14 nights · Puerto Rico · Departs San Juan · Visiting St Georges Grenada, Bequia Island, Mayreau Island, Iles des Saintes, Marigot, Catalina Island, Santo Domingo, Cartagena Colombia, San Blas Islands Panama, Colon · Aboard Windstar Cruises on the Star Pride
Image courtesy of Windstar Cruises ©
| Cruise line | Windstar Cruises |
|---|---|
| Ship | Star Pride |
| Duration | 14 nights |
| Port calls | 11 |
| Departures | 1 sailings |
| From fare | $3,875 per person |
| Year built | 1988 |
| Guests | 343 |
| Cabins | 156 |
| Crew | 190 |
| Length | 159 m |
| Beam | 19 m |
| Cruising speed | 15.0 kn |
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.
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.
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.
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.
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.
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.
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.
Arrive in La Romana, where the Dominican Republic’s sugar coast meets one of the Caribbean’s most polished resort enclaves. Casa de Campo’s golf courses and marina are nearby. Altos de Chavón, a 16th-century-style village, overlooks the Chavón River. Further east, Bayahibe offers boat trips to Saona Island and its protected beaches. Choose La Romana for a day that moves from elegant leisure to coastal wilderness.
Step ashore in Santo Domingo, where the New World’s history is written in streets you can still walk. Founded by Europeans in 1498, it is the oldest continuously inhabited European-established city in the Americas. In the UNESCO-listed Colonial Zone, visit the first cathedral in the Americas, the Alcázar de Colón, and Ozama Fortress. Then trade stone lanes for a waterfront meal or the capital’s lively cafés.
A short ride from Cartagena’s cruise port brings you to its UNESCO-listed historic centre and handsome colonial streets. Inside the old walls, flower-draped balconies, shaded plazas and broad stone lanes lead to cafés, churches and lively markets. Visit Castillo San Felipe de Barajas, the great fortress built to defend the harbor, then explore colorful Getsemaní. Come early, before the midday heat settles over the plazas, and save time for a cool drink beside the Caribbean.
San Blas is no conventional cruise port. More than 300 islands and cays fringe Panama’s Caribbean coast. Here, clear water and white-sand beaches meet Guna Yala, an Indigenous territory with a distinct culture. Choose a boat outing for reef snorkeling, or visit a Guna community and discover mola textiles, sewn by Guna women. Access and transport require advance planning, typically through a local operator or community.
Colón puts you at Panama’s Caribbean gateway, where the Atlantic meets the Panama Canal. At Agua Clara Locks, watch ships pass through the expanded canal toward Gatun Lake. Nearby, Portobelo and San Lorenzo preserve Spanish colonial fortifications built to guard Caribbean trade routes. Colón is best approached as a gateway, with its strongest draws found in the canal, historic coast and surrounding rainforest.
Published September 28, 2026
Last updated October 3, 2026
Author: J. Richard
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