Key West is a two-by-four-mile island, so the days are about the water and the evenings about Duval Street. Morning one: a reef snorkel trip to the only living coral reef in the continental US, six miles out (from $31 for a two-hour sail, $47 with breakfast and mimosas). Afternoon: the Conch Train or trolley through Old Town (from $39), the Hemingway House and its six-toed cats, and the Southernmost Point. Evening: a sunset sail with an open bar (from $64), or the free street show at Mallory Square. Day two: a mangrove kayak and dolphin-watching eco tour in the backcountry (from $64), or the big one — the Dry Tortugas catamaran to Fort Jefferson, 70 miles west (from $215, books out weeks ahead). December to April is high season with the calmest seas; summer is hot, cheap and best for snorkelling visibility.
352 tours · prices per person, book with partner