Key West

Key West feels like a small island town where the past lives side by side with the present. The Old Town area around Duval Street is the most walkable, with pastel houses and narrow lanes that lead to the water. Just a short walk south you’ll find Bahama Village, a neighborhood that still carries the rhythm of the Bahamian immigrants who built much of the island’s early culture. Prices for a night in a boutique guesthouse in Old Town run $150-$200, while a modest inn in Bahama Village can be found for $100-$130. Meals at casual spots on Duval average $12-$18 for a plate of conch fritters or a grouper sandwich, and a dinner at a waterfront restaurant can hit $35-$55 per person.

If you love seafood, try the key lime pie at a bakery on Whitehead Street – it’s usually $6-$9 per slice, and the flavor is as bright as the sunsets you’ll watch from Mallory Square. The Ernest Hemingway Home and Museum is a must-see; admission is $14 for adults, and the historic Fort Zachary Taylor park costs $6 for entry. A sunset drink at the iconic Southernmost Point Buoy costs about $12 for a cocktail, and you can explore the lighthouse for $8. All of these experiences keep the pace relaxed, so you can wander at your own speed without feeling rushed.