We are open today until 6:30 pm. Call 020 7590 0610

Star Collector: Windward Islands, Spanish Cities & Costa Rica

Summary

Begin among the Windward Islands, sailing into St. George’s, Bequia, Mayreau, and Les Saintes, where coral-rich waters, quiet anchorages, and easygoing beaches set the tone for the opening days of your journey. Continue on toward Isla Catalina, Santo Domingo, and an overnight in Cartagena, exploring colonial plazas, sea-worn fortifications, and offshore islands known for excellent snorkeling and diving. From the San Blas Islands to Colón, the route carries you through remote stretches of coastline before your daylight transit of the Panama Canal offers a rare, close-up perspective. The voyage concludes along Costa Rica’s Pacific shore, with time in Isla Parida, Golfito, Puerto Jiménez, and Quepos—places where rainforest trails, calm bays, and abundant wildlife reward unhurried exploration.

Cruise line Windstar Cruises

Ship Star Pride

Duration 21 nights

Type Ocean Cruise

Regions Europe,
Southern Europe,
Mediterranean

Itinerary & Map

San Juan (Puerto Rico) → Puerto Caldera 22 days · 18 ports · 1 sea day
Day 1 San Juan (Puerto Rico) Embark

If you associate Puerto Rico's capital with the colonial streets of Old San Juan, then you know only part of the picture. San Juan is a major metropolis, radiat...

Full description
Day 3 Saint George's

Nutmeg, cinnamon, cloves, cocoa those heady aromas fill the air in Grenada (pronounced gruh-nay-da). Only 21 miles (33½ km) long and 12 miles (19½ km) wide, the...

Full description
Day 4 Port Elizabeth, Bequia

Bequia is a Carib word meaning "island of the cloud." Hilly and green with several golden-sand beaches, Bequia is 9 miles (14½ km) south of St. Vincent's southw...

Full description
Day 5 Mayreau Island

The small island of Mayreau, just one and 1/2 square miles in area (3.9 square kilometres) is the smallest inhabited island of The Grenadines, and is part of th...

Full description
Day 6 Terre-de-Haut
Day 7 Marigot

French and Dutch have lived side by side on St. Maarten/St. Martin for hundreds of years—with no border patrols or customs between them. The French side has a m...

Full description
Day 8 San Juan (Puerto Rico)

If you associate Puerto Rico's capital with the colonial streets of Old San Juan, then you know only part of the picture. San Juan is a major metropolis, radiat...

Full description
Day 9 Isla Catalana
Day 10 Santo Domingo

Santo Domingo is the capital of the Dominican Republic and one of the Caribbean's oldest cities. Its walled, cobblestoned historic core, the Zona Colonial, has...

Full description
Day 12 Cartagena Overnight

Cartagena's magnificent city walls and fortresses, now a UNESCO World Heritage Site, enclose a well-restored historic center (the Cuidad Amurallada, or walled c...

Full description
Day 13 Cartagena

Cartagena's magnificent city walls and fortresses, now a UNESCO World Heritage Site, enclose a well-restored historic center (the Cuidad Amurallada, or walled c...

Full description
Day 14 San Blas Islands

The San Blas archipelago is located off the Caribbean coast, east of Colon, and is made up of 365 islands that range in size from tiny ones with a few coconut p...

Full description
Day 15 Colón

The provincial capital of Colón, beside the canal's Atlantic entrance, is named for the Spanish-language surname of Christopher Columbus, though the Americans c...

Full description
Day 16 At Sea and Fuerte Amador
Day 17 Fuerte Amador
Day 19 Isla Parida
Day 20 Golfo Dulce

Wild, scenic and incredibly bio-diverse, Golfo Dulce is not on most tourists itineraries. The name, says it all, Golfo Dulce or sweet gulf, in English. After a...

Full description
Day 21 Quepos (Puerto Quepos)

Quepos allows tourists to experience a once in a lifetime nature experience in Manuel Antonio National Park without leaving any of the familiar amenities behind...

Full description
Day 22 Puerto Caldera Disembark
Scroll for all 22 days
Route overview map
Day 1 San Juan (Puerto Rico) Embark

If you associate Puerto Rico's capital with the colonial streets of Old San Juan, then you know only part of the picture. San Juan is a major metropolis, radiat...

