Sail to St. Kitts and Nevis

Board in Basseterre and begin with a short run down the leeward coast toward the Southeast Peninsula. Anchor off a calm bay for an easy first swim and a gentle tender cruise along the headland. If you want a low effort first afternoon ashore, aim for Cockleshell Bay for a simple beach stop and an early dinner back on board while the peninsula quiets down.

Cross the Narrows to Nevis and settle off Charlestown or Pinney’s Beach with time still in the day. Ashore, take a short walk through Charlestown’s historic streets, then return to the yacht for an afternoon swim. For guests who appreciate a small museum done with care, the Nevis Historical and Conservation Society hosts an exhibition on Alexander Hamilton inside Trott House. 

Keep the yacht close and treat Nevis as a day of details rather than distance. Start with a long morning at Pinney’s Beach, ideal for paddleboarding and an extended swim before the afternoon breeze arrives. In the afternoon, consider a private car transfer inland to one of the island’s old plantation sites for a quieter look at Nevis beyond the shoreline, then return on board for a dinner service that feels entirely off schedule, in the best way.

Begin with a short reposition and plan the day around Nevis’s hot spring history. The Bath Hotel sits near the springs just south of Charlestown and was built around 1800, tied to the island’s long standing association with therapeutic waters. After a calm on shore visit, return to the yacht and shift to Oualie Bay for a quieter evening anchorage, with time for a sunset swim and a low key night on board.

Cross back to St. Kitts and reenter Basseterre with the afternoon open. This is the best day to add one of St. Kitts’s signature land experiences without rushing the week. The St. Kitts Scenic Railway began as a sugar transport line, built between 1912 and 1926 to move cane from plantations to the factory in Basseterre, and it now runs as a coastal viewing experience. Return to the yacht for dinner and an early night before the western coast day ahead.

Cruise north along St. Kitts’s leeward side to Sandy Point and plan a morning ashore at Brimstone Hill Fortress National Park. UNESCO describes it as an outstanding, well preserved example of seventeenth and eighteenth century military architecture in the Caribbean, with the site linked to colonial expansion and the Atlantic slave trade. After the visit, return for a long lunch on board and an afternoon swim stop in a nearby bay, letting the day settle instead of stacking more plans.

Take a relaxed final leg back to Basseterre, with the option of one last swim stop en route if conditions suit. Keep the last hours practical and calm: rinse down gear, pack without hurry, and step ashore for a short harbor walk before disembarkation. The week finishes the way it began, with the islands close and clear in view, and nothing feeling overworked.