Authentic Key West Sailing

The Schooner Jolly II Rover


Key West Sailing

Sail back in time to capture the bygone days of a highly romanticized period in Key West sailing history when merchant ships, smugglers, and pirates plied the very waters we sail today. The Jolly II Rover, with plenty of seating, smooth ride, and signature red sails will ignite your passion for traditional tall ship sailing. Join the crew and hoist the sails or sit back, relax and take in the experience.

Day Sail | Sunset Sail

Drink and eat what you want – bring your favorite food and beverages while we supply the bottled water, lots of ice, ice chests, cups and bottle openers.

Lots of seating and room to walk about on its 65’ length deck. Plus two heads (bathrooms) are located down below via easy access full size stairs with railing (not the usual awkward ladder!)


Day Sail


2 Hour Sail | Times Vary By Season
Book Online

Sailing daily out of the Historic Seaport of Key West on Key West’s longest day sail with a Hint of Piracy!

A full 2 hours on the water, your Key West sailing tour departs from the Historic Seaport (locals call it the Key West Bight). The Bight was famous for its shrimp boats and is rich in history and waterfront culture.

On reaching open waters, Jolly II Rover’s distinctive red sails unfurl as you take in Key West sites from the water including:

  • Mallory Square
  • Civil War-era Fort Zachary Taylor
  • Navy Mole submarine base
  • Truman Annex with President Truman’s famous “Winter Whitehouse”,
  • Christmas Tree Island
  • The opulent Sunset Key and more.

Key West’s waters teem with wildlife. Look for dolphins, turtles, flying fish, manta rays and man o’ war jellyfish. Overhead, frigates glide high above you while pelicans bob on the calm, warm waters and ospreys dive bomb for fish.

See more pictures of Key West’s most photographed ship on our Gallery Page.

Fire the Cannons!

Find your inner pirate while sailing Key West’s emerald waters. Join the crew and show your muscle hoisting the sails! Grab the wheel and prove your salt steering the ship! Let your intrepid spirit shine and fire the cannons!

A Jolly II Rover day sail is a BYOB excursion making it one of the most affordable Key West activities!

Book your day sail now!


Sunset Sail


2 Hour Sail | Times Vary By Season
Book Online

A must-do for all Key West trips is to soak in the sunset Key West style – from the decks of our majestic tall ship. Our Key West sunset sail, like our day sail, departs from Key West’s Historic Seaport.

Be the focal point of Mallory Square’s World Famous Sunset Celebration!

As we sail by, cameras flash as another evening’s worth of pictures are snapped of Key West’s most photographed schooner. Watch, wave and smile as other vessels sail in close to give their passengers a glimpse of our magnificent sailing ship with its distinctive tanbark sails and tall square rig. Sunsets in Key West are one of life’s most romantic moments.

See more pictures of Key West’s most photographed ship on our Gallery Page.

Picture yourself and your loved one sharing this exquisite view aboard the Jolly Rover. This experience is sure to be the highlight of your trip! Take in the beautiful sights as we sail past historic Fort Zachary Taylor, the submarine base, the Truman Annex – President Truman’s “Winter Whitehouse”, “Christmas Tree Island” and the celebrities’ multi-million dollar homes on glamorous Sunset Key.

Watch for numerous Florida wildlife – dolphins, turtles, flying fish, pelicans, frigates, and ospreys are just a few of the creatures inhabiting our emerald waters.

As you sail into the glorious Key West sunset, scan the horizon for the world-renowned Key West Green Flash – that elusive split second where the disappearing sun changes color.

  • Steer The Ship!
  • Fire The Cannons!

Let out your inner pirate as the Rover crew trains the cannons and prepares for a broadside cannon fire exchange with a rival tall ship! Of all the beautiful sunsets you’ll experience in Key West, the most memorable will be from the decks of the Jolly Rover.

Book Your Sunset Sail Now!


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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 $15 off your second sail and your third sail is FREE!

*Within 30 days.

Where to
Find Us

Click HERE for the Map