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Day 1: Puerto Caldera
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.
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Day 2: 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.
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Day 3: 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.
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Day 4: Curú, Costa Rica
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.
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Day 5: Quepos
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. 
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Day 6: 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 with a wet landing.
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Day 7: Punta Leona, Costa Rica
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.*
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Day 8: Puerto Caldera
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.
Itinerary at a Glance
Date
Port
Arrive
Depart
Watersports
PlatformWatersports Platform: 
Sat Dec 21
Puerto Caldera
Arrive:  
Depart:  6:00 PM
Watersports Platform: 
Sun Dec 22
Playa Flamingo
Arrive:  10:00 AM
Depart:  
Watersports Platform: 
Mon Dec 23
Playa Flamingo
Arrive:  
Depart:  3:00 PM
Watersports Platform: 
Tue Dec 24
Curú, Costa Rica
Arrive:  7:00 AM
Depart:  9:30 PM
Watersports Platform: 
Wed Dec 25
Quepos
Arrive:  6:00 AM
Depart:  4:00 PM
Watersports Platform: 
Thu Dec 26
Golfo Dulce
Arrive:  7:00 AM
Depart:  4:00 PM
Watersports Platform: 
Fri Dec 27
Punta Leona, Costa Rica
Arrive:  10:00 AM
Depart:  10:00 PM
Watersports Platform: 
Sat Dec 28
Puerto Caldera
Arrive:  6:00 AM
Depart:  
Watersports Platform: 
Wind Star
Wind Star is a sleek, 4-masted sailing ship accommodating 148 guests. With four decks and a gross tonnage of 5,307, Wind Star feels like your own private yacht.
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Accommodations & Pricing
Boutique cruising with fewer than 350 guests. Our expertly designed itineraries and unexpected shore excursions bring you closer to each destination.
The Windstar Life
The Windstar staff-to-guest ratio is 1:1.5, and it shows.The moment you board you’ll feel it: an ever-attentive crew at your service, providing you with what you want and need, when you want and need it.
Friendly and Relaxed Atmosphere
Signature Onboard Barbecue
Cooking Demonstrations
Genuine and Thoughtful Crew
Crew Talent Show
Open Bridge
Local and Live Performances
Relax at the Pool or Hot Tub
Complimentary 24 Hour Room Service
Signature Sail Away
Shopping With The Chef
Take In The Sun
Watersports Platform
Enjoy regionally inspired treatments at World Spa by Windstar
Relax With A Morning Yoga Session