Tours/Key West/Key West Schooner Sunset Sail with Bar & Hors d'oeuvres
Viator · group up to 68 pax

Key West Schooner Sunset Sail with Bar & Hors d'oeuvres

4.9(893)Key West1 hour
VIATOR4.9(324)TRIPADVISOR4.9(569)

Description

Enjoy an exquisite 2-hour sunset sailing adventure aboard a stunning modern-built schooner! Take in the sights aboard Schooner America 2.0, the most elegant schooner in Key West, as you sail by Mallory Square, Sunset Pier, Sand Key Light Tower and more. Enjoy complimentary beverages throughout your sail along with individually plated hors d'oeuvres. Sit back and relax as your captain sails you effortlessly through the emerald green Key West waters and off toward the horizon for a quintessential Florida sunset experience.

Tour Options

Peak Holiday Option
  • Duration: 2 hours: This experience is 2-hours. Please check in at the ticket booth 30-45 minutes prior to the departure time for boarding passes Bar & Food included Peak Holiday Rates Apply
Sunset Sail Wine Upgrade
  • Duration: 2 hours: Please check in at the ticket booth 30-45 minutes prior to the departure time for boarding passes White Wine Upgrade: This option includes a bottle of white wine & souvenir glassware. Beer, wine, soda, water, & light snacks are also included. Requirement: There is a 2 ticket purchase minimum for this upgrade option
Sunset Sail Champagne Upgrade
  • Duration: 2 hours: This experience is 2-hours. Please check in at the ticket booth 30-45 minutes prior to the departure time for boarding passes Champagne upgrade: This option includes a bottle of champagne & souvenir glassware. Beer, wine, soda, water, & light snacks are also included. Requirement: There is a 2 ticket purchase minimum for this upgrade option
Key West Sunset Sail
  • Duration: 2 hours: This experience is 2-hours. Please check in at the ticket booth 30-45 minutes prior to the departure time for boarding passes Bar & food included: This option includes our house beer, wine, sparkling wine, and hors d'oeuvres
Holiday Premium Option
  • Duration: 2 hours: This experience is 2-hours. Please check in at the ticket booth 30-45 minutes prior to the departure time for boarding passes Bar & Food included Premium rates apply

Itinerary

Pass by

Enjoy views of some famous Key West landmarks from the water as the boat sails along the coast and onward into the sunset!

Pass by

See the famous Fort Zachary from the water as you sail by.

Pass by

Enjoy great waterside views of Sunset Pier and other famous Key West landmarks as the captain sails America 2.0 alongside the coastline and onward!

Highlights

Your 2-hour sailing experience aboard America 2.0
Individually plated hors d'oeuvres
Complimentary beer, wine, Champagne and soda

What's included

Included
Your 2-hour sailing experience aboard America 2.0
Individually plated hors d'oeuvres
Complimentary beer, wine, Champagne and soda
Not included
Gratuities
Hotel pickup and drop-off

Traveller Ratings

4.9
893 reviews
5
848
4
20
3
11
2
6
1
8

Important Information

  • Infants and small children can ride in a pram or stroller
  • Service animals allowed
  • Public transportation options are available nearby
  • Suitable for all physical fitness levels
  • We recommend bringing a light jacket as it's often cooler on the water.
  • Must be 21 years or older to consume alcohol.
  • Meet at Key West Bight Marina 30-45 minutes prior to your selected departure time to check in at ticket booth and board the sailboat for your sunset cruise

Reviews(893)

S
Saundra D
May 29, 2026
Disappointing

They cancelled the tour same day with no reason given. We were lucky to get on another cruise tour the same day.

Operator response

Saundra, thank you for booking a sail with us and taking some time to provide your valuable feedback. We sincerely apologize for the short notice cancellation, which is rare and something we very much try to avoid. We understand how disappointing this must have been, but we are glad that you were still able to get out on the water. Our team did call, text, and email to try to help arrange an alternate experience since we are connected with the other sailing experiences in the area, and we had reached out to them to hold space for you. We hope to be able to provide you with a great experience on another occasion. - Classic Harbor Line Key West

M
mattdR4861BG
May 27, 2026
Sunset cruise key west

Captain Janet and her two crew mates made the experience very fun. The boat was easy to find and the overall experience was great. Janet was very friendly and answered all kinds of questions from people while also steering and guiding the boat masterfully. It’s always a pleasure to see people great at their jobs and enjoying it. The two guys helping out were very sweet and made sure everyone had drinks and the three plates served (veggies with ranch, shrimp cocktail, and cheese and crackers) were all tasty. I don’t think anyone on board had a bad time.

