Romantic Getaways in Boston

October 20, 2026

Boston suits couples who like to walk, look at art and eat well, and the list of reliable date-night options is short. Some well-known restaurants and venues in the city have closed, so this page keeps to ideas that are open now and notes where to confirm details first. Most evenings here are built from a museum, a stroll and a dinner reservation.

Gardner Museum courtyard

The Isabella Stewart Gardner Museum at 25 Evans Way is built around a courtyard and is a good pick for a slow afternoon together. Tickets are timed, so book ahead. Adults pay $25, seniors 65 and over $22 and students $15. It opens Monday, Wednesday and Friday 11 to 5, Thursday 11 to 9 and Saturday and Sunday 10 to 5, and it is closed on Tuesday. Cafe G is on site for coffee or lunch. See gardnermuseum.org .

An evening at the MFA

The Museum of Fine Arts stays open until 10 pm on Thursday and Friday, which makes a later start possible. Adults pay $30. It is closed on Tuesday, and the last entry is 30 minutes before closing. Check mfa.org for the current hours.

Beacon Hill in the evening

Acorn Street and Louisburg Square are real streets of Federal-style rowhouses, and gas lamps line the street. People live here, so keep to the sidewalk, keep your voices down and do not step onto doorsteps for photos. Allow an hour for a slow loop, then walk down to the Public Garden. The Esplanade along the Charles River, near the Hatch Shell, is an easy place for a picnic. Stay on the paths and keep out of the water. Swimming in the Charles is allowed only at permitted events.

Sunset schooner sail

Liberty Fleet runs a 2 hour sunset sail from Fan Pier Marina on the schooners Liberty Star and Fame, at about $68 per adult. Sails are seasonal, spring to autumn, so check libertyfleet.com for the current schedule. Dress in layers, as the harbor is cooler than the city once the sun goes down.

Dinner

Two restaurants have been reported open in recent reviews: 75 Chestnut on Beacon Hill, which has a patio in season, and Row 34 at 11 Stillings St in Fort Point. Check menus, prices and hours, and book ahead. On Hanover Street in the North End, Modern Pastry at 257 Hanover St reportedly takes cards. At Mike’s Pastry, 300 Hanover St, payment rules have been reported both ways, so bring some cash.

Skating after dark

Frog Pond on Boston Common is a winter rink with late opening hours, so it works as an evening outing. Admission was $12 for skaters 58 inches or taller in the 2025-26 season, rentals were $18 for adults and lockers $7. Confirm the opening date and evening hours at bostonfrogpond.com .

Winter and timing

Boston winters, roughly December to March, bring nor’easters, heavy snow and wind chill. Check the forecast and MBTA service alerts, and expect seasonal outings such as sails and the Swan Boats to be closed. For a longer stay, compare hotels on Booking.com .