Windstar: Cruises from Boston & Montreal

Windstar Cruises from Boston & Montreal

Discover the allure of the Northeast and beyond with Windstar Cruises. Embarking from Boston or Montreal, these luxurious yachts offer unforgettable journeys through stunning coastal landscapes, vibrant Canadian cities, and the enchanting islands of Bermuda and the Caribbean. Experience the epitome of small-ship cruising with Windstar’s luxurious amenities, personalized service, and enriching itineraries. Whether you seek historical charm, breathtaking natural beauty, or tropical paradise, let us curate your perfect Windstar adventure.

Featured Voyages

11 Days Caribbean-Eastern

Boston, Hamilton, St. George/Bermuda, Gustavia, Basseterre, Virgin Gorda, San Juan

Departure date: Oct 23, 2024

From: $2,799pp

11 Days US & Canada Eastern

Boston, Portland/Maine, Lunenburg, Halifax, Louisbourg, Cap-aux-Meules, Gaspe, Quebec City, Montreal

Departure date: Sep 26, 2025

From: $4,999pp

11 Days US & Canada Eastern

Montreal, Quebec City, Gaspe, Cap-aux-Meules, Louisbourg, Halifax, Lunenburg, Portland/Maine, Boston

Departure date: Sep 15, 2025

From: $5,299

12 Days US & Canada Eastern

Montreal, Quebec City, Gaspe, Cap-aux-Meules, Louisbourg, Halifax, Portland/Maine, Cape Cod Canal, New York City

Departure date: Oct 07, 2025

From: $5,299pp

11 Days US & Canada Eastern

Montreal, Quebec City, Gaspe, Cap-aux-Meules, Louisbourg, Halifax, Portland/Maine, Boston

Departure date: Oct 12, 2024

From: $5,699pp

22 Days US & Canada Eastern

Montreal, Quebec City, Gaspe, Cap-aux-Meules, Louisbourg, Halifax, Portland/Maine, Boston, Hamilton, St. George/Bermuda, Gustavia, Basseterre, Virgin Gorda, San Juan

Departure date: Oct 12, 2024

From: $7,599pp

11 Days US & Canada Eastern

Boston, Portland/Maine, Halifax, Louisbourg, Cap-aux-Meules, Gaspe, Quebec City, Montreal

Departure date: Oct 01, 2024

From: $8,109pp