Boating and sailing in the Florida Keys is among the most beautiful and relaxing experiences of a lifetime. Cruise beneath the warm sun through crystal-clear waters, lunch on the shores of uninhabited islands, and find all the comforts of home at the many harbors scattered throughout the archipelago. Novices and master shipmen alike can enjoy the tropical splendor of this unique American paradise.

If you decide to cruise through the island waterways, it’s advisable to reserve a harbor slip in advance, as there are often more boats than available transient slips. Most marinas do maintain these slips for tourists, though private yacht clubs may not allow reservations. Slips rates are per foot, per day, and generally include access to fresh water, 30- and 50-amp hook-ups, and local shops and restaurants. Be sure to inquire in advance about additional amenities and channel and slip depths. Some marinas institute minimum and maximum stay lengths, minimum boat length, and additional charges (live-aboard fees, electricity, and taxes) may apply to dockage rates.

The two primary routes along the Florida Keys are the Intracoastal Waterway through Florida Bay and Hawk Channel in the Atlantic. Which you choose depends upon your boat, your boating experience, and the islands, harbors, and attractions you want to visit on your way. Boaters along either route must watch for shallow reefs and sea grass beds, and areas marked “idle speed” to protect manatees and divers. Always pack current NOAA nautical charts, GPS navigation, radios, and safety equipment. If you run into trouble offshore, dial VHF channel and call for SeaTow, the boater assistance service that operates throughout the Keys. The Coast Guard and Florida Marine Patrol vessels also constantly monitor channel 16.

The Intracoastal Waterway has a 5-ft draft limitation and is marked by red buoys along the shore and green buoys that separate the channel from the open gulf. Though it’s narrower than Hawk Channel, the Intracoastal is well marked and easily followed.

In the Atlantic Ocean, Hawk Channel runs alongside the eastern edge of the Florida Keys in the Atlantic Ocean, and is a deeper, broader route. Especially from the Middle Keys southward, Hawk Channel is considered the safer choice, since you’re less likely to run aground.

If you’re truly a novice, book a couple nights at a Florida Keys hotel and sign up for any of the various boating and sailing lessons offered throughout the islands. You can obtain experience and certification privately or in a group setting; contact either the U.S. Sailing Association or the American Sailing Association for more information. When you’ve completed your course you’ll be ready to sail the open seas safely and confidently.

Florida Keys Boat Rentals

Forego the expense and hassles of owning a boat without sacrificing the enjoyment of sailing the open tropical seas – rentals of every imaginable type of watercraft are widely available throughout the Florida Keys. Choose your boat, your period of rental, and prepare for the experience of your dreams.

An endless list of watercraft can be rented for half-day, full day, weekly, and monthly terms, from schooners to powerboats to catamarans to Hobie cats. You can handle all the details yourself (called a “bareboat charter”) or hire a crew – options include “bareboat with a skipper,” which means a part-time captain who lets you handle the helm as you wish, or “full crew yachting,” which gets you a luxury yacht plus a full-time captain and cook. If you’re going it alone, be sure to bring a fishing license, a camera, sunscreen, and plenty to eat. Stop by a local bait & tackle shop for up-to-date information on fishing and great islands to explore.

Boaters can also choose whether to cruise in luxury or minimalism; many rental boats come equipped with decadent amenities and the latest electronics, while those wishing a simpler trip can find scaled-down models. Specific items to inquire about include GPS navigation equipment, cell-phones, radios, depth & fish finders, Scuba/snorkeling equipment, live wells & tackle, iceboxes, canopied decks, hot tubs, and upscale interiors.

Renting Powerboats

All rental powerboats are outfitted according to Coast Guard specifications (which means they’re equipped with VHF marine radios & life vests), and most range from 14 to 27 feet. Various options include cuddy cabin, center console, pontoon, or bowrider configurations. Some are outfitted to the specific needs of fishermen; others are better suited to sightseeing or pleasure cruising.

In order to rent a boat without a captain, you may be required to pass a written or verbal exam on safe boating practices, or show proof of previous safe boating experience. Some rental agencies restrict how far offshore, or specifically where, a boat may travel; during inclement weather, these restrictions often tighten or the boat may be kept in harbor.

Renting Sailboats

Sailboat rentals generally are available at daily and weekly rates, with the option of a charter captain for an additional fee. Rentals are available at many marinas and sailing clubs, and may require proof of previous successful seamanship or certification.

Four of the largest sailing clubs are the Key West Sailing Club, Florida Keys Sailing in Marathon, the International Sailing Center on Key Largo, and the Offshore Sailing School on Duck Key, MM 61. All offer sailing courses of varying lengths and experience levels.

Renting Personal Watercraft

“Personal watercraft” includes kayaks, jet skis, jet boats, Hobie Cats, paddleboats, floating lounge chairs, two-person glass bottom boats and more. Adventurers can also find parasailing and water skiing charters throughout the Florida Keys.

Prices vary widely based on your choice of water sport and whether you’d like the accompaniment of a guide. Many shops also rent wetsuits and windsurfing equipment.