Saint Vincent and the Grenadines

Tobago Cays are five small islands that were never permitted year-round settlement, and Horseshoe Reef — the coral barrier curving around the group — breaks the open-ocean swell before it reaches the anchorage, which is what keeps the water calm and clear enough for turtles to swim right up to snorkellers in the shallows. Marine park status since 2006 formalised protections that were already informal practice among sailors — no anchoring directly on coral (moorings are provided instead), no fishing, no touching the turtles — which is why the reef and marine life here have stayed intact while more accessible, more developed islands elsewhere in the Caribbean lost theirs. The Cays are reachable only by boat, either a day-trip catamaran from Union Island or an overnight stop on a yacht charter.

The Grenadines' 32 islands sit close enough together for line-of-sight navigation — sailors can almost always see the next island ahead — while steady trade winds and minimal tidal variation make for consistent, predictable conditions rather than the gusty or tide-driven sailing found elsewhere in the Caribbean. That combination is why a week-long charter can comfortably island-hop from Bequia down to Union Island with a secure anchorage most nights, rather than requiring long open-water passages between stops. Bareboat charters (sailing yourself, with certification) and crewed charters (captain and chef included) both operate from bases in Blue Lagoon on Saint Vincent and Union Island.

Bequia's boat-building tradition predates the tourism economy entirely — families like the Sargeants have built traditional wooden sailing boats on the beach at Port Elizabeth for generations, a skill that survived because Bequia's economy was built on fishing and inter-island trade long before yacht charters arrived. That same maritime self-sufficiency is why Bequia functions as the Grenadines' practical hub for provisioning, repairs and crew changes, not just its cultural one. A limited, closely regulated tradition of hand-harpoon whaling of humpback whales is still permitted here under an International Whaling Commission exception, capped at a small annual quota — a genuinely rare and controversial holdover from the island's whaling heritage rather than a tourist activity.

Saint Vincent is mountainous and volcanic rather than beach-fringed, which is a large part of why most sailing itineraries treat it as a starting point rather than a destination — La Soufrière, the island's active volcano at 1,234 metres, last erupted in April 2021 with evacuations and ashfall across the island, and the guided crater hike (check current eruption status before planning) is a genuinely demanding full-day trek rather than a casual walk. Kingstown's botanical gardens, established in 1765, are the oldest in the Western Hemisphere and still grow breadfruit trees descended from the ones Captain Bligh brought to the Caribbean — a direct link between the island's colonial-era plant-transfer history and what's growing in the gardens today.

Wallilabou Bay's natural, undeveloped harbour was exactly what filmmakers needed to double for 17th-century Port Royal in the Pirates of the Caribbean films, and rather than dismantling the set afterward, the bar, dock structures and props were left in place and turned into a standalone attraction — which is why visitors can walk through a genuine film set built for the movies rather than a themed replica built for tourists. Petit Tabac, one of the Tobago Cays, served as the deserted-island location in the same film series, giving sailing itineraries through the Grenadines an unplanned but genuine film-tourism thread alongside the sailing and snorkelling.

Argyle International Airport, which opened on Saint Vincent in 2017, finally gave the country direct international flights, replacing a small airstrip that could only handle regional turboprops — but once you're in the country, moving between islands still depends on which island you're headed to: small SVG Air flights reach the larger Grenadines, a regular ferry connects Saint Vincent to Bequia, and everywhere smaller than that is reached only by water taxi or private charter boat. That patchwork is a direct consequence of the islands' small size and scattered geography rather than underdevelopment — there's no room for airstrips on most of the smaller Grenadines, and yacht access was always the practical way to reach them.