Frequently Asked Questions
Classic Harbor Line
Frequently Asked Questions
Our Key West Sails often sell out in advance, especially our sunset sail and special event cruises. Guests are encouraged to book as early as possible to ensure they secure tickets for their desired cruise. To check availability for a cruise, please visit our online calendar or call us at 305-293-7245.
We are happy to add you to a waitlist, and will contact you if we have a last-minute cancellation, or if we add additional trips (in the event of a specialty cruise). However, if a trip is sold out and you are waitlisted, we cannot guarantee we will be able to offer you tickets. Please book as early as you are able to ensure you can cruise with us on your desired date.
Due to the limited availability of tickets for our trips, tickets may only be rescheduled or refunded up to 24 hours in advance of the departure date. We highly encourage that you purchase “Trip Cancellation Protection” during the booking process. This allows you to reschedule or refund your full ticket value up to 1 hour in advance of your departure for an added non-refundable fee. For any reschedule/refund questions, please contact us at 305-293-7245.
All passengers, regardless of age, must have a ticket, so please make sure your entire party is accounted for during the booking process. For children 2-12, please choose a Child ticket and for children under 2, please choose an Infant ticket, where applicable.
Parking in Key West is very limited. Please be advised that we are unable to honor cancellations or no-shows due to parking issues. 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, and a municipal parking garage a few blocks away. Parking for both is $5 per hour, or $40 for 24 hours. They only take credit card. We are not affiliated in any way with these lots.
Yes, the boat is equipped with two bathrooms that are always available for use by our guests. We call them “marine heads” and they are very easy to use! The captain will provide more information once you are on board.
There is food offered on some of our key West sailing boat rides. Please visit our website and read the description of the event in which you are interested to learn more about what is offered.
If you or a member of your party has an allergy/dietary restriction, we encourage you to bring additional snacks aboard, as we are unable to defer from our menus.
No, it is illegal for you to bring alcohol of your own on board. Alcohol is available on all our sailing trips, whether included or for-purchase. One quick note, however- We are not a “booze cruise.” We aim to create an elegant, relaxing, peaceful, and safe experience for all our guests.
Looking for recommendations on what to bring? Or what to wear? We recommend wearing comfortable clothing and footwear. High heels are not recommended. It can often be cooler on the water than on land, so we recommend bringing a light jacket. And don’t forget your sunscreen and sunglasses!
Our route is set by the captain based on wind and weather, but guaranteed crystal blue seas and a water side view of Fort Zachary Taylor are a given. Additional sites include Sand Key Reef, Mallory Square, Sunset Pier, marine wildlife, and fellow schooners within the Key West fleet!
The Schooner America 2.0 is a United States Coast Guard certified vessel with all the necessary safety gear for a vessel her size per Coast Guard regulations and receives regular inspections. All our captains are USCG-licensed. The crew conducts emergency drills on a regular basis.
We carry the required number of “Type 1” life jackets specified by the USCG. They are rigid, bright orange life jackets that are designed for emergency use and are designed to keep your head afloat at sea. For the most part, they are not comfortable to wear while sitting on a boat. The life jackets for children are also “Type 1” life jackets. If you would like to comfortably wear a life jacket or have one for a child to wear while cruising or sailing with us, we suggest bringing your own.
Along with your captain, there is a minimum of two crew members on every sail to ensure your safety, and to make sure you feel comfortable. We are stocked with water, beverages, blankets, pillows should you feel you need one. There are also private marine heads (bathrooms) below.
The Schooner America 2.0 is a very steady vessel. It is rare for our guests to become seasick. While most people do not experience any seasickness on the schooner, you may want to consider light medication if you normally take it for motion sickness on land. We cannot officially advise you to take any medication, however, and we are unable to offer you any medication while on board.
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.
No, smoking of any kind, including e-cigarettes, is not permitted aboard Schooner America 2.0.
Our sails depart and return to our dock behind Schooner Wharf Bar at 202 Williams Street.
The sail usually runs in light rain and other moderate weather situations. Our captains and Management team monitor the radar on days when inclement weather is possible. Weather-related cancellations will be 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 due to weather concerns, you will have the opportunity to reschedule your tickets (subject to availability), receive a full refund or receive full value credit towards a future event.
Don’t worry, we won’t melt! Trips with a little added excitement due to weather have proven to be some of the most memorable 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. If the weather becomes such that the captain deems conditions unsafe before the trip is completed, the boat will return to the dock and your Captain will review your options.
For most of our trips, 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. You may also include a gratuity with your ticket purchase during the booking process. A few of our special events include gratuity with ticket purchase, but this is outlined during the booking process.
No, Schooner America 2.0 is not ADA-accessible. In many cases, however, we are able to accommodate guests who need mobility assistance.
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 charter, please fill out a Private Charter Request form and someone from our Charter Sales team will get back to you!
Yes. All our captains in Key West can perform marriage ceremonies aboard the Schooner America 2.0. For further details and arrangements, fill out a Contact Us form and let us know you’d like more information!
Yes, we offer gift certificates which make perfect gifts for holidays, birthdays or any other occasion!