Drive around the North Shore for a while, and it can seem like everybody has a boat in their yard—everybody but you.
But even if you’ve never been out on the water before, you don’t need to miss out this summer on dockside bloody marys, sunburnt shoulders, or tall tales about the 40-pound striper you reeled in all by yourself.
We caught up with Gloucester harbormaster Chris Lucido for tips on ways to hit the water, where to explore, and how to make sure you end up safely back on dry land.
Tours & Water Shuttles
Lucido recommends keeping it simple for your maiden voyage, hopping aboard a scheduled group tour. One option, the Gloucester Water Shuttle, connects the city’s Harbortown and Rocky Neck districts. At $15 for adults, and with an experienced captain at the controls, it may be the cheapest, easiest way to begin your boating life. “You can hop on, and they take you around the city and drop you off at a dock,” Lucido says. “It’s one fee for the whole day.”
For a more festive day (or evening) on the water, Mahi Cruises out of Salem offers harbor cruises, sunset cruises, and music cruises with a full bar and grill, as well as fireworks cruises on July 3 and 4. The sunset cruise explores the shorelines of Salem, Beverly, Manchester-by-the-Sea, and Marblehead, depending on the wind and waves. There’s no narration, so you’ll be able to kick back and relax—as long as you’re up for an occasional Jimmy Buffett singalong.
Essex River Cruises offers narrated sightseeing tours ranging from 90 minutes to seven hours. The company doesn’t operate on the open ocean, but instead explores the salt marshes of Essex Bay. Depending on the day, you might spot egrets, ospreys, or great blue herons. And on an early morning cruise, there’s a decent chance you’ll see a sleeping seal floating belly-up in the water.

Charters
If you want to escape the crowds, but aren’t yet ready to don your captain’s hat, a private charter boat is a perfect fit. “A charter can take you out on a private sunset cruise or lighthouse tour,” Lucido says. “Often, you can bring up to four people at one rate, and they’ll take you out for a three- or four-hour tour in one price range. And then if you do a whole day, it brings you to another price range.”
Since you’ll essentially be getting your own boat—and crew—for the day, you’ll pay significantly more for a charter than for a group tour. Compass Rose Yacht Charters out of Newburyport starts at $190 per hour with a two-hour minimum, and prices go up for trips that require constant high speed (such as whale watch cruises) or longer travel to locations like the Isles of Shoals, the Annisquam River, or the Maine Coastline.
Out of Gloucester, Cape Ann Cruises offers birdwatching, seal watching, lighthouse tours, and longer charters that circumnavigate Cape Ann (three hours minimum) and go to Boston (four to five hours roundtrip).
Some charters will allow you to bring your own food and drinks (including alcohol) aboard, sometimes charging a “catering” fee. Others offer their own catering and bar packages.
Fishing
Deep sea fishing excursions are a step up the ocean adventure ladder. Typically, you’ll be on the water for at least several hours, honing your balance as you adjust to casting and reeling from a deck instead of a dock.
Lucido notes that the fishing boat companies know the best spots to pull in haddock, striped bass, or cod, increasing the chances that you’ll bring a trophy home with you at the end of the day. “These charters are constantly talking to each other and finding the hot spots so their customers can go out and catch a really big fish and have a great time,” he says.
Yankee Fleet out of Gloucester runs half-day fishing trips starting at $50 (including rod, reel, bait, and hooks), as well as full-day trips, “marathon” 12-hour trips, and even overnight trips to Platts Ledge, seven miles out to sea.
North Shore Anglers, also out of Gloucester, offers private charters for between four and six people, with most charters lasting between four and six hours, targeting haddock or striped bass. If you’re looking to battle a true sea beast (and you’re a morning person), 4 a.m. and 5 a.m. charters that range between $1,200 and $1,500 for four to six people will have you hunting bluefin tuna that can grow up to more than half a ton in weight.

Rentals
If you think you’re ready to graduate from Gilligan to Skipper, you can consider taking a boat out on your own. The Mariners Club at Gloucester Boat Rental offers five half-day powerboat rentals per month, starting at a flat $185 monthly fee.
Adults in Massachusetts aren’t currently required to have a boating license (although safety training certificates will be phased in starting next year). However, Lucido warns that any newbies taking the helm for the first time should at minimum bring an experienced boater with them to help with basics like navigation, operation, and safety. On any given day in the summer, he notes, there might be a dozen boats stranded on the sandbar at Wingaersheek Beach all day while their inexperienced operators wait for the tide to come back in. Even worse, boaters could end up accidentally driving into rocky waters or find themselves on a collision course with a larger vessel that can’t slow down.
“You need to know how to work a VHF radio, how to call for a mayday, how to anchor your boat,” Lucido says. “Recreational access to the ocean is a great thing, but it’s important that you know what you’re doing.”