2 hrs
All Ages
Minimum Age
Key West

Key West Sunset Sail on Schooner America 2.0

  • 2-hour romantic sailing excursion on Schooner America 2.0
  • $96 per person
  • Includes complimentary beer, wine, champagne, and soft drinks. Cocktails are available for purchase.
  • Includes complimentary hors d’oeurves- cheese and crackers, veggies and dip, and shrimp cocktail
  • Enjoy the iconic Key West sunset on a premier sailing vessel
  • Reduced capacity and other safety precautions, including zoned seating (see Health and Safety for full list of safety precautions)

Enjoy your romantic sunset sail aboard Key West’s most elegant sailboat, the 105-foot, 1851 revival, Schooner America 2.0.

Take in the vibrant colors of Key West’s famous sunset as you sip champagne and glide through the crystal clear surrounding waters of the beautiful Florida Keys.

This two-hour sunset sail features complimentary champagne, wine, beer, soft drinks, and water, and hors d’oeurves.

Schooner America 2.0 is a state-of-the-art vessel built-in 2011. She features teak decks, mahogany-trimmings, and 3600 square feet of canvas! Sit back and relax while she plies effortlessly through the turquoise green Key West sailing waters and off towards the horizon for the quintessential Key West Sunset experience!

Some of the sights on this two-hour sailing adventure include:

  • A waterside view of Fort Zachary Taylor
  • The famed Sand Key Lighthouse, Mallory Square, and Sunset Pier
  • Close-up encounters with dolphins, sea turtles, and rare waterfowl
  • The famous Key West “Green Flash” at sunset

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

Meeting Location

  • The Key West Bight (Key West, FL)
  • (Exact meeting location details will be provided immediately upon purchase of tickets.)

Key West Sunset Sail on Schooner America 2.0

Ages 13 and up
Ages 4 – 12
Ages 0 – 3
Bow Section Buyout
Privately reserve a port or starboard bow section of the boat for up to 12 guests
Cockpit Section Buyout
Privately reserve the entire cockpit section of the boat for up to 12 guests

This adventure is operated by Classic Harbor Line – Key West

We are currently offering a “no questions asked” 24-hour refund policy. Should you need to, you may cancel your reservation for a full refund, reschedule, or gift card conversion up to 24 hours in advance of your trip. Day-of cancellations are non-refundable/non-reschedulable unless you have purchased Trip Cancellation Protection.

This policy is in effect until 05/31/2022

Classic Harbor Line

Classic Harbor Line (operators of a series of classic style vessels in Newport, RI, New York City and Boston, MA) bring the 105-foot Schooner America 2.0 (of NYC, NY) to Key West, FL for the winter months of November through April.

This 105 foot sailboat, certified for 75, was designed and built by the same boat-builders who crafted Key West’s former pride, Schooner AMERICA. Scarano Boat Building of Albany, also crafted all the vessels in the famed Classic Harbor Line fleet: the 1920s style yacht “Manhattan” of NYC, and the schooner Adirondack of NYC as well as the Adirondack III of Boston MA, and Adirondack II of Newport RI.

Classic Harbor Line is well known for their outstanding captains and crew and standard of hospitality. Whether you sail with them in Newport, Boston, New York, or Key West, guests are known to not only rave about the beauty and maintenance of the boats, but of the lasting warm impression that their hosts provide. Guests are treated like royalty, beverages are cold and the vessels sail like a dream.

Do sails sell out frequently?

Sails do sell out. We are currently operating at approximately 50% or less capacity. Potential guests are encouraged to check the website or call the week of the date you would like to attend to check availability for public trips and to book as early as possible. Please see Health & Safety for important information regarding COVID-19 updates.

What happens if the sail is sold out?

Unfortunately, we do not have a wait-list for our sails, so please book in advance. We do sail 7 days a week!

Is there parking, where? And how much is it?

Parking in Key West is very limited, and operates on a first come, first serve basis. There is a local municipal parking lot at the corner of Caroline Street and Margaret Street, very close to our ticket booth where you check in! Further information will be provided upon purchasing your tickets.

Do I need a ticket for my young child?

All passengers, regardless of age, must have a ticket for capacity purposes. Please be sure to take this into account when purchasing tickets for your party. Children ages 3 and younger ride for free on all of our trips, but you’ll still need to enter the appropriate number of Infant tickets labeled “Free” when purchasing. Children over the age of 3 must purchase a full priced “Child” ticket.

What exactly do we see on the sail?

Our route is indicative of the breeze we are given, but we guarantee crystal clear blue-green seas and a water side view of Key West Harbor. Additional sites may include Fort Zachory Taylor State Park, Sand Key Reef, Mallory Square, Sunset Pier, marine wild life of many varieties, and fellow vessels within the Key West fleet. We may also be lucky enough to catch the magnificent “Green Flash” (just as the sun is about to disappear from the horizon, it changes for a moment to a bright green color).

