A Weekend on Culebra Island

View of Keys and St. Thomas from Culebra

 Zain Deane

Culebra enjoys a well-deserved reputation as Puerto Rico’s undeveloped paradise. The majority of the hotels, bars, restaurants and facilities have a decidedly rustic air to them. There is only one town, Dewey, and it is little more than a few intersecting roads. There are only two gas stations, one of which is used by boats; the largest luxury hotel had to shut its doors because the island’s infrastructure and labor force wasn’t sufficient enough to keep it going. And half the island lives in relative isolation. And no Culebrense would have it any other way.

A weekend on Culebra Island is an escape not just from the rest of the world, but from the rest of Puerto Rico. There is one world-famous beach that most visitors flock to, along with several not-so-famous beaches that can hold their own against pretty much any other stretch of sand in the Caribbean. In season, nesting turtles enjoy rock-star status and the preferential treatment that comes with it. Snorkeling; diving; swimming; hiking; fishing; boating: these are the engines that drive the tourist trade. Having said that, you’ll need to book your hotel, car rentals and even restaurant reservations (at the town’s most popular eateries) well in advance, because people love to come here.

What do you need to bring on your trip to Culebra? Better yet, here’s what you need to leave behind:

  1. Suits and formal clothing
  2. Notions of five-star hotels and upscale restaurants
  3. Your flashy club threads
01 of 03

Day One: Ferries, Flights, and Flamenco

Culebra's magnificent Flamenco Beach

Zain Deane

Like Vieques, Culebra is accessible by water and air, but I’d recommend flying if you can afford it. The only problem with the small planes that make the trip is that you can’t pack too much, but then again, you don’t need a lot of clothing on the island. The ferry is a slow and lumbering, but dirt cheap. Once here, you’ll want to get settled in, and then do what everyone has come here to do: head to Flamenco Beach.


  1. Once you reach the ferry dock or the airport, you’ll want to pick up your car rental. While there is ample public transportation to Culebra’s sandy jewel, you’ll want a car to putter around the island. Carlos Jeep Rental and Jerry’s Jeeps (787-742-0587) are both reliable options. If you want a funky (read: adventurous) alternative to a regular car or jeep, rent one of Dick & Cathie’s “Things,” a collection of dilapidated, noisy, manual-drive, old-fashioned Volkswagen buggies that are a lot of fun but certainly aren’t flashy (787-742-0062).
  2. Head to your hotel, or, if you want to live it up, Culebra-style, your rented villa. Club Seabourne is the top option; Harbour View Villas is a good moderate choice; and Posada La Hamaca and Casa Ensenada (787-742-3559) are among the best budget hotels.
  3. Check in and change into your bathing suit. Then take an hour or so to explore Dewey, Culebra's only town. When you’re ready for lunch, head back out toward the airport and stop at Barbara-Rosa’s (787-397-1923), about as down-home a place as you’ll find anywhere in Puerto Rico, and the place to go for killer crab soup and shark nuggets.
  4. After lunch, drive (or take a público) out to the one and only Flamenco Beach.
  5. When you’re ready for dinner, you have a few options. If you’re here during peak season, make sure you’ve booked a table (again, in advance) at Juanita Bananas, the consensus number one pick for dining in Culebra.
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02 of 03

Day Two: Getting Off the Island

Walter Rieder of Culebra Divers

Zain Deane

To really enjoy your visit to Culebra, you’ll need to leave Culebra. That might sound contradictory, but scuba divers and visitors to the all-natural cayo, or key, of Culebrita will agree heartily. You can probably even do both in one day, with some advanced planning, a good picnic lunch, and a water taxi or two.


  1. Contact Culebra Divers to arrange a morning trip. Walter and Monika Rieder are your underwater hosts, and they know where to go and how to entertain you, whether you’re a novice or an expert. If you prefer fishing to diving, call Chris Goldmark.
  2. After your morning on the water, make your way to El Eden (787-742-0509), a grocery-bar-deli on the outskirts of Dewey where you can get terrific sandwiches, soups, wine, beer, and other essentials for a picnic lunch.
  3. You’re now ready to hail a water taxi and head out to Culebrita. The price of the ride may seem a bit steep, but it’s worth it. Culebrita is an unspoiled, beach-heavy, snorkel-friendly paradise. There is only one manmade structure on the island: a lighthouse that is no longer in use. Playa Tortuga is a close second on the spectacular scale to Flamenco Beach, and the views from the easternmost point of the beach, where a promontory juts out into the ocean, are fantastic (you can see St. Thomas in the distance.) Spend the afternoon in this blissful, quiet, natural retreat.
  4. Returning to Culebra, relax at your hotel until dinner, and then head to Mamacita’s (787-742-0322), the main social gathering place in Dewey. Not only is the food great (and the homemade peanut butter pie tremendous), but the bar scene is about as hopping as it gets on the island. As far as nightlife goes, this place will serve your needs.
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03 of 03

Day Three: Before You Get Off the Island

The Island Woman's shack is one of the most photographed spots in Dewey

Zain Deane

Begin your last day on the island by hiking to a difficult-to-reach pristine beach, and then finish off your visit with lunch and shopping, such as it is, in Dewey.


  1. Reserve the morning for a hike to Brava Beach. Lesser known and less accessible than Flamenco Beach, Brava Beach is also less crowded than its famous neighbor. To get here, you have to drive to the end of a residential road and then hike through a trail that goes from tall grass to cool forest. A trail to the beach leads off from the right of the main path, but it’s unmarked and very easy to miss, so keep an eye out for it. If you make the effort, your reward is a beautiful beach that is completely undeveloped. Note: the rough surf and no lifeguard makes swimming inadvisable.
  2. A journey to Brava Beach is guaranteed to make you hungry. Two good, but very different options for lunch are the Dinghy Dock Bar-B-Q Restaurant (787-742-0024), for hearty fare in a rustic, casual ambience (check out the massive tarpon swimming below the dock), and White Sands Restaurant for award-winning, nouveau ‘Rican cuisine in a pleasant, manicured setting at Club Seabourne.
  3. Spend the rest of your time checking out Dewey’s shops. There’s not a whole lot here, but Fango (787-435-6654) and Paradise Gift Shop (787-742-3569), are among the more unique stores. Before you leave, snap a picture at Island Woman’s shack, one of the most photographed spots in town for its “open some days, closed others” sign on display when the place is closed.