key west sailing

The Ultimate Guide to an Unforgettable Key West Sailing Vacation

Balmy temperatures, Caribbean flavors, 800 islands to explore and 6,000 reefs—the Florida Keys is where it’s at.

The Florida Keys, also called simply “the Keys”, is home to thousands of miles of reefs, beaches, six-toed cats, a national park and the southernmost point of the continental United States.

But with so many options available, a trip to the Keys can be overwhelming. Where should you go? What should you see?

Whether you’re a liveaboarder seeking a change of view or a landlubber looking for a liveaboard dive trip, read on to find my favorite places to help you have an unforgettable Key West sailing vacation.

Book a Boat Charter or Room?

First things first. While high-class resorts with amazing pools are available in the keys, it’s truly the ultimate playground for those who love boating.

An archipelago of 1,700 islands makes up the Florida Keys, along with 43 residential islands connected by bridges. Available are hundreds of reef locations to snorkel and multiple islands with white sandy beaches. And only with a boat is it possible to visit everything on your vacation, which makes the Florida Keys a great place to discover.

Don’t book that resort, no matter how classy. Book the boat charter. You won’t regret it.

When to Visit Key West and the Florida Keys

The best time to visit Key West and the Florida Keys is between the off-peak seasons of March and May, when winter crowds thin out and rates go down. Not only that, but the weather is remarkable this time of year, finding yourself on the beach, 77 degrees and sunny, is the best way to vacay.

A Note About Hurricane Season

Between June and November is the season for you, if you’re a gambler. Hotel rates drop lower than spring rates, but, well… it’s hurricane season. Chances for a hurricane are greatest between mid-August and the first of October.

According to Monroe County, “the Keys are very popular with vacationers in the summer and fall months.” So between March and May timeframe, you can absolutely travel. Chances are, historically, that you’ll avoid a hurricane ruining your vacation. Just be aware that you may experience cooler weather, windy and overcast days.

Fantastic Key West Festivals

Key West Pride Festival and Parade

The Key West Pride Festival offers visitors a weeklong celebration of PRIDE in the one-and-only Key West. Take part in play readings, talent shows, pool parties, free wine tastings and the famous Pride Parade.

When: Annually on the first weekend of June

Stay: Hotels and lodging prices skyrocket during the festival. Don’t forget price boat charters, Airbnb and VRBO as well as traditional lodging.

Why? To have fun, of course! And to “discover the island’s One Human Family philosophy.”

Fantasy Feast

With a motto of “it’s not just FUN—its GOOD BUSINESS!” it’s no surprise that a group of business owners founded the event, tempting snowbirds to travel to Key West for Halloween (instead of waiting until after New Year). Since the early days of 1979, the festival grew into an economic boosting party.

When: Annually on the third weekend of October

Where: Key West’s Duval Street

How long: 10-days with 75,000 party goers (growing each year). Make sure to check out each year’s theme and book your travel early.

Where to Rent Charter Boats

Some boats are excellent and durable enough for offshore fishing, while others are simply for scooting about the reefs and beaching for a picnic. Before booking a charter for your trip to the Florida Keys, understand the various types of recreational boats available.

In other words, don’t book a pontoon if ya wanna catch a Kingfish. Once you’ve figured out what works for you and your family, check out these great boat charter rental companies in Key West:

Key West Boat Rentals

key west sailing

Take a speedboat out for a day or entire week with Key West Boat Rentals. For the best prices, I encourage calling the company to book your vacation. They offer deckboats, pontoons and center consoles, ranging from $275 for four hours to $525 for the full day.

The Moorings

key-west-sailing

The Moorings is known worldwide for their exceptional service and quality of boats. You can charter a sailboat or yacht by yourself and make your own adventure. But if you need a captain, they offer that, too. Head out with The Moorings for a half or full day of sailing, snorkeling and sunset cruises.

The Moorings also specialize in Bareboat Charters, Captain Only Charters and even provide you with a path toward boat ownership. For the best prices, call them directly or book your dream charter online.

Key Largo Fishing Adventures

key west sailing

Don’t forget to book a fishing charter! Key Largo Fishing Adventures offers the best care whether it’s your first or fiftieth outing. They offer bigger ocean fishing boats and specialize in providing Deep Sea and offshore fishing, where your catch of the day could include mahi-mahi, tuna, wahoo and Kingfish.

Email them for the best rates. You may even score a reduced rate hotel with Holiday Inn Key Largo, Marriott Courtyard Key Largo, Marina Del Mar, or the Key West Inn.

My Favorite 5 Key West Spots to Visit

Southernmost Point Buoy

One of the most photographed attractions in Key West is the permanently anchored Southernmost Point Buoy, where visitors can stand at the most southernmost point in the continental United States.

Ernest Hemingway Home and His Six-Toed Cats

Six-toed cats, also called polydactyl cats, aren’t unusual if you venture over to the Ernest Hemingway Home in Key West. Decades ago Ernest Hemingway was given a six-toed cat from a ship captain as a gift. Over the years, they’ve produced about 40-50 offspring in all colors and sizes, which call Hemingway’s house their home.

Dry Tortugas National Park

Dry Tortugas National Park lies almost 70 miles off Key West’s coast. A relatively small national park at only 100-square-miles and consists of mostly open water with seven small islands, reachable only by boat or seaplane. The park is famous for its coral reefs and marine life, and Fort Jefferson. You can visit for a few hours or if you are adventurous stay the night at the campground. Either way, you don’t want to miss this excursion.

Islamorada

Islamorada literally means the “village of islands” and is a fantastic spot for your family holiday! With family-friendly events year-round, this island is where it’s at with Trunk or Treat at Founders Park in October, music festivals monthly, golfing and miles of beaches to enjoy. This island offers something special for everyone.

Marathon

Marathon is the heart of the Florida Keys and consists of 13 smaller islands, steeped rich in railroad history. Its location along Seven Mile Bridge makes this island a great halfway point from Key West and Key Largo. Marathon is quiet, calm, and full of great fishing spots and beaches, which makes it one of my favorite destinations.

Navigation Challenges

The Florida Keys isn’t the place to be in a hurry. But while the slower pace of life contributes to taking it easy, don’t be taken by surprise. The keys present even advanced sailors with a few challenges. With navigational challenges like wildlife sanctuaries, strong winds, depth changes, low bridges and tall riggings, it’s difficult to stay calm at the helm.

  • Navionics — It’s important to keep the electronic navigation charts of the local marine areas
  • Marine debris — After recent hurricanes, keep a watchful eye on debris from boats, trees or houses
  • Seamanship — Know where you’re going and if you don’t, take time to figure it out

A Few Last Thoughts

Sailing through the Florida Keys is a dream come true for any boat enthusiast. When you plan your next vacation, consider a boating trip through the Keys.

Sailing is a unique way to experience more locations than just one during your vacation and it may be your new mode of transportation. Boats of all types and sizes frequent the Keys, and the island’s lifestyle will bring you back year after year to explore.


Nicole Anderson is a communication professional and freelance writer. She learned to sail on the Great Salt Lake and enjoys being out on the water as much as possible, as well as camping, hiking, and traveling the world. Anderson resides in the Salt Lake valley with her husband, Mike, and her border collie, Luke.