15 nights · Barbados · Departs Bridgetown (Barbados) · Visiting Funchal, Porto Santo Island Madeira, Casablanca, Lisbon · Aboard Windstar Cruises on the Star Legend
Image courtesy of Windstar Cruises ©
| Cruise line | Windstar Cruises |
|---|---|
| Ship | Star Legend |
| Duration | 15 nights |
| Port calls | 5 |
| Departures | 1 sailings |
| From fare | $2,946 per person |
| Year built | 1992 |
| Guests | 343 |
| Cabins | 156 |
| Crew | 190 |
| Length | 159 m |
| Beam | 19 m |
| Cruising speed | 15.0 kn |
Bridgetown rewards travelers who leave the ship and walk into Barbados’ compact capital. Its UNESCO-listed Historic Bridgetown and Garrison trace the island’s colonial history; Broad Street offers a lively glimpse of daily life. Pause beside the Careenage, where boats thread the old harbour, then browse shops for local rum and Bajan crafts. Carlisle Bay’s pale sand and clear water lie just beyond the city.
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.
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.
Casablanca is Morocco’s commercial capital, where Atlantic breezes meet broad boulevards and a lively medina. Begin at the Hassan II Mosque, whose vast prayer hall and soaring minaret stand beside the ocean. Then explore the French-era Art Deco centre, or browse the lanes of the Habous quarter for pastries, crafts and bookshops. Casablanca rewards curiosity with a modern Morocco shaped by trade, architecture and daily life.
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.
Published September 8, 2026
Last updated October 3, 2026
Author: J. Richard
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