7-Night Itinerary

After waking up and enjoying a relaxed breakfast, consider taking one final snorkel at Pyramid Reef before setting out east toward Culebra and Cayo Luis Peña. The sail is roughly 13 NM, and you’ll find anchorage or moorings on the island’s southwest side. This area is a sea turtle sanctuary with an excellent snorkeling reef and a beautiful white-sand beach. You’re welcome to stay overnight here, though you may prefer to continue a couple of miles farther east to Playa Melones on Culebra. There, moorings sit just off a lovely beach known for great snorkeling.

The main advantage of Melones is its proximity to the town of Dewey, Culebra’s capital, and the ferry port—just a short dinghy ride away. Dewey offers small shops along with a variety of unique restaurants and cafés. It’s a great place to plan dinner at the island’s favorite, Mamacita’s, a charming spot accessible by dinghy about halfway up the channel that runs through the island. Mamacita’s also hosts live music on weekends, and spontaneous performances by local musicians can pop up any night of the week.

After your time on Culebrita, enjoy a pleasant downwind sail toward the southern channel leading into Ensenada Honda, Culebra’s main harbor. Drop anchor just behind Cayo Pirata, then take the dinghy ashore and tie up at the Dinghy Dock Restaurant. It’s a perfect spot to savor a late breakfast or early lunch while overlooking Ensenada Honda. The Dinghy Dock also makes a convenient place to leave your tender as you explore the rustic town of Dewey. Here you can browse local shops, restock provisions, or even rent a scooter or jeep to tour the island.

You can choose to spend the evening here and have dinner at Sally’s, another great local favorite. Alternatively, sail farther down Ensenada Honda to the Dakiti anchorage, which offers numerous moorings in a calm, reef-protected harbor. Just around the bend from Dakiti is Bahía Fulladoza, home to Club Seaborne—a boutique hotel with one of the island’s best restaurants—as well as the Bahia Bay Resort, an ideal stop for drinks with a stunning view. Another excellent mooring option for the night is Bahía Aldomovar, located just outside and east of Ensenada Honda. This peaceful mangrove-lined harbor, protected by a coral reef, faces east toward St. Thomas.

After breakfast, and perhaps a morning snorkel or hike, cast off and sail at a relaxed pace along Vieques’ undeveloped south coast to Sun Bay. Anchor on the eastern side of the bay and enjoy some snorkeling or a stroll along the beach. Just around the bend from Sun Bay is Puerto Real, home to the vibrant town of Esperanza. Here, the “Malecón,” or waterfront walk, is lined with charming shops and a variety of dining options. For casual drinks and bar fare, check out Lazy Jacks. Duffy’s is ideal for lunch or dinner, while Bili or El Quenepo offer a more refined gastronomic experience—all conveniently located along the Malecón.