About Old Town

Photo courtesy of Amber Nolan

From the days of Hemingway drinking at local waterholes, to today's festivals and parades, Old Town Key West has always contained a magical and contagious essence that draws tourists year after year. An eclectic nightlife, top-notch restaurants, a variety of accommodations, historical and adventure attractions, and unique shopping opportunities add to its appeal.

See & Do

Key West's iconic lighthouse was built in 1847 and originally powered by 15 oil lamps that helped guide sailors to the island. Although it no longer serves as a functioning lighthouse, visitors can climb the 88 winding steps to the top for 360-degree views of the city and the ocean. Admission includes entrance to the museum (the former keeper's quarters), where audio and visual recordings are available as well as glass display cases of the previous owner's possessions.

Eat

From the outside, Pepe's doesn't look like much, and this restaurant doesn't claim to be anything it's not - which may be why it's been open for more than 100 years. Breakfast consists of good-old-fashioned Chock Full O' Nuts coffee, homemade sweetbreads, fresh orange juice, chipped beef on toast, and traditional omelets. As the oldest eatery in the Keys (a Cuban fisherman opened it in 1909), Pepe's is worth a visit for the history alone.

Old Town's Best Restaurants

Better Than Sex

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El Siboney

AZUR

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Party

This Key West institution is just a ways down from the Hemingway House on Whitehead Street, and during the day it's the typical stale-popcorn serving saloon. At night, the place is packed with a motley crew anxious to see what's on the musical roster. One night may be a Cuban jam session; the next is Gypsy Jazz followed by a meeting of The Green Parrot Ukulele Association.

Stay

On a less-crowded side of quirky Duval Street, rests Southernmost on the Beach, an upscale (yet unpretentious) hotel that boasts a private pier and beach, poolside bar, and on-site restaurant. The resort offers complimentary use of beach chairs, parking, and WiFi, and special events such as beer school, live music, wine tastings, and water aerobics.

Shop

Take home some flavors of the tropics at Peppers of Key West, which lets shoppers sample their spicy sauces at the hot sauce bar. The "tasting staff" entertains and makes helpful suggestions while visitors try everything from jerk sauce and steak sauce to dips and only-if-you-dare hot sauces. Cheese and crackers help return taste buds to normal, and each sample comes with a description about what it is you are trying.