Windstar 70 Nights Caribbean

Star Collector: Grand Mediterranean And Latin America Adventure

Star Legend • Embarkation: Istanbul

Voyage Overview

Embark Date 19-Oct-2026
Disembark Date 28-Dec-2026
Duration 70 Nights
Vessel Star Legend

Day-by-Day Itinerary

Day 1: ISTANBUL

Ah, Constantinople, Queen of Cities and the Door to Happiness. Istanbul is the only city in the world built on two continents-Europe and Asia-and its appeal is truly universal. The Romans, Byzantines, and Ottomans all ruled their empires from here, leaving behind some of their finest monuments and a fascinating blend of cultures. Visit the harem at Topkapi Palace, where the clatter of silver soles once warned concubines of the approaching sultan. Admire the Iznik tiles and stained glass windows of the Blue Mosque, and the mystical light bathing the nave of Hagia Sofia. Shop the Grand Bazaar for a coffee cezve, magic lamp, embroidered slippers, or hand-woven kilim. Temper a tiny cup of potent Turkish coffee with bites of sweet lokum (Turkish delight). 

Day 2: MYRINA / LEMNOS

Limnos is a delightful, off the beaten path island with wild mountainous geology and large, uncrowded, sandy beaches all along the coastline. Windsurfing is becoming increasingly popular here. Sites to see here include the Medieval Castle of Myrina, Ancient Poliochni, Ancient Kavirio and the legendary cave of Philocetes.

Day 3: MYKONOS

Wake this morning to the postcard-like scene of Mykonos, the classic Greek isle dotted with hundreds of whitewashed churches and thatch-roofed windmills, in a harbor bobbing with fishing boats and luxurious private yachts. An optional  tour including a scenic ferry ride takes you back to the 6th   century B.C. to the tiny island of Delos, a UNESCO site and the mythical birthplace of Apollo.

Day 4: KUSADASI

Few places offer such a rich combination of history and scenic beauty. In Ephesus, one of the greatest outdoor museums in the world, you'll explore legendary sites steeped in history. Also visit the houses of Bulbul Mountain, where the roof of one forms the terrace of the next. This evening we present our Destination Discovery Event -- dinner in the moonlight and a concert near the  Celsus Library or on Harbour Street in ancient Ephesus.  

Day 5: BODRUM

The 15th century Castle of St. Peter, built by the Crusaders, presides over the city's dual harbors. Colorful peacocks strut their stuff trying to claim your attention, but they have nothing on the white sugar cube houses, palm-lined boulevards, and shockingly blue Aegean below. For a picture-perfect seaside playground, Bodrum offers a surprisingly rich history, or maybe it's the other way around. Visit the Mausoleum of Halicarnassus, one of the original Seven Wonders of the Ancient World. Surrender to the captivating magic of bathtub-warm waters and the Marina. Shop the bazaar for Milas cloth scarves and silver jewelry. Stroll the marina to see the other private yachts in port. (None as grand as yours, of course.)

Day 6: SANTORINI

As our yacht approaches the spectacular cliffs rising from the deep azure sea, you'll understand the magic of this area, where some say the ruins of Atlantis remain hidden. Visit the village of Oia and see the iconic Santorini blue domes or take a guided tour of Bronze Age excavations at the UNESCO site of Akrotiri. Toast the day with a crisp, cold glass of local Assyrtiko wine and appreciate the magic accessible to small ships like ours.

Day 7: SEAD

SEAD

Day 8: ITEA, DELPHI

Before there were fortune cookies there was the oracle of Delphi, dating back to 1400 B.C. The oracle gave cryptic guidance to the leaders of the day and was so highly respected that Delphi, now a UNESCO World Heritage Site, became known as the center of the world. An optional tour lets you go exploring, from the Temple of Apollo to the Delphi Archaeological Museum, which contains some of the finest works of art in Greece. 

Day 9: CRUISING THE CORINTH CANAL

You'll want to be on deck today as we transit the narrow Corinth Canal with other private yachts and Greek mail steamers. It's a shortcut reserved for petite ships like ours, and as we cruise between the narrow limestone walls we are the envy of all the ancient Romans who once portaged their ships along this very route before there was a canal.  Transit through the Corinth Canal is subject to local conditions and may occasionally be impacted by closures due to natural causes or construction activity beyond Windstar’s control. Should a closure occur, the itinerary will be updated accordingly, and booked guests will be notified as soon as information becomes available.

