10-DAY ITINERARY IN THE LEEWARD ISLANDS

Depart the main harbour on Saint Kitts and follow the coastline south, with the slopes of Mount Liamuiga falling to a series of beaches and small bays. Rounding the south eastern tip, the channel to Nevis opens while Cockleshell Bay curves in as a gently shelving anchorage with views across to Nevis Peak. Swell is usually modest here, giving an easy first night within sight of the next island.

Daily Highlights:

• Coastal shakedown passage along Saint Kitts
• Afternoon swim from the yacht in Cockleshell Bay
• Time ashore for a casual beach bar visit at the south end of the island
• Sunset at anchor with Nevis on the horizon

Cross the Narrows from Cockleshell Bay to Nevis, a short channel run that still gives a clear sense of moving between islands. The cone of Nevis Peak rises directly from shore, with a long sweep of sand at Pinneys Beach and mooring fields set in good sand over gentle depths. The passage can carry choppy water when the trades freshen but is normally a swift and straightforward hop.

Daily Highlights:

• Quick inter island crossing with both shores in constant view
• Swim and snorkel off Pinneys Beach
• Option to go ashore for a walk into Charlestown’s historic streets
• Dinner on board anchored under the lee of Nevis Peak

Leave Nevis on a south easterly course into more open water, with rolling ocean swell and steady trade winds building a purposeful day under way. Montserrat appears gradually, its northern ridges green while the southern half is marked by the scar of the Soufrière Hills volcano and exclusion zones ashore. Approaching the authorised anchorage on the northwest coast, depths fall steadily over sand and rubble with dramatic views of the volcanic flanks inland.

Daily Highlights:

• Full day passage across open sea between Nevis and Montserrat
• Offshore views of the active volcanic summit and exclusion area
• Late afternoon arrival and secure anchoring on the northwest coast
• Quiet evening watching steam and cloud drift over the crater

From Montserrat, shape a course north or north east toward Antigua, often with a quartering sea and the island’s profile rising ahead as a low, indented coastline. Entering the wide bay of Jolly Harbour, the sea state calms behind the outer reefs and low headlands, leading into a full service marina and nearby anchorage fields. This is one of Antigua’s main yachting hubs, with sheltered water and straightforward access to shore services.

Daily Highlights:

• Open water leg from a remote volcano island to a major sailing centre
• Landfall on Antigua’s west coast with its sequence of coves and beaches
• Secure berth or anchorage at Jolly Harbour with provisioning and marina facilities
• Evening stroll along the waterfront or dinner ashore

Leave Jolly Harbour and track north along the coast through shallow, generally protected water that reveals sand bars and reefs off the points. Deep Bay opens as a narrow inlet with steep sides, good sand holding and the wreck of the Andes lying in the middle at snorkelling depth. The surrounding headland carries the ruins of Fort Barrington, giving an elevated vantage over the anchorage and the entrance to Saint Johns.

Daily Highlights:

• Short, relaxed coastal passage with time to stop in a cove along the way
• Snorkelling on the Andes wreck in clear, protected water
• Walk up to Fort Barrington for views over the bay and western coastline
• Overnight at anchor in one of Antigua’s classic small harbours

From Deep Bay, continue north along the shore past Fort James and the approaches to Saint Johns, then curve into the open arc of Dickenson Bay. The bay offers a long sandy beach, several offshore islets and a coral reef set just beyond the anchorage, with depths that remain comfortable for anchoring close to shore. This is a livelier stop, with water sports and shore venues lining part of the beach while still leaving quieter corners for the yacht.

Daily Highlights:

• Coastline run past the entrance to Saint Johns
• Anchor off Dickenson Bay’s main beach for easy tender access
• Option for water sports and shore dining
• Late afternoon swim with the reef and small islands as a backdrop

Head north from Antigua into more open sea, with the low outline of Barbuda appearing slowly as you close the island across its surrounding banks. The west coast is a near continuous stretch of pale sand with few buildings, protected offshore by reefs that leave a calm strip of water for anchoring in settled conditions. Entry demands attention to depth and colour changes, but rewards with one of the region’s most spacious and undeveloped anchorages.

Daily Highlights:

• Satisfying day passage across the channel between Antigua and Barbuda
• Arrival off a long, lightly populated beach with wide anchor room
• Swimming and snorkelling over sand and patches of coral in clear water
• Dinner on board or a simple lobster meal ashore where available

Depart the west coast of Barbuda and run south toward the more rugged eastern side of Antigua, aiming for Nonsuch Bay and Green Island. The approach passes reef lines and outer breakers before entering the more sheltered waters behind Antigua’s eastern barrier reef. Green Island is uninhabited, with several anchor pockets over sand and good protection from the prevailing trades, making it a favourite among crews seeking a quieter, nature focused stop.

Daily Highlights:

• Open sea return to Antigua with a different coastal character from the west side
• Careful pilotage into Nonsuch Bay and the channels around Green Island
• Snorkelling in clear water with reef and sea grass habitats
• Evening at anchor in a remote feeling setting, despite being close to Antigua

From Green Island, follow the south east coast of Antigua, where cliffs and coves alternate before the entrance to English Harbour opens as a narrow cut leading into a well protected natural harbour. Inside, Nelson’s Dockyard presents restored eighteenth century naval buildings around a basin that remains a major Caribbean yachting centre. The harbour offers excellent shelter, shore facilities and the sense of arriving at a historic end point for the voyage.

Daily Highlights:

• Short, scenic run along Antigua’s south coast
• Entry into one of the Caribbean’s most storied natural harbours
• Berth or anchor with easy access to Nelsons Dockyard, trails and viewpoints such as Shirley Heights
• Final dinner ashore or on board, reflecting on the full Saint Kitts to Antigua passage

Keep the yacht based in English Harbour for a final day to explore its maritime and cultural setting without further repositioning. Ashore, the dockyard museums, restored workshops and hillside trails give context to Antigua’s long sailing heritage, while nearby Falmouth Harbour provides additional yacht watching and shore venues. The lay day also allows for unhurried handover, logistics and a measured close to the itinerary.

Daily Highlights:

• Dockyard history and shoreline walks
• Optional short sail or tender run to nearby coves
• Time for final provisioning or relaxation on board
• Departure preparations carried out at a calm, fully serviced base