Full description
Day 3 Saint George's

Nutmeg, cinnamon, cloves, cocoa those heady aromas fill the air in Grenada (pronounced gruh-nay-da). Only 21 miles (33½ km) long and 12 miles (19½ km) wide, the...

Full description
Day 4 Port Elizabeth, Bequia

Bequia is a Carib word meaning "island of the cloud." Hilly and green with several golden-sand beaches, Bequia is 9 miles (14½ km) south of St. Vincent's southw...

Full description
Day 5 Mayreau Island

The small island of Mayreau, just one and 1/2 square miles in area (3.9 square kilometres) is the smallest inhabited island of The Grenadines, and is part of th...

Full description
Day 6 Terre-de-Haut
Day 7 Marigot

French and Dutch have lived side by side on St. Maarten/St. Martin for hundreds of years—with no border patrols or customs between them. The French side has a m...

Full description
Day 8 San Juan (Puerto Rico)

If you associate Puerto Rico's capital with the colonial streets of Old San Juan, then you know only part of the picture. San Juan is a major metropolis, radiat...

Full description
Day 9 Isla Catalana
Day 10 Santo Domingo

Santo Domingo is the capital of the Dominican Republic and one of the Caribbean's oldest cities. Its walled, cobblestoned historic core, the Zona Colonial, has...

Full description
Day 12 Cartagena Overnight

Cartagena's magnificent city walls and fortresses, now a UNESCO World Heritage Site, enclose a well-restored historic center (the Cuidad Amurallada, or walled c...

Full description
Day 13 Cartagena

Cartagena's magnificent city walls and fortresses, now a UNESCO World Heritage Site, enclose a well-restored historic center (the Cuidad Amurallada, or walled c...

Full description
Day 14 San Blas Islands

The San Blas archipelago is located off the Caribbean coast, east of Colon, and is made up of 365 islands that range in size from tiny ones with a few coconut p...

Full description
Day 15 Colón

The provincial capital of Colón, beside the canal's Atlantic entrance, is named for the Spanish-language surname of Christopher Columbus, though the Americans c...

Full description
Day 16 At Sea and Fuerte Amador
Day 17 Fuerte Amador
Day 19 Isla Parida
Day 20 Golfo Dulce

Wild, scenic and incredibly bio-diverse, Golfo Dulce is not on most tourists itineraries. The name, says it all, Golfo Dulce or sweet gulf, in English. After a...

Full description
Day 21 Quepos (Puerto Quepos)

Quepos allows tourists to experience a once in a lifetime nature experience in Manuel Antonio National Park without leaving any of the familiar amenities behind...

Full description
Day 22 Puerto Caldera Disembark

San Juan (Puerto Rico)

If you associate Puerto Rico's capital with the colonial streets of Old San Juan, then you know only part of the picture. San Juan is a major metropolis, radiating out from the bay on the Atlantic Ocean that was discovered by Juan Ponce de León. More than a third of the island's nearly 4 million citizens proudly call themselves sanjuaneros. The city may be rooted in the past, but it has its eye on the future. Locals go about their business surrounded by colonial architecture and towering modern structures.By 1508 the explorer Juan Ponce de León had established a colony in an area now known as Caparra, southeast of present-day San Juan. He later moved the settlement north to a more hospitable peninsular location. In 1521, after he became the first colonial governor, Ponce de León switched the name of the island—which was then called San Juan Bautista in honor of St. John the Baptist—with that of the settlement of Puerto Rico ("rich port").Defended by the imposing Castillo San Felipe del Morro (El Morro) and Castillo San Cristóbal, Puerto Rico's administrative and population center remained firmly in Spain's hands until 1898, when it came under U.S. control after the Spanish-American War. Centuries of Spanish rule left an indelible imprint on the city, particularly in the walled area now known as Old San Juan. The area is filled with cobblestone streets and brightly painted, colonial-era structures, and its fortifications have been designated a UNESCO World Heritage Site.Old San Juan is a monument to the past, but most of the rest of the city is planted firmly in the 21st century and draws migrants island-wide and from farther afield to jobs in its businesses and industries. The city captivates residents and visitors alike with its vibrant lifestyle as well as its balmy beaches, pulsing nightclubs, globe-spanning restaurants, and world-class museums. Once you set foot in this city, you may never want to leave.

