Specialty & Themed Cruises
A cruise aboard any of the Maine Windjammer Association’s member vessels is certainly special. Each of the vessels is individually owned and operated and the offerings tend to be just as unique as the Captain and his or her crew.
For example, no matter what vessel you sail on or what month of the sailing season it is, you’ll be treated to an authentic beach-side lobster bake, the food will be amazing, the gorgeous scenery will always be photography worthy, and you are virtually guaranteed to sail past one of Maine’s many light houses or catch a glimpse of a seal, porpoise, whale, puffin, heron, osprey, etc. And every year, each vessel of the fleet participates in MWA’s seasonal events. No matter who you sail with, you won’t be disappointed.
However, the captains agreed it might be helpful to highlight some of the themed cruises the fleet offers so that you can quickly hone in on the particular specialty that attracts you. We’ve combined similar themes together for simplicity.
![]() Schooner GamKick off the summer season with a windjammer gathering of the entire fleet! Relive the age of sail during this quiet rendezvous of more than a dozen 19th-century-style sailing ships. Location is determined by the weather of the day! Live music and festivities. |
![]() Boothbay Harbor Windjammer DaysWindjammer Days marks the kick off to summer in the Boothbay region and is a time to reconnect with family, friends and neighbors after the long winter, an opportunity to support local businesses and welcome visitors. It is a time to honor our maritime history and celebrate the vital role it plays in the lives of all who live here. See https://www.boothbayharborwindjammerdays.org for more details. |
![]() Great Schooner RaceMaine’s tall ship fleet gathers for an exciting race from Islesboro to Rockland, followed by a festive Awards Ceremony/Party with live music. This year marks the 44th anniversary of the Great Schooner Race, North America’s largest annual gathering of tall ships! Pre-Race festivities include small boat races. |
![]() Camden Windjammer FestivalThe fleet gathers in picturesque Camden Harbor for festivities reminiscent of the days when hundreds of coastal schooners lined the waterfront. Festivities include a parade of sail, flag-raising ceremonies, live music, dancing and fireworks. |
![]() WoodenBoat Sail-InNow in its 34th year, the fall gathering of the fleet takes place in Brooklin, Maine, headquarters of WoodenBoat Magazine and WoodenBoat School. A spectacular sight locals and passengers look forward to every year. |
![]() For Fathers and GrandparentsSorry Moms! Your special day comes too early in the season, but you still matter! Surprise the parents in your life with an experience they never thought you would give them and one they won’t ever forget! A number of vessels in the fleet are offering a dedicated cruise to Dad and Grandparents this season: Schooners Ladona, Stephen Taber, Angelique, and J. & E. Riggin, also have cruises that include Father’s Day! |
![]() Health & Wellness CruisesAs if relaxing on a windjammer for three to ten days wasn’t “zen” enough, some of the vessels of the fleet are offering cruises this season that include additional activities such as hiking, cycling, kayaking, yoga, meditation, and soul-refreshing accompanied by healthy and supportive meals to help bring body, mind and soul back to center. All ages are encouraged to participate. |
![]() Learn the Adventure of Windjamming & SeamanshipSome of the most frequent questions we get are “Can I help drive the boat?”, “Can I take a turn at the helm?”, and “Will I bug the captain or first mate if I ask too many questions?” The answers are yes, yes, and no. All of the vessels will permit you to help sail the boat, conditions and time permitting, and the captains are ever-ready to answer any question you have about windjamming. A couple of the vessels in the fleet, however, make the educational aspect of sailing a core theme. |
![]() Perseid Meteor Showers / Star GazingThe Perseid Meteor Showers will reach their peak in August. All nine vessels of the Maine Windjammer Association have cruises during this time. The vessels with the Perseids on their calendars are: |
![]() Music! Glorious Music…and ArtMusic & the sea goes together like peanut butter & jelly, wine & chocolate, yin & yang… Most of the vessels in the fleet offer dedicated music cruises, where you’ll hear local artists and maybe the captain and the crew as well! |
![]() Wine TastingYour taste buds will visit a different country every evening from the deck of a Maine Windjammer. Enjoy the evening meal with a wine pairing that complements the menu while discussing the wine’s varietals and viticultural history. |
![]() Art / Photography / Film-makingEvery windjammer cruise aboard any Maine Windjammer Association vessel offers prime shutterbug scenery for photography enthusiasts. A number of MWA’s vessels offer more specific instruction and guidance for people looking to hone their skills: |
![]() Maine’s Iconic LighthousesNo matter which vessel you sail on you are guaranteed to see one, if not more, of Maine’s lighthouses on your windjammer cruise. A couple of the vessels take lighthouse sightseeing to a more competitive level and attempt to bring you to as many as Mother Nature will permit. |
![]() Wildlife / Nature / Captain’s ChoiceFrom osprey and puffins, to seals and porpoises (maybe even a whale!), to hundreds of uninhabited islands, a windjammer cruise with any of the vessels in the Maine Windjammer Association fleet offers ample opportunity for wildlife sightings and exploration. A few of the vessels have cruises dedicated to this aspect of sailing the Maine coast: |
![]() Acadia National Park / DowneastMany of the vessels in the fleet venture off the beaten path a bit to take passengers to see and/or explore one of the most famous destinations in Maine – Acadia National Park on Mount Desert Island. If you’ve always wanted to visit this part of Maine, then hop aboard a windjammer – you’ll be treated to a view like no one else. |
![]() Autumn Colors / Fall FoliageAutumn offers stunning views of Maine’s coastal fall foliage. Every vessel in the MWA fleet lays claim to this time of year. With warm days, cooler nights, and spectacular hues, September and October are some of the best months to sail the Maine coast on a windjammer. |