Waypoints

Sailing the Spanish Virgin Islands: The Summer Charter You Haven’t Considered Yet

Spanish Virgin Islands

If your ideal summer vacation involves open water, uncrowded anchorages, and a place that genuinely feels undiscovered, the Spanish Virgin Islands should be at the top of your list. Just 22 miles west of St. Thomas, a charter through Culebra, Culebrita, and Vieques is one of the Caribbean’s best kept secrets — and summer is one of the finest times to go.

Spending time in the Spanish Virgin Islands means experiencing a distinctly Spanish-Caribbean culture, Puerto Rican rhythms on the waterfront, and a pace of life that has no interest in hurrying. No resort infrastructure. No cruise ship docks. No marina complexes. By June the trade winds have shifted southeast, opening up comfortable passages along the south shores of both islands. 

In this guide, we’ll walk you through what makes Culebra, Culebrita, and Vieques worth the trip: the best anchorages, what to do ashore, why summer is one of the best times to sail here, and everything you need to know before you go.

What Awaits You on the Islands

Culebra

The small town of Dewey is where most sailors arrive first, and it earns the welcome. Two-story wooden homes, a non-lifting lift bridge, a handful of bars and restaurants whose owners may or may not choose to open on any given day. That’s island time, and you’ll adjust quickly. Tie the dinghy at the town dock, walk across to Mamacita’s for a whole red snapper, and settle into it.

For the beach, a $10 roundtrip taxi gets you to Playa Flamenco — a sweep of powder-white sand that ranks among the finest in the entire Caribbean. Beyond the beaches, over a third of Culebra’s interior and its entire coastline fall within the Culebra National Wildlife Refuge, managed by the US Fish and Wildlife Service and home to endangered leatherback sea turtles and some 50,000 seabirds. The reefs here are federally protected, and the snorkeling reflects it.

When it comes to anchoring, most boats drop the hook off Cayo Pirata for easy dinghy access to Dewey. A better move is to tuck a little further west past Cayo Pirata, where the depth runs about 13 feet and you’ll be downwind of most other boats. The bottom is sea grass, so lay out at least 5:1 scope and back down hard before heading ashore. 

For one of the finest anchorages on the island, Bahia de Almodovar is hard to beat. Sailor and cruising author Don Street calls it one of the finest in the entire Eastern Caribbean — clear water, white sand bottom, a reef to windward that breaks the seas. At night, St. Thomas lights up 15 miles to the east as the sun sets.

Culebra quick takes:

  • Anchor west of Cayo Pirata in 13 feet — quieter and less crowded than the main field
  • Bahia de Almodovar is one of the finest anchorages in the Eastern Caribbean — clear water, sand bottom, reef to windward
  • Taxi to Playa Flamenco ($10 roundtrip) rather than sailing in unless conditions are ideal
  • Mamacita’s for dinner — order the whole red snapper

Culebrita

Northeast of Culebra sits a small uninhabited island that tends to be the one sailors talk about when they get home. Bahia de Tortuga is a 700-yard crescent of white sand framed by surviving palms, with excellent snorkeling just offshore and natural tide pools a five-minute hike away on the island’s north side.

The hike to the lighthouse takes 15 to 20 minutes and is worth every step. Built by the Spanish between 1882 and 1886, destroyed by a hurricane in 1932, blacked out during World War II for security reasons, and finally shuttered in 1959, the ruined lighthouse sits at 305 feet with panoramic views stretching west to Culebra and Puerto Rico, south to Vieques, and east toward St. Thomas. Bring water, a camera, and sturdy footwear.

Culebrita quick takes:

  • Bahia de Tortuga is best avoided when ground swell exceeds 2-3 feet
  • Hike to the lighthouse — 15-20 minutes, 305 feet up, views in every direction
  • Natural tide pools are a 5-minute walk from the beach

Vieques

Twenty-one miles long and largely untouched by development — a direct consequence of its decades as a US Navy bombing range, the last of which fell in 2003 — the island is home to wild paso fino horses that roam freely and a population that still travels some stretches by horseback.

