Florida Keys Sailing Itinerary

Chart your course with confidence and explore our handcrafted Florida Keys sailing itinerary.

For an offshore passage to visit the Dry Tortugas from Key West, I would plan for a minimum of a week. Use this sailing itinerary as a starting point for your planning! 

Day 1: Travel day & Sleepaboard

Arrive, get settled in, and stow away your provisions. Familiarize yourself with the boat's systems if you'd like. Crack a beer! Let's get this vacation underway.
Epic sunsets at the Boca Grande anchorage

Day 2: Head first for Boca Grande Key

Raise your sails for an early am departure for Boca Grande key. If you have time, grab a mooring ball for some snorkeling and a lunch stop at one of the Marine Sanctuary sites. If you are making great time, you can push on to the Marquesas Keys.
Exploring Fort Jefferson

Day 3: Arrive at the Dry Tortugas

Sail the rest of the way to the Dry Tortugas and get those fishing lines out. Explore the magic of Fort Jefferson after most of the tourists have left for the day on the ferry.
Loggerhead Key

Day 4: Daytrip to Loggerhead Key inside the Park

Motor over to Loggerhead Key for the day. Check out the sandbars, explore the lighthouse, and consider snorkeling the Windjammer wreck on the west side. Return to Garden Key in the evening (you aren't allowed to stay overnight at Loggerhead).
Sunset over the Marquesas Keys

Day 5: Back east to the Marquesas Keys

Get an early start to start making your way back towards Key West. The Marquesas Keys makes for a good overnight anchorage. Keep your eye out for lost Spanish galleon treasure!
Key West anchorage

Day 6: Night out on Duval Street

Complete the last leg of your passage and celebrate your return to civilization in Key West. Grab a bite and check out the scene on Duval street.

Day 7: Checkout and travel day

You've done it! Allow enough time to refuel and complete check-out procedures with the charter company back at the marina.

Florida Keys charter planning?

Consider booking with the Yacht Warriors.