States

Our sunset sail on the Key West Schooner was truly unforgettable! Captain Janet, along with Dan, Tom, and Milo, were all incredibly attentive and friendly, making sure everyone was comfortable and having a great time. We enjoyed delicious canapés and drinks as we cruised, soaking in the beautiful ocean views. One of the highlights was seeing dolphins play near the boat — such a magical moment! And of course, the sunset itself was absolutely breathtaking, painting the sky in stunning colors. This experience was the perfect mix of relaxation, great service, and natural beauty. Highly recommend if you’re in Key West and want a special evening on the water!

C
Chuck – United States

Great crew, nice ship, food was great, drinks were cold. Awesome experience. No changes needed.

Select participants and date

Participants

Highlights

  • Feel the wind in your hair as you sail to watch the sun set over Key West
  • Experience the atmospheric phenomenon at sunset known as the Green Flash
  • See Key West's wildlife like playful dolphins, sea turtles, and water birds
  • Sip on your favorite drink and nibble on delicious hors d'oeuvres as you sail
  • Marvel at the beautiful colors of the sunset reflected in the water around you

Full description

Take in the vibrant colors of Key West's fabulous sunset as you glide through the waters on one of the finest boats in the Key West Schooner Fleet. Watch the sun fade into the horizon and the stars emerge into the deep blue sky.

America 2.0 features teak decks, mahogany-trimmings, and 3,600 square feet of canvas! Sit back and relax while she plies effortlessly through the crystal-clear waters off Key West, heading towards the horizon for the quintessential Florida sunset experience!

Some of the sights on this sailing adventure include a view of Fort Zachary Taylor from the water, and views of the famed Sand Key Reef, Mallory Square, and Sunset Pier.

Keep your eyes peeled for wildlife such as dolphins, sea turtles, and water birds – and for the famous Key West "Green Flash" at sunset.

Bring your family or friends and join the courteous and professional crew for this sunset sail that completes the Key West experience in comfort and elegance.

Special offerings: Select the sunset departure on Christmas Eve or Christmas day and enjoy complimentary holiday treats and the opportunity to take a holiday photo at the helm. Select the sunset departure on New Year's Eve or New Year's Day and enjoy a special champagne toast and a complimentary souvenir flute.

Includes

  • Sailboat tour
  • Complimentary alcoholic and non-alcoholic drinks
  • Personal hors d'oeuvres plate
  • Champagne (if option selected)
  • Gratuity

Meeting point

202 William Street, Key West, FL 33040 (directly behind the Schooner Wharf Bar)

Open in Google Maps

Important information

What to bring

  • Passport or ID card
  • Driver's license

Not allowed

  • Smoking

Know before you go

  • Seating may be assigned.

From $116 per person

Customer reviews

Overall rating

4.9 /5

based on 304 reviews

Review summary

  • Transportation
    4.9/5
  • Value for money
    4.7/5

Customer photos

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A
Alison – United StatesMay 28, 2025 – Verified booking
Our sunset sail on the Key West Schooner was truly unforgettable! Captain Janet, along with Dan, Tom, and Milo, were all incredibly attentive and friendly, making sure everyone was comfortable and having a great time. We enjoyed delicious canapés and drinks as we cruised, soaking in the beautiful ocean views. One of the highlights was seeing dolphins play near the boat — such a magical moment! And of course, the sunset itself was absolutely breathtaking, painting the sky in stunning colors. This experience was the perfect mix of relaxation, great service, and natural beauty. Highly recommend if you’re in Key West and want a special evening on the water!
C
Chuck – United StatesMay 7, 2025 – Verified booking
Great crew, nice ship, food was great, drinks were cold. Awesome experience. No changes needed.
C
Cynthia – United StatesMarch 9, 2025 – Verified booking
everything the captain and crew the boat is beautiful the food and drinks are great and the scenery beautiful well worth every penny 😀

Product ID: 31302

Activity provider:Classic Harbor Line - Key West
  • United States
  • Florida
  • Things to do in Key West
  • Tours in Key West

Top Attractions in Key West

  • 1Ernest Hemingway Home and Museum
  • 2Key West Butterfly & Nature Conservatory
  • 3Bagatelle Key West
  • 4Mallory Square
  • 5Key West Aquarium
  • 6Key West First Legal Rum Distillery
  • 7Duval Street
  • 8Key West International Airport
  • 9Key West Lighthouse
  • 10Southernmost Point Buoy
  • 11Florida Keys National Marine Sanctuary
  • 12Key West Shipwreck Museum
  • 13Mel Fisher Maritime Museum
  • 14Smathers Beach
  • 15Truman Little White House
  • 16Sunset Key
  • 17Fort East Martello Museum
  • 18St. Paul's Episcopal Church, Key West
  • 19The Roost
  • 20US1 – Mile Marker 0

Experiences in Key West

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  • 2Key West Snorkeling
  • 3Key West Family-friendly activities
  • 4Key West Swim with dolphins
  • 5Key West Day trips
  • 6Key West Jet Skis
  • 7Key West Hop-on Hop-off tours
  • 8Key West Dolphin & whale watching
  • 9Key West Diving
  • 10Key West Sunset tours
  • 11Key West Dinner & lunch cruises
  • 12Key West Boat parties
  • 13Key West Entry tickets
  • 14Key West Air & helicopter tours
  • 15Key West Hidden gems
  • 16Key West Sailing trips & boat tours
  • 17Key West Canoe & kayak tours
  • 18Key West Ghost & vampire tours
  • 19Key West Transfers
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