You shouldn’t have much trouble finding a company ready to put you out on a boat with all the water gear you’ll need. Up and down Duval Street , in front of restaurants, on street corners, and of course down near the port area, there are kiosks and sales booths touting the services of Fury Watersports (2 Duval St., 305/296-6293, snorkeling cruises from $40 per person, parasailing from $40 per person, sunset sailing from $37) and Sebago (201 William St., 305/292-4768, parasailing from $55 per person, snorkeling cruises from $49 per person, sailing from $39, Jet Ski tours from $150).
Both companies offer an array of parasailing and snorkeling excursions, powerboat trips, Jet Ski tours, catamaran trips, and scenic cruises. The differences between their offerings are minimal, so just grab a few brochures and figure out which trip seems the most appealing to you and your group.
Sunset Watersports (201 William St., 305/296-2554, water sports activity cruise from $109 per person) offers similar activities but bundles it all in a “party boat” atmosphere; your ticket price includes a day of Jet Skiing, sailing, windsurfing, waterskiing, kayaking, and more.
Like Fury, Sebago, and Sunset Watersports, it’s hard to miss the advertising blitz employed by Danger Charters (407 Caroline St., 305/296-3652, snorkeling cruises from $75, sunset cruises from $70, kayak tours from $75). The sunset “wind and wine” sailing cruises, snorkeling excursions, and guided kayak trips offered are some of the best in town.
Also noteworthy are the passenger cruises available on The Western Union (202 William St., 305/292-1766, sailing cruises from $55 per person, reservations required); the historic vessel was originally used to lay telegraph cable among Key West , Cuba , and the rest of the Caribbean and is a justifiable local landmark. In addition to the sunset cruises, The Western Union also offers day sailing and a thoroughly unique “stargazer” cruise that takes advantage of the area’s relative lack of light pollution.
Kitehouse (1801 N. Roosevelt Blvd., 305/294-8679, www.thekitehouse.com , lessons from $200 for 4 hours) specializes in kiteboarding or kitesurfing lessons and excursions out to nearby flats where the winds are high and the shallow water is perfect for the sport. Although there are other kiteboarding outfitters in town, Kitehouse strongly advocates extensive training for beginners and has designed two-day and five-day courses with the right combination of instruction and activities to get novices comfortable with the sport.
Lazy Dog Charters (5114 Overseas Hwy., 305/293-9550, kayak rentals from $20 per half-day, fishing charters from $400 per half-day) and Blue Planet Kayak Eco-Tours (2933 Seidenberg Ave., 305/294-8087, kayak rentals from $30 per half-day, kayak tours from $50 per person per 2.5-hour tour) also offer canoe and kayak rentals, guided nature tours, and flat-water fishing excursions.
Finding a charter fishing excursion in Key West is about as difficult as finding a bar. There are dozens of single-boat operators like Charter Sea-Clusion (5950 Peninsula Ave., 305/295-0774) and Triple Time (700 Front St., 305/296-8210), which run large boats out into the deep water where snapper, cobia, barracuda, sailfish, and tuna reside. Larger charter companies like Almost There (5001 5th Ave., 305/295-9444) offer a dozen boats that include flats boats, backcountry boats, and wreck-and-reef boats, providing a little more flexibility.
Though there aren’t quite as many scuba and snorkeling charters as there are fishing charters, it’s still pretty tough to swing a cat in Key West  and not hit an air tank or a pair of fins. The biggest gear shop in town is Divers Direct (535 Green St., 305/293-5122), but Dive Key West (3128 N. Roosevelt Blvd., 305/296-8865) also offers air, repairs, rentals, and gear, along with their lessons and certification, custom charters, and dive trips (reefs, wrecks, night dives).
Reef Raiders (617 Front St., 305/295-8748) is another good option, especially for visitors looking to get scuba-certified quickly (their $175 resort course consists of 2 hours of pool instruction followed by two one-hour reef dives). They also offer custom charters, snorkeling excursions, deep-reef dives, wreck dives, and dolphin-spotting trips.
Unlike the rest of Florida , there’s not much golfing going on in the Keys. The only course on Key West is the Key West Golf Club (6450 E. College Rd., 305/294-5232, from $70). There you can find an 18-hole Reese Jones–designed course that has recently been renovated. The 6,500-yard par-70 course is beautifully landscaped with lots of tropical foliage.