Is food served during the sails?

Yes! We serve complimentary hors d’oeurves, including cheese and crackers, veggie and dip, and shrimp cocktail.

How about drinks? Should I bring those?

Outside alcoholic beverages are not permitted. This romantic sunset sail features complimentary champagne, wine, beer, soft drinks, and water. (One quick note: We are not a unlimited booze-cruise. We aim to create an elegant, relaxing, peaceful, and safe experience for all of our guests.) Cocktails are available for purchase.

Is the Schooner America 2.0 safe?

Absolutely. While known for its speed, the Schooner America 2.0 is a safe and gentle vessel. Along with your captain, there is a minimum of two crew members on every sail to make sure you feel comfortable and at home on the water. We are stocked with water, beverages, blankets, pillows, and life jackets should you feel you need one. There are also private marine heads (bathrooms) in the salon below.

How steady is the sailing? Am I likely to get seasick?

The Schooner America 2.0 is a steady, gentle vessel. It is very rare for our guests to become seasick. While most people do not experience any sea sickness on the schooner, you may want to consider light medication if you normally take it for motion sickness. We cannot officially advise you to take any medication, however.

Is there a bathroom on the boat?

Yes, the boat is equipped with two bathrooms that are accessible at all times. We call them “marine heads,” and they are very simple to use. The Captain will explain directions for their use once you are on board the vessel.

Can I stow anything (eg, my luggage) during the sail?

There is an area below deck where you may store your belongings. Please keep in mind that this area is not guarded, so we cannot take responsibility for any broken, lost or missing items.

What should I wear?

For our sunset sail we recommend wearing comfortable clothing and footwear (high heels are not recommended). Feel free to come in light, casual clothing, but bring a light jacket just in case, especially since we’ll be out on the water in the evening!

Where does the sail finish?

Our sails will end at the same dock from which they departed.

Can I get a refund or reschedule my tickets after buying them?

Because of COVID-19 precautions, we are currently offering a “no questions asked” refund policy up to 24 hours in advance of your trip. Should you need to, you may cancel your reservation for a full refund, reschedule, or convert to gift credit up to 24 hours in advance of your trip. Exceptions within the 24-hour period may be made under extenuating circumstances.

Do you ever cancel sails due to bad weather?

The sail usually runs in light rain and other moderate weather situations. The only time we cancel a trip is in the event of severe or unsafe weather conditions. Our captains monitor the radar to watch fronts and cells in the area on days when inclement weather is possible. Cancellations are made on the day of the sail, by the Captain, up to one hour prior to sail time. If you have purchased tickets for a sail that is canceled, you will have the opportunity to reschedule your tickets (subject to availability), take a full refund or receive credit towards a future event.

What happens if it starts raining when we’re out on our sail?

Don’t worry, we won’t melt! Trips with a little added excitement due to weather have proven to be some the most memorable bonding experiences for our guests. (This all depends on attitude of course…) Our captains will never take the boat off the dock if they believe the weather conditions to be unsafe, however, and are constantly monitoring the weather once off the dock.

Is gratuity included in the price of the sail?

Because of COVID-19 precautions, we have added a “pre-paid gratuity” option to our ticket purchasing to encourage touchless interactions. Gratuity is not included in the base ticket price. Cash tips are greatly appreciated at the end of the trip. Gratuities can be handled via Venmo as well. Thank you in advance for taking care of the crew!

Is the schooner wheelchair accessible?

No, unfortunately America 2.0 is not wheelchair-accessible.

Can I book a private charter sail?

Yes, private sails on the Schooner America 2.0 can be a unique and elegant event for your group. If you are interested in booking a private sail, please contact us by calling 305-890-6485 or by clicking the “Contact SailKeyWest” link and writing us a message!

Can I get married aboard America 2.0 in Key West?

Yes. All of our captains in Key West are licensed in the state of Florida to perform marriage ceremonies aboard the America 2.0. For further details and arrangements, please call 305-890-6485 or click on the “Contact SailKeyWest” link and write us a message!

Are gift certificates available for this sail?

Yes, we offer gift certificates which make perfect gifts for holidays, birthdays or any other occasion! To purchase a gift certificate for this sail, please click on the “Gift Certificates: Purchase” link in the box above.


Refund/Rescheduling Policy
Customers will receive a full refund with 24 hours notice of cancellation. Customers will also receive a full refund in case of operator cancellation due to weather or other unforeseen circumstances. Contact us by phone to cancel or inquire about a cancellation. No-shows will be charged the full price.

Other Policies
Activity may be cancelled due to severe weather.
The activity usually runs in light rain and other moderate weather conditions, but the seller may cancel the activity up to an hour before the start time in the event of severe or unsafe weather conditions. If the seller cancels the event, ticket-holders will be allowed to reschedule tickets (subject to availability), receive credit for a future event, or receive a full refund.