The anchorages on the south shore are exceptional. Bahia de la Chiva, code-named Blue Beach by the Navy during training exercises, has been rated among the best beaches in the world by Condé Nast. 

Anchor northwest of Isla Chiva in 12 to 15 feet, or tuck east of the island right under Punta Conejo for what many sailors find the more settled of the two spots. The shallows in between are the warmest water you’ll find anywhere in the Virgin Islands chain at any time of year.

The island’s most singular experience is Mosquito Bay at night. Home to the highest concentration of bioluminescence on the planet, a kayak through the bay produces an otherworldly blue glow with every paddle stroke. The best viewing falls in the two-week window from three days after the full moon to three days after the new moon, when the skies are darkest. Seek out a smaller group tour with glass-bottom kayaks over the larger 40-person trips.

Vieques quick takes:

  • Bahia de la Chiva anchorage #2 (east of Isla Chiva) tends to be the more settled of the two spots
  • Bioluminescence tours are best in the two-week window around the new moon — book ahead
  • Do not go ashore at Isla Chiva — the Navy is still clearing unexploded ordnance

Why Summer Works for the Spanish Virgin Islands

By June the trade winds have rotated from northeast to southeast, which changes the sailing geometry here in your favor. Anchorages like Bahia de la Chiva and Bahia de Almodovar are well-suited to southeast conditions, and passages along the south shores of both islands become comfortable reaches.

The one leg that rewards careful planning is the return to St. Thomas. With the prevailing winds behind you on the way out, heading home means going upwind across 15 miles of exposed open water. 

Keep an eye on the 10-day forecast and aim to return in conditions under 15 knots with seas below five feet. The crossing is perfectly manageable in the right window, and rewards patience over stubbornness.

4 Things Only the SVI Offers

The Spanish Virgin Islands sit in a category of their own. Here’s what you won’t find anywhere else in the Virgin Islands chain:

  1. The world’s most concentrated bioluminescence – Mosquito Bay on Vieques holds the highest concentration of bioluminescence on the planet. A nighttime kayak here has to be seen to be believed.
  2. Federally protected reefs – The waters around Culebra are managed by the US Fish and Wildlife Service. Decades of serious conservation show in marine life, resulting in some of the best snorkeling in the Caribbean.
  3. A culture that’s entirely its own – From the Spanish spoken in Dewey’s small restaurants to the Puerto Rican rhythms drifting from Esperanza’s waterfront Malecon on a Friday evening, the SVI has a personality distinct from anything you’ll find in the USVI or BVI.
  4. Less development – No large resorts, no cruise ship docks, no marina complexes. Just good sailing, beautiful water, working wildlife refuges, and wild horses roaming the hills of Vieques.

FAQs About Spanish Virgin Island Charters

Do I need to clear customs when arriving from the USVI? 

Yes. Crossing from the US Virgin Islands to the Spanish Virgin Islands requires reporting arrival to US Customs and Border Protection as you are entering a different US jurisdiction. The easiest method is the CBP ROAM app on your smartphone, which handles the process via video call without going ashore. Have all crew present and passports ready.

Is provisioning available on the islands? 

Limited provisioning is available in Dewey and Esperanza, but neither island has a large supermarket and there are no marinas anywhere in the SVI. Provision fully in St. Thomas before you depart, take on fuel and water there, and plan to top up with basics only once you arrive.

What’s the sailing distance from St. Thomas? 

Culebra’s main anchorage is approximately 22 nautical miles from St. Thomas — around three hours at a comfortable pace. Culebrita is about 17 miles, and Vieques at Esperanza is roughly 35 miles. The outbound passage is typically a lovely downwind run. Factor more time and thought into the return.

What’s the best gateway for a summer SVI charter? 

St. Thomas (STT) is your hub, with regular direct service from major US cities. From there the SVI is a single day sail away.

Start Planning Now

Summer charters in the SVI fill up, and the season rewards those who plan ahead. If you’ve been looking for a sailing destination with real character, protected waters, world-class snorkeling, wild horses, and that rare feeling of arriving somewhere that hasn’t been packaged for tourists, this is it. 

Get in touch with our Waypoints Yacht Charter Consultants today to check availability and start putting your itinerary together.