Windstar

Windstar Cruises from Boston, Massachusetts

Historic Acorn Street in Boston.

Upcoming Windstar Cruises from Boston, Massachusetts

6 Results

Taxes and fees included in all prices shown

Sort

A picturesque view of a red and white lighthouse on a rocky cliff overlooking the vast Atlantic Ocean in St. Anthony, Newfoundland and Labrador.

Up to $500 FREE Onboard Credit*+ 2 more offers

Windstar

25-night Star Collector Cruise: Autumn In Newfoundland And New England From Boston, Massachusetts

Halifax (Nova Scotia)

Sydney (Nova Scotia)

Aboard

Star Pride

From

Boston, Massachusetts

1 Sailing

Sep 14, 2026

1 Sailing

Sep 14, 2026

Published prices from

$13,498

per person*

taxes & fees included

A historic castle fortress illuminated at night, located on a small island surrounded by calm water under a deep blue evening sky.

Up to $500 FREE Onboard Credit*+ 2 more offers

Windstar

11-night Southeast Canadian Explorations Cruise From Boston, Massachusetts

Halifax (Nova Scotia)

Sydney (Nova Scotia)

Aboard

Star Pride

From

Boston, Massachusetts

2 Sailings

Sep 14, 2026 - Sep 16, 2027

2 Sailings

Sep 14, 2026 - Sep 16, 2027

Published prices from

$6,641

per person*

taxes & fees included

A turquoise and white ferry boat cruises through the harbor in Hamilton, Bermuda, with a backdrop of pastel-colored buildings and houses along the waterfront.

Up to $500 FREE Onboard Credit*+ 2 more offers

Windstar

8-night Bermuda Bliss Cruise From Boston, Massachusetts

Aboard

Star Pride

From

Boston, Massachusetts

1 Sailing

Oct 20, 2026

1 Sailing

Oct 20, 2026

Published prices from

$2,907

per person*

taxes & fees included

Historic Halifax waterfront buildings.

Up to $500 FREE Onboard Credit*+ 1 more offer

Windstar

25-night Star Collector: Autumn In Newfoundland And New England Cruise From Boston, Massachusetts

Halifax (Nova Scotia)

Aboard

Star Pride

From

Boston, Massachusetts

1 Sailing

Sep 16, 2027

1 Sailing

Sep 16, 2027

Published prices from

$15,818

per person*

taxes & fees included

A panoramic view of Gustavia, Saint Barthélemy, featuring a bay filled with luxury yachts and sailboats, framed by lush, green hillsides dotted with houses.

Up to $500 FREE Onboard Credit*+ 1 more offer

Windstar

17-night Star Collector Cruise: Bermuda & Caribbean Island Explorer From Boston, Massachusetts

Aboard

Star Pride

From

Boston, Massachusetts

1 Sailing

Oct 22, 2027

1 Sailing

Oct 22, 2027

Published prices from

$4,394

per person*

taxes & fees included

A panoramic view of Gustavia, Saint Barthélemy, featuring a bay filled with luxury yachts and sailboats, framed by lush, green hillsides dotted with houses.

Up to $500 FREE Onboard Credit*+ 1 more offer

Windstar

10-night Bermuda Bliss Cruise From Boston, Massachusetts

Aboard

Star Pride

From

Boston, Massachusetts

1 Sailing

Oct 22, 2027

1 Sailing

Oct 22, 2027

Published prices from

$3,027

per person*

taxes & fees included

*Rates and offers are per person, in US Dollars, based on double occupancy, capacity controlled, subject to availability and confirmation, and may change without notice. Government taxes and fees are included. Rates and offers are available for select dates and categories only. Additional restrictions may apply. Call 1-800-377-9383 for full terms and conditions.