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Monday 9am - 5pm Tuesday 9am - 5pm Wednesday 9am - 5pm Thursday 9am - 5pm Friday 9am - 5pm Saturday 9am - 5pm Sunday 9am - 5pm

Schooner Jolly II Rover

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United States
Key West, FL
Schooner Jolly II Rover

Come sail Key West’s famous Red Sails in the Sunset most photographed ship! The Tall Ship Schooner Jolly II Rover. Traditional sailing with a Hint Of Piracy!
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The only square rigged topsail schooner in the Historic Seaport of Key West!

02/15/2024

Thank you for sailing with us 🤩

If you had a fantastic time, please leave us a review

02/07/2024

Just wait... these cannons are prepped & ready to fire 💥

A fun tradition on our schooner that makes you feel like a true pirate!

01/30/2024

We are living the tall ship life, and loving every salty moment ⛵️🌊

Book a trip with us soon!

01/24/2024

Chasing sunsets, where the day meets its most beautiful goodbye ✨

01/16/2024

Cherishing these precious moments as our guests create lasting memories with their loved ones aboard ❤️

Head to our website to book a sail with us soon!

01/11/2024

Capturing the mesmerizing magic of our island one sail at a time 🌅✨

01/04/2024

Get ready to experience the magic ⛵

We’ll take you back in time on our classic 80’ tall ship to an era of pirates, rum runners and privateers seeking freedom and solitude. Their spirit of independence lives on daily on the Jolly II Rover.

Book 👉 https://buff.ly/3FVLxQa

01/02/2024

Thank you for sailing with us 🤩

If you had a fantastic time, please leave us a review on Google and TripAdvisor!

12/31/2023

As the sun sets, our tradition ignites the sky ⭐

Join us as we mark each sunset with cannon fire—a salute to the day's end and the night's beginning!

12/29/2023

Postcard from Key West 🌊 🌴🌞

There’s nowhere we’d rather be!

12/27/2023

As we near the end of the year, here's to the breathtaking journeys awaiting on the open seas! 🥂

12/25/2023

Merry Christmas from The Conch Republic!

12/25/2023

Merry Christmas from the Jolly II Rover family!

May your holiday season be filled with joy, peace, and smooth seas ahead. 🎄

12/23/2023

Where dreams set sail 🌟⛵

12/21/2023

to sailing in Cuba!

During the years 2015-2017, we had the honor of leading the boat parade into Havana Harbor—an unforgettable and thrilling experience!✨

12/20/2023

The greatest adventure for your family!

Have you sailed with us this year? 😃

12/19/2023

Give the gift of sailing this holiday season ⛵

Unwrap moments under the setting sun aboard our schooner in Key West. 🌅

Book a trip - https://buff.ly/3FVLxQa

12/17/2023

A new perspective 💫

Step aboard and immerse yourself in every detail, every breeze, and every whisper of the sea's melody⚓

12/15/2023

Thank you for choosing to sail with us! 😃

If you had a fantastic time on board, we'd be honored if you could share your experience with others on Google and TripAdvisor.

12/13/2023

We sure do love our passengers & crew! 🙌

Did you know we have a Frequent Sailor Discount? Many locals as well as visitors are repeat sailors. And we love seeing familiar faces, so we offer $15 off your second sail and your third sail is FREE (within 30 days)!

📷: Sabrina Harvill

12/11/2023

Chasing sunsets & embracing golden hour every night 🧡 ✨

Book your next trip 👇
https://buff.ly/3T6rQNf

12/09/2023

Smooth sailing with little sailors onboard! ⛵

Setting sail isn't just an adventure—it's a chance for kids to learn, grow, and create lasting memories.

12/07/2023

As the sun sets, experience the mesmerizing glow along the tranquil waters 🌊

We can’t wait to sail with you soon!

