21 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, Panama Canal, Panama City, Isla Gamez Panama, Golfito, Quepos, Puntarenas · Aboard Windstar Cruises on the Star Pride
Image courtesy of Windstar Cruises ©
| Cruise line | Windstar Cruises |
|---|---|
| Ship | Star Pride |
| Duration | 21 nights |
| Port calls | 17 |
| Departures | 1 sailings |
| From fare | $6,417 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.
Few journeys change your sense of scale like a passage through the Panama Canal. This 50-mile waterway links the Atlantic and Pacific, lifting ships through locks and across Gatun Lake. Watch the gates close, water rise, and a vast vessel move within inches of concrete walls. On deck, the engineering is the spectacle; beyond it, rainforest edges the route. Bring binoculars, and stay outside for the crossing.
Balboa sits at the Pacific entrance to the Panama Canal, where ocean-going ships begin their passage between continents. From the port, Panama City’s skyline rises beyond the canal’s working waters. Visit Casco Viejo for restored colonial streets, independent cafés and views across the bay. Or follow the Amador Causeway toward the Biomuseo and sweeping views of ships awaiting transit. Balboa rewards travelers who look beyond the canal to a capital shaped by trade, history and the sea.
Isla Gámez lies in Panama’s Gulf of Chiriquí, reached by boat from Boca Chica. Within the Gulf of Chiriquí National Marine Park, it offers a quieter encounter with Panama’s Pacific coast. Expect a palm-fringed shore, warm water and opportunities to snorkel among coral and tropical fish. Bring sun protection; shade and facilities can be limited. Swim, stroll the beach and enjoy a pause in this island seascape.
Golfito lies between the forested slopes and sheltered waters of Golfo Dulce, on Costa Rica’s southern Pacific coast. The town grew around a banana port built by the United Fruit Company in the 1930s. Boat trips cross the gulf, with chances to see dolphins, sea turtles and migrating whales. Inland, steep green hills lead toward Piedras Blancas National Park and its rainforest.
Quepos puts Costa Rica’s central Pacific within easy reach. The town grew around its harbor and remains a working gateway to sport fishing, coastal excursions and rainforest. Manuel Antonio National Park lies just south, where forest trails descend toward white-sand coves and Pacific waters. Browse the marina, sample fresh seafood or watch afternoon light settle over the bay. Bring swimwear, walking shoes and time to linger.
Step ashore in Puntarenas, Costa Rica’s long, narrow port city on the Pacific coast. From here, rainforest reserves, coffee country and the Nicoya Peninsula lie within reach. Walk the waterfront promenade for seafood and views across the Gulf of Nicoya. Or head inland to Monteverde’s cloud forest. Plan one excursion and allow time for the road; Puntarenas is best enjoyed at an unhurried pace.
Published September 21, 2026
Last updated October 3, 2026
Author: J. Richard
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