Florida Keys & Key West

Florida Keys and Key West overview, cruising conditions, sailing itinerary, and yacht charter guides

Beautiful sunset with our sailboat at Boca Grande Key

Interior of Fort Jefferson with no crowds

Sunset at Garden Key at the Dry Tortugas

Key West is a unique yacht charter destination that many don’t consider. It perhaps isn’t a place to return year after year, like the Exumas or British Virgin Islands, but I thoroughly enjoyed our bareboat trip. I’d recommend adding it to your bucket list!

Why visit?

Key West, itself, is a really fun city to explore. And then you have direct access to the Dry Tortugas, about 60 nautical miles to your west. Lastly, if you prefer, you have the rest of the Florida Keys and Miami to explore, also within reach.

I think, however, the number one reason to visit is for an offshore passage to the Dry Tortugas – go see this special National Park as most other visitors are not able to. History, seclusion, and pristine natural beauty are top reasons to go.

Highlights of a Key West and Dry Tortugas yacht charter

Anchor in the National Park near Garden Key and explore Fort Jefferson after the other tourists have left for the day
Take a day trip inside the park to Loggerhead Key and snorkel the Windjammer Wreck
Sail to and snorkel one of the many protected areas of the Florida Keys National Marine Sanctuary, such as Sand Cay
Enjoy epic sunsets over the Marquesas Keys
Go shopping or perhaps enjoy a night out on bustling Duval Street in Key West
Catch mahi, mackerel, and tuna on the shelf or drop areas along the way to the Dry Tortugas

Squalls near Dry Tortugas — Sailing past a typical pop-up squall en route to the Dry Tortugas

The Key West, Florida Keys, and Dry Tortugas charter area is not considered a place for beginners.

Protected anchorages are few, there are navigational hazards, and you need to pay close attention to the weather. Furthermore, if you go offshore to the Dry Tortugas, you may be out of cell phone service for multiple days and should have a plan to monitor weather conditions during certain times of the year (in particular for keeping check on tropical systems and cold fronts).

Here’s what you need to know about chartering in the Key West area:

When to go
How long to plan your trip for
What is the sailing route like?
Fishing

When to visit Key West and the Dry Tortugas

I did this trip in August…and I would not recommend boating to the Dry Tortugas this time of year (doable maybe if you have reliable air conditioning aboard). South Florida is then very hot and the wind is also at it’s weakest and most variable. I slept on the catamaran trampoline every night it was that bad!

I think the Spring or early Fall are the best time to take a private boat to the Dry Tortugas. Why?

Less risk of tropical mischief
The heat is less intense and the weather is more settled
There is less risk of cold fronts which can barrel down with intense winds and squalls
Fishing in the fall as the water cools offers great chances at catching wahoo along the drop

Weather is the biggest factor to plan for. You want your best chance of a settled weather window. Aside from the anchorage at Fort Jefferson, there are really very few protected anchorages along this route.

How many days to plan for your Key West yacht charter

What is the sailing route to the Dry Tortugas like?

Little tunny caught near key west florida — Little tunny we caught between Key West and the Dry Tortugas

Fishing on the way to the Dry Tortugas

You have great chances at catching fish boating to the Dry Tortugas. Depths range from 40-60 feet along the way – expect to catch king mackerel, little tunny, and barracuda.

I also like the idea of fishing the drop which will take you on a slight detour south if you can afford the time. Here you’ll have better chances of landing tuna, mahi, and wahoo.

There are also several spots to bottom drop, such as at Rebecca Shoal – here you have decent chances of hooking snapper and grouper.

Before you enter the park boundaries, make sure you stow away your equipment. Park rangers also ask you to report any catch that you are bringing into the park. You can do this on Channel 16.

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!

Travel day

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.

Travel day

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.

Epic sunsets at the Boca Grande anchorage

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.

Exploring Fort Jefferson

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).

Loggerhead Key

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!

Sunset over the Marquesas Keys