Frequently Asked Questions


These are some of the most common questions we’re asked about our tours. If you want the answer to the question “What is the meaning of life?”… try viewing a Key West sunset from the deck of the Jolly Rover. It will all become quite clear.

Do I have to purchase tickets in advance?

We highly recommend that you purchase tickets in advance, as sails do sell out quickly. To maximize your chances of getting the day that you prefer, please book well in advance!

What happens if the sail is sold out?

Unfortunately, we do not have a waiting list for our sails, so please book well in advance to ensure getting the day of your preference.

What happens if it rains?

The Jolly II Rover will run in all light weather conditions (a little rain never hurt anyone!). In the rare event that we have to cancel a sail due to severe weather, you will have the opportunity to reschedule your tickets subject to availability or receive credit for a future event.

Are food and beverages available on board?

We do have iced bottled water on board that is included in your ticket price. There are no other foods and beverages available on board, but we encourage you to bring your own picnic with you! You are permitted to bring alcoholic beverages on board as well, and can bring a small picnic basket sized cooler if you so wish.

Can children go on the sail?

We love children! Children are more than welcome to attend the sunset sail. Children between 4 and 12 years of age have a reduced ticket price, and children 3 years of age and under are free but must secure a ticket.

How far will the boat go out?

The boat will go anywhere between 2 and 3 miles out on the water depending on the day’s weather.

How fast does the Schooner go?

The Schooner cruises at an average of 5 knots with a maxim of 10 knots.

Can I bring a personal cooler/ice chest with me?

You may bring a small personal cooler (the size of a knapsack or picnic cooler), but please do not bring any large coolers with you. We have ice chests on board for you to store your food and beverages in!

What should I wear on the sail?

We advise you to wear layers, as it is often cooler out on the water than on land. If you get warm, you can always peel off a layer or two!

Are there bathrooms aboard the schooner?

Yes, there are two clean heads (bathrooms) on the schooner for your use.

Do you have life jackets on board?

Yes! The Jolly Rover is US Coast Guard certified for safety, and has life jackets on board for each and every passenger. However, you are not required to wear the life jackets during the trip!

Will I get seasick?

Probably not. Luckily the Key West waters are friendly and typically not very choppy, and our crew does a fantastic job navigating out of the extremely windy areas. If you do get seasick, we will seat you at the steering section and that should help. If you have a tendency towards motion sickness, please take preventative measures beforehand.

Is there public parking nearby?

There is a public parking lot on Caroline Street between Margaret and William Streets in the Historic Seaport, just two blocks from the meeting location. Rates are $2.50 an hour, with a $16.25 daily maximum.

Should I tip the crew?

Gratuities are not mandatory but greatly appreciated! Your crew works very hard to ensure that your sunset sail is a superior experience. If you enjoyed the sail, please tip the crew accordingly!

Can I book a private charter?

Yes! The Jolly Rover is available for private party trips, daytime sails, overnight adventures, and any other types of special events! For more information, please click on the “Contact JollyRover” link.

Are gift certificates available?

Yes! If you are interested in gift certificates, please “Contact JollyRover” for more information.

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Frequent Sailor Discount!

Many locals as well as visitors are repeat sailors. And we love seeing familiar faces, so we offer $10 off your second sail and your third sail is FREE!

*Within 30 days.

Where to
Find Us

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