Cruising the Eastern Caribbean: An Island-by-Island Guide for Bluewater Sailors

The Eastern Caribbean is where most Atlantic sailors make landfall and where many spend their first full cruising season. The chain of islands stretching from the Virgins to Grenada offers everything the brochures promise — trade wind sailing, warm water, spectacular anchorages — plus a few things they don't mention, like complex inter-island clearance procedures, rolly anchorages, and the particular chaos of anchoring in Admiralty Bay on a Saturday afternoon.

This is a working guide for the sailor moving through the Leewards and Windwards on a typical season — November through May — covering the practical realities of each stop rather than rehashing the tourist highlights.

The Virgins: BVI and USVI

The BVI remains the charter capital of the Caribbean, which means crowded anchorages, mooring balls everywhere, and a well-developed infrastructure for sailing visitors. The Baths at Virgin Gorda, the caves at Norman Island, and the anchorage at Jost Van Dyke are iconic for good reason, but in peak season (December-March) you'll be sharing them with dozens of charter boats.

For the visiting cruiser, the BVI's value is as a shakedown ground after the Atlantic crossing — well-marked waters, short passages, reliable trades, and help available if something breaks. The SailClear system handles customs pre-clearance, though you'll still need to visit the office in person at Road Town or West End, Tortola.

The USVI (St. Thomas, St. John, St. Croix) requires separate US customs clearance. St. Thomas has the best provisioning and marine services in the Virgins. Christmas Cove and the north shore of St. John offer quieter anchorages than the BVI, and the national park waters around St. John are genuinely beautiful.

Antigua

Antigua is the serious sailor's island. English Harbour and Falmouth Harbour form the epicenter of Caribbean yachting — world-class boatyards, riggers, sailmakers, and marine services clustered around the historic Nelson's Dockyard. If you need boat work done in the Caribbean, Antigua is where you do it.

The clearance process uses eSeaClear (different from eSailClear — yes, it's confusing). Clear in at Jolly Harbour or English Harbour. The annual Antigua Sailing Week in late April draws a serious racing fleet, but the island is worth visiting regardless of the regatta calendar. Barbuda, Antigua's sister island 30 miles north, offers spectacular deserted beaches and a massive frigate bird colony.

Anchoring in English Harbour requires awareness of the current mooring situation — space is limited and the harbor can be crowded. Falmouth Harbour has more room and better holding in most conditions.

Guadeloupe and Martinique

The French islands are a different world. Better food, better wine, better bread — and French bureaucracy, Schengen visa implications for non-EU passport holders, and higher prices. Clearance is online through French customs systems. Deshaies on the northwest coast of Guadeloupe is a charming first stop, with a well-protected bay and a waterfront lined with restaurants.

Martinique's Fort-de-France has the best provisioning in the French Caribbean — the supermarkets stock French cheeses, charcuterie, and wines at prices that would make a Med cruiser weep. The anchorage at Anse Mitan across the bay is more pleasant than the city waterfront. St. Pierre, on the northwest coast, is a haunting anchorage — the town was destroyed by the eruption of Mont Pelee in 1902, and the underwater ruins are a remarkable dive site.

Remember: time spent in Guadeloupe, Martinique, St. Martin (French side), and St. Barts counts toward your Schengen 90/180-day limit.

Dominica

Dominica is the wild card of the Eastern Caribbean — mountainous, volcanic, covered in rainforest, and dramatically less developed than its neighbors. The island doesn't have a single beach that compares to Antigua or the BVI. What it has is waterfalls, hot springs, hiking trails through primary rainforest, and an authenticity that the more touristed islands have traded away.

The Portsmouth Association of Yacht Security (PAYS) operates in Prince Rupert Bay — call them on VHF Channel 16 as you enter. Local boat boys will guide you to a mooring and provide tours, laundry service, and provisioning assistance. The system works well and supports the local economy. The Indian River tour by rowing boat through the mangrove forest is one of the great experiences in Caribbean cruising.

Holding in Prince Rupert Bay is poor in places — sand over hard pan. Set your anchor carefully and dive on it to confirm. The Cabrits anchorage at the north end is better protected from the swell.

