Barbados Cruise from Bridgetown to Oranjestad — 16 Days

15 nights · Barbados · Departs Bridgetown (Barbados) · Visiting Les Anses d'Arlet, Pigeon Island, Castries, Mayreau Island, St Georges Grenada, Bequia Island, Scarborough, Willemstad Curacao, Oranjestad Aruba · Aboard Windstar Cruises on the Star Legend

Windstar Cruises logo
Cruise lineWindstar Cruises
ShipStar Legend
Duration15 nights
Port calls10
Departures1 sailings
From fare$5,987 per person
Year built1992
Guests343
Cabins156
Crew190
Length159 m
Beam19 m
Cruising speed15.0 kn
  1. Day 1

    Bridgetown, Barbados

    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.

  2. Day 2

    Les Anses d'Arlet, Martinique

    Les Anses-d’Arlet is a fishing village on Martinique’s Caribbean coast, where the church of Saint-Henri faces the sea. Come ashore for clear water, a wooden pier and a village still rooted in island life. Grande Anse offers a broad beach, while nearby Anse Dufour is known for snorkeling and sea turtles. Creole cafés and a scenic coastal road make this a fine place to slow down and explore Martinique’s south.

  3. Day 3

    Pigeon Island

    Pigeon Island is more than a beach stop: this 44-acre national landmark joins Saint Lucia’s history to its northwest coast. Walk the causeway, then climb to Fort Rodney, where British guns once guarded the channel against French attack. From Signal Peak, the view sweeps across Rodney Bay and the Caribbean toward Martinique. Afterward, swim at one of the island’s small beaches or visit the museum in its restored military buildings.

  4. Day 4

    Castries

    Castries brings Saint Lucia’s capital close to the water, with cruise ships entering a sheltered harbor beneath green hills. Start at the lively Castries Market, where vendors sell spices, produce, and local crafts. Nearby, the Cathedral of the Immaculate Conception and Derek Walcott Square offer a quieter glimpse of the city’s past. For island views, visit Morne Fortune; for a beach day, arrange transport beyond town.

  5. Day 5

    Mayreau Island

    Mayreau is one of the Grenadines’ smallest inhabited islands, with a village reached by a steep road from the shore. Its appeal is quiet beaches, clear water and Salt Whistle Bay, a sheltered crescent popular with sailors. Walk uphill to the compact settlement and its Catholic church, then look across the neighboring Grenadines. For a day ashore, Mayreau rewards unhurried exploration rather than a packed itinerary.

  6. Day 6

    St Georges Grenada, Grenada

    St George’s is one of the Caribbean’s most handsome harbour towns, its pastel waterfront curving around a horseshoe-shaped bay. Walk the Carenage, where fishing boats and yachts share the water beneath Fort George. Grand Anse Beach lies a short drive south, with clear water and a long sweep of sand. In town, market stalls sell nutmeg, cocoa and cinnamon, helping earn Grenada its title, the Spice Isle.

  7. Day 7

    Bequia Island

    Port Elizabeth sits on Bequia’s Admiralty Bay, where fishing boats and yachts share a sheltered anchorage. Step ashore into a compact waterfront of cafés and shops, then follow the Belmont Walkway towards Princess Margaret Beach. Bequia’s boatbuilding tradition remains visible in its working yards and local craft. Come for unhurried island life, swimming in clear water and views across the Grenadines.

  8. Day 8

    Bridgetown, Barbados

    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.

  9. Day 9

    Pigeon Island

    Pigeon Island is more than a beach stop: this 44-acre national landmark joins Saint Lucia’s history to its northwest coast. Walk the causeway, then climb to Fort Rodney, where British guns once guarded the channel against French attack. From Signal Peak, the view sweeps across Rodney Bay and the Caribbean toward Martinique. Afterward, swim at one of the island’s small beaches or visit the museum in its restored military buildings.

  10. Day 10

    Scarborough

    Scarborough is Tobago’s capital, a busy port town with a market, local shops and views across the water. Begin at Fort King George, high above town, for broad sea views and a small museum tracing Tobago’s layered past. Then browse the central market or take a short drive to Store Bay, known for calm water and local food. Scarborough rewards travelers who want history and everyday Tobago before heading for the island’s beaches.

  11. Day 11

    Bequia Island

    Port Elizabeth sits on Bequia’s Admiralty Bay, where fishing boats and yachts share a sheltered anchorage. Step ashore into a compact waterfront of cafés and shops, then follow the Belmont Walkway towards Princess Margaret Beach. Bequia’s boatbuilding tradition remains visible in its working yards and local craft. Come for unhurried island life, swimming in clear water and views across the Grenadines.

  12. Day 12

    Mayreau Island

    Mayreau is one of the Grenadines’ smallest inhabited islands, with a village reached by a steep road from the shore. Its appeal is quiet beaches, clear water and Salt Whistle Bay, a sheltered crescent popular with sailors. Walk uphill to the compact settlement and its Catholic church, then look across the neighboring Grenadines. For a day ashore, Mayreau rewards unhurried exploration rather than a packed itinerary.

  13. Day 13

    St Georges Grenada, Grenada

    St George’s is one of the Caribbean’s most handsome harbour towns, its pastel waterfront curving around a horseshoe-shaped bay. Walk the Carenage, where fishing boats and yachts share the water beneath Fort George. Grand Anse Beach lies a short drive south, with clear water and a long sweep of sand. In town, market stalls sell nutmeg, cocoa and cinnamon, helping earn Grenada its title, the Spice Isle.

  14. Day 15

    Willemstad Curacao, Netherlands

    Willemstad is one of the Caribbean’s most distinctive ports, built around the deep inlet of St. Anna Bay. Punda and Otrobanda showcase Dutch colonial architecture and form part of the city’s UNESCO-listed historic area. Walk across the Queen Emma Bridge, a floating pontoon span linking the two districts. Beyond the harbor, Curaçao offers sheltered coves, clear water and beaches for an unhurried afternoon.

  15. Day 16

    Oranjestad Aruba, Netherlands

    Oranjestad makes a striking first impression: Dutch gables in Caribbean colors line streets beside a busy harbor. Beyond the waterfront, the capital’s compact center rewards a walk, with shops, cafés and landmarks including Fort Zoutman. Aruba’s dry, sunlit landscape feels close at hand, while beaches and clear water are an easy ride away. Come ashore for a relaxed city stroll, then choose whether to linger over lunch or head for the coast.

Star Legend Cruises

Published August 16, 2026
Last updated October 3, 2026
Author: J. Richard


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