Key West Boating Guide

Key West is a delightful destination any time of year. From the shops on Duval Street to exciting annual events, there’s always something to do! One of our personal favorite activities is boating in Key West. Whether you want to drop a line and head out on a fishing charter or just want to set out on a romantic sunset cruise, you can find it all here!

If you want to get out on the water during your trip, you’re in the right place! We’re here to set the record straight on all things related to Key West Boating.

Key West is a dream destination for boaters—and once you get out on the water, you’ll understand why. With warm, clear waters year-round and easy access to both the Gulf of Mexico and the Atlantic Ocean, this little island offers big adventure. Whether you’re reeling in trophy fish, exploring coral reefs, or cruising into a postcard-perfect sunset, boating in Key West is one of the best ways to experience the Florida Keys.

Without further ado, let’s dive in. Follow along with our Key West Boating Guide!

Key West Fishing Charters

Want to go fishing on your trip? That’s perfect! Key West is a fishing paradise. There are so many kinds of fish to find, too!

Deep-sea fishing trips target mahi-mahi, tuna, sailfish, and marlin, while backcountry and flats fishing offer chances to catch tarpon, permit, bonefish, and snapper. Don’t worry about bringing all your gear; most charters include it in their packages, and you’ll have a captain there to show you the ropes should you need any help along the way.

Here are a few of our top options for fishing charters in Key West:

Dream Catcher Charters

Gulfstream Fishing

Fish Key West

Scuba Diving Experience

The Florida Keys are home to the only living coral barrier reef in the continental U.S.—and Key West is your jumping-off point for exploring it underwater. Sound exciting?

Top Dive Sites include Sand Key, Western Sambo, and the Vandenberg wreck, but you’ll have a great time no matter where your scuba tour takes you. Key West has several diverse forms of marine life; expect to see angelfish, parrotfish, nurse sharks, rays, and vibrant coral formations.

If it’s your first time exploring scuba diving, it’s normal to be nervous, but you have nothing to worry about when you head out on your trip with an experienced Key West Company. 

Check out these Key West Scuba Diving Tours:

Southpoint Divers

Captain’s Corner

Dive Key West

You will need to have a scuba diving certification to head out on these adventures. If you don’t want to spend the time getting certified, check out Snuba Key West! Their scuba diving/snorkeling hybrid is the closest you can get to scuba diving without a certification.

Romantic Sunset Cruises

If you’re heading out on vacation with your partner, what better activity to explore than a romantic sunset cruise? We can picture it now: the two of you watching the sunset over the endless blue ocean, with gorgeous hues of orange, red, and yellow combining for a truly once-in-a-lifetime view. It sounds like the perfect romantic activity to us. If that sounds good to you, check out these companies that offer sunset cruises!

Marathon Snorkeling & Sunset Cruise

Danger Charters

You can even book a private charter through them! Coastal Living named this one of the top two sunset sails in North America, so don’t miss out.

Fury Cat

How does a live music sunset cruise sound to you? If your answer is “amazing, count me in!” then you simply must book your sunset cruise with Fury Cat. Grab a drink and appetizers as you watch the sun disappear over the deck, all while listening to music from local Key West talent.

Key West Sebago Watersports

One of Sebago’s unique offerings is its Tipsy Tiki Sunset Cruise. Try refreshing beer, wine, sangria, and frozen margaritas as you watch the sunset!

Sailboats in Key West

Sometimes, you want to take a step back from fast-paced, high-powered boat rentals and take it easy for a bit. Set sail on a peaceful sailboat ride during your time in Key West! Whether you want to set out on a full-day, half-day, or sunset sailing experience, you can find it all here. Some companies even offer wedding packages if you’re feeling like you want to tie the knot out at sea!

These are our recommended Key West Sailing companies:

Key West Sailing Adventure

Key West Sailing Charters

Argo Navis

Private Boat Rentals

If you want to rent a boat of your own, be our guest! Several local companies offer private boat rentals. That way, you can explore the waters of Key West on your own time.

Want to experience all the joys of renting a boat here?

Check out these companies for your private boat rentals:

Aqua Boat Rentals

Sunset Water Sports

Please note: Those born on or after January 1, 1988, must have a boating license. Check out full rules and regulations on the Florida Fish and Wildlife Commission website.

Book Your Stay in Key West Directly with Dwell Key West!

Now that you know everything there is to know about boating in Key West, it’s time to book that trip! Enjoy the wind in your sails during the day, and then relax back at your home away from home in the comfort of the best vacation rentals in Key West.

Our boutique hotel rentals near Duval Street are perfect for your Key West Vacation. With amenities like rentals with a full kitchen or pool access, we’re confident you’ll find the ideal rental in our extensive catalog.

What are you waiting for? There’s no time like the present to book your accommodations. Browse our available boutique rentals now and book your next trip to Key West directly with Dwell Key West!