Yacht charter in the Greater Antilles
Cruising the Greater Antilles on a crewed yacht offers varied passages across Puerto Rico, the Dominican Republic, and Jamaica. The region features expansive coastlines, deep-water sounds, and barrier reefs, suitable for charterers who enjoy combining open-water sailing with coastal exploration. It suits experienced sailors and guests seeking cultural heritage, nature reserves, and quieter anchorages away from the more congested routes of the eastern Caribbean.
Best time to charter
The primary charter season runs from December to April, characterised by reliable north-easterly trade winds between 15 and 20 knots, minimal rainfall, and temperatures around 27°C. Peak demand occurs from Christmas through March. May and November offer calmer conditions with fewer visiting yachts. The Atlantic hurricane season spans June to November, bringing higher humidity, variable winds, and increased rain.
Anchorages and harbours to know
Palomino Island, Puerto Rico
Offers clear water and secure holding in sand, providing shelter from the prevailing north-easterly trade winds off Fajardo.
Isla Saona, Dominican Republic
Provides an expansive anchorage in the Parque Nacional del Este with calm shallows protected from north-easterly swells.
Port Antonio, Jamaica
A deep natural double harbour on Jamaica's north-east coast that offers exceptional shelter and designated customs clearance facilities.
Samaná Bay, Dominican Republic
A vast, sheltered bay known for seasonal humpback whale breeding, featuring secure holding near Santa Bárbara de Samaná.
Cayo Aurora, Puerto Rico
Also known as Gilligan's Island, this mangrove cay on the southern coast offers tranquil, shallow anchorages protected by barrier reefs.
Practical tips
- Getting there: San Juan (SJU), Punta Cana (PUJ) and Montego Bay (MBJ). Fajardo's marinas are about 1 hour from San Juan airport; Cap Cana marina is about 15 minutes from Punta Cana.
- Fajardo's marinas are about 1 hour from San Juan airport; Cap Cana marina is about 15 minutes from Punta Cana. Montego Bay (MBJ) serves northern Jamaica.
- In the Dominican Republic, vessels must obtain a naval despacho for every movement between ports, whereas Puerto Rico arrivals can often clear remotely using the CBP ROAM app.
- Charter taxes and cruising fees vary by island and are not included, so ensure individual entry fees and cruising permits are factored in across jurisdictions.
- Passages between main islands, such as crossing the Mona Passage, involve open-ocean swells and require careful monitoring of weather windows prior to departure.