Here Is the Best Place to Go Sailing in Maine

It’s true that sailing is Maine’s favorite pastime. Fishing, hiking, and dining upon fresh seafood are all important to us here, but there’s nothing quite like seeing the region’s unique and beautiful landscape from the open ocean. Below, we’ll explain why Boothbay Harbor is the best place to go sailing in Maine!

Before setting sail in the waters of Boothbay Harbor, let us take care of the tedious part of planning a trip. As residents of Boothbay Harbor, we want to help visitors experience the area through the eyes of a local. That’s why we’ve compiled the best attractions, activities, restaurants, events, and places to go sailing in Maine. For all of our top recommendations, access our complimentary Midcoast Maine Vacation Guide today!

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

There’s a Sailing Festival Every Year

Every summer, Boothbay Harbor’s Windjammer Days Festival brings all kinds of nautical fun to coastal Maine. This is the town’s way of paying homage to its storied maritime past. Enjoy signature events including The Blessing of the Fleet, an Antique Boat Parade, and much more.

There’s a Maine Sailing Charter for Every Interest

For Wildlife Lovers

Cap’n Fish’s Whale Watch

Cap’n Fish’s Whale Watch is Boothbay Harbor’s original whale tour company! Going whale watching with this company is an environmentally friendly way to see the region’s many species, including the majestic humpback whale and intelligent pilot whale. The best part? Visitors are 94% likely to experience a sighting!

Audubon Puffin Cruise

For visitors looking for a truly unique activity, a puffin cruise is a great choice. Also offered by the Cap’n Fish’s company, one of these tours is an entertaining way to experience sailing in Maine while enjoying rare wildlife sightings! Each trip is narrated by a certified marine biologist, so prepare for an educational journey for the whole family. Audubon Puffin Cruises are held between April and August.

For Nautical Sightseers

Schooner Eastwind Tours

In addition to plentiful wildlife, the Boothbay Harbor region is home to historic lighthouses (like the Cuckolds Lighthouse), remote islands, and gorgeous rocky coastlines. See it all from the deck of the 65-foot Schooner Eastwind! This company offers some of the best boat tours in Boothbay Harbor, so don’t miss out.

Sailing in Maine

After a Day on the Water, Relax at Newagen Seaside Inn!

Newagen Seaside Inn is just a few minutes away from all of the best sailing in Maine! Located just off the beaten path in Southport, Maine, this serene and historic place offers comfortable accommodations with charming coastal decor and premium amenities like free Wi-Fi and fun activities. Guests can choose between a private oceanfront cottage or traditional guest room, each equipped with everything needed for a memorable stay. During the summer, guests can even attend exciting on-property events like our signature lobster bakes!

There’s nothing finer than a relaxing nautical retreat in Midcoast Maine. Start planning one by checking our availability today!