Day 10: PIRAEUS, ATHENS

With 3,000 years of history, you can't turn around in Athens without encountering the past. The Acropolis, a UNESCO site, the Plaka, and the Acropolis Museum are must-sees. But leave time if you can to climb Pnyx Hill for photos of the Parthenon at sunset, to buy your own set of Greek komboloi (worry beads), and to explore the metro stations that serve as mini-museums for the relics that are constantly being unearthed. 

Day 11: CRUISING THE CORINTH CANAL

You'll want to be on deck today as we transit the narrow Corinth Canal with other private yachts and Greek mail steamers. It's a shortcut reserved for petite ships like ours, and as we cruise between the narrow limestone walls we are the envy of all the ancient Romans who once portaged their ships along this very route before there was a canal.  Transit through the Corinth Canal is subject to local conditions and may occasionally be impacted by closures due to natural causes or construction activity beyond Windstar’s control. Should a closure occur, the itinerary will be updated accordingly, and booked guests will be notified as soon as information becomes available.

Day 12: ITEA, DELPHI

Before there were fortune cookies there was the oracle of Delphi, dating back to 1400 B.C. The oracle gave cryptic guidance to the leaders of the day and was so highly respected that Delphi, now a UNESCO World Heritage Site, became known as the center of the world. An optional tour lets you go exploring, from the Temple of Apollo to the Delphi Archaeological Museum, which contains some of the finest works of art in Greece. 

Day 13: CORFU

One of the most beautiful and popular islands, located on the Ionian Sea, Corfu has wonderful beaches and small villages throughout the island. Take in the Venetian influence at the two fortresses located in Old Town, a UNESCO World Heritage Site. 

Day 14: ARGOSTOLI, KEPHALONIA

Argostoli, the vibrant capital of Kefalonia, is known for its picturesque harbor, lively waterfront, and charming squares. The harbor is also home to resident sea turtles, often spotted swimming near the fishing boats in the clear waters. With its relaxed atmosphere, seaside cafés, and easy access to the island’s beautiful beaches and natural sights, Argostoli offers an inviting introduction to Kefalonia.

Day 15: MESSINA, TAORMINA

The cobblestone streets of Messina, Sicily, are the perfect launching point for an optional visit to nearby Taormina. Stroll along flower-filled streets in search of a delightful lunch or an artist's palette of colorful gelati. The ancient Greek Theater is an ideal place to sit back and admire shimmering waters below and Mount Etna, languidly smoking in the distance.

Day 16: TRAPANI

At once ancient and contemporary, Trapani is a city of contrasts. From the salt marshes that produce much of the Mediterranean's signature colored salts, to the intricate mosaics of Mozia and the famous wines of Marsala, to the best view in all of Sicily from the medieval hill town of Erice where the colorful gardens are rivaled only by the cannolis for pure sensory delight. The line of 17th century windmills, still hard at work in ancient Phoenician salt marshes beckons you to return to Trapani again and again. 

Day 17: CAGLIARI, SARDINA

Cagliari is known for Il Castello, a hilltop medieval walled quarter majestically watching over the town. Beautiful Poetto Beach sits on the edge of town with sparkling blue waters and lively activity. Other sites to see include the 13th century Cathedral di Santa Maria, the Torre Dell'Elefante and the Museo Archeologico Nazionale di Cagliari with its displays of bronze objects, Roman ceramics and artifacts from the Nuragic age to the Byzantine era.

Day 18: SEAD

SEAD

Day 19: BARCELONA

The old meets the new in this sunny Catalan metropolis, where narrow alleyways contrast with grand boulevards, trendy cuisine meets homemade tapas, and everywhere you're greeted by the warm, welcoming smiles of the fashionable locals. Don't miss UNESCO sites like the mind-boggling architecture of Antoni Gaudí or La Sagrada Familia Cathedral, with its eight decorative spires soaring hundreds of feet into the sky.

Day 20: MYSTERY PORT 1

Today is a surprise! Prepare to be captivated as anticipation builds with the unveiling of our mystery port, revealed only 36 hours before our ship arrives at its destination. Rest assured that you will still explore new places, meet amazing people and make unforgettable memories - because that's what you do on a Windstar cruise.

