Cuba

Cuba runs two charter itineraries under one flag. On the north coast, Marina Hemingway sits a short run from Havana's Malecón and its working fleet of pre-revolution Detroit iron, with the Caribbean's largest marina now built out along Varadero's Hicacos Peninsula an easy day's run east. On the south coast, reached separately, Cienfuegos and the cobbled colonial streets of Trinidad open onto the Bay of Pigs' cave-diving and, further out again, the permit-only bonefish and tarpon flats of Jardines de la Reina and the coral walls of Maria la Gorda at the island's western tip. The season runs November to May, ahead of the Atlantic hurricane months; the marina network, almost without exception, is state-run — which matters more here than in most charter grounds.

Havana's streets still run on 1950s Detroit iron — the same embargo, redrawn every decade since, that keeps most of the world's charter fleet on the far side of the Florida Straits.

The sanctions reality

What follows applies specifically to US-flagged yachts and US passport holders, not to the rest of the charter fleet.

Since June 2019, the US Commerce Department has withdrawn the export licence exception that let American-flagged pleasure craft sail to Cuba at all, and the general policy on any fresh application since has been denial. Separately — and this is the part that catches owners who assume a foreign flag settles it — the US Treasury's Office of Foreign Assets Control (OFAC) regulates the person, not just the vessel: a US passport holder's travel to Cuba is only lawful under one of twelve specific licence categories, among them family visits, journalism, professional research and support for the Cuban people, and tourism is explicitly not one of them. Chartering a foreign-flagged yacht for a leisure week at Marina Hemingway does not change who is doing the travelling.

The direction of travel has hardened rather than eased. Cuba was returned to the US State Sponsor of Terrorism list in January 2025, the State Department's Cuba Restricted List was reinstated and then expanded to around 250 entities that summer, and a further executive order in May 2026 added secondary sanctions reaching foreign companies doing business with Cuba's state sectors. GAESA, the Cuban military's holding company, is itself already blocked, and Gaviota — GAESA's tourism arm, whose marina and dive-centre subsidiaries appear on the Restricted List by name — is the operator, directly or through its Marlin marina brand, behind most of the marinas named in this dossier, Varadero included. A foreign-flagged yacht that does call here should also take advice on the 180-day rule and its companion passengers-on-board restriction before its next US port: a vessel that has carried passengers to or from Cuba can be barred from entering US waters afterwards outside a narrow licensed exception. None of this touches the rest of the charter market — European, Latin American and Canadian owners and guests cruise Cuba routinely — but it rules out the US-flag and US-passport segment almost entirely.

Signature anchorages

Two coasts, not one circuit — the distances between them are real, and the itineraries below are built accordingly.

• Marina Hemingway, HavanaFour kilometre-long channels cut through the reef at Santa Fe, west of the city; official capacity around 400 vessels with LOA (length overall) to 70 metres on paper, though usable, fully serviced berths run to a fraction of that and several pontoons still await repair. Draft to about 3.6 metres. Present-day home of the Hemingway International Billfish Tournament, which has run most years since its first Havana staging in 1950.
• Varadero — Marina GaviotaThe Caribbean's largest marina by berth count, built out along the Hicacos Peninsula with draft to about 4 metres and dockage advertised toward 1,200 berths as the build-out continues. Fronts the near-20-kilometre beach that gives Varadero its name; the marina basin is fully protected, the open roadstead beyond it exposed to the north.
• Cienfuegos — Punta GordaA UNESCO-listed neoclassical grid of a city on a deep, almost landlocked bay — good holding and all-round shelter once inside. Marina Cienfuegos at Punta Gorda runs to around 20 berths, LOA to roughly 25 metres; a working transient marina rather than a superyacht dock, and often full with resident charter fleets midweek.
• Trinidad — Casilda & the Ancón peninsulaTrinidad's cobbled UNESCO old town sits inshore of Casilda, which is not itself a port of entry — clear in at Cienfuegos and take a despacho (Cuba's port-to-port cruising permit) for the leg on. The shoal-draft dock at Cayo Blanco, in the mangroves south of Casilda, has room for two or three boats stern-to with water and diesel; better draft and more berths, to around 26, sit at the marina on the Ancón peninsula opposite.
• Jardines de la ReinaOver 160 kilometres of cayos (low sand-and-mangrove islets) and reef along Cuba's south-central shelf, a national park with a fishing and diving area larger than the entire Florida Keys — and access is a single exclusive concession, held by the operator Avalon, whose own liveaboards are effectively the only vessels permitted inside it. No yacht marina, no casual entry; the gateway is the small mainland port of Júcaro, reached overland, not by sea from Havana or Varadero.
• Maria la Gorda, Guanahacabibes PeninsulaCuba's westernmost anchorage, inside a UNESCO biosphere reserve at the tip of the Guanahacabibes Peninsula — steep coral walls starting close to shore, among them the Salón de María and the Black Coral Valley, spread across some 60 charted dive sites. No marina; anchor off the dive centre's pier and clear in via Cabo San Antonio, the nearest port of entry, a run around the cape.

The scene

Havana ashore, and the marlin tournament that put Marina Hemingway on the chart in the first place.

Table & stay ashore

Havana's paladares — privately run restaurants, legal since the food-service reforms of the 1990s — sit alongside the city's grand hotel dining rooms; Michelin does not rate Cuba, so the record here is reputation and history rather than stars.

A week, sketched

Built around the north coast's only two marinas — the south coast, described above, runs as a separate charter out of Cienfuegos, not a single week's extension.