St. Lucia

Rodney Bay in the north is the cruiser hub — a full-service marina, good provisioning, and a lively restaurant scene. It's where most boats clear in and where many do their laundry, fill water, and stock up before heading south.

The Pitons — the twin volcanic spires on the southwest coast — are the most photographed landfall in the Caribbean. The anchorage between the Pitons is dramatic and uncomfortable — deep water, poor holding, and open to afternoon swells. Many boats take a mooring rather than anchoring. The view is worth one night; the rolly conditions usually enforce a one-night stay regardless.

Marigot Bay, just north of Soufriere, is a landlocked hurricane hole that's become a marina resort development. It remains a beautiful and well-protected anchorage.

St. Vincent and the Grenadines

The Grenadines are the crown jewels of Eastern Caribbean cruising. Bequia, Mustique, Canouan, Mayreau, the Tobago Cays, Union Island, and Petit St. Vincent form a chain of islands with some of the most spectacular sailing and anchorages in the Caribbean.

Bequia's Admiralty Bay is one of the great cruiser gathering spots — a large, well-protected anchorage with a waterfront town, excellent restaurants, a functioning boatyard, and a community of local boat builders carrying on a tradition that dates to whaling days. Clear in at the customs office on the waterfront. The holding is good in sand with some patches of grass.

The Tobago Cays — a cluster of small islands inside a horseshoe reef — are the Caribbean's underwater Eden. The snorkeling inside the reef is extraordinary. It's also a marine park with mooring balls and strict no-anchoring zones on the reef. Arrive early for the best mooring positions; the Cays are popular and space is limited.

The passage between St. Vincent and Bequia can be rough — the wind accelerates through the channel and the current can be strong. Take it on the nose and it's a wet, slow beat. Time it to carry the current and it's manageable.

Grenada

Grenada is where many cruisers spend hurricane season — it's at the southern edge of the hurricane belt, has multiple haul-out yards, and offers a warm, welcoming culture that makes extended stays genuinely enjoyable.

Prickly Bay and Clarkes Court Bay on the south coast are the cruiser hubs, with boatyards, chandleries, and regular cruiser events. St. George's, the capital, has the best market in the southern Caribbean — the Saturday market is a provisioning event worth building your week around.

Clear in at St. George's or at Carriacou (Tyrell Bay). If you clear in at Carriacou, you don't need to re-clear at Grenada proper. Carriacou itself is worth several days — a quieter, more traditional island with good anchorages and a functioning boatbuilding tradition.

Trinidad

Trinidad is the workshop of the Caribbean. Chaguaramas Bay on the northwest peninsula has the highest concentration of boatyards, marine services, and hauling facilities in the Eastern Caribbean. If you need serious boat work — a refit, a re-rig, engine work, fiberglass repair — Trinidad is where you go.

The island is below the hurricane belt (though not immune to late-season storms), making it a traditional season storage location. The culture is distinct from the rest of the Caribbean — a multicultural blend of African, Indian, Chinese, and European influences that produces extraordinary food and one of the world's great carnivals (February/March).

The anchorage in Chaguaramas is industrial rather than scenic. Scotland Bay, further west in the Bocas, is prettier but further from the yards. Provisioning is excellent and cheap — the supermarkets and wholesale outlets in Port of Spain and Chaguaramas are the best-stocked in the southern Caribbean.

The Northbound vs. Southbound Question

Most boats arriving from the Atlantic make landfall in the southern Windwards (Martinique, St. Lucia, or Barbados) and work north toward the Virgins. The return trip south in the spring means beating into the trades — the prevailing northeast winds make southbound passages a hard slog of tacking or motorsailing.

The alternative strategy: sail north early in the season, explore the Leewards, then let the trades carry you south through the Grenadines and to Grenada or Trinidad for hurricane season. This puts the wind at your back for the best cruising grounds and saves the windward work for the shorter passages.

Either way, give yourself time. The Eastern Caribbean isn't a checklist — it's a season. The sailors who rush through see islands. The ones who slow down find communities.

References: Doyle Guides, Chris Doyle's Sailors Guide to the Windward Islands, Noonsite Caribbean, SailClear, cruising community reports