Store Bay, Tobago
Pigeon Point, Tobago
Charlotteville (Man O’ War Bay), Tobago
Chaguaramas, Trinidad
Englishman’s Bay, Tobago
Snorkel Buccoo Reef and the Nylon Pool
Watch scarlet ibis return to roost at the Caroni Swamp
Hike the trails of the Main Ridge Forest Reserve
Join the Carnival festivities in Port of Spain
Dive the wreck-strewn waters off Speyside
Port of Spain
Scarborough
Charlotteville
Speyside
Crown Point
December through May offers the driest, most settled sailing weather, with steady northeast trade winds across Tobago’s anchorages. Trinidad sits far enough south, close to the Venezuelan coast, that many charter yachts use it as a hurricane-season base between June and November rather than sailing north during those months. Visiting in February or March around Carnival adds an unmissable cultural layer to a Trinidad stop, though Port of Spain’s marinas book out well in advance.
Trinidad’s Piarco International Airport (POS), near Port of Spain, is the main international gateway, with direct flights from North America and Europe as well as connections across the Caribbean. Tobago has its own airport, A.N.R. Robinson International (TAB), close to Crown Point at the island’s southwestern tip, roughly 11 kilometres from Scarborough and a short taxi ride from most charter anchorages on the leeward coast.
Store Bay and Pigeon Point, both close to Crown Point, offer easy access to Buccoo Reef and the airport for guests joining or leaving a charter. Charlotteville, tucked into a deep bay on the wilder north coast, provides good shelter and a genuine fishing-village atmosphere for an overnight stop. Man O’ War Bay, beside it, is regarded as one of the best natural harbours in the southern Caribbean.
A week gives enough time to explore Tobago’s calmer leeward anchorages around Store Bay and Pigeon Point, cruise up to the wilder northeast coast at Charlotteville, and still allow a day or two in Trinidad for Carnival, the Caroni Swamp or the capital’s restaurants. Many charters treat Tobago alone as a shorter, standalone week, since the open-water passage between the two islands can be rough and is best planned as a full day’s sail.
Trinidad sits at around 10.5 degrees north, close enough to the South American coast that it falls outside most insurers’ official hurricane zone, unlike islands further north in the Caribbean chain. Chaguaramas, on Trinidad’s northwest peninsula, has grown into one of the region’s largest boatyards, with haul-out facilities, chandleries and skilled marine trades supporting hundreds of yachts laid up each year between June and November.
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