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Key West Literary Tour

Block for block, Key West has to be the smartest town in America.
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Rating: 4 out of 5 by EveryTrail members
Difficulty: Easy
Duration: Full day

Overview:  Despite the slap of vulgarity that is the circa-1829 Duval Street, which attracts an eternal honky-tonk herd of cruise-ship gawkers,... more »

Tips:  Bicycles are the best way to explore the area.

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Points of Interest



Address:
1500 Reynolds St.
Key West, Florida
United States

Phone:
(888) 303-5717

Order the conch salad for a lunch treat.

Address:
801 Eaton St.
Key West, Florida
United States

Phone:
(305) 295-3474

This boutique B&B housed in a circa-1870 plantation-style mansion is the most graceful place to stay on the island. Beginning in 1930, former owner Peggy Mills spent nearly 40 years on the gardens, adding orchids, palms, winding brick pathways, fountains, and enormous Cuban earthenware jars. Since then, subsequent owners have introduced a... More

With its old-school fishing shacks and shrimp boats, Stock Island harks back to Key West circa the 1970’s. Dine at tables overlooking a dock crowded with shrimp boats at this funky dive that has live music on weekends.

Address:
6810 Front St.
Stock Island, Florida
United States

Phone:
(305) 293-4041

The museum dates to 1834. Since the 1930’s, the property has been owned by the Porter family, one of the founding clans of Key West: Robert Frost wintered in a garden cottage here between 1945 and 1960, with his hostess, Miss Jessie Porter, entertaining such legends of wit as Tallulah Bankhead.

Address:
410 Caroline St.
Key West, Florida
United... More

The circa-1891 Key West Museum of Art & History at the Custom House features a dripping-with-malice portrait of Truman Capote, waving a 1976 American Bicentennial flag and pistol, a Vote for the Man sign and a bloody young couple in the foreground: it was done by Capote’s fellow all-star of writing, Tennessee Williams.

Address:
281 Front St.
... More

7. Reach Resort

The sister property to the Casa Marina features an outpost of the Strip House. All 150 breezy rooms at the Reach Resort have coconut-shell headboards, bathrooms with abstract art, and private balconies.

Address:
1435 Simonton St.
Key West, Florida
United States

Phone:
(800) 626-0777

At the improbably first-rate theater, local boy Richard Wilbur once helped out with Molière translations.

Address:
319 Duval St.
Key West, Florida
United States

Phone:
(305) 296-9911

9. Saluté Ristorante Sul Mare

The oceanfront restaurant attracts lunching writers.

Address:
1000 Atlantic Blvd.
Key West, Florida
United States

Phone:
(305) 292-1117

Catch an art film at the nonprofit Tropic Cinema (founded, in part, by writer Jean Carper and George Cooper, a retired law professor and author).

Address:
416 Eaton St.
Key West, Florida
United States

Phone:
(877) 761-3456