Key West Schooner

The amazing Schooner Jolly II Rover is proudly owned by Bill Malone and is operated out of Key West’s Historic Seaport. He purchased the Jolly II Rover in 2003 to fulfill a lifelong dream of operating a classic, square rigged, topsail schooner.

At the time of purchase, the Jolly Rover was in Fort Myers, Florida. With the help of enthusiastic friends, Bill sailed the Jolly Rover back to his adopted home of New Orleans. With his new team, “The Pirates of Lake Pontchartrain” he offered day and evening sails on Lake Pontchartrain with daily sailing trips, sunset sails and sailing charters.

Several years later you could say that fate intervened. Hurricane Katrina passed through New Orleans and blew the Jolly II Rover back to Florida where the tall ship belongs – among the traditional sailing ships, both mercenary and merchant, of the Historic Seaport of Key West.

Follow the Adventures of the Jolly Rover!

Key West Sailing Adventure
Over the years, the Schooner Jolly Rover has been featured in countless magazines, newspapers and blogs for our iconic red sails and legendary sunset cruises. We have hand picked several of our favorite articles from USA Today, National Geographic and more.

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Schooner Jolly Rover Details

The tall ship Schooner Jolly II Rover was designed by Naval Architect Meritt Walter as a mercenary vessel and was built in 1994 by Bock Marine of Beaufort, North Carolina. The Rover’s hull is constructed out of steel and at 80′ long with her trademarks sails, topmast and square rig she is a magnificent sight under sail as well as sitting quietly dockside. You can learn more about Meritt Walter and his designs, including the Jolly 2 Rover, at

For a little extra history on what brought The Jolly Rover the the Key West Historic Seaport check out “North Shore icon finds a new home in Key West” from the Greater New Orleans Times Picayne Newspaper.

The Crew

The Crew

Traditional sailing vessels is a shared interest of Jolly Rover’s captains and owner who want to share their love of old world sailing with you. Our experienced captains and crew have been sailing with us for years and take great pride in providing you with amazing memories aboard the Jolly Rover

Capt Bill

Capt Bill

Bill, a long-time arm chair salior now proudly owns and operates the Schooner Jolly II Rover. He grew up on the shores of Long Island Sound in Connecticut, where he first fell in love with old world sailing ships. Years later, living in New Orleans and after a career in healthcare administration, the ocean called him back to his first love.

Capt Rio

Capt Rio

Content for Capt Rio

Captain Rhondi

Capt Rhondi

Content for Capt Rhondi

Capt Jen

Captain Chris

Capt Chris

Chris taught himself to sail the hard way, on a Windsurfer (sailboard) in the 1980's. In the late nineties he sailed with a friend on his wooden sloop to Cuba and back. Soon after he bought his first sailboat and has been sailing ever since.