Come aboard the Schooner Jolly II Rover for an unforgettable sunset sailing experience - With a Hint of Piracy!- in the glistening waters of the Florida Keys.
This square-rigged, 80 foot topsail schooner, built in 1994, will transport you back in time with its tanbark colored sails and cannons. Enjoy an exciting, romantic, sailing adventure while basking in the amazing views of a Florida sunset.
See Key West's gorgeous Historic Seaport, known locally as the Key West Bight. Once known for its shrimp boats, it is today both a beautiful sight and rich with history and waterfront culture.
During the sail, you will see:
This square-rigged, 80 foot topsail schooner, built in 1994, will transport you back in time with its tanbark colored sails and cannons. Enjoy an exciting, romantic, sailing adventure while basking in the amazing views of a Florida sunset.
See Key West's gorgeous Historic Seaport, known locally as the Key West Bight. Once known for its shrimp boats, it is today both a beautiful sight and rich with history and waterfront culture.
During the sail, you will see:
- The renowned Key West sunset (and maybe even the "green flash" when the sun changes color for a moment if you're lucky)
- Ocean wildlife, including schools of dolphins
- Mallory Square, home of the Key West historical sculpture garden
- Fort Zachary Taylor
- The Navy Mole, a submarine base
- Truman Annex, President Truman's "Winter Whitehouse"
- "Christmas Tree Island"
- Sunset Key, known for its multi-million dollar celebrity homes
What Is Not Included?
Food and beverages other than bottled water are not included on the sail. Please bring your own picnics and alcoholic or non-alcoholic beverages aboard in a small picnic basket sized cooler! We have ice chests aboard for you to use to store your snacks and drinks.
Meeting Location
Historic Harbor, near Elizabeth and Greene Streets (Key West, FL)
(Exact meeting location details will be provided immediately upon purchase of tickets.)
- 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.
- 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 goes on average at a speed ranging from 7-10 knots.
- 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 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.
Schooner Jolly II Rover
The Schooner Jolly II Rover (an 80', square rigged, topsail schooner) is owned by Bill Malone and operated by Captains James "Mac" Reddy and Rhondi Opiela. Their shared interest in traditional sailing vessels, and their combined desire to expose old world sailing to others, has resulted in their being able to offer (at a very reasonable cost) exciting, traditional sailing adventures - with a hint of piracy! (Yes, they have cannons!).
The Schooner Jolly II Rover offers two hour Sunset sails, Day Sails, Full Moon Sails and one and one half hour Stargazer Sails in the heart of Key West. They depart daily from the Historic Seaport of Key West.
During the summer they host the Boy Scouts of America National High Adventure Seabase Program.
This magnificent tall ship is a replica of an 18th century coastal schooner. 80' in overall length, the Schooner Jolly II Rover has tanbark colored sails and carries several cannons. Join the crew and get transported back in time on this exciting traditional sailing adventure!
Hoist the Sails! Steer the Ship! Fire the Cannons!
The Schooner Jolly II Rover offers two hour Sunset sails, Day Sails, Full Moon Sails and one and one half hour Stargazer Sails in the heart of Key West. They depart daily from the Historic Seaport of Key West.
During the summer they host the Boy Scouts of America National High Adventure Seabase Program.
This magnificent tall ship is a replica of an 18th century coastal schooner. 80' in overall length, the Schooner Jolly II Rover has tanbark colored sails and carries several cannons. Join the crew and get transported back in time on this exciting traditional sailing adventure!
Hoist the Sails! Steer the Ship! Fire the Cannons!