Operator response

Matt, thank you for booking a sail with us and taking some time to provide your valuable feedback. We are delighted to hear that Captain Janet and our crew made your sunset experience so enjoyable. Your kind words about Janet's expertise and friendliness, along with the excellent service from our crew, truly mean a lot to us. We're thrilled that you enjoyed the food offerings and had such a wonderful time on the water. We hope to have the pleasure of hosting you again soon! - Classic Harbor Line Key West

H
hotelfanOrlando_FL
May 27, 2026
Great ending to our Girls trip!

Amazing Sail! Captain Janet and her incredible crew gave us the experience of a lifetime! Never having been on a schooner before we weren't sure what to expect but it was exciting and was also the last sail of the season in Key West!! What a hard working group who were expert in getting to and from, providing snacks and beverages and raising and lowering the sails which is something I will never forget. If you are in Key West or New York, you must experience a sail on America 2.0!! You will not be disappointed in the least. Thank you!!

Operator response

Thank you for booking a sail with us and taking some time to provide your valuable feedback and recommendation. We are delighted to hear about your amazing experience on America 2.0! Captain Janet and our crew work hard to create memorable moments, especially for special occasions like your girls trip. We're thrilled you enjoyed the excitement of sailing on a schooner and witnessing the sail handling. We hope to have another opportunity to host you on the water! - Classic Harbor Line Key West

S
Shawn_E
May 27, 2026
Windy day = awesome

We went out on a very windy day and what an awesome time it was. Great crew, great service, great fun !!! Awesome sunset !!

R
R3319ZNlucyl
May 22, 2026
We went on The America 2.0 for the hors d'oeuvres, cocktails, and sunset trip. It was breathtaking and relaxing. Definit

Our Captain and tour guides were amazing!

Operator response

Lucy, thank you for booking a sail with us and taking some time to provide your valuable feedback. We are delighted to hear that your hors d'oeuvres, cocktails, and sunset trip aboard The America 2.0 was breathtaking and relaxing. Our crew takes great pride in creating memorable experiences. We hope to have the pleasure of hosting you again soon! - Classic Harbor Line Key West

E
E8844GYbarbaraw
May 20, 2026
The highlight of our vacation!

A wonderful experience! The booking process is so easy. So was the boarding process. The captain and crew were amazing – thank you so much to Captain Jana, and her crew, Chelsea and Milo. They made the sail so much fun! The ship is beautiful, the ride was fantastic, the drinks and hors d’oeuvres, were yummy, and the sunset never disappoints. It was our favorite thing to do on this vacation. Will definitely do it again.

Operator response

Barbara, thank you for booking a sail with us and taking some time to provide your valuable feedback. We are delighted to hear our experience was the highlight of your vacation! We're thrilled you enjoyed a seamless booking and boarding process and that our crew made your sail so enjoyable. It's wonderful you loved the style of the ship, delicious drinks and hors d'oeuvres, and stunning sunset. We look forward to hosting you again soon! - Classic Harbor Line Key West

J
Jane_C
May 19, 2026
The Best

Worth it! Pay the extra money for this over the catamaran boats. Food and wine was great but the sailing and crew were even better.

B
Barb_T
May 19, 2026
It was an awesome...

It was an awesome experience. The crew, Ray, Chelsea, and Brad were wonderful. Best experience so far in Key West.

S
Stuart_G
May 18, 2026
A Great time

The crew is fantastic. Not just sailors, but great hosts. Our wine glasses were never empty, and the snacks just kept coming.

A
Ajay_K
May 17, 2026
Best expererinece ever

Best experience ever. The crew was awesome and the vibe was abwesome. It’s pure dialling boat so we loved it

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