Yankee Freedom Dry Tortugas Ferry

Marine sanctuary visitors center featuring interactive ecology exhibits & a 2,500-gallon reef tank.

Upscale resort on the beach offering seafood dining, a spa & an outdoor pool, plus free Wi-Fi. Overlooking the Gulf of Mexico, this upscale waterfront resort is a 5-minute walk from Mallory Square and a mile from the Southernmost point buoy. All the chic, contemporary rooms have balconies and feature flat-screen TVs, iPod docks and pillow-top mattresses, plus minifridges and free Wi-Fi. Upgraded rooms add gulf views and/or additional sitting areas. Amenities include beach access, a heated outdoor pool and a hot tub with a sundeck, and a spa, plus a fitness center, a seafood eatery and a bar. Jet ski rentals and breakfast are available, and there's a business center. Parking is extra.

Stylish old house with a big patio for globally accented American fare, plus a late-night wine bar.

Lively clothing-optional resort for gay men, plus a poolside cafe/bar, free happy hours & a gym. An 8-minute walk from the Key West Bight Ferry Terminal this buzzing resort for gay men is less than a mile from restaurants and bars on Duval Street. Inspired by Ernest Hemingway’s Havana home, the rooms feature tropical style and original art. All offer ceramic tile floors, and complimentary Wi-Fi and flat-screen TVs offering premium adult channels, plus iPod docks. Freebies consist of limited parking, and regular happy hours. There’s a poolside cafe/bar, a heated outdoor pool and a clothing-optional sundeck, as well as hot tubs, and a health club offering a gym with a sauna and a steam room. An erotic lounge shows videos 24 hours a day.

At the southernmost tip of the continental U.S., Key West offers a lively mix of iconic photo ops and vibrant local charm, all just 90 miles from Cuba.

Since 1890, this classic dive bar in Key West offers cold beer, live music by talented bands, and a chill atmosphere perfect for mingling.

Chill takeaway window with a beach-shack vibe for breakfast/lunch sandwiches with local seafood.

Chic hotel with posh sundecks on all floors, plus free breakfast & a courtyard with an outdoor pool. A 5-minute walk from the Ernest Hemingway Home and Museum, this stylish hotel is a half mile from trendy dining on bustling Duval Street. Modern, boldly decorated rooms offer built-in desks, leather chairs, and bathrooms with tile showers, and marble countertops and vanities, as well as nightly turndown service; some rooms have balconies. Suites add separate sitting areas. Wi-Fi is free, and there are furnished sundecks on every floor. Amenities include complimentary continental breakfast and covered parking. A courtyard features an outdoor pool and a sundeck surrounded by palm trees and plants. Minimum-stay rules may apply.

Longtime open-air hangout for seafood complemented by live music & dockside views.

Chill, inviting eatery with classic Creole & island comfort eats, including renowned Key lime pie.