easy
1.5 hours
Suitable for all fitness levels as sailing requires minimal physical exertion; mostly sitting or light movement on deck.
Sail into the night on the Schooner America 2.0 and enjoy the breathtaking full moon over Key West’s waters. This tranquil 1.5-hour adventure creates unforgettable memories under the stars.
From $64 • 1.5 hrs
Embark on a magical 1.5-hour moonlight sail aboard the stunning Schooner America 2.0 in Key West. Experience the tranquility of night sailing, with breathtaking views of the full moon and starry skies. This limited-time adventure promises romance and serenity, making it an unforgettable evening on the water.
This special sail is only offered for a limited time every month! Ticket price includes 1.5 hours of sailing. Drinks and snacks available for purchase.
America 2.0 features teak decks, mahogany-trimmings, and just under 3600 square feet of canvas! Sit back and relax while she sails silently through the evening, basking in the golden moonlight that dances in the night waters.
Bring your family and/or friends and join our courteous and professional crew for this adventurous late night sail that will highlight your Key West experience!
Do sails sell out frequently?
Sails do sell out. 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.
What happens if the sail is sold out?
Unfortunately, we do not have a wait-list for our sails, so please book in advance.
Is there parking, where? And how much is it?
Parking in Key West is very limited. 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.
What type of ticket should I buy if I'm bringing a very young child?
All passengers, regardless of age, must have a ticket purchased for them.
What exactly do we see on the sail?
Our route is determined by the direction of the wind and up to the discretion of the captain, but on this sail you will enjoy the adventure of a nighttime sail, with great star-gazing opportunities and the fantastic moonlight! You may be able to see some attractions along the way, but the focus of this trip is on the moonlit night sailing itself!
Is food served during the sails?
Light snacks are are available for purchase during the booking process or while on board.
How about drinks? Should I bring those?
No, it is illegal for you to bring alcohol of your own on board. Schooner America 2.0 is fully stocked with beer, wine, champagne, and cocktails, all of which are available for purchase either during the booking process, or while on board. Soda and water are complimentary throughout the trip.
Is the Schooner America 2.0 safe?
Absolutely. While known for its speed, the Schooner America 2.0 is a safe and gentle vessel. In addition to your captain, there is a minimum of two crew members on every sail to make sure you feel safe and comfortable on the water. We are stocked with beverages, blankets, and life jackets should you feel you need one.
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 located in our below-decks main salon area. This area is accessible by a short flight of stairs. We call our toilets "heads," but they are very much like the bathroom you have at home. The Captain will give directions on their use during the safety speech at the beginning of the trip.
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 Full Moon 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?
All our sails begin and end at the same location, Schooner Wharf Bar in the Historic Key West Bight.
Can I get a refund or reschedule my tickets after buying them?
Tickets may be rescheduled or refunded up to 72 hours in advance of the departure date. You may also add a 8% "Trip Cancellation Protection" fee during the online booking process which allows you to reschedule or refund your tickets (less taxes and fees) up to 1 hour in advance of your departure.
Do you ever cancel sails due to bad weather?
Weather in Key West is very moderate during the winter months. However, we will cancel a trip is in the event of severe or unsafe weather conditions. Our captains closely monitor the weather on days when inclement weather is possible. Cancellations are made on the day of the sail, by the Captain, up to 1 hour prior to sail time. If you have purchased tickets for a sail that is canceled, we will gladly reschedule your tickets, issue a full refund, or issue credit towards a future sail with us.
What happens if it starts raining when we're out on our sail?
Trips with a little rain have proven to be some the most memorable experiences for our guests. This all depends on attitude, of course! Our captains closely monitor the weather on days when inclement weather is possible. As guest safety is of utmost concern, if the weather looks to be more severe than a passing sprinkle, the captain will bring our guests back to the dock.
Is gratuity included in the price of the sail?
Gratuity is not included in the price of the sail. It is customary to show your crew appreciation for their hard work with cash tips following the trip. If you prefer, you may also add a gratuity during the booking process.
Is the schooner wheelchair accessible?
No, unfortunately the schooner is not wheelchair-accessible.
Can I book a private charter sail?
Yes, private charter 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 clicking the "Contact SailKeyWest" link.
Can I get married aboard America 2.0 in Key West?
Yes. All of our captains are licensed to perform marriage ceremonies aboard the America 2.0. For further details and arrangements, please click on the "Contact SailKeyWest" link.
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
Tickets may be rescheduled or refunded up to 72 hours in advance of the departure date. You may also add "Trip Cancellation Protection" during the booking process which allows you to reschedule or refund your tickets (less taxes and fees) up to 1 hour in advance of your departure for an added fee.
Other Policies Activity may be cancelled due to severe weather. The activity 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.
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 85, 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 impressions that their hosts provide. Guests are treated like royalty, beverages are cold and the vessels sail like a dream!
Plan to arrive 15 minutes before departure to ensure a smooth check-in and boarding process.
Even in warm Florida, evenings on the water can get cool, so bring a light jacket or sweater.
Capture stunning moonlit views and starry skies, but use a night mode or low-light setting for best results.
This is a private or small group experience, so book early to secure your spot.
The Schooner America 2.0 is modeled after the original 19th-century America, a celebrated racing yacht, reflecting Key West’s rich maritime heritage.
Classic Harbor Line supports sustainable tourism by minimizing waste onboard and educating guests about protecting Florida Keys ecosystems.
Stay warm during cooler evening breezes while sailing.
fall specific
Capture sharp photos of the full moon and stars.
Ensure safe footing on the boat’s deck during the sail.
Protect yourself from mosquitoes during warmer months.
summer specific