Weekend City Picks: Caribbean

Blue skies and tranquil waters draw millions to the islands of the Caribbean, but there’s more to the region than perfecting a tan.

Caribbean Weekend City Picks

Arts & Entertainment

National Museum of Fine Arts, Cuba

Founded in 1913, the museum is made up of two buildings. The Palace of Fine Arts highlights Cuban art, with one gallery entirely devoted to works from 1970s, including the hyperrealism movement and more modern symbolic works, while The Palace of the Asturian Center features European paintings and sculptures as well as ancient works.

La Placita de Santurce

This plaza in the heart of San Juan is an open market by day but hosts the mother of all street parties at night (particularly on Thursdays and Fridays). Eat, drink and dance to salsa bands as long as you can stay awake.

Nuyorican Café

If salsa is your pleasure, then this bohemian-style café in Da House Hotel might just be heaven. It draws an energetic crowd with live music, drinks and a late night menu. Dancing is not required, but it may as well be.

Food & Drink

Casa Bacardi

If you love rum – and why wouldn’t you? – you don’t want to miss a tour of this distillery, where you can taste rum, learn to mix drinks and even bottle your own personal sherry cask of Bacardi Special Reserve rum straight from the barrel.

Rhumb Lines


Owned and operated by longtime residents of St. John, this restaurant blends the flavors of the Caribbean with Pacific Rim favorites, creating what’s considered one of the best Asian fusion restaurants in the islands. Grilled Banana Mahi Mahi is a favorite, as is the shrimp Pad Thai.


Discover Australian warmth and Chef Ron Hargrave’s Aussie-Caribbean cuisine (including kangaroo sausages!) while overlooking the beach on Grand Cayman. There are vegetarian options and plenty of beef on the menu, too, and the Sunday brunches are a favorite with visitors.


Sustaining a farm-to-table sensibility isn’t easy on a small island, but this restaurant and wine bar focuses on supporting small producers and local farmers. The menu includes seafood and meat, but Marmalade stresses a firm commitment to vegetarian dining as well.

Bonito St. Barth

Reservations are always a good idea at this Latin American restaurant on St. Bart’s, although walk-ins are always welcome and casual attire is not frowned upon. Seafood specialties reign, and you can indulge yourself while enjoying a lovely view from Bonito’s hilltop location.

Luquillo Food Kiosks

If variety is what you’re seeking, the Luquillo Food Kiosks are the place to go. Diners can browse 50 or so restaurants along an outdoor strip, with offerings ranging from empanadas to scallops. 


Stingray City


In the North Sound of Grand Cayman, a charter boat deposits visitors on this series of shallow sandbars where they can interact with and feed stingrays. There are also other snorkeling trips available, as well as a trip to a turtle farm and fishing charters.

El Yunque Rain Forest

The only tropical rain forest in the national park system, El Yunque sprawls over almost 29,000 acres, offering day hiking trails, swimming and great views of nature. It’s open every day except on Christmas. 

Healthy Living 

Rincon Surf School


Everybody wants to surf! The longest-running surf school in Rincon offers lessons for beginners and advanced surfers, with group and private lessons and guided adventure tours for the bold.

Kite Club Cabarete

If surfing is too pedestrian for you, why not try kitesurfing, kiteboarding or – if you’re really brave – kite foiling? Kite Club Cabarete offers lessons at a variety of levels or, if you know what you’re doing, just rents gear. There also training courses for instructors.


Waterlemon Cay

Considered the home of the best snorkeling on St. John, Waterlemon Cay is a small cay surrounded by a reef in Leinster Bay. You don’t even need a boat – you can hike a mile on the relatively flat Leinster Bay trail to the beach and snorkel into the turquoise waters.

Castillo San Felipe


Originally built in 1539 by Spanish troops and shored up in the 1700s, the Castillo San Felipe del Morro launched many battles over its strategic location over the centuries. Now it’s a National Historic and a World Heritage Site offering guided tours.

Bioluminescent Bay Vieques Island

Along the coast lies one of the world’s most popular bioluminescent bodies of water (thanks to the microorganisms that live there). The Island Adventures Biobay Boat Tour offers nightly trips out on the bay on a pontoon boat so you can witness the phenomenon.


Stella Nolasco Boutique

A graduate of Drexel University and the SACI art school in Italy, Nolasco is Puerto Rico’s most famous designer, one who focuses on artisan handwork in her designs

Guy Harvey Gallery & Shoppe

At this 4,000-square-foot store and art gallery devoted to the work of the famous conservationist and angler, shoppers can browse Guy Harvey art work, merchandise and apparel for men, women and children.

Calle San Sebastian


Whether you’re looking for food, drink or something to buy, the shops of Calle San Sebastian beckon many travelers with a lively and colorful atmosphere.

Hotels featured in this article

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