Day 21: MYSTERY PORT 2

Today is a surprise! Prepare to be captivated as anticipation builds with the unveiling of our mystery port, revealed only 36 hours before our ship arrives at its destination. Rest assured that you’ll still explore new places, meet amazing people and make unforgettable memories — because that’s what you do on a Windstar cruise.

Day 22: MYSTERY PORT 3

Today is a surprise! Prepare to be captivated as anticipation builds with the unveiling of our mystery port, revealed only 36 hours before our ship arrives at its destination. Rest assured that you’ll still explore new places, meet amazing people and make unforgettable memories — because that’s what you do on a Windstar cruise.

Day 23: MYSTERY PORT 4

Today is a surprise! Prepare to be captivated as anticipation builds with the unveiling of our mystery port, revealed only 36 hours before our ship arrives at its destination. Rest assured that you'll still explore new places, meet amazing people and make unforgettable memories; because that's what you do on a Windstar cruise.

Day 24: MYSTERY PORT 5

Today is a surprise! Prepare to be captivated as anticipation builds with the unveiling of our mystery port, revealed only 36 hours before our ship arrives at its destination. Rest assured that you’ll still explore new places, meet amazing people and make unforgettable memories — because that’s what you do on a Windstar cruise.

Day 25: MYSTERY PORT 6

Today is a surprise! Prepare to be captivated as anticipation builds with the unveiling of our mystery port, revealed only 36 hours before our ship arrives at its destination. Rest assured that you’ll still explore new places, meet amazing people and make unforgettable memories — because that’s what you do on a Windstar cruise.

Day 26: MYSTERY PORT 7

Today is a surprise! Prepare to be captivated as anticipation builds with the unveiling of our mystery port, revealed only 36 hours before our ship arrives at its destination. Rest assured that you'll still explore new places, meet amazing people and make unforgettable memories; because that's what you do on a Windstar Cruise.

Day 27: MALAGA

Here, on the shores of Costa del Sol, the Andalusian spirit thrives. Be sure to include an optional visit to see the brilliant and comprehensive collection of Picasso's work at Museo Picasso Málaga, a tribute to this artistic genius in the city of his birth. Or you may choose to opt for a visit to the beautiful village of Mijas, where picturesque Andalusian country life creates some of the world's best wines. 

Day 28: TANGIER

Fascinating Tangier is a traveler's delight with beautiful vistas, lovely unspoiled beaches, intriguing history and friendly people. Separated from Spain by only 20 miles across the Strait of Gibraltar, Tangier is considered by many to be the gateway to Africa. With its cosmopolitan mix of African and European influences, there are many interesting sites in Tangier.  The two UNESCO sites of the Medina (the old-walled city) a bustling place, and the Kasbah which offers beautiful views and fine Moroccan art, and the Place de France in the heart of the new city is an entertaining place to sip mint tea and enjoy the view.

Day 29: CASABLANCA

The siren call of Morocco is irresistible. Amid the whitewashed alleyways and stunning ocean views, make time for an optional excursion to the medina of Marrakech, a UNESCO World Heritage Site.  Explore the souks and medinas in the footsteps of Sir Winston Churchill and Yves St. Laurent, who both called this extraordinary blend of east and west their home.

Day 30: SEAD

SEAD

Day 31: FUNCHAL, MADEIRA

Considered one of Portugal's main tourist attractions and home of world-famous footballer Cristiano Ronaldo, Funchal is known for its style and beauty.  Visit Cabo Girao, the highest sea cliff in Europe or take a trip to the Pica da Torre for an incredible view of Camara de Lobos, a delightful fishing village. With a long history of Madeira winemaking, there'll be time here for a little wine tasting, a meal at one of the many 5-star restaurants, sightseeing to 15th century Cathedral of Our Lady of the Assumption, shopping the bargains to be found here, or experiencing the vibrant night life.

