Get a Quote

Windstar: Sail from Boston

Hurry! Limited Time Offer! 1 (800) 498 7245
From $2,499 pp
All Inclusive Windstar Cruises from Boston with Up to $150pp Onboard Credit
Get This Deal
Skyline of Boston Massachusetts including Faneuil Hall and Quincy Market at dusk.
Skyline of Boston Massachusetts including Faneuil Hall and Quincy Market. Credit: SeanPavonePhoto - stock.adobe.com
Old fortress called Royal Naval Dockyard in Bermuda jetting into a beautiful blue ocean.
Royal Naval Dockyard at Bermuda's King's Wharf. Credit: MaryK - stock.adobe.com
Historic buildings sit on a waterfront with many boats in Lunenburg, Nova Scotia.
Historic waterfront in Lunenburg, Nova Scotia. This UNESCO World Heritage Site is home to many tall boats, schooners, dories, fishing vessels and even floating docks. Credit: Maurizio De Mattei - stock.adobe.com
Pink sand beach during sunset in Bermuda.
Horseshoe Bay Beach, a pink sand beach on Bermuda's south shore. Credit: romylee - stock.adobe.com

Southeast Canadian Explorations (2023)

Quebec’s French-flavored history, the fusion of Acadian and Scottish cultures in Nova Scotia—each province distills its own blend of Old World and New, bucolic and urbane.

Sail DateNightsShipPortsAll Inclusive FromCruise Only From
10/4/202311 DaysStar PrideBoston to Montreal$6,278pp$5,299pp
Itinerary: Boston, Portland, Bar Harbor, Lunenburg, Halifax, Louisbourg, Cap Aux Meules, Gaspe, At Sea, Quebec City (overnight), Montreal

Boston Sights, Warm Caribbean Nights (2023)

Venture from cosmopolitan Boston to warm Bermuda beaches and the picturesque Caribbean shorelines during this 11-day cruise.

Sail DateNightsShipPortsAll Inclusive FromCruise Only From
10/26/20239 DaysStar PrideBoston to St. Maarten$3,300pp$2,499pp
Itinerary: Boston, At Sea (overnight), Hamilton (overnight), St. George’s (overnight), At Sea (overnight), Gustavia, St. Maarten

Southeast Canadian Explorations (2024)

Quebec’s French-flavored history, the fusion of Acadian and Scottish cultures in Nova Scotia—each province distills its own blend of Old World and New, bucolic and urbane.

Sail DateNightsShipPortsAll Inclusive FromCruise Only From
10/1/202411 DaysStar PrideBoston to Montreal$6,778pp$5,799pp
Itinerary: Boston, Portland, Bar Harbor, Lunenburg, Halifax, Louisbourg, Cap Aux Meules, Gaspe, At Sea, Quebec City (overnight), Montreal

Boston Sights, Warm Caribbean Nights (2024)

Venture from cosmopolitan Boston to warm Bermuda beaches and the picturesque Caribbean shorelines during this 11-day cruise.

Sail DateNightsShipPortsAll Inclusive FromCruise Only From
10/23/202411 DaysStar PrideBoston to San Juan$3,978pp$2,999pp
Itinerary: Boston, At Sea (overnight), Hamilton (overnight), St. George’s (overnight), At Sea (overnight), Gustavia, Basseterre, Virgin Gorda/Prickly Pear, San Juan

Choose from All Inclusive or Cruise Only Fares

All-inclusive fares offer the ultimate in convenience and value with Wi-Fi, unlimited beer, wine, and cocktails, and gratuities. Just relax and enjoy!

Windstar’s Cruise Only fares include:

  • All meals
  • Dining at specialty restaurants and 24-hour room service
  • Non-alcoholic beverages, including sodas, specialty coffee & tea, bottled water, and zero-proof cocktails
  • Complimentary Watersports Platform equipment & snorkel gear

Bonus Offers

  • Up to $150pp Onboard Credit
  • Choose Cruise Only or All Inclusive Rate

Get This Deal

  • Please select one:
  • Please select one:
  • Please tell us about the cruise or deal you're interested in. Be specific if you can.
    You'll gain access to exclusive savings. You can unsubscribe at any time.
  • This field is for validation purposes and should be left unchanged.
Deal Terms and Conditions

Additional terms and conditions apply. See agent for details. Can be removed at anytime. Capacity controlled.

Get This Deal