Things to Do in Boston

October 20, 2026

Boston is compact and walking-first, so most of its activities sit a short subway ride apart. The picks below cover a ballpark tour, ice skating, whale watching, paddling on the Charles and a schooner sail. Several are seasonal, so check each operator before you plan around them.

Fenway Park tour

The public tour lasts 60 minutes and departs at the top of each hour, daily all year. It costs about $30 for adults and $21 for children 3 to 12. Buy at the ticket counter at Gate D. Bags must be a single compartment no larger than 12 x 12 x 6 inches, and backpacks are not allowed. Sitting on top of the Green Monster belongs to the separate Pregame Tour, which costs about $55 and runs on game days three hours before first pitch. Details are on the Red Sox tour page .

Frog Pond ice skating

The rink on Boston Common charged $12 for skaters 58 inches or taller in the 2025-26 season, with children under 58 inches free. Skate rentals were $18 for adults and $12 for children, and lockers were $7. The opening date for the coming winter is announced late, so check bostonfrogpond.com or call 617-635-2120. The carousel nearby is $4 a ride and runs in the warmer months.

Whale watching

The New England Aquarium sails with Boston Harbor City Cruises from Central Wharf, with aquarium naturalists on board, roughly May through November. Boats head to Stellwagen Bank National Marine Sanctuary and the trip takes about 3.5 to 4 hours. Fares are not printed on the official pages. Booking sites show roughly $75 and up for adults, with lower child fares and under-3s free. Ask the operator what the rain-check or refund terms are if no whales appear. Dress warmer than the forecast on the water.

Paddling the Charles

Paddle Boston rents kayaks and paddleboards at Kendall Square in Cambridge (15 Broad Canal Way) and in Allston/Brighton (1071 Soldiers Field Rd). Recent press coverage put adult rentals from about $35 for 90 minutes and children’s rentals around $17. Community Boating on the Esplanade is membership based, not a walk-up rental. Swimming in the Charles is allowed only at permitted events, so stay in your boat. Check for bacteria or algae advisories before you go, wear the life jacket you are given, and keep out of the rowing lanes.

Schooner sails

Liberty Fleet sails from Fan Pier Marina on the schooners Liberty Star (67 feet) and Fame (70 feet). A day sail lasts about 1.5 hours and a sunset sail about 2 hours. Day sails ran roughly $35 to $70 for adults, and the sunset sail was about $68. The season is spring to autumn, so check libertyfleet.com for current dates.

Harbor Islands and the skyline

Ferries to the Boston Harbor Islands, including Georges Island with its fort, run seasonally from roughly May to October. Check the operator for the current schedule and fares. For a view from above, the View Boston observation deck was listed at $34 for adults and $15 for children 6 to 12 on the CityPASS price table.

Planning notes

Boston winters, roughly December to March, bring nor’easters, heavy snow and wind chill. Check the forecast and MBTA and ferry service alerts, and expect seasonal attractions such as the Swan Boats, Harbor Islands ferries and whale watches to be closed or reduced. The Boston Marathon is on Monday 19 April 2027, which is Patriots’ Day. Some sites close that day and hotels fill early.

The subway costs $2.40 a ride and a 1-Day Pass is $11.00. Contactless tap-to-pay works on the subway and buses. Fares are on mbta.com . To compare harbor cruises and sails, browse Boston boat tours on GetYourGuide .