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Leeward Islands Explorer

St Martin to St Martin

Feb 21st to February 28th 2026 / Duration 7 Days

350 Nautical Miles

PN032026

$4,250

Bunks Available: 2

Passage summary

This passage is designed as a relaxed, daylight cruising and exploration experience, offering a comprehensive tour of the Leeward Islands. Starting and ending in Sint Maarten, the route includes planned stops at Saba or St. Eustatius, St. Kitts and Nevis, and possibly Montserrat. The itinerary emphasizes coastal island navigation, daytime sailing, and time ashore to experience the unique culture and sights of each island. The schedule includes one overnight passage on the final leg back to Sint Maarten, providing an introduction to night sailing under manageable conditions. This trip is ideal for sailors interested in hands-on coastal cruising and those seeking a balance of sailing and island exploration by sea.

Leeward Islands Explorer

Route Overview

 

Departure: Sint Maarten

 


Primary Possible Route:

Sint Maarten – Saba – St. Eustatius – St. Kitts – Nevis – Montserrat – Sint Maarten

 

Estimated Distance:

250–300 nautical miles, depending on exact anchorages and routing

    • Key Points: Daytime coastal hops between islands, time allocated for local exploration, one overnight passage on the return to Sint Maarten

 

 

Passage Breakdown

 

Sint Maarten to Saba

  • Crew briefing and vessel checks in Sint Maarten prior to departure

  • Short sail to Saba with anchoring and opportunity for shore excursions

 

Down the Chain (Leeward Islands)

  • Day sails from Saba to St. Eustatius, then onward to St. Kitts, Nevis, and Montserrat

  • Each leg planned to arrive in the afternoon or early evening to allow time ashore

  • Flexible itinerary accommodates local conditions and client interest

  • Shore time includes options for local sightseeing, dining, and exploring island communities

 

Final Leg: Montserrat to Sint Maarten

  • One overnight passage back to Sint Maarten

  • Night watch rotation established for this final leg

  • Arrival and trip wrap-up in Sint Maarten

 

Training Focus

  • Coastal navigation: route planning, waypoints, and visual piloting

  • Chartplotter, radar, AIS, and paper chart skills in short- and medium-range passages

  • Docking, anchoring, and tender operations at various island harbors

  • Crew coordination for frequent arrivals and departures

  • Introduction to night sailing and overnight watch routines on the final passage

  • Safety procedures, local regulations, and customs protocols at each stop

 

Expected Conditions

Winds: Predominantly E–ESE, 12–20 knots typical for late February, lighter than deep trade wind offshore routes
Seas: 3–6 feet in open channels, generally moderate with some wind chop between islands
Weather: Warm and mostly dry, with isolated squalls possible, high visibility, comfortable sailing conditions throughout
Hazards: Local ferries, small craft, anchoring considerations at less-developed harbors, occasional strong currents in channels

 

Why This Passage is Relevant

 

  • Offers experience in coastal navigation, day sailing, and multi-island cruising

  • Combines hands-on sailing with meaningful time ashore for  exploration

  • Features a single overnight leg, providing a manageable introduction to night passage-making

  • Suited for sailors interested in both adventure and relaxation, with a flexible daily schedule

 

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