Sunny Florida skies, year-round warmth, nightlife, and a diverse culture define this cosmopolitan city. South Beach draws crowds, while the Art Deco District is the world's largest collection of Art Deco architecture. Shop from Bal Harbour to Lincoln Road and Coconut Grove, enjoy Cuban culture on Calle Ocho, or visit the historic Venetian Pool. There's something for everyone in this "Gateway to the Americas."

Puerto Plata is rich in local color. Founded around 1500, its name-"silver port"-was given by Christopher Columbus, who thought the cloud-covered mountaintop looked silvery. The main public beach, Playa Dorada ("Golden Beach"), is named for its sunlit sand and is great for tanning. In town, the Museo del Ámbar offers many shades of amber, plus jewelry for sale.

Old San Juan, the oldest city under U.S. jurisdiction and second-oldest European settlement in the Americas, blends historic landmarks, pristine beaches, great cuisine, and resilience. Walk cobblestoned streets past Spanish Colonial sites, browse colorful plazas, and visit Castillo San Felipe del Morro, Castillo San Cristobal, and Museo de Arte de Puerto Rico. Then explore El Yunque's rainforest and waterfalls before relaxing on Luquillo Beach.

St. Maarten is the smallest piece of land shared by two sovereign states. Legend has it that the Dutch and French boundaries of the island were determined by two men who challenged one another in a race around the island, with the Frenchman walking faster and claiming more land. Legend or not, both the Dutch and French settled here in the 1630s and despite occupancy by the British twice, the Dutch and French have lived peacefully together ever since they arrived.

One of the Caribbean's true gems, St. Barts is where Riviera chic meets Caribbean cool. Day-trippers come from nearby islands for the duty-free shopping, excellent dining and to lounge on the soft, white sands in a secluded palm-fringed cove. Tour Fort Gustav and Fort Carl, historic reminders of Sweden's short-lived Caribbean possession. Excursions abound, inviting guests to snorkel, sail over the clear blue waters on a catamaran, or horseback ride through shaded jungle trails.

Antigua, especially St. John's, is a classic British Caribbean destination, with 365 beaches, coral reefs, forts, and colonial architecture. See St. John's Cathedral, rebuilt on the same spot three times after earthquakes, and the Museum of Antigua & Barbuda, with island history and semiprecious stones. For nature, visit Nelson's Dockyard National Park or the Shirley Heights trail. St. John's also has nightlife and live music, and local restaurants serve buttery "flying fish."

Spend a glorious day swimming at famed Cane Bay Garden Beach, hiking the island's rainforest and enjoying a scenic drive around this lush island. Swim with dolphins, go sea kayaking or head over to Virgin Gorda and climb down to the famous Baths for a day of swimming and exploring this natural phenomenon. Take home charming local crafts, straw items, artwork and resort wear. Enjoy local fish dishes or perhaps a pub lunch or burger!

Sunny Florida skies, year-round warmth, nightlife, and a diverse culture define this cosmopolitan city. South Beach draws crowds, while the Art Deco District is the world's largest collection of Art Deco architecture. Shop from Bal Harbour to Lincoln Road and Coconut Grove, enjoy Cuban culture on Calle Ocho, or visit the historic Venetian Pool. There's something for everyone in this "Gateway to the Americas."