Netherlands Antilles Cruise from Philipsburg to Lisbon — 16 Days

15 nights · Netherlands Antilles · Departs Philipsburg St Maarten (Netherlands) · Visiting Funchal, Porto Santo Island Madeira, Lisbon · Aboard Windstar Cruises on the Wind Surf

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st martin of tours roman catholic church Funchal (Madeira) Cruise Port: Shore Excursions & Expert Guide Porto Santo Island Cruise Port Lisbon Cruise Port: Shore Excursions & Expert Expert Guide

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Cruise lineWindstar Cruises
ShipWind Surf
Duration15 nights
Port calls4
Departures2 sailings
From fare$2,580 per person
Year built1990
Guests376
Cabins171
Crew178
Length187 m
Beam20 m
Cruising speed15.0 kn
  1. Day 1

    Philipsburg St Maarten, Netherlands

    Philipsburg rewards a shore day spent beyond the cruise terminal. It sits on a narrow strip between Great Bay and the Great Salt Pond. The Dutch-side capital is compact and easy to explore on foot. Front Street pairs duty-free shops with the 1793 courthouse, while the Boardwalk follows Great Bay Beach. Cross the open border into French Saint-Martin for French bakeries, lively markets and another stretch of coast.

  2. Day 12

    Funchal, Portugal

    Funchal sits in a broad, sunlit amphitheatre above Madeira’s deep Atlantic harbour. Its compact centre rewards exploration, from the Old Town’s painted doors to the cathedral’s carved cedar ceiling. Ride the cable car uphill to Monte for sweeping views, then descend through gardens or by traditional wicker toboggan. Madeira’s wines and market produce offer a taste of the island before your ship sails.

  3. Day 13

    Porto Santo Island Madeira, Portugal

    Porto Santo rewards travellers who prefer substance to spectacle. Set in Madeira’s Atlantic archipelago, this small island is known for a remarkable nine-kilometre sweep of golden sand. Vila Baleira, its compact main town, offers cafés, a harbour and the house associated with Christopher Columbus. Beyond the beach, volcanic hills and dry, open landscapes invite unhurried walks and island-wide views. Come for clean horizons, long swims and a gentler pace than Madeira’s livelier resorts.

  4. Day 16

    Lisbon, Portugal

    Lisbon is a city best approached with time and comfortable shoes. Its seven hills rise above the Tagus, linking tiled lanes, grand squares and viewpoints with wide river views. In Alfama, narrow streets preserve the feel of old Lisbon. In Belém, the Jerónimos Monastery and Tower recall Portugal’s age of discovery. Pause for coffee and a warm pastel de nata between sights.

Wind Surf Cruises

Published August 11, 2026
Last updated October 3, 2026
Author: J. Richard

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