Special themed-cruises aboard our Windjammers: lighthouses, kayaking, hiking, knitting, photography, and more!
Our vessels offer cruises which cater to a variety of interests. Some offer additional activities like hiking, kayaking, or yoga. Some offer knitting, painting, or photography workshops to inspire your inner artist. And there are cruises which provide extra sailing instruction or extra opportunities to see lighthouses and Maine’s historic sites. Think of these themed cruises as Windjamming “with a twist”!
Photography cruises
Take vacation pictures that your friends will actually want to see! These cruises offer optional photography workshops with professional New England photographers for those who want to take their skills to the next level. Most of these cruises don’t require an investment in a fancy camera – our photographers are happy to give tips on making the most out of your cell phone camera!
Angelique, June 30-July 6 (6-Nights)
Heritage, June 8-12 (4-nights)
J.&E. Riggin, Sept 25-29 (4-nights)
Mary Day, June 16-June 22 (6-nights)
Lighthouse cruises
No matter which windjammer you sail on, you’re bound to see lighthouses as Penobscot Bay is home to over a dozen! However, some windjammer trips offer a few more opportunities to sail close to, photograph, and learn more about these magnificent structures.
Schooner Heritage, June 17-21 (5-nights)
Schooner Mary Day, June 8-11 (3-nights) and Sept 15-19 (4-nights)
Windjammer Angelique, July 28-31 (3-nights)
Schooner Lewis R. French, July 16-20 (4-nights) and Sept 24-28 (4-nights)
Tallship sailing and seamanship course
Schooner Mary Day invites you for a week of experiential instruction. Would you like to learn to read a nautical chart? Plot a course? Grab your gear and plan on getting your hands dirty!
Schooner Mary Day, July 28-Aug 3 (6-nights)
Coastal kayaking cruises
Guests have the opportunity to spend one afternoon kayaking among the protected islands of the bay accompanied by professional guides. No experience necessary.
Schooner Lewis R. French, July 18-22 (4-nights) and August 20-24 (4-nights)
Island hiking cruises
Each cruise offers guests opportunities to go ashore and explore. Sometimes the boats anchor at a small coastal town, sometimes at a small deserted island. These hiking trips offer a little extra time ashore to explore Maine’s island trails. All hiking is optional.
Lewis R. French, May 28-June 1 (4-nights)
American Eagle, July 27-Aug 1 (5) and Aug 18-22 (4)
Yoga and Wellness cruises
This is an all-levels yoga, mediation, breathwork and sailing experience. Enjoy creative healthy meals to support your body and soul.
American Eagle, June 14-18(4 nights)
Angelique, August 1-5 (4-nights)
Knitting/Fiber Arts/Rug Hooking cruises
Finally, a cruise for both the knitting addict and their non-knitting partner! Whether you’re hoping to start a new project, finish that knitting project you tucked away years ago, or just want to sail and relax, you’ll find your niche on one of these cruises.
Knitting cruises: J. & E. Riggin, June 14-18 (4-nights) and Sept 1-7 (6-nights)
Rug Hooking cruise: J. & E. Riggin, August 20-24 (4-nights)
Watercolor Painting cruises
Capture the beauty of Maine’s coast via watercolor! The changing light, glistening waves and water, and bold islands are fascinating subjects. There trips include instruction from professional Maine artists and are great for both experienced painters and new students.
Angelique, August 6-10 (4-nights)
Wildlife and Whale-watching cruises
Many first-time sailors tell us that they didn’t realize just how many islands there would be and how much wildlife they’d see. Bald eagles, osprey, cormorants, seals, porpoises are easily seen. On a few trips though, you’ll have a chance to sail a bit further to look for whales and/or puffins – both have feeding grounds near some of the rocky ledges off the coast.
Angelique, Whales and seabirds: July 21-27 (6-nights)
Cruises for history buffs
Journey through the little-known history of Penobscot Bay. With historian Sam Collins as your guide, learn about mid-coast Maine’s industrial and ancient past.
Traces of the past: American Eagle, June 23-29 (6-nights)
Murder Mystery Tour
Join the Heritage for a trip to parts unknown as we track down clues on deserted islands and in small close-knit fishing villages. Channerl your inner detective to solve the mystery.
