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It’s diminutive, to be sure, but “Little Grape Island” has a big claim to historical fame: Christopher Columbus landed here in 1502, anchoring his ships for repairs. Since then, a lot has happened (and been rumored to have happened) on this now-uninhabited island. It even once served as a quarantine site during a leprosy outbreak. Today, it’s an easy and interesting day trip for beach lounging, surfing and hiking. Take a boat over to the quiet spot and play modern-day explorer, keeping an eye out for colorful bird and fish species.

Old San Juan offers historically and culturally significant experiences including a walk through 500-year-old forts, visits to UNESCO sites, historic churches, museums, the second oldest cathedral in the Americas and Ponce de Leon’s mansion. Cobblestone streets and pastel buildings are perfect for exploration during the day and variety of restaurants and shops make for a complementary evening.

Restaurante Whapin is a great option for getting to know—and love—authentic Caribbean cuisine, with its unusual spices and unmistakable coconut infusions. A yummy snapper, Cahuita-style, does plenty to breach the distance between San José and the Caribbean. And that’s what good eating is all about: building bridges to the world’s farthest corners, one delicious bite at a time.

This Madrid-style tavern specializes in Spanish as well as Italian, Lebanese, and Mediterranean tapas. Like many other spots in Barrio Escalante, Olio is known for its lively atmosphere—yet not so lively you can’t carry on a conversation. Its exposed-brick walls and eclectic decor lend it a particular warmth. The restaurant is also famed for cocktails, European wines, and fusion sangrias in locally inspired flavors like pineapple or watermelon.

A shared love for southern Italian comfort food and a chance encounter in the supermarket drew chefs Antonio d’Alaimo and Ciro Genova into this gastronomic venture. The Italian duo, known to everyone as Ciro and Tony, personally welcome every guest to their small dining room. The menu features, among other things, veal marsala, snapper in wine sauce with fresh tomato and laurel, and tortellini Alessandro (pasta stuffed with chopped ham and cream). A wide-ranging wine list and tempting dessert menu help round out the evening.

Get down and dirty on an unforgettable spelunking experience at the Venado Caves, 45 minutes from La Fortuna. The caves were formed some 15 to 20 million years ago by tectonic shifting and erosion from underground streams. In them, you’ll see stalagmites and stalactites galore, and get the chance to check out colorful frogs and fascinating marine fossils and learn about the bat communities hanging right over your head. The experience is real (and really humid)—so wise adventurers bring insect repellent, knee pads, and an extra change of clothes. Waterproof your camera, too.

This itinerary trades busy beaches for cloud forests, quiet rivers, and rural communities.

December 2, 2025 | 18:00–19:30 CET

Watch the recap of AFAR and the USTOA’s virtual panel discussion.

Taste your way around the Caribbean Island—from chocolate and coffee to ice cream and roasted pork—on this self-guided road trip.

On this episode of View From Afar: Live From ILTM, Nayara CEO and cofounder Leo Ghitis reveals how his resorts blend sustainability, social impact, and extraordinary natural beauty to create meaningful luxury for the next generation of travelers.

Puerto Rico is one of the most musical places in the Caribbean. On this week’s episode of Unpacked, we tune in.

Learn more about Puerto Rico through its creativity and rich heritage, from street art to world-renowned paintings and more.