San Juan, Puerto Rico, Castillo San Felipe del Morro
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San Juan's Castillo San Felipe del Morro iStock.com / Bkamprath
St. John, US Virgin Islands, Charlotte Amalie, Cruz Bay
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St. John's Cruz Bay iStock.com / Sean Pavone
St. Maarten, Netherlands Antilles
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Philipsburg, St. Maarten iStock.com / Sean Pavone
St. Thomas, US Virgin Islands, Magens Bay Beach
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St. Thomas' Magens Bay Beach iStock.com / SashaBuzko
St. Thomas, US Virgin Islands
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St. Thomas iStock.com / Songquan Deng

Eastern Caribbean

Trunk Bay, St. John, US Virgin Islands, Annaberg Sugar Plantation Annaberg Sugar Plantation on St. John iStock.com / connerscott1

If your main goal on vacation is going home with a tan, then this itinerary has your name written all over it. This is classic Caribbean: sand, sun, and lots of people having a ball in paradise for a week. This part of the Caribbean ranges from large, heavily touristy islands — such as St. Thomas, St. Maarten, and Puerto Rico — to much quieter places, including Jost Van Dyke in the British Virgin Islands, where you’ll find quiet beaches, yacht-filled harbors, and beach bars that let you sip with your feet in the sand.

What We Love

The Energetic Vibe: If you're into making new friends and the buzz of bustling beach bars and busy shopping areas, the Eastern Caribbean is for you.  

The History: Sure, you have to look for it, but there are old forts, cobblestone streets, sugar mills, and other vestiges of the islands' colonial past. In San Juan, Puerto Rico, check out the 16th-century, seaside El Morro citadel, and in Charlotte Amalie, St. Thomas, explore 17th-century, red-brick Fort Christian.

Best Known For

Beautiful Beaches: This part of the Caribbean has some of the best strands of sand in the world — wide, white, and soft. Favorites include St. Barts' Saline Beach, Trunk Bay on St. John, and Orient Bay on the French side of St. Maarten. 

Shopping: If you enjoy spending a morning browsing through jewelry, watches, perfumes, and cosmetics, you'll love that the shops in the Caribbean are duty-free for Americans — up to $1,600 per family member. That said, finding a bargain can be tricky: In most cases, you could get the same price back home.

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Best Ports

St. John: If your ship calls on nearby St. Thomas, you'll want to take the short ferry ride to St. John. Head to the sugar-white sands of gorgeous Trunk Bay for its marked underwater snorkeling trail, or chill out on nearby Hawksnest, Cinnamon, or Maho beaches. Why is it so pristine? More than half of the island is protected as U.S. National Park land.

St. Barts: This hilly little island is home to gorgeous beaches and lots of boutique hotels and chic restaurants where celebrities and jet-setters hang out. Despite the fact its main port town, Gustavia, was named after a Swedish king, St. Barts is very French. You'll find great croissants and better champagne here.

Puerto Rico: Old San Juan, with its cobblestone streets, churches, chapels, and townhouses, is lovely. Many of the buildings date as far back as the 16th and 17th centuries.

Don't Say We Didn't Warn You

There are Maddening Crowds: St. Thomas, St. Maarten, and Puerto Rico get really packed on days when multiple megaships are in town at the same time. And we don't just mean "busy day at the mall"-level crowding: More than 15,000 cruise passengers all pouring off ships en masse means traffic jams, crowded beaches, and waiting in line ... for everything.

Heidi Sarna

Heidi Sarna is a Singapore-based contributor to ShermansCruise who has also written for Condé Nast Traveler and USA Today.

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