Florida Keys Cruising Conditions

Uncover the cruising conditions you can expect on the water and find out the best times to visit.

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.
Our catamaran at anchor at Boca Grande Key, one of the anchorage areas along the route

How many days to plan for your Key West yacht charter

I think you need at least a week to charter to the Dry Tortugas. It can be done in fewer, but I wouldn't recommend it unless you have a speed boat. Check out the Sailing Itinerary tab for a suggested week-long plan.

What is the sailing route to the Dry Tortugas like?

It’s approximately 80 nautical miles to the Dry Tortugas from Key West. If you are on a sailing charter vacation, plan for two days to get there and the same for the return. Yes, that can be done with a very early am departure, but don’t plan on checking out until mid morning. You know the drill with those check-out briefings.

It’s a great sail! The water is beautiful and the fishing is excellent.

With prevailing winds, you are most likely to have a downwind sail on the way there. Returning to Key West, you might be beating to windward and it might make sense to throw in the towel and motor.

As far as planning guides go, I picked up a copy of the Water Way Guide for the Keys. We also relied heavily on Garmin Active Captain for anchoring advice.

Anchorages along the route

Main anchorage near downtown Key West

I like this anchorage at the end of the trip. Celebrate your final night and share stories about your adventures boating to the Dry Tortugas during a night on the town.

Boca Grande Key

Boca Grande is next up. In settled conditions, you can anchor in ~10 feet to the west of the popular beach (Boca Grande – 2 on Garmin Active Captain). You will swing some on the tide here as it flows between the Gulf of Mexico and the Gulf Stream at about 1 knot.

You can also anchor further up the channel that leads to the interior of the key, but be prepared for 180 shifts and swings on the tide.

Marquesas Keys

The final anchorage before you reach the Dry Tortugas (and you still have about 50 miles to go) is the Marquesas Keys. It is less protected than Boca Grande, so keep that in mind if you are planning around some weather events.

Anchor within a few hundred yards of the beach. If the bugs are bad, you can venture farther out – look for the Brown Pelican anchorage on Active Captain which is about a mile offshore.
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.

Florida Keys charter planning?

Consider booking with the Yacht Warriors.