Saint George's

Nutmeg, cinnamon, cloves, cocoa those heady aromas fill the air in Grenada (pronounced gruh-nay-da). Only 21 miles (33½ km) long and 12 miles (19½ km) wide, the Isle of Spice is a tropical gem of lush rain forests, white-sand beaches, secluded coves, exotic flowers, and enough locally grown spices to fill anyone's kitchen cabinet. St. George's is one of the most picturesque capital cities in the Caribbean, St. George's Harbour is one of the most picturesque harbors, and Grenada's Grand Anse Beach is one of the region's finest beaches. The island has friendly, hospitable people and enough good shopping, restaurants, historic sites, and natural wonders to make it a popular port of call. About one-third of Grenada's visitors arrive by cruise ship, and that number continues to grow each year. Grenada's capital is a bustling West Indian city, much of which remains unchanged from colonial days. Narrow streets lined with shops wind up, down, and across steep hills. Brick warehouses cling to the waterfront, and pastel-painted homes rise from the waterfront and disappear into steep green hills. The horseshoe-shaped St. George's Harbour, a submerged volcanic crater, is arguably the prettiest harbor in the Caribbean. Schooners, ferries, and tour boats tie up along the seawall or at the small dinghy dock. The Carenage (pronounced car-a-nahzh), which surrounds the harbor, is the capital's center. Warehouses, shops, and restaurants line the waterfront. The Christ of the Deep statue that sits on the pedestrian plaza at the center of The Carenage was presented to Grenada by Costa Cruise Line in remembrance of its ship, Bianca C, which burned and sank in the harbor in 1961 and is now a favorite dive site. An engineering feat for its time, the 340-foot-long Sendall Tunnel was built in 1895 and named for Walter Sendall, an early governor. The narrow tunnel, used by both pedestrians and vehicles, separates the harbor side of St. George's from the Esplanade on the bay side of town, where you can find the markets (produce, meat, and fish), the Cruise Ship Terminal, the Esplanade Mall, and the public bus station.

Port Elizabeth, Bequia

Bequia is a Carib word meaning "island of the cloud." Hilly and green with several golden-sand beaches, Bequia is 9 miles (14½ km) south of St. Vincent's southwestern shore; with a population of 5,000, it's the largest of the Grenadines. Although boatbuilding, whaling, and fishing have been the predominant industries here for generations, sailing has now become almost synonymous with Bequia. Admiralty Bay is a favored anchorage for both privately owned and chartered yachts. Lodgings range from comfortable resorts and villas to cozy West Indian—style inns. Bequia's airport and the frequent ferry service from St. Vincent make this a favorite destination for day-trippers, as well. The ferry docks in Port Elizabeth, a tiny town with waterfront bars, restaurants, and shops where you can buy handmade souvenirs—including the exquisitely detailed model sailboats that are a famous Bequia export. The Easter Regatta is held during the four-day Easter weekend, when revelers gather to watch boat races and celebrate the island's seafaring traditions with food, music, dancing, and competitive games.To see the views, villages, beaches, and boatbuilding sites around Bequia, hire a taxi at the jetty in Port Elizabeth. Several usually line up under the almond trees to meet each ferry from St. Vincent.

Mayreau Island

The small island of Mayreau, just one and 1/2 square miles in area (3.9 square kilometres) is the smallest inhabited island of The Grenadines, and is part of the independent state of St.Vincent in the eastern Caribbean Sea. Two of the best known islands in The Grenadines are Mustique and Bequia, the second largest island in this group. The Grenadine Islands are strung out in a gentle sweep between St.Vincent and Grenada. Most visitors to Mayreau arrive from cruise ships, on the regular ferry, or by yacht. There are no proper roads on the island, only a few vehicles, no airport and only a single unnamed village. Mayreau and the neighboring Tobago Cays are very popular for divers and snorkellers. Saline Bay, on the west coast of the island, has a wonderful broad beach and a few local vendors selling T-shirts and local craft. A climb up the road to the hilltop village on the island provides breathtaking views across Mayreau, Canouan, the Tobago Cays and Carriacou.

