Set Sail From Gloucester Harbor: 7 Coastal Adventures Around Cape Ann

August 16, 2024 / A Local Favorite, Outdoor Adventures, Things to Do & See

Gloucester, MA, offers endless ways to experience its coastal beauty, and there’s no better way to do it than by getting out on the water. Whether you’re seeking adventure, relaxation, or a deeper connection to the area’s rich maritime history, Gloucester has something for everyone.

From exciting whale-watching tours to relaxing sunset sails, we’re sharing some of the best ways to enjoy the ocean breeze and explore the waters around Gloucester Harbor this summer:

Whale Watches

Whale watching from Gloucester offers an incredible opportunity to witness some of the ocean’s most majestic creatures up close. Both Cape Ann Whale Watch and 7 Seas Whale Watch provide unforgettable experiences, taking you into the Stellwagen Bank National Marine Sanctuary, a major destination for whale sightings.

Aboard their well-equipped vessels, you’ll have the chance to spot humpback, finback, and minke whales, among others, while learning from expert naturalists who share fascinating insights into the marine life and ecosystems.

Schooner Sails

Schooners are an important part of Gloucester’s maritime heritage, and sailing aboard one offers a unique way to experience the city’s storied connection to the sea.

For a classic sailing experience where you can help raise the sails while taking in stunning views of the coastline, hop aboard Schooner Lannon. The ship is named after owner Tom Ellis’ maternal grandfather who fished out of Gloucester Harbor in the early 20th century, and was designed by Capt. Harold A. Burnham, whose family has been a part of Essex’s shipbuilding tradition since 1650. In addition to daytime sails, sunset sails, and special events like fireworks and music sails, the Lannon is a favorite Gloucester experience for private charters and groups.

Captained by shipwright Harold Burnham, Schooner Ardelle offers public sails aboard a traditional Gloucester fishing schooner throughout the season. The Ardelle offers several unique sailing opportunities, with live Celtic music sails, circumnavigation trips, weekly schooner challenges, and more. And, each sail includes admission to Maritime Gloucester’s exhibits and aquarium, located right where the ship docks.

Schooner Adventure is a restored 1926 dory-fishing schooner, offering its guests a glimpse into local maritime history aboard a National Historic Landmark. As one of the last surviving Grand Banks dory-fishing schooners, Adventure serves as an important artifact not only here in Gloucester, but as part of Massachusetts and American history. Also docked at Maritime Gloucester, the ship features several ways to learn about maritime history through public sails and programming designed for local students and groups.

Harbor Cruises

For lunch, dinner, drinks, and dancing on the water, be sure to check out Beauport Cruiselines. Departing from Cruiseport Gloucester, Beauport Cruiselines offers everything from lobster lunch cruises, to themed events for St. Peter’s Fiesta, Independence Day, and more. This summer’s live music cruises feature favorite acts like Lisa Love Experience and Annie Brobst, and the fall’s Harvest Cruises offer a way to spend time on the water well into October. In addition to everything happening on board, the experience comes with incredible views of Gloucester Harbor, Rocky Neck, Eastern Point, Ten Pound Island, Stage Fort Park, and Hammond Castle, all from the comfort of your indoor dining space, or outside on the deck.

Cape Ann Cruises‘ Wejack yacht cruises Gloucester Harbor with a packed calendar of public events like live music cruises and sunset cruises, plus special offerings during Gloucester Schooner Festival and nearby fireworks shows. In addition to public cruises, Wejack is a go-to option in Gloucester for private events like weddings and corporate outings, as well as fishing charters.

Harbor Shuttles

Getting to and from points of interest around Gloucester Harbor is a breeze with Cape Ann Harbor Tours. Their harbor shuttle connects Harbor Loop/Jacobs Landing, Saint Peter’s Town Landing, and Rocky Neck aboard M/V Lady Jillian. The shuttle is $10 to ride all day, with season passes available. And, it runs free of charge during Culture Splash, an annual celebration of Gloucester’s art and culture on Rocky Neck and in Harbortown on Thursday nights each July and August.

Cape Ann Harbor Tours also operates lobster tours, lighthouse cruises, river trips (perfect for bird watching!), and private events like business outings, birthday parties, and burials at sea, just to name a few.

Kayak Rentals

To get a closer look at the beauty of Cape Ann, consider booking a kayak tour with North Shore Adventures. In addition to watercraft and bike rentals, this local outdoor adventures company features guided excursions to locales like Straitsmouth Island, Thacher Island, The Great Marsh/Plum Island Sound, the Dry Salvages, and more. You can even book a guided paddle to Thacher Island as part of an overnight camping trip!

New for 2024, North Shore Adventures has begun offering limited edition tours. This year’s included a trip to Misery Island, Ipswich River Watershed in Topsfield, and a Motif#1 paddle in Rockport. Be sure to follow them on social media for the latest updates on future trips!

Sailing Charters

For a luxurious day at sea, Artemis Sails can help you explore the coast of Cape Ann in style. Book a private charter on Artemis, a beautifully equipped yacht featuring a full galley, air conditioning, comfortable berths, a cushioned lounge area, and even a swim platform with a hot water shower.

Whether you’re interested in a three-hour day sail around Cape Ann, a romantic sunset sail with a farm-to-table cheese tray, or a full-day offshore adventure with the possibility of whale sightings, Artemis has a charter to fit your needs.

Fishing Charters

If having your own Wicked Tuna moment is on your must-do list, a fishing charter could be the highlight of your visit to Gloucester Harbor.

Several local charters are available, including Tuna Hunter (pictured above), which offers deep sea fishing charters for giant bluefin tuna, striped bass, cod and haddock, sharks, flounder, bluefish and more.

For two and three-day distant water trips, along with half-day and all-day charters, Yankee Fleet is another local option that has been running since 1944.

If the whole family is coming along and you are looking for deep sea fishing perfect for all ages, Gloucester Fleet is a small family-owned and operated business here in town.

And, Charlie’s Charters offers fishing by private charter, along with sightseeing tours, seal and bird watching, and photo excursions.

Taking your own boat to Gloucester?

Book your mooring with Dockwa and pick up a VIP Port Package when you arrive! You can find them right by the Transient Boater Facility and Mariners Lounge on your way into town. The package includes maps and information on everything there is to see in do downtown all within a short stroll of the harbormaster’s dock, including restaurants, museums, galleries, boutiques, and more.