Puerto Rico Cruise from San Juan — 12 Days

11 nights · Puerto Rico · Departs San Juan · Visiting St John Island USVI, Gustavia St Barths, Basseterre St Kitts, Falmouth Antigua, Iles des Saintes, Pigeon Island, St Georges Grenada, Jost Van Dyke Island BVI, Virgin Gorda Island BVI · Aboard Windstar Cruises on the Star Pride

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Star Pride
coastal cityscape historic fort Cruz Bay Cruise Port Gustavia Cruise Port Basseterre Cruise Port
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Image courtesy of Windstar Cruises ©

Cruise lineWindstar Cruises
ShipStar Pride
Duration11 nights
Port calls10
From fare$5,778 per person
Year built1988
Guests343
Cabins156
Crew190
Length159 m
Beam19 m
Cruising speed15.0 kn
  1. Day 1

    San Juan

    San Juan puts a remarkable piece of Caribbean history within easy reach of your ship. Founded in 1521, Old San Juan is a compact district of blue cobbles, pastel façades and Spanish colonial landmarks. Walk its steep lanes to El Morro, the 16th-century fortress that guards the harbor. From its ramparts, the Atlantic comes into view. Beyond the old walls, cafés, galleries and contemporary restaurants show a city still shaped by its maritime past.

  2. Day 2

    St John Island USVI

    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.

  3. Day 3

    Gustavia St Barths, France

    Gustavia makes a polished first impression, but its appeal is more than designer boutiques and superyachts. Swedish rule left its mark in the town’s name and the ruins of Fort Gustav above the harbor. From the waterfront, cafés, galleries and shops sit within easy walking distance, while Shell Beach lies just beyond the center. Come ashore for French-Caribbean style, with history close at hand.

  4. Day 4

    Basseterre St Kitts

    Begin in Basseterre, St Kitts’s compact capital, where Georgian buildings and busy market streets reveal the island’s layered past. At Independence Square, once a slave market, pause among mature trees before browsing nearby shops and cafés. Then leave town for Mount Liamuiga’s volcanic slopes, former sugar estates and beaches of dark volcanic sand. Brimstone Hill Fortress, a UNESCO World Heritage site, rewards the drive with stone ramparts and wide Caribbean views.

  5. Day 5

    Falmouth Antigua

    Falmouth sits on Antigua’s sheltered south coast, where two deep natural harbours draw yachts from around the world. A short journey brings you to Nelson’s Dockyard, the restored Georgian naval base and UNESCO World Heritage site. Walk its stone lanes, browse the marina, then climb to Shirley Heights for a sweeping view over English Harbour. Beyond the historic waterfront, Antigua’s coves and pale-sand beaches invite an easy afternoon by the sea.

  6. Day 6

    Iles des Saintes, Guadeloupe

    The Îles des Saintes reward visitors who prefer a quieter Caribbean. Most calls centre on Terre-de-Haut, where pastel houses, fishing boats and cafés line a compact waterfront. Above town, Fort Napoléon surveys one of the world’s most beautiful bays and houses a small museum and botanical garden. Rent a scooter or walk to Pain de Sucre, a sheltered beach with clear water and good snorkeling. Try the island’s famed tourment d’amour, a coconut-filled pastry, before returning to the harbor.

  7. Day 7

    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.

  8. Day 8

    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.

  9. Day 10

    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.

  10. Day 11

    Virgin Gorda Island BVI

    Virgin Gorda swaps city bustle for clear water, quiet coves and a dramatic coastline. At The Baths, granite boulders form a maze of sea pools and narrow passages beside the beach. Some routes involve ladders and slippery rocks, so wear shoes with grip. Spanish Town is the island’s main settlement; North Sound is known for sheltered anchorages and sailing. Go early to explore The Baths before the busiest hours, then cool off in the Caribbean.

  11. Day 12

    San Juan

    San Juan puts a remarkable piece of Caribbean history within easy reach of your ship. Founded in 1521, Old San Juan is a compact district of blue cobbles, pastel façades and Spanish colonial landmarks. Walk its steep lanes to El Morro, the 16th-century fortress that guards the harbor. From its ramparts, the Atlantic comes into view. Beyond the old walls, cafés, galleries and contemporary restaurants show a city still shaped by its maritime past.

Star Pride Cruises

Published August 27, 2026
Last updated October 29, 2026
Author: J. Richard

Cruise Disclosure

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