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. There is only one town, Dewey, which consists of little more than a few intersecting roads. With only two gas stations—one of which caters to boats—the island’s largest luxury hotel had to close due to insufficient infrastructure and labor force. Consequently, half of the island lives in relative isolation, and no Culebrense would have it any other way.

A weekend on Culebra Island represents an escape from the rest of the world and even from the remainder of Puerto Rico. There is one world-famous beach that most visitors flock to, alongside numerous lesser-known beaches that hold their own against almost any other stretch of sand in the Caribbean. During nesting season, turtles gain rock-star status and the special treatment that follows. Activities such as snorkeling, diving, swimming, hiking, fishing, and boating significantly drive the tourist trade. Therefore, you’ll need to arrange accommodations, car rentals, and even dining reservations at popular local eateries well in advance, as this island is a favorite among travelers.

What do you need to bring on your trip to Culebra? Here’s what you should leave behind:

1. Suits and formal clothing
2. Expectations of five-star hotels and upscale restaurants
3. Your flashy club attire

Day One: Ferries, Flights, and Flamenco

Like Vieques, Culebra is accessible by water and air; however, flying is recommended if it fits your budget. One minor drawback to using small planes is the limited packing capacity; nevertheless, you won’t require much clothing for your stay. The ferry option is inexpensive but a slow journey. Upon arrival, you’ll want to settle in before embarking on the popular visit to Flamenco Beach.

Itinerary

1. Upon reaching the ferry dock or airport, pick up your car rental. Although Culebra has several public transportation options, having a rental car gives you the freedom to explore the island conveniently. Notable options include Carlos Jeep Rental and Jerry’s Jeeps (787-742-0587). For a more adventurous ride, consider renting one of Dick & Cathie’s quirky Volkswagen buggies (787-742-0062).
2. Head to your hotel or, for a taste of local living, your rented villa. Club Seabourne is a top choice, whereas Harbour View Villas offers a more moderate experience, and Posada La Hamaca along with Casa Ensenada (787-742-3559) represent affordable options.
3. Check in and change into your swimwear before taking an hour to explore Dewey, Culebra’s only town. When lunchtime arrives, head back toward the airport and stop at Barbara-Rosa’s (787-397-1923) for an authentic dining experience featuring excellent crab soup and shark nuggets.
4. Post-lunch, drive (or take a público) to the renowned Flamenco Beach.
5. For dinner, enjoy several dining options. If visiting during peak season, ensure you’ve reserved a table well in advance at Juanita Bananas, a favorite among diners in Culebra.

Day Two: Getting Off the Island

To truly appreciate your time on Culebra, you’ll need to venture beyond its shores. This might seem paradoxical, yet scuba divers and fans of the natural key, Culebrita, will wholeheartedly agree. With some advanced planning, a picnic lunch, and perhaps a couple of water taxis, you can enjoy both activities in a single day.

Itinerary

1. Contact Culebra Divers for a morning scuba diving trip, guided by Walter and Monika Rieder, who excel in providing memorable underwater experiences for both novices and experts. Should you prefer fishing, reach out to Chris Goldmark.
2. Following your underwater adventure, head to El Eden (787-742-0509), a local grocery-bar-deli where you can acquire delicious sandwiches, soups, and other picnic essentials.
3. Your next stop is a water taxi to Culebrita. Although the fare may seem slightly high, experiencing this unspoiled, beach-laden, snorkel-friendly paradise is worth it. Culebrita features only one manmade structure, a defunct lighthouse, while Playa Tortuga ranks closely behind Flamenco Beach in terms of beauty and boasts stunning vistas, including a view of St. Thomas in the distance. Dedicate your afternoon to relishing this tranquil retreat.
4. When you return to Culebra, unwind at your hotel before dining at Mamacita’s (787-742-0322), the social hub of Dewey. The food is exceptional, and their homemade peanut butter pie is a must-try. In terms of nightlife, this venue fulfills your needs.

Day Three: Before You Get Off the Island

Conclude your island experience with a morning hike to a remote, stunning beach, followed by lunch and some shopping in Dewey.

Itinerary

1. Start your morning with a hike to Brava Beach. Lesser-known and more secluded than Flamenco Beach, Brava Beach is an ideal escape from crowds. To access it, drive to the end of a residential road, then hike through a pathway that transitions from tall grass to a cool forest. Watch for an unmarked trail leading to the beach as you explore. If successful, you’ll be rewarded with a beautiful and completely undeveloped beach. Note: due to rough surf and a lack of lifeguards, swimming is not recommended.
2. Your trek to Brava Beach will undoubtedly work up an appetite. Two excellent yet contrasting lunch options are the Dinghy Dock Bar-B-Q Restaurant (787-742-0024) for hearty food served in a casual setting (don’t miss the massive tarpon swimming below the dock) and White Sands Restaurant, which serves award-winning, innovative Puerto Rican cuisine in a beautifully maintained atmosphere at Club Seabourne.
3. Use the remaining time to browse the shops in Dewey. Although the choices are limited, Fango (787-435-6654) and Paradise Gift Shop (787-742-3569) offer unique shopping experiences. Before departure, make sure to capture a photo at Island Woman’s shack, famous for its “open some days, closed others” sign.