📷: irismoorephoto

12/06/2023

Your journey’s success is anchored in our team's dedication. They're the true stars making your trip truly spectacular! ⛵

12/04/2023

The sparkle of paradise ✨

We’ve been sailing for years & would love to hear your favorite memories on our ship!

Comment below 👇

12/03/2023

An authentic Key West Sailing Experience!

With the holidays approaching fast it’s the perfect time to book a sail with your friends and family. Head to our website to book your trip today 😃

www.schoonerjollyrover.com

12/01/2023

What a magical moment! 💫

Congratulations to the newlyweds - Jake & Madi!

Aboard the Schooner Jolly II Rover we do customized private charters, contact us today to plan your next special event.

📷: irismoorephoto

11/30/2023

Meet Crew Member - Elio ⚓

She has been sailing with us for 13 years! Originally from El Salvador, Elio joined the Jolly Rover family in 2009. Her love for sailing sparked when her first husband, a sailor, brought her to Key West. Elio pursued art in Virginia, where she fell in love with sailing even more.

Have you sailed with Elio before? Comment below!

11/28/2023

What brings you peace as the day bids farewell? 💙

Let us know in the comments below👇

11/26/2023

Allow the hues of the sky to paint the backdrop for your seafaring memories. 🌅

Please visit our website for more information👇
https://buff.ly/3FVLxQa

📸: Jennifer Smith

Address

631 Greene Street
Key West, FL
33040

Opening Hours

Monday	9am - 5pm
Tuesday	9am - 5pm
Wednesday	9am - 5pm
Thursday	9am - 5pm
Friday	9am - 5pm
Saturday	9am - 5pm
Sunday	9am - 5pm

Telephone

+13053042235

Website

http://schoonerjollyrover.com/

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Videos

Just wait... these cannons are prepped & ready to fire 💥 A fun tradition on our schooner that makes you feel like a true pirate! . #jollyrover #tallshipsailing #keywestvacation #sunsetsailing #sailinglife #schooner #keywestsunset #floridakeys #lovefl #sunsetcruises

Capturing the mesmerizing magic of our island one sail at a time 🌅✨ . #jollyrover #tallshipsailing #keywestvacation #sunsetsailing #sailinglife #schooner #keywestsunset #floridakeys #lovefl #sunsetcruises

If there’s one thing that never loses its charm, it’s the thunderous excitement of the cannons! ✨ What’s your go-to thrill when sailing with us? ⚓️ . #jollyrover #tallshipsailing #keywestvacation #sunsetsailing #sailinglife #schooner #keywestsunset #floridakeys #lovefl #sunsetcruises #cannons

Experience the allure of the open sea with us and set your sails for an unforgettable adventure! ⛵️ Check out our website for details on how to book👇 schoonerjollyrover.com . #jollyrover #tallshipsailing #keywestvacation #sunsetsailing #sailinglife #schooner #keywestsunset #floridakeys #lovefl #sunsetcruises

Discover the beauty of Key West from a new perspective on our elegant schooner 🌊⛵️ . #jollyrover #tallshipsailing #keywestvacation #sunsetsailing #sailinglife #schooner #keywestsunset #floridakeys #lovefl #sunsetcruises

Take a Seat & Enjoy the View 🌞 Join us for an unforgettable Key West sunset sail departing from the Historic Seaport and be the star of Mallory Square’s sunset celebration! Head to our website to book your next sail. . #jollyrover #tallshipsailing #keywestvacation #sunsetsailing #sailinglife #schooner #keywestsunset #floridakeys #lovefl #sunsetcruises

Sit back & enjoy authentic Key West sailing ⛵ You will see us raise sails, hear us tell some jokes, and learn something about the history of our ship. Head to our website to book! https://schoonerjollyrover.com

Sights and sounds of the Florida Keys winter. Our almond tree leaves turned red on New Years Day. It has been raining leaves ever since and the Key Deer are loving it! Happy New Years everyone! #jollyrover #redleavesinthesunset #floridakeys