
The Leeward Loop
Clear water, short hops, the best kitchens on the circuit. For first-time charterers.
- 01St Barths
- 02Anguilla
- 03St Martin
- 04Saba
- 05St Kitts
- 06Nevis

Eight suggested itineraries across the Caribbean, Bahamas, and South Florida. You can take them as drafts — the Captain will happily redraw any of them over a coffee the morning of.

Clear water, short hops, the best kitchens on the circuit. For first-time charterers.

Remoter, quieter, rawer. Snorkel the Cays at dawn, eat at Basil's by lunch.

The ur-Caribbean itinerary. Protected waters, iconic anchorages, no passports.

The signature Bahamas run — gin-clear water over white sand, iguanas on Allan's, swimming pigs on Big Major, the Thunderball Grotto off Staniel.

New England-white villages on pink-sand beaches. Loyalist history, Bahamian rum bars, and the best mail-boat lunches in the country.

From Biscayne Bay down the Keys to the empty anchorage off Fort Jefferson — 70 miles west of Key West, where the birds outnumber the boats.

Puerto Rico's east coast into the Dominican Republic — bioluminescent kayak nights, humpback whales off Samaná in season, and the finest fishing off Punta Cana.

Arguably the clearest water in the Atlantic. The Columbus Passage between Grand Turk and Salt Cay is humpback highway from January through March.
Dec – Apr. Trade-wind weather, low humidity, the quintessential charter months. Peaks at Christmas, New Year's, President's Week, and Easter — book by September.
Year-round, best Nov – Jun. Exumas and Abacos sit outside the hurricane belt relative to Florida; Turks & Caicos is similar.
Orca cruises anywhere from the Dry Tortugas to Grenada. Fuel-dense, range-capable, stable at sea — write us an idea, we'll price a week.