Marigot

French and Dutch have lived side by side on St. Maarten/St. Martin for hundreds of years—with no border patrols or customs between them. The French side has a more genteel ambience, more fashionable shopping, and a Continental flair. The Dutch tends to be less expensive, has casino hotels, and more nightlife. Water sports abound all over—diving, snorkeling, sailing, and windsurfing are all top draws. And it's easy to while away the day relaxing on one of the 37 beaches, strolling the boardwalk of Dutch-side Philipsburg, and exploring the very French town of Marigot. Although luck is an important commodity at St. Maarten's 13 casinos, chance plays no part in finding a good meal at the island’s excellent eateries. The best way to explore St. Maarten/St. Martin is by car. Though often congested, especially around Philipsburg and Marigot, the roads are fairly good, though narrow and winding, with some speed bumps, potholes, roundabouts, and an occasional wandering goat herd. Few roads are marked with their names, but destination signs are common. Besides, the island is so small that it's hard to get really lost—at least that is what locals tell you. If you’re spending a few days, get to know the area with a scenic "loop" around the island. Be sure to pack a towel and some water shoes, a hat, sunglasses, and sunblock. Head up the east shoreline from Philipsburg, and follow the signs to Dawn Beach and Oyster Pond. The road winds past soaring hills, turquoise waters, quaint West Indian houses, and wonderful views of St. Barth. As you cross over to the French side, turn into Le Galion for a stop at the calm sheltered beach, the stables, the butterflies, or the windsurfing school, then keep following the road toward Orient Bay, the St-Tropez of the Caribbean. Continue to Anse Marcel, Grand Case, Marigot, and Sandy Ground. From Marigot, the flat island of Anguilla is visible. Completing the loop brings you past Cupecoy Beach, through Maho and Simpson Bay, where Saba looms in the horizon, and back over the mountain road into Philipsburg.

Santo Domingo

Santo Domingo is the capital of the Dominican Republic and one of the Caribbean's oldest cities. Its walled, cobblestoned historic core, the Zona Colonial, has buildings that date to the 1500s, including the cathedral, which was the first built in the New World. On the cafe-lined Plaza de España is the Alcázar de Colón palace. It’s now one of the city’s many museums, displaying notable medieval and Renaissance art

Cartagena

Cartagena's magnificent city walls and fortresses, now a UNESCO World Heritage Site, enclose a well-restored historic center (the Cuidad Amurallada, or walled city) with plazas, churches, museums, and shops that have made it a lively coastal vacation spot for South Americans and others. New hotels and restaurants make the walled city a desirable place to stay, and the formerly down-at-the-heels Getsemaní neighborhood attracts those seeking a bohemian buzz. The historic center is a small section of Cartagena; many hotels are in the Bocagrande district, an elongated peninsula where high-rise hotels overlook a long, gray-sand beach.When it was founded in 1533 by Spanish conquistador Pedro de Heredia, Cartagena was the only port on the South American mainland. Gold and silver looted from indigenous peoples passed through here en route to Spain and attracted pirates, including Sir Francis Drake, who in 1586 torched 200 buildings. Cartagena's walls protected the city's riches as well as the New World's most important African slave market.

San Blas Islands

The San Blas archipelago is located off the Caribbean coast, east of Colon, and is made up of 365 islands that range in size from tiny ones with a few coconut palms to islands on which hundreds of Kuna Indians live. Only about fifty are inhabited. The Kuna rule the San Blas Territory with internal autonomy, and have tightly preserved their language and cultural traditions over the centuries despite influences from European colonies. In addition to their own language, Spanish is widely spoken and many men work on the mainland, but live on the islands. Women wear costumes with unique designs based on local themes, geometric patterns, and stylised fauna and flora. The island of El Porvenir is one of the main seats of government for the Kuna Indians. Many Kunas from the other islands came to settle on El Porvenir, bringing with them their traditional arts and crafts, including the famous molas. These intricately hand-sewn designs are made by the women of the tribes as part of their blouses and dresses. With the increased tourism, molas are now a favoured souvenir and craft item for visitors.

