Portugal Cruise from Lisbon to Philipsburg — 16 Days

15 nights · Portugal · Departs Lisbon (Portugal) · Visiting Funchal, Jost Van Dyke Island BVI, Philipsburg St Maarten · Aboard Windstar Cruises on the Wind Surf

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

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Cruise lineWindstar Cruises
ShipWind Surf
Duration15 nights
Port calls4
Departures1 sailings
From fare$2,580 per person
Year built1990
Guests376
Cabins171
Crew178
Length187 m
Beam20 m
Cruising speed15.0 kn
  1. Day 1

    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.

  2. Day 4

    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 15

    Jost Van Dyke Island BVI

    Cruz Bay is St. John’s harbor town, where ferries, cafés and island roads meet. From here, much of the island opens quickly: Virgin Islands National Park protects roughly two-thirds of St. John. Follow North Shore Road to white-sand beaches and clear water, or visit the sugar plantation ruins at Annaberg. Back in town, browse the shops at Mongoose Junction, then choose a waterfront table for dinner.

  4. Day 16

    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.

Wind Surf Cruises

Published August 29, 2026
Last updated October 3, 2026
Author: J. Richard

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