Why Boothbay Harbor Is the Best Place to Go Sailing in Maine

There are few places better suited for nautical adventures than Boothbay Harbor, Maine. This seaside town located in Maine’s Midcoast region offers so many ways to enjoy the open ocean. Sailing is one of the most prominent! This ancient water activity has shaped the state of Maine for generations, and it remains an exciting way to explore this beautiful part of New England. Below, we’ve compiled everything visitors need to know before taking advantage of the best sailing in Maine.


Before setting sail in Boothbay Harbor, be sure to create an itinerary! Planning a trip to Maine’s most charming coastal town doesn’t have to be stressful. As Boothbay Harbor residents, we want to help visitors experience the area through the eyes of a local. That’s why we’ve created a comprehensive list of the best restaurants, attractions, events, and places to go sailing in Maine. Access our complimentary Vacation Guide to Boothbay Harbor today!

Why Boothbay Harbor Is the Best Place to Sail in Maine

Touring ancient lighthouses (like the Monhegan Island Light), reeling in a big Striped Bass, viewing Eastern Egg Rock (where a colony of puffins nests each summer), and watching for whales are just a few of the many activities to enjoy while sailing off the coast of Boothbay Harbor. Here’s everything visitors need to know about this popular pastime.

Beginners Are Welcome

While sailing in Maine is a special tradition for so many people, beginners are welcome, too! Whether visitors have never set foot on a boat before or want to sharpen rusty skills, Boothbay Harbor is the best place to perfect the art of sailing. We recommend visiting during the summer (the height of boating season) and receiving sailing lessons.

Windjammer Days: A Sailing Festival You Won’t Want to Miss

The Windjammer Days festival is Boothbay Harbor’s way of paying homage to its storied maritime past. It’s also a wonderful time to reconnect with friends while enjoying a series of signature events like The Blessing of the Fleet, Antique Boat Parade, and more.

There Are Plenty of Maine Sailing Charters to Enjoy

Don’t have your own vessel? Not to worry: Boothbay Harbor offers a wide variety of boat tours and charters! Below are just a few of our favorite ways to experience sailing in Maine.

Cap’n Fish’s Whale Watch

Boothbay Harbor’s original whale tour company is Cap’n Fish’s Whale Watch. This company offers an environmentally friendly and locally owned way to see the region’s many species, including the majestic Humpback Whale. The best part? Visitors are 94% likely to experience a sighting!

Audubon Puffin Cruise

In addition to whale watching tours, the Cap’n Fish’s company offers a noteworthy Audubon Puffin Cruise. A journey aboard one of their boats is narrated by a certified marine biologist, so prepare for an educational experience filled with rare bird sightings! These tours are held between April and August.

Schooner Eastwind

Another one of the best boat tours in Boothbay Harbor is offered by the Schooner Eastwind.

This company’s 65-foot wooden vessel is a family-owned and built by hand. It takes guests around the harbor to see the beautiful Maine coastline, lighthouses, lobstermen, wildlife, remote islands, and more.

Stay at The Russell House Bed & Breakfast and Go Sailing in Maine!Sailing in Maine

For a truly unforgettable sailing experience in Maine, stay at The Russell House Bed & Breakfast in downtown Boothbay Harbor! This beautiful and historic B&B is just minutes from all of the best sailing the town has to offer, as well as the charms of the downtown district. Each of our chic, modern guest rooms features cozy furnishings and premium amenities that make everyone feel right at home. Plus, wake up to a freshly made gourmet breakfast each morning of your stay!

Ready for a nautical adventure to remember? Check our availability today and start looking forward to coastal charm, fun activities, and our warm Maine hospitality.