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The most adventurous things to do in Boston happen on the water and on the wall: paddle a kayak or stand-up paddleboard on the Charles River, climb at one of the city's indoor gyms, ride the Codzilla thrill boat out of Long Wharf, or take a ferry to the Boston Harbor Islands. Water trips are seasonal, roughly spring to mid-fall; the climbing gyms and escape rooms are open year-round.
Boston adventures at a glance
| Adventure | Where | When | Cost cue |
|---|---|---|---|
| Kayak or paddleboard the Charles | Esplanade or Allston-Brighton | Spring to fall | $40 for a full day at Community Boating |
| Indoor climbing | North Station, Fenway, South Boston | Year-round | Day passes |
| Codzilla thrill boat | Long Wharf | Seasonal | Book with City Cruises |
| Harbor Islands by ferry | Long Wharf | May to October | Round-trip ferry ticket |
| Guided bike tour | 103 Atlantic Avenue | In season | Tour or rental fee |
| Open-air roof deck, 51 floors up | Prudential Tower | Year-round | From $32 |
| Escape room | Downtown | Year-round | Per player |
Kayak or paddleboard the Charles River
Two rental docks sit inside the City of Boston. Community Boating, the public sailing center that has run from the Charles River Esplanade since 1946, rents single kayaks, tandem kayaks and stand-up paddleboards for $40 a person for the whole day. You can come back to the dock and head out again later. From the water you see Back Bay, Beacon Hill, MIT on the Cambridge bank, and the Zakim and Longfellow Bridges. In 2026 rentals run until October 31. Weekday hours start at 1 p.m. in spring and fall and 3 p.m. in midsummer, weekends start at 9 a.m., and rentals end 30 minutes before sunset. On red-flag days, when the wind is high, paddlers stay in the Storrow Lagoon.
Upriver, Paddle Boston rents kayaks, canoes and paddleboards at 1071 Soldiers Field Road in Allston-Brighton. Reservations are optional and walk-ups are welcome. The nine-mile stretch has no current, so out-and-back trips are easy; paddle downstream toward Boston University, MIT and the skyline, or book a one-way trip to the company's Kendall Square dock in Cambridge. Life jackets are included and must be worn. The last boat launches one hour before closing.
Climb indoors at a Boston gym
Boston's climbing gyms are the year-round answer to a rainy day. Central Rock Gym has two gyms in the city, at 99 Beverly Street by North Station and at 5 David Ortiz Drive in the Fenway. Both sell day passes, and first-timers do a facility and bouldering orientation, plus an auto-belay orientation for the roped walls. Rock Spot Climbing at 30 Old Colony Avenue in South Boston sells day passes too, at a discount if you buy at least two days ahead. Central Rock Gym asks for a signed participation agreement, which you can fill in online before you go.
Ride the Codzilla thrill boat
Codzilla is a high-speed thrill boat that City Cruises runs from 1 Long Wharf on the downtown waterfront in season. Check the operator for this year's dates, prices and height and age rules. For a slower day on the same water, see our Boston whale watching guide and things to do on the water.
Take the ferry to the Boston Harbor Islands
The Boston Harbor Islands National and State Park is 34 islands and peninsulas, and public ferries leave Long Wharf from May to October. The ride is about 30 minutes to Spectacle Island, with hilltop trails and skyline views, and about 45 minutes to Georges Island, home of Fort Warren. The 2026 season ends October 12; in the fall schedule Spectacle runs Friday to Sunday and Georges Thursday to Sunday.
Bike the city or the Emerald Necklace
Urban AdvenTours, at 103 Atlantic Avenue on the North End waterfront, runs guided bike tours, including a Boston City View tour, an Emerald Necklace tour through Olmsted's chain of parks and an electric-bike option. It also rents bikes if you would rather ride on your own.
Stand on an open-air deck 51 floors up
View Boston occupies the top three floors of the Prudential Tower in Back Bay. The 52nd floor is an indoor panorama, and the 51st-floor Cloud Terrace is an open-air roof deck. It is open daily from 10 a.m. to 10 p.m., general admission starts at $32 plus a $3 booking fee, and the operator recommends sunset.
Beat an escape room
For a group, a locked room with a clock running is its own kind of thrill. Three established operators are downtown: Escape the Room Boston at 33 West Street, Trapology Boston at 177 Tremont Street and Boxaroo at 55 Court Street.
What about helicopter tours and flying lessons?
Older guides to Boston adventures promise both, but we found no helicopter tour operator flying from inside the City of Boston, so we have left them out rather than send you to the wrong place. For the view from above, View Boston is the reliable option.
More ideas: our best outdoor things to do in Boston, thrilling things to do for a group and, after dark, spooky things to do in Boston.