Key West Suggested Itineraries

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The self-styled Conch Republic has always danced to its own drumbeat, on the southernmost, and perhaps most eccentric point of continental USA. A party island, artists’ haunt, cruise-ship favorite and GLBT-friendly resort, Key West floats off the west coast of Florida’s southern tip.

Day 1: Key West Characters

When you’re talking characters and Key West, the name Hemingway is bound to crop up. The notoriously macho author lived on Key West for more than a decade from 1928, and raffish Key West characters and locations feature in his novel To Have and Have Not. You can visit Hemingway’s lovely Old Town home and meet the 60-plus descendants of the author’s cats, many inheriting the extra toes of his original felines. Old Town was also where US President Harry S. Truman chose a Caribbean-style getaway as his winter White House on Key West. Eisenhower and Kennedy also stayed at the house at 111 Front Street, which is open for guided tours.

Day 2: Conch tours and mansions

Get with the conch theme and jump aboard the Conch Train , a hit with young and old since 1958. The 90-minute train ride begins on Front Street and loops through Old Town Key West. Bone up on the island’s conch history at Heritage House, browse pirate plunder at the Pirate Museum, and see treasures from the deep at the Shipwreck Museum. Salvage from shipwrecks was used to decorate many a mansion on Key West, including the Classic Revival Audubon House which features original artworks by the great bird artist J. J. Audubon.

Day 3: Dip your toe in the water

This being Key West, you’re going to get your feet wet at some stage, whether your favorite outdoor activity is dolphin-watching, snorkeling, parasailing, fishing or jet-skiing. If you can’t decide where to start, the full-day Power Adventure combines a catamaran sail across the Gulf of Mexico, kayaking in the mangroves, parasailing, kayaking and snorkeling. Go for a cruise and view Key West from the water, or clink champagne flutes on a romantic sail into the sunset.

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