Barcelona Spain
Edinburgh Castle, Scotland
Venice, Italy

Windstar Cruises

Recently voted the World’s Best Small Ship Cruise Line by Conde Nast Travelers prestigious Readers' Choice Awards, Windstar Cruises' small ships are exactly the right size - large enough to pamper and entertain you, yet small enough to tuck into the tiny harbors and hidden coves others can't reach. With only 148 to 310 guests cruising with you, each moment is all about you, yours to enjoy, yours to explore.
Call Our Dedicated Cruise Desk at 877-287-2835

Europe Cruises

Santorini Greece

Treasures of the Greek Isles Cruise

Discover the magic and mythology of the Greek Isles — one of the most storied regions of the world.

Barcelona Architecture

Spanish Symphony Cruise

Poised as if to kiss the continent of Africa, Andalusia hugs the southern coast of Spain and embraces cultural influences from both sides of the strait

Athens, Greece

Enchanting Greece & The Amalfi Coast Cruise

Idyllic islands, charming cobbled villages, spectacular scenery, intriguing history. Capture the heart of the Mediterranean in a single voyage.

Waterfall, Iceland

Around Iceland Cruise

Dramatic scenery and curious communities coalesce on this weeklong circumnavigation of Iceland.

Dubrovnik, Croatia

Classic Italy & Dalmatian Coast

Explore the shores of Italy, Croatia and Montenegro, discovering the charm of Venice, the magnificence of Rome, and the vast beauty of the Dalmatian Coast.

Edinburgh, Scotland

Gaelic Explorers

From the pubs of Dublin to the castles of Edinburgh, journey through hills and highlands, idyllic islands, and lyrical landscapes.

Baltic Sea Cruise

Baltic Delights Cruise

Visit seven magical countries and nine delightful cities as you travel through the Baltic's most fascinating cultures and breathtaking scenery.


Caribbean Cruises

St. Maarten

Windstar Cruises Caribbean

This classic Caribbean cruise allows you to get to the heart of local cultures with Windstar Cruises shore excursions, which are created to provide authentic experiences. Set sail from St. Maarten and discover the best of this region with a Caribbean cruise.


Tahiti Cruises

Windstar Tahiti

Windstar Tahiti

A graceful sailing ship is the perfect way to experience the true wonder of Tahiti. We’ll let the trade winds fill our sails as we visit one legendary island after another, staying overnight in some to give you time to swim and snorkel in crystal-clear lagoons, meander through lush rainforests, and experience the fascinating Polynesian culture from tikis to tiare flowers.


Panama Cruises

Windstar Central America

Windstar Panama and Costa Rica

Natural and man-made wonders combine in this exotic region where you are an explorer by day with cocktails on the fantail of your luxury yacht by night. Costa Rica is one of the most ecologically diverse places on earth over landscapes of rainforest, lakes, cloud forests, volcanoes, and more, boasting an impressive variety of wildlife.

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pre- and post-cruise stays, onboard accommodations, activities and more
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Not responsible for errors or omissions. [Pleasant Holidays acts only as an agent for the various travel providers shown above.]