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 2 Rover is an amazing deal and more affordable than you think.

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

Florida Keys Private Charters

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

Key West Pirate Ship

Charter a day sail for your childs 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.

Jolly Rover Proposal

Wedding Ceremony

Vow Renewal

Family Reunions

Company Holiday Party

Milestone Birthdays

Kids Birthday Party

Private Sightseeing Tour

Private Key West Charters

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

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.

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!

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