23 nights · Barbados · Departs Bridgetown (Barbados) · Visiting Funchal, Porto Santo Island Madeira, Casablanca, Lisbon, Cadiz, Gibraltar, Malaga, Cartagena Spain, Palma de Mallorca, Barcelona · Aboard Windstar Cruises on the Star Legend
Image courtesy of Windstar Cruises ©
| Cruise line | Windstar Cruises |
|---|---|
| Ship | Star Legend |
| Duration | 23 nights |
| Port calls | 11 |
| Departures | 1 sailings |
| From fare | $5,815 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.
Cádiz is one of Europe’s oldest continuously inhabited cities, set on a narrow peninsula where Atlantic light reaches every street. Its compact old quarter is made for unhurried exploration, with watchtowers, shaded plazas and the cathedral’s golden dome. At the Mercado Central, fishmongers display the day’s catch; nearby taverns serve fino sherry and local seafood. Beyond the walls, La Caleta beach and the seafront promenade offer a bracing taste of Cádiz’s maritime life.
Gibraltar stands at the southern tip of the Iberian Peninsula, looking across the Strait towards Morocco. The Rock rises above a compact town shaped by British, Spanish and Mediterranean influences. A taxi tour of the Upper Rock Nature Reserve brings far-reaching views and close encounters with Barbary macaques. Below, explore the Great Siege Tunnels and Moorish Castle, then browse Main Street’s shops and cafés.
Málaga is more than a gateway to Andalusia; it is a port city with a confident life of its own. In the old centre, the Roman Theatre sits below the Moorish Alcazaba, while the cathedral rises above nearby streets. Visit the Picasso Museum or his birthplace, then try grilled sardines and local wine at a pavement table. The Mediterranean is close: city beaches, Atarazanas Market and palm-lined promenades make lingering easy.
Cartagena rewards visitors who look beyond its busy harbor. Founded by the Carthaginians in 227 BC, this compact port city carries layers of Roman, military, and maritime history. Follow the waterfront to the Roman Theatre, uncovered in 1988 and now paired with a museum. Explore the old quarter’s elegant Modernista buildings and naval landmarks. Cartagena is easy to navigate, yet rich enough to hold your attention all day.
Palma rewards an unhurried first walk. From the waterfront, the Gothic towers of La Seu rise above the old city, a landmark shaped over centuries. Inside, soaring columns and Antoni Gaudí’s modernist contributions add a striking note. Beyond the cathedral, lanes lead to shaded courtyards, shops and cafés serving local ensaimada. For a wider view, take a taxi to Bellver Castle, whose circular form overlooks the bay.
Barcelona is a Mediterranean port city built on Roman foundations, with Gothic lanes and striking modernist architecture. La Rambla runs from Plaça de Catalunya towards the waterfront and the old town. Gaudí’s Sagrada Família and Park Güell show the city at its most distinctive. Set aside time for a market lunch and a walk through El Born, where medieval streets meet lively cafés. Barcelona’s beaches offer a welcome pause between visits.
Published September 4, 2026
Last updated October 3, 2026
Author: J. Richard
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