14 best Boston cruises and boat tours to sightsee the city

This classic harbor vessel recently got a top-to-bottom makeover after a fire in 2023: its four levels are newly renovated with more modern fixtures and finishes. Brunch, lunch and dinner cruises are fan-favorite events on board, thanks in part to the boat’s huge buffet. And for nighttime entertainment, there’s typically a DJ on the upper deck—making for a dazzling way to spend an evening under the stars. Spirit of Boston is one of the many city experiences from Boston Harbor City Cruises.

Care for a side of modern art with your harbor exploration? Consider taking the Institute of Contemporary Art’s water shuttle from its Seaport location over to the seasonal exhibits in East Boston at the ICA Watershed, or vice versa. Admission to the museum covers your shuttle ride, provided through Red Top Boats, and vessels run every 15 minutes. Just make sure to select a boat departure time when you buy your museum ticket.

Classic Harbor Line offers a variety of ticketed cruises around Boston Harbor all year long. Choose from their yacht, Northern Lights, or the seasonal schooner, Adirondack III. You can take a standard sightseeing cruise, a sunset sail, or peruse one of the many themed cruises on offer: barbecue and beer series, holiday brunch cruises, jazz cruises, fireworks cruises and more. 

What’s a day on the water without oysters and caviar? Navy Yard Hospitality, which operates splashy seaside restaurants in East Boston, the Seaport and beyond, has tapped Boston Launch Company to provide water shuttle service to its waterfront properties. The boat makes stops at Pier 6 in Charlestown, the Tall Ship floating bar in East Boston, and ReelHouse locations in both Eastie and the Seaport.

Dinner cruises on the Odyssey, part of Boston Harbor City Cruises’ fleet, combine good food, a relaxing ride and a bit of sightseeing in one buoyant outing. Enjoy a plated dinner (grilled peach and arugula salad, anyone?) as you gently circle the harbor. You’ll get a front-row seat to the skyline at sunset, not to mention views of landmarks like the USS Constitution and the Nantucket lightship. Reserve a window table for the best view, and when you’re finished eating, mosey over to the cash bar and DJ deck.

The Boston Harbor Islands provide an overwhelmingly pleasant escape from city life—with hikes, swimming, camping and more—just a 30-minute ferry ride away. Hop on a ferry to Spectacle, Georges or Peddocks Island to learn about the history of the numerous islands dotting the harbor. And do make time to walk around to the back side of Georges for views of Boston Light in the distance. 

The newest offering from Boston Harbor City Cruises, the “Alive After Five” cocktail cruise is aimed at folks pouring out of work on a weekday. Board at 5:30pm from Long Wharf for 90 minutes of fun after a day at the office. The plan? Sip cocktails, enjoy a live DJ and forget about screens for a while.

Prefer to keep the shore at an arm’s length as you sail? Set out on a Charles River architecture tour, courtesy of Charles River Boat Company. You’ll drink in spectacular views of both modern and historic architecture in Boston, with a guide to narrate the most impressive design facts and features. Highlights include the Prudential Building, the Hancock Tower and Marriott’s Custom House, among other more contemporary projects. Tours depart from Lechmere Canal in Cambridge.

Maybe you don’t feel like inching up I-93 on a summer’s day to get to the Encore. Why not make a day of it by cruising over to the Everett casino by boat? Free water shuttles depart from Long Wharf every 20 minutes between May 1 and September 30—just check the schedule before heading out.

Get up close and personal with one of Boston’s most famous historical landmarks as part of this offering from Boston Harbor City Cruises. The 45-minute tour takes you over to Old Ironsides, one of the very first ships commissioned by the US Navy in 1797. You’ll have the option to disembark at the Charlestown Navy Yard to tour the USS Constitution Museum, and then hop back on for a quick harborside swing around to other historical landmarks, including Bunker Hill Monument and Old North Church.

Stellwagen Bank National Marine Sanctuary, just off the coast of Massachusetts, is one of the best spots for whale watching in the world. Each summer, around 50 individual humpback whales return to this hotbed of biological activity. Take a whale-watching cruise and you'll see not only these majestic mammals, but also other species of marine life, from dolphins and seabirds to ocean sunfish and sea otters. On your tour, you’ll also learn all about the marine life you encounter from a knowledgeable on-board naturalist.

Spend 90 minutes dancing in the moonlight aboard a Mass Bay Lines moonlight cruise. Seeing the skyline from the water at night is a treat in itself, though doing so with a glass of wine in hand feels like the cherry on top. Mass Bay Lines also offers a full moon cruise when the stars (or, uh, moons) align, as well as plenty of sunset cruise options.

The city’s most iconic tour lends both land and sea perspectives to Boston’s history and architecture, all injected with a Bostonian sense of humor. These vessels are revamped, World War II-era amphibious vehicles (and occasional sports champion chariots). Hop on and you'll cruise the streets of Boston, then plunge into the Charles River for views of both the Boston and Cambridge skylines. You’ll get the chance to intermingle with sailboats, kayaks and, yes, local ducks. Along the way, you'll be educated and entertained by a ConDUCKtor, who will surely encourage you to quack at the locals.

The Seaport Ferry provides ferry service to commuters coming to and from Lovejoy Wharf near North Station and Fan Pier in the Seaport. That’s not to say any old Bostonian can’t join in the seafaring fun on a weekday—you could try grabbing an after-work cocktail in the Seaport and then taking a boat over to Alcove, Night Shift Brewing on Lovejoy Wharf, or the North End for a plate of pasta.