Heritage, June 23-29 (6-nights)
Longer cruises
Want to escape for a little longer? A few vessels offer cruises over six-nights in length.
Sail Downeast: Schooner American Eagle, July 16-25 (9-nights)
As close to Canada as you can get without needing a passport! Dramatic coastlines beckon us northward across waters less traveled.
Gloucester Schooner Race: Schooner American Eagle, August 27-Sept 5 (9-nights)
This nine-night cruise takes you down the coast, through whale feeding grounds, to Gloucester, MA, America’s oldest fishing port. Includes a day of participating in the Gloucester Schooner Race!
Schooner Ladona, Ports Unknown: July 7-14 and August 15-22 (7-nights)
Secrets of the Outer Islands! Travel far off the grid in search of the outer islands!
The Great Seven Night Adventure, Schooner Grace Bailey, Aug 10-17 (7 nights)
The name says it all. Sail an extra day because you won’t want to go home!
Culinary adventures aboard Maine Windjammer
On a Windjammer cruise, we know that great food is essential to your daily enjoyment. That’s why we don’t skimp on the homemade meals and hors d’oeurves. From freshly baked morning treats to after dinner desserts, our cooks and galley crew work hard to provide our guests the best all day long. A few cruises have a special culinary emphasis for those who want to take their food journey to the next level!
All cruises below are 2024 offerings
Wine, Dine and Chocolate aboard Schooner Stephen Taber
May 23-27 (4-nights)
July 28-Aug 2 (5-nights) with chocolatier Kate Schaffer
“Chocolate lovers will sail on a sea of delight, buoyed by desserts featuring Maine’s award winning Ragged Coast Chocolate in addition to our daily-prepared gourmet fair and generous evening wine pairings.”
Culinary Explorations aboard Schooner Ladona or Schooner Stephen Taber
June 3-7 (4-nights) – Schooner Ladona
June 13-17 (4-nights) – Schooner Ladona
June 26-29 (3-nights) – Schooner Stephen Taber
“On this trip, we focus on our partnership with Fiore Olive Oils and Vinegars. Our chef will demonstrate how two seemingly simple ingredients — you guessed it, olive oil and vinegar — can transform any dish.”
Gourmet Gastropub aboard Schooner Stephen Taber
July 13-17 (4-nights)
“Owner of gastropub Frog and Turtle, Chef James will not only cook for us but also be on hand to discuss techniques, inspirations, and his passion for housemade charcuterie.”
Maine Sip and Sail Cruises aboard Schooner J. & E. Riggin
June 24-28 (4-nights) – craft beers of Maine
July 12-15 (3-nights) – craft cocktails with bar craft professional Lara Nixon
Sept 15-19 (4-nights) – craft cocktails with bar craft professional Lara Nixon
“Enjoy craft cocktails or craft beers from Maine distillers and brewers that we love paired with the fabulous meals you have come to expect from the Riggin galley.”
Local Culinary Heroes aboard Schooner Stephen Taber
August 18-22 (4-nights)
“Our home town of Rockland has a well-deserved reputation as a foodie’s paradise, and on this trip, we’ll celebrates that diverse culinary culture. The first evening will feature a welcome dinner at a local restaurant. Throughout the rest of our sail, we’ll treat you to an olive oil and vinegar tasting, a rendezvous with North Haven Oyster Company, and a tour of a local coffee roaster.”
Farm-to-table Barn Dinner aboard Windjammer Angelique
August 21-25 (4-nights)
Angelique sails to the island of North Haven one afternoon to enjoy a farm-to-table barn dinner at Turner Farm. The feast features vegetable and meats raised on the farm. Wander the grounds while sampling appetizers and cocktails before sitting down to a gourmet five course meal.
Wine, Dine and Cheese aboard Schooner Stephen Taber
Sept 15-21 (6-nights)
Each day will culminate with a journey to a country through its cheese, wines, and viticultural history. The evening’s meal will include wine pairings which perfectly complement the menu that Jane and our chef have created. View our cheese and wine menu from our recent sailing season.
Categories: Specialty cruises, The Maine Coast