Windjammer Sailing Packages

Convenience, Comfort, & Adventure All in One!


Special Air, Sea & Land Windjammer Sailing Packages

Air & Sea Package

Get a jump on your windjammer vacation with a non-stop flight from Boston to Rockland! Cape Air offers 5 flights a day, so you can enjoy your windjammer cruise entirely car-free. Package includes round-trip airfare and ground transportation to our dock in Rockland. Add $150 to any of our cruises. Please mention Air & Sea Package at time of booking.

For more information about transportation from Boston to Rockland or to the docks:

Cape Air: (800) 352-0714
Schooner Bay Taxi and Limo: (207) 594-5000

Rockland Land & Sea Package

Enjoy the best of both worlds—land and sea—with a windjammer cruise and a stay at an historic inn in Rockland, where you can enjoy the culture of a seaside town that is famous for its museums, galleries and fine dining. Package includes 2-night accommodations, gourmet breakfasts, expert concierge services and an a la carte menu of discounts to local area attractions. Add-on Inn packages start at $270/couple, based on double occupancy. Please mention the Rockland Land & Sea Package.

For more information about the Land portion of this package: Historic Inns of Rockland: 207-596-6611

Camden Inn & Picnic Package

Explore the natural beauty of Camden with a 2-night stay at one of a dozen premier inns either before or after your windjammer cruise. Package includes accommodations in a queen room with private bath, full breakfasts and amenities, gourmet picnic lunch and 2-day pass to the Camden Hills State Park or a guided tour up Beech Hill. Miles of well-groomed trails offer excellent hiking as well as spectacular views of Camden Harbor, Penobscot Bay and the islands beyond. Enjoy a “Specialty of Maine” backpack lunch featuring lobster rolls and lots of local goodies. Add $399/couple to any regular 3-night or longer windjammer cruise. Please mention the Camden Inn & Picnic Package at time of booking.

For more information about the Camden Inns: Premier Bed and Breakfast Inns of Camden