A Heritage Travel Itinerary for Puerto Rico

Experience art history, tropical rainforests, and the world's best rum in San Juan.

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Number of Bostonians with Puerto Rican Heritage: 35,082

While the effects of Hurricane Maria still linger on some parts of the island, San Juan and the surrounding areas—as well as heritage-inspired trips like this one, planned by local luxury travel expert Tiffany Dowd—are open for business once again.

Day 1

After a four-hour flight from Boston to San Juan, you’ll drop your luggage off at the 1919-built Condado Vanderbilt hotel and head to the Old 
San Juan district, where centuries of history and culture await. The first stops are 
the El Morro and San 
Cristóbal forts, the first of which was built in 1539 to protect San Juan from sea attacks and the second some 200 years later to guard against invaders on land. Admire the colorful architecture and pop into contemporary art and craft galleries on your way to the Museum of Art and History, where you’ll view centuries-old artifacts in a neoclassical building that was once a popular gathering spot for intellectuals.

Day 2

Today you’ll leave the big city behind to immerse yourself in Puerto Rico’s lush natural heritage. One of the oldest reserves in the Americas, El Yunque National Forest takes its name from the language of the indigenous Taino people, who celebrated it as a spiritual place. A 40-minute drive is all it takes to reach this biologically diverse tropical rainforest (visit the government’s hurricane recovery website for the latest updates on which trails are open). Feeling parched after your adventure? The piña coladas at Old San Juan’s Barrachina Restaurant, where the frozen libation was created in 1963, should quench your thirst.

Day 3

For generations, Puerto Ricans have been growing sugar cane—and producing some of the world’s best rum. Book a tour of Casa Bacardí, in nearby Cataño, and you’ll hear all about the famous spirit-maker’s history, see the distillery, and, of course, toast to the Island of Enchantment. Continue the party by celebrating another famous Puerto Rican export: hand-rolled cigars. The Cigar House in Old San Juan offers a wide selection of stogies to puff on—and to take home.

Read more: The Ultimate Guide to Planning Your Heritage Travel Journey