Colón

The provincial capital of Colón, beside the canal's Atlantic entrance, is named for the Spanish-language surname of Christopher Columbus, though the Americans called it Aspinwall in the 19th century.. The city was founded in 1850 by Americans working on the Panama railroad and named Aspinwall for one of the railway engineers. Following completion in 1855, Colon gained in importance, which was furthered by the plans for an isthmian canal. During the time of the French canal attempt, a fire in 1885 burned the city nearly to the ground and left thousands of people homeless. Colon was rebuilt in the architectural style then popular in France. Buildings from that era plus the ones constructed by Americans between 1904 and 1914 are still in use today, although the majority is on the verge of collapse. In addition to its importance as a port, Colon boasts the world’s second largest duty-free zone, known as Zona Libre, which is contained in a huge fortress like, walled-off area with giant international stores. However, most of the merchandise is sold in bulk to commercial businesses throughout the country.

Golfo Dulce

Wild, scenic and incredibly bio-diverse, Golfo Dulce is not on most tourists itineraries. The name, says it all, Golfo Dulce or sweet gulf, in English. After a well justified visit to the Golfo Dulce, located in the South Pacific region of Costa Rica, and adjacent to the Osa Peninsula, visitors will be delighted and perplexed, wondering why they would ever leave this wonderland. Several coastal hamlets reside along this enchanting gulf, namely Puerto Jiménez, Golfito, Zancudo and Pavones, as well as the Piedras Blancas National Park. This is one stop on the itinerary that won’t soon be forgotten. Easily one of the wettest and most humid sections in the country, Golfo Dulce and the southwest can receive more than 200 inches (500 cm) of rainfall per year. This assures the surrounding area will be thriving with wild and plant life, perfect for aspiring adventurers. Surrounded by Corcovado National Park to the southwest, and Costa Rica’s mainland to the northeast, Golfo Dulce serves up a large platter of entertainment for all who visit. Sprouting along the edges of the Golfo Dulce are mangroves and estuaries full of wildlife. Explore these ecosystems crowded with crocodiles, river otters, waterfowl, monkeys and much more. Fed by the Coto Colorado River, the Coto River Swamps are an excellent choice for discovering these uncanny wetlands and the secrets that lay within.

Quepos (Puerto Quepos)

Quepos allows tourists to experience a once in a lifetime nature experience in Manuel Antonio National Park without leaving any of the familiar amenities behind. The close proximity of the park, located just 4.3 miles (7 km) to the south, and a wide array of services makes Quepos the perfect place to visit for those who wish to explore this enchanting area. The amenities available include everything from banks, restaurants, hotels, gift shops, bakeries, bars, a hospital, supermarket and even a post office. The area was once dependent on banana plantations which used to line the surrounding area. After disease infiltrated the harvest, interest transferred to African Palms as the prominent crop. Now, tourism has deemed itself the major economic factor, contributing to just about everything in the area. Quepos lures in many tourists for its fantastic sport fishing. In fact, some have come solely to participate in this world class experience and have never left, but besides sport fishing, many other activities are available. Exploring this maze of wetlands by boat is amazing but not the only way to see crocodiles, monkeys, herons, raccoons and more. This small paradise has the perfect balance between nature and the comfort and facilities someone might need.

Date & price

Departs

Mon 22 Nov 2027

from £4,903 pp

Enquire now Call 020 7590 0610

Per person, based on two sharing, cruise only. Updated daily and confirmed when you book.

Why book with Wexas Travel?

At Wexas, we specialise in bespoke travel experiences. Our itineraries are just samples of what we can arrange, and can be changed depending on your precise needs, finances and ideas by our experienced destination specialists.

Contact one of our consultants on 020 7590 0610 to discuss how we can tailor your holiday.

Learn why Wexas is the leader in creating luxury holidays. What is tailor-made travel?

Expert advice & support

Visit us in our London office

Let our travel specialists curate the perfect holiday:

  • Inspirational ideas based on experience
  • Established for over 50 years
  • Tailor a holiday to your precise requirements
  • Personalised quotes and documentation

Every step of the way

Every step of the way

Our services are with you from start to finish:

  • Dedicated personal consultants
  • Free airport lounges on qualifying bookings
  • Care and guidance pre, post and during holiday
  • Full financial security: ATOL & ABTOT protected
Mon 22 Nov 2027
Enquire