Customized Private Charter

Aboard the Schooner Jolly II Rover


Private Charter Aboard The Jolly II Rover

Make your Key West, Florida vacation memorable and create your own Florida Keys sailing trip on a private charter aboard a replica of an early 1800’s American Coastal Topsail Schooner! A private charter on the Jolly II Rover is an amazing experience and more affordable than you think.

Call us to customize your Florida Keys sailing adventure at 305.304.2235 or email at

Imagine the stories your kids will tell of camping out on their very own pirate ship!

Charter a day sail for your child’s birthday party, or anchor overnight, or multiple nights for the experience of a life time. We love kids and look forward to sharing our knowledge and passion for sailing the high seas with the next generation.

Possibilities are endless – picture you and your loved one exchanging wedding vows with the sun setting in the background. Or a milestone birthday celebration to be remembered and memories cherished. You can even book the Jolly Rover for a convenient dockside party or as your own private hotel for an overnight stay. Our rates are kept low since you provide your own food and drink while we supply the bottled water, lots of ice, ice chests, cups and bottle openers.

Wedding Ceremony

Vow Renewal

Family Reunions

Company Holiday Party

Milestone Birthdays

Kids Birthday Party

Private Sightseeing Tour


Bring your fishing rods and snorkel gear and our captains will share their knowledge of the bountiful ocean. On a private charter, we can sail to isolated reefs where your group snorkels in solitary splendor away from the crowds. We even have a fresh water hose on deck to spray off the salt water after a day of fun in the ocean. Then cook your catch on deck. We’ll provide the grill and propane.


For The More Adventurous

For The More Adventurous

An overnight excursion on the Jolly Rover is like camping out on the water! Experience life on the ocean as a sailor. Charter your own sailing trip for one night or many. Some favorite trips include:

Educational cruise for a youth group, nature/environmental group or anyone interested in learning more about sailing, wildlife and our magnificently unique Florida Keys ecosystem.

A wildlife adventure to the Dry Tortugas National Park known for its fantastic bird and marine life and anchor overnight.

For your private Florida Keys sail charter, call 305.304.2235.
Or email


Stargazer Sail


Enjoy an exciting, romantic, sailing adventure while looking up at the stars! Away from all light pollution, watch the sky come alive as your eyes adjust.

Elio Hinds, the schooners official on board star tracker, will teach you all about the solar system, galaxies, and beyond! Experience how the ancient mariners used the stars to chart their course, identify constellations, and spot your Zodiac sign!

Star gazing sleepover. See the night sky in all its glory and count the constellations as you spend the night anchored at sea. No light pollution here – be amazed at how many stars are visible at night. Time your excursion with a full moon rise!

Coast Guard Inspected

The Jolly Rover is U.S. Coast Guard inspected and certified for 41 day passengers and 20 overnight.

Heading down a full size stair case with railings (opposed to the usual awkward ladder) you will find sleeping quarters, and two full bathrooms.

Pet Friendly!

Jolly Rover is a pet friendly vessel but please remember that cannons are fired and not all pets have inner pirates!

We Love Kids!

We are proud to charter for the Boy Scouts of America and their National High Adventure Sea Base. We welcome the opportunity to work with your organization!