Day 32: SEAD

SEAD

Day 33: SEAD

SEAD

Day 34: SEAD

SEAD

Day 35: SEAD

SEAD

Day 36: SEAD

SEAD

Day 37: SEAD

SEAD

Day 38: SEAD

SEAD

Day 39: SEAD

SEAD

Day 40: SEAD

SEAD

Day 41: SEAD

SEAD

Day 42: BRIDGETOWN, BARBADOS

Jolly old England comes to life in the city and its garrison, both UNESCO World Heritage Sites. Further afield, you'll find historic sugar plantations and the fairyland magic of Harrison's Cave.

Day 43: ANSE MITAN, MARTINIQUE

Martinique offers a delightful and distinctive blend of French and Caribbean influences, with a bounty of historical sites, museums and a wide array of excellent shopping. Be sure to take a tour of the beautiful Jardin de Balata Botanical Gardens with exotic plants from around the world and a treetop walkway affording mountain views.

Day 44: RODNEY BAY

Rodney Bay, Saint Lucia

Day 45: RODNEY BAY

Rodney Bay, Saint Lucia

Day 46: CASTRIES, ST LUCIA

The capital and largest city of St. Lucia is a bustling port where shoppers flock.  Most of the city's historic buildings were destroyed in major fires between 1785 and 1948 but you'll see the beautiful, scenic backdrop of Morne Fortune (elev. 2,795 ft.) and the bustling harbor.  Visit the Castries Market for handicrafts, fruits and vegetables, see the murals painted by a local artist and housed in the Cathedral of the Immaculate Conception, and check out one of the many restaurants or Derek Walcott Square.

Day 47: SUNSET CRUISING PITONS

Located near the town of Soufriere, St. Lucia the Pitons are a UNESCO World Heritage Site and a spectacular landmark. Gros Piton is 2,619 feet high (798 meters) and Petit Piton is 2,438 feet high (743 meters). Gros Piton is home to at least 148 plant species and 27 bird species (5 of them endemic) and Petit Piton has 97 plant species with 8 rare tree species.

Day 48: MAYREAU

Mayreau is the smallest inhabited island of St. Vincent and the Grenadines, covering just about 1.5 square miles with a population of only a few hundred people. Tucked between Union Island and the Tobago Cays in the southern Grenadines, it's known for its laid-back, off-the-grid charm—there are no airports, no banks, and only one small village (Old Wall) perched on a hillside.

Day 49: ST GEORGES, GRENADA

Inhale the intoxicating aroma of the "Isle of Spice" as your eyes feast on what is widely claimed to be the most beautiful city in the Caribbean. Spend the day on 2-mile-long Grand Anse beach, and before you go, a taste of nutmeg ice cream is a must.

Day 50: BEQUIA

The only ships in port are those small enough to anchor alongside the yachts and fishing boats in Admiralty Bay. Bequia's whaling heritage is on display in the museum in pretty Port Elizabeth, or watch the island's famed model boat builders at work on their miniature masterpieces.

Day 51: BRIDGETOWN, BARBADOS

Jolly old England comes to life in the city and its garrison, both UNESCO World Heritage Sites. Further afield, you'll find historic sugar plantations and the fairyland magic of Harrison's Cave.

Day 52: RODNEY BAY

Rodney Bay, Saint Lucia

Day 53: SUNSET CRUISING PITONS

Located near the town of Soufriere, St. Lucia the Pitons are a UNESCO World Heritage Site and a spectacular landmark. Gros Piton is 2,619 feet high (798 meters) and Petit Piton is 2,438 feet high (743 meters). Gros Piton is home to at least 148 plant species and 27 bird species (5 of them endemic) and Petit Piton has 97 plant species with 8 rare tree species.

Day 54: SCARBOROUGH, TOBAGO

Scarborough, Tobago

Day 55: BEQUIA

The only ships in port are those small enough to anchor alongside the yachts and fishing boats in Admiralty Bay. Bequia's whaling heritage is on display in the museum in pretty Port Elizabeth, or watch the island's famed model boat builders at work on their miniature masterpieces.

Day 56: MAYREAU

Mayreau is the smallest inhabited island of St. Vincent and the Grenadines, covering just about 1.5 square miles with a population of only a few hundred people. Tucked between Union Island and the Tobago Cays in the southern Grenadines, it's known for its laid-back, off-the-grid charm—there are no airports, no banks, and only one small village (Old Wall) perched on a hillside.

