Take to the water on the newest addition to our fleet - the schooner America 2.0, just completed in 2011. This stunning 105-foot boat features teak decks, mahogany trimmings and padded bench seating. Her 3,600 square feet of sail will propel you smoothly through the crystal green waters of Key West.
This exciting day sail features a full bar. Drinks are just $1.00! Water and soda are free of charge. Guests are encouraged to make the most of the event by bringing aboard their own picnic lunch!
Some of the sights on this 1.5 hour sailing adventure include:
This exciting day sail features a full bar. Drinks are just $1.00! Water and soda are free of charge. Guests are encouraged to make the most of the event by bringing aboard their own picnic lunch!
Some of the sights on this 1.5 hour sailing adventure include:
- A waterside view of Fort Zachary Taylor
- The famed Sand Key Lighthouse, Mallory Square, and Sunset Pier
- And keep your eyes peeled for wildlife: dolphins, sea turtles, and waterbirds
What Is Not Included?
Food is not included, but guests are encouraged to pack their own or pick up a picnic from the local Schooner Wharf Bar right near our meeting location.
Meeting Location
The Key West Bight (Key West, FL)
(Exact meeting location details will be provided immediately upon purchase of tickets.)
- 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 may be somewhat 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?
- For children between the ages of 4 and 12 you should purchase a reduced price Child ticket. Children ages 3 and younger ride for free on Day Sails, but you’ll still need to enter the appropriate number of Infant tickets labeled “Free” when purchasing. All passengers, regardless of age, must have a ticket, so please make sure your entire party is accounted for in this way.
- What exactly do we see on the sail?
- Our route is indicative of the breeze we are given, but guaranteed crystal green seas and a water side view of Fort Zachary Taylor are a given. Additional sites may include Sand Key Reef, Mallory Square, Sunset Pier, marine wild life, and fellow schooners within the Key West fleet.
- Is food served during the sails?
- Food is not served on the Day Sail, but guests are welcome and encouraged to bring a picnic.
- How about drinks? Should I bring those?
- No, it is illegal for you to bring alcohol of your own on board. A full bar with beer, wine and champagne is available with drinks at just $1. Soft drinks and water are provided free of charge. (One quick note: We are not an unlimited booze-cruise. We aim to create an elegant, relaxing, peaceful, and safe experience for all of our guests.)
- 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 three 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 unlike the bathroom you use at home. The Captain will give directions in the safety speech.
- 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. But we have not had any problems with items being left on prior sails.
- What should I wear?
- For our day sail we recommend wearing comfortable clothing and footwear (high heels are not recommended). Feel free to come in a bathing suit, but bring a light jacket just in case!
- 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 we are guaranteeing your space on the sail, tickets cannot be refunded once purchased.
- 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 1 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 wetness have proven to be some the most memorable bonding experiences for our guests. (This all depends on attitude of course...) If we are caught in a rain shower we have ankle-length button-down raincoats available for all of our guests aboard the America 2.0.
- Is gratuity included in the price of the sail?
- Gratuity is not included in the price of the sail. It is customary to reward your hosts with cash tips following the trip.
- Is the schooner wheelchair accessible?
- No, unfortunately the schooner 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 clicking the "Contact SailKeyWest" link.
- Can I get married aboard America 2.0 in Key West?
- Yes. Two of our operators in Key West are capable of performing 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
- Non-refundable, cannot be rescheduled.
- Once purchased, tickets cannot be refunded and cannot be rescheduled because your space is being guaranteed at the event.
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.
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 1920's 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.
The year-round vessel of Key West is the Yacht Beacon, a 52 foot classic yacht which is equipped for Snorkeling, Kayaking, Morning Mimosa Cruises and Classic Sunset Cruises!
Classic Harbor Line is well known for their outstanding captains and crew and standard of hospitality. Whether you sail with them in Newport, 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!
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 1920's 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.
The year-round vessel of Key West is the Yacht Beacon, a 52 foot classic yacht which is equipped for Snorkeling, Kayaking, Morning Mimosa Cruises and Classic Sunset Cruises!
Classic Harbor Line is well known for their outstanding captains and crew and standard of hospitality. Whether you sail with them in Newport, 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!




