Is there anything more timeless or beautiful than a summer spent sailing up and down the Maine coastline? Penobscot Bay, in particular, with its rugged islands, wind-swept lighthouses, and endless horizon, is an iconic stretch of the Maine Coast that just begs for a sailing adventure (or two). Whether you’re taking the helm of your own vessel or settling in on the deck of a classic schooner with a glass of wine, sailing in Maine is an unforgettable experience.
The calm, protected waters of Penobscot Bay, Maine, make it ideal for everything from half-day sailing tours to multi-day windjammer cruises. It’s no wonder this area has been drawing sailors, artists, and explorers for generations. The bay is full of character, with wild coastlines, bobbing lobster buoys, and seals lazing on the rocks all adding to its quiet magic. Of course, the sailing is just the beginning of your Midcoast adventures this summer.
Rockland is a vibrant little city in the heart of Midcoast Maine, with plenty to explore when you’re back on land. The Farnsworth Art Museum is home to an incredible collection of works by the Wyeth family, while the Maine Lighthouse Museum offers a fascinating glimpse into the maritime history of the region. You can browse charming boutiques downtown, enjoy a fresh lobster roll on a waterfront patio, or take in a live show at the Strand Theatre. In summer, the harbor buzzes with activity, while fall brings crisp air and jaw-dropping foliage along the shoreline. Whether you’re into sailing adventures, coastal hikes, or just sipping coffee with a harbor view, there are so many rewarding things to do in Rockland.
To make your Midcoast getaway even more special, stay at the Berry Manor Inn. As Rockland’s top-rated bed and breakfast in Maine, this stately Victorian inn combines historic charm with luxurious comfort. Located just a short walk from the harbor and downtown shops, it’s the perfect place to relax after a day on the water or out exploring the coast. Whatever your day has in store, our Maine Bed and Breakfast makes it easy to enjoy everything Penobscot Bay and the surrounding area have to offer. Book your stay today!
Your Guide to Sailing on Penobscot Bay
If sailing on Penobscot Bay in Maine isn’t on your calendar yet, it should be. This stretch of Maine’s coast offers some of the best conditions, most breathtaking views, and most rewarding destinations for sailors of all stripes. Dotted with pine-covered islands, working harbors, and quiet coves, Penobscot Bay is a paradise for anyone who loves to be on the water.
The sailing season on Penobscot Bay typically kicks off in late May and runs through mid-October. Summer brings steady breezes, warm days, and cool nights, ideal for everything from relaxing day sails to longer windjammer cruises. September and early October, with their dramatic foliage and quieter harbors, offer some of the most memorable experiences you can have on the water. Whether you’re chasing the summer sun or catching the color-drenched coastline in fall, Penobscot Bay is sailing in Maine at its absolute best.
One of the great joys of sailing Penobscot Bay, Maine, is the variety of destinations you can reach in a day or two. Both Rockland and Camden Harbors are popular favorites, of course. Both towns are renowned for their scenic waterfronts and excellent dining options. Further east, Castine offers rich maritime history and peaceful anchorages. Vinalhaven and North Haven—two of the bay’s largest islands—are worth visiting for their rugged charm, hiking trails, and quiet beaches. Further away, you won’t want to miss a stop at Isle au Haut if you’re up for adventure. Much of the island is part of Acadia National Park, offering stunning views and uncrowded trails.
Sailing in Maine can be as hands-on or as relaxed as you want. You can book a guided tour, charter a boat, or join a traditional windjammer cruise where the crew does the heavy lifting and you just enjoy the ride. Packing layers is essential, even in summer, as temperatures can dip when the sun goes down. Sunscreen, a good hat, and a camera are musts. Local outfitters and captains are excellent resources, as they are well-versed in the intricacies of Penobscot Bay.
5 Best Sailing Tours Near Rockland, Maine
If you’re not planning to captain your own ship, there are plenty of fantastic sailing tours near Rockland that offer unforgettable views, salty breezes, and insight into the region’s maritime culture. Here are a few top options to consider.
- We recommend starting your Penobscot Bay adventures with A Morning in Maine. They offer Rockland Harbor Tours on a 55-foot ketch that departs directly from Rockland. Their two-hour sails highlight local landmarks and history, and are a great intro to sailing on the Bay. Captain Bob’s storytelling is a pure delight. This charter company also offers sails to Monroe Island, and other sailing adventures around Penobscot Bay.
- We also recommend Maine Sailing Adventures based out of nearby Camden, aboard Schooner Olad and Cutter Owl. These two classic boats offer a variety of Maine sailing adventures throughout the summer and fall, from private charters to public day sails. Wherever you go, you’ll enjoy scenic views of Penobscot Bay islands, lighthouses, and wildlife.
- Schooner Heron offers unforgettable sailing adventures in Rockport, just a short drive from Rockland. The Schooner Heron offers elegant two-hour sailing tours with views of Penobscot Bay and the Camden Hills. You can choose from a daytime eco tour, a sunset sail, or an elevated private morning tour.
- For a deeper dive into the history and romance of sailing Penobscot Bay, book a multi-day trip on one of the historic schooners aboard the historic Rockland & Camden Fleet of the Maine Windjammer Association. Many depart right from Rockland Harbor. These windjammer cruises take you island-hopping, offer incredible meals onboard, and often include lobster bakes on the beach.
- For a more laid-back tour of Penobscot Bay, consider hopping aboard one of the Lobster and Lighthouse Tours with Camden Harbor Cruises. These tours offer a unique blend of sightseeing and hands-on experience, including lobster hauling demos and narrated scenic sails. It’s a fun and educational option, especially for families or first-time visitors.
Stay in Style at Our Maine Bed and Breakfast
After a day filled with sea spray, coastal views, and unforgettable moments on Penobscot Bay, there’s nothing better than returning to a place that feels like home—but better. The Berry Manor Inn is the perfect match for your sailing getaway. Located in the heart of Rockland, this award-winning bed and breakfast offers the kind of comfort, charm, and thoughtful hospitality that elevates your entire trip. Whether you’re heading out on a full-day windjammer cruise or booking one of the many shorter sailing tours near Rockland, the Inn’s central location makes it easy to get to the harbor, enjoy downtown, and relax in between adventures.
Inside, you’ll find beautifully appointed guest rooms, spa-like bathrooms, and all the amenities you want for a restful retreat. From the warm welcome and fresh-baked pie and other treats in the evenings to the elegant decor and lush gardens, there’s an attention to detail found here that you can’t find anywhere else. The staff is happy to help you plan your Maine sailing adventures or recommend their favorite things to do in Rockland, including places to eat, shop, and explore along the coast. With free parking, quiet spaces to unwind, and a gourmet breakfast each morning, it’s everything you’d want from a Midcoast Maine stay.
Sailing trips on Penobscot Bay Maine are a memory in the making. With the Berry Manor Inn as your home base, you’ll experience the best of both worlds: exhilarating days on the water and peaceful nights in one of Rockland’s most iconic inns. Whether you’re visiting for a weekend escape or a week-long adventure, your perfect base for sailing in Maine starts right here. Book your stay today!