Day 57: ST GEORGES, GRENADA

Inhale the intoxicating aroma of the "Isle of Spice" as your eyes feast on what is widely claimed to be the most beautiful city in the Caribbean. Spend the day on 2-mile-long Grand Anse beach, and before you go, a taste of nutmeg ice cream is a must.

Day 58: SEAD

SEAD

Day 59: WILLEMSTAD, CURACAO

Savor the pastel colors of the historic UNESCO site Old Town and the way the elaborate Dutch gables cut baroque curlicues from the sky. It's the perfect appetizer for a day of watersports or an adventure below ground at the magical Hato Caves-filled with eerie limestone formations and ancient petroglyphs.

Day 60: ORANJESTAD, ARUBA

Known for having some of the best beaches in the Caribbean, this Dutch port makes it easy to just ... take it easy. Walk through town to choose your favorite carved wooden door, or spend the day like the Arubans do playing dominos at a beachside table.

Day 61: SEAD

SEAD

Day 62: CARTAGENA, COLOMBIA

Welcome to the sparkling city of Cartagena, where the gold and jewels of the Spanish Main awaited shipment across the Atlantic. No pirate could resist, nor will you be able to when you visit this historic city. The Old Town, a UNESCO World Heritage Site, is surrounded by 400-year-old walls and contains a plethora of churches, fortresses, and restored colonial mansions. Outside the walls are more treasures: Climb the massive Castillo de San Felipe to investigate its maze of hidden tunnels, or shop for the perfect emerald.

Day 63: CARTAGENA, COLOMBIA

Welcome to the sparkling city of Cartagena, where the gold and jewels of the Spanish Main awaited shipment across the Atlantic. No pirate could resist, nor will you be able to when you visit this historic city. The Old Town, a UNESCO World Heritage Site, is surrounded by 400-year-old walls and contains a plethora of churches, fortresses, and restored colonial mansions. Outside the walls are more treasures: Climb the massive Castillo de San Felipe to investigate its maze of hidden tunnels, or shop for the perfect emerald.

Day 64: SEAD

SEAD

Day 65: BOCAS DEL TORO

Bocas del Toro on Bastimentos island was visited by Columbus in 1502 and then built up with colorful and Caribbean-style clapboard houses by the United Fruit Company in the early 20th century.   Situated on the beautiful Bocas del Toro archipelago, the laid-back and friendly community is a great combination of races and ethnicities living harmoniously. West Indians, Latinos and Extraneros (the resident gringos) make this an easy place to feel right at home and embrace the relaxed Caribbean vibe of the town. Not far from town is the Smithsonian Tropical Research Institute, as well as two national parks, La Amistad and many banana plantations.

Day 66: SAN BLAS ISLANDS, PANAMA

The San Blas Islands of Panama is an archipelago comprising approximately 378 islands and cays, of which 49 are inhabited, some by the Kuna people.  Scattered over an area of about 100 square miles, the islands are the number 1 vacation destination in Panama although the Kuna work hard to protect their land against overwhelming tourism and keep the islands healthy and lovely, unique and untouched by culture. These white-sand and palm tree lined islands are encompassed by a coral reef and warm, crystal-clear water that is perfect for snorkeling and is home to a variety of marine life including dolphins, sharks and giant manta rays.

Day 67: PANAMA CANAL TRANSIT

At nearly 48 miles long, on your transit through the Panama Canal you will enter three sets of locks that raise and lower the vessel 85 feet between the calm Pacific Ocean and the shimmering waters of the Atlantic. Your voyage features a daylight hours transit with numerous observation vantage points for outside viewing and comfortable indoor air-conditioned lounges. Expert onboard commentary enhances your journey as you watch the day to day workings of this bucket list experience.

Day 68: FUERTE AMADOR, PANAMA CITY

One of the entrances to the Panama Canal on the Pacific side, Balboa/Fuerte Amador was founded in 1519 and is a short distance from Panama City.  In 2012 Balboa was ranked #1 in Latin America in the category of world's busiest container ports. Sightseeing highlights include the colonial homes, the Administration Building, the Goethals Memorial, the Prado, and the local handicraft markets of traditional Panamanian crafts.

Day 69: SEAD

SEAD

Day 70: ISLA PARIDA

Located within a Nature Preserve of 50 islands, and part of Chiriqui Marine National Park lovely Isla Parida boasts magnificent beaches, one of which is over 1,300 feet long.  The crystal clear waters stay at 82 degrees year round and are filled with marine life. There are numerous hardwood trees like teak, mahogany, and eucalyptus, and fruit trees like mango, banana and coconut trees. Here you will be treated to Windstar's Signature Beach Party on a secluded beach that faces the Pacific Ocean. This port is accessed via a wet landing, where guests arrive by Zodiac and step directly into shallow water ashore. For more information, please visit our Wet Landings page under our Life On Board section.

Day 71: PUERTO JIMENEZ, GOLFO DULCE

Picture Jurassic foliage growing down steep hillsides all the way to the waterline, the hoots  of monkeys echoing through trees choked by orchids. Golfo Dulce is one of Costa Rica's most biodiverse areas, where both the jungle and the sea brim with life. Explore the canals by kayak in search of javelinas, butterflies, and more bird species than in all of North America. This port is accessed via a wet landing, where guests arrive by Zodiac and step directly into shallow water ashore. For more information, please visit our Wet Landings page under our Life On Board section.

Day 72: QUEPOS, MANUEL ANTONIO NATL PK

The former banana-exporting town of Quepos is your basecamp for a day of rainforest adventure. Take a walk along trails that weave up to waterfalls, or ride horseback to a beautiful jungle pool. A float trip through a mangrove swamp populated by monkeys, crocodiles, egrets, and herons is also available. Or you may choose a nature walk through Manuel Antonio National Park, with its lovely beaches, easy trails, and abundant animal life. 

Day 73: PUNTA LEONA

Your wet landing will drop you off at Punta Leona Beach Club, a well-known private beach resort community located on the Pacific coast of Costa Rica. Nestled amidst lush tropical rainforests, Punta Leona offers visitors a pristine and picturesque environment to unwind and enjoy the natural beauty of the region. The resort is known for its stunning white sand beach, Playa Mantas, and clear turquoise waters. Traverse the suspended cable bridges over the forest canopy in Carara National Park, or board a jungle cruise boat up the Tarcoles river to see one of the largest colonies of crocodiles in Costa Rica. Whether seeking relaxation or adventure, Punta Leona provides a captivating destination for nature enthusiasts and beach lovers alike. *This port is accessed by a wet landing and there may be a fee for using the resort amenities. Taxis and tours organized independently will need to be added to the resort guest list.*

Day 74: CURU

Located along Costa Rica's Pacific coast, the Curu Wildlife Reserve is an impressive nature reserve spanning 12 square kilometers. This biodiverse paradise is a haven for nature enthusiasts and wildlife lovers alike looking for a responsible way to experience Costa Rica's forest and pristine beaches. Wander through dense tropical dry forests teeming with howler monkeys, capuchins, and a plethora of exotic birds or relax and bask in the sun on the beach.

Day 75: PLAYA FLAMINGO

Playa Flamingo is considered one of Central America's most beautiful beaches with it pristine blue water, exotic marine life, and some of the best deep sea fishing to be found. Located in Punta Salinas on the country's Gold Coast, Playa Flamingo is the only full-service marina between Acapulco and Panama. Other water activities include year-round SCUBA diving, swimming, and snorkeling. The stunning and unspoiled white-sand beaches will remain in your memory for years to come. This port is accessed with a wet landing.

Day 76: PUERTO CALDERA, SAN JOSE

Located on the Gulf of Nicoya, the small town of Puerto Caldera is one of Costa Rica's top attractions, perfect for travelers who like more off the beaten path destinations where the native Tico lifestyle can be experienced. It is the gateway to San Jose, Jaco and the big city of Puntarenas, plus Los Suenos and Tortuga Island. Carara National Park is nearby, the rainforest home to crocodiles, over 400 species of birds and is considered the most likely place to see scarlet macaws.

About Star Legend

Star Legend
  • Cruise Line: Windstar
  • Guest Capacity: 3 guests
  • Vessel Type: Ocean Liner / Mega-Cruise Ship
  • IMO Registration: 9008598
Starting From
$25,744
per person / based on double occupancy
Category Estimates
Inside Cabin: Call
Oceanview Cabin: $25,744
Private Balcony: $40,444
Luxury Suite: $25,744
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