We may earn a commission from links on this page, at no cost to you. Disclosure
The best date ideas in Boston pair one thing to do with one place to eat or drink: a sunset visit to View Boston at the top of the Prudential Tower, a Thursday evening at the Isabella Stewart Gardner Museum (free from 5 to 9 p.m.), live jazz at Wally’s Café or a harbor-view dinner at Woods Hill Pier 4. In warm months, add a Swan Boat ride in the Public Garden or a ferry to the Harbor Islands.
Below are 15 date ideas in the City of Boston, checked against each place's own website, with the season or night that suits each one. Two old favorites are gone: Meritage at the Boston Harbor Hotel closed in 2020, and the cocktail bar Drink in Fort Point closed in 2024.
15 date ideas in Boston at a glance
| Date idea | Neighborhood | Best time |
|---|---|---|
| Swan Boats and the Public Garden | Public Garden, Downtown | Mid-April to early September |
| Sunset at View Boston | Back Bay | Any evening, open until 10 p.m. |
| Thursday night at the Gardner | Fenway | Thursdays, 5 to 9 p.m. |
| A late night at the MFA | Fenway | Thursday or Friday, until 10 p.m. |
| The Boston Symphony Orchestra | Symphony Hall | September to May |
| Harbor-view dinner at Woods Hill Pier 4 | Seaport | Dinner nightly |
| Rooftop Italian at Contessa | Back Bay | Dinner or weekend brunch |
| A North End dinner at Mamma Maria | North End | Dinner nightly |
| Oysters at Row 34 | Fort Point | Lunch or dinner |
| Jazz at Wally’s Café | South End | Every night |
| A ticketed show at Scullers Jazz Club | Allston | Show nights |
| Live music at The Beehive | South End | Every night, weekend brunch |
| The speakeasy at Carrie Nation | Beacon Hill | Evenings |
| A ferry to the Harbor Islands | Downtown Waterfront | Mid-May to mid-October |
| Charles Street and Beacon Hill Chocolates | Beacon Hill | Daytime |
Outdoor and view dates
1. Swan Boats and the Public Garden
The Public Garden is free, open every day and made for a slow walk: a serpentine lagoon, a footbridge from the 1860s and the Make Way for Ducklings statue at the corner of Beacon and Charles streets. The Swan Boats, pedaled by a driver since 1877, give a 10- to 15-minute ride around the lagoon, but only from mid-April to early September; the 2026 season ended September 7 and the boats return in April 2027. Arlington station on the Green Line is across the street.
2. Sunset at View Boston
View Boston fills the top three floors of the Prudential Tower, with a glassed-in deck on the 52nd floor and an open-air terrace that wraps around the building a floor below. It is open daily until 10 p.m. and suggests sunset for the skyline; the Sips and Sights ticket adds one beer, wine or cocktail. The Prudential stop on the Green Line E branch exits into the building. The Prudential's old Top of the Hub restaurant closed in 2020, so older guides that send you there for dinner are out of date.
3. A ferry to the Harbor Islands
Boston Harbor Islands ferries leave Long Wharf North and reach Spectacle Island in about 30 minutes and Georges Island, with its Civil War fort, in about 45. The park has no entrance fee, but the ferries run only from mid-May to mid-October; in 2026 the last sailing day is October 12.
Museum and music dates
4. Thursday night at the Gardner
The Isabella Stewart Gardner Museum stays open until 9 p.m. on Thursdays, and admission is free from 5 to 9 p.m., with tickets released two days ahead. Its galleries surround a glass-roofed courtyard garden that flowers all year, so it works as well in February as in June. Book ahead; timed tickets sell out.
5. A late night at the MFA
The Museum of Fine Arts stays open until 10 p.m. on Thursdays and Fridays. On the third Thursday of each month, entry after 5 p.m. is pay what you wish, with a $5 minimum, sold in person only.
6. The Boston Symphony Orchestra
The Boston Symphony Orchestra plays its 2026–27 season at Symphony Hall from September 18 to May 9, under music director Andris Nelsons. It pairs well with dinner in the South End or Back Bay beforehand.
7. Jazz at Wally’s Café
Wally’s Café Jazz Club on Massachusetts Avenue has had live music every night since it opened on New Year's Day 1947. There are no reservations and no dress code: come for the jam session from 7 to 9 p.m., Tuesday to Saturday, or the night set from 10 p.m. to midnight, and expect to stand close to the band.
8. A ticketed show at Scullers Jazz Club
For a seated, booked evening instead, Scullers Jazz Club presents touring and local jazz acts on the ground floor of the DoubleTree Suites by Hilton at 400 Soldiers Field Road in Allston, which is in Boston despite the hotel's "Boston-Cambridge" name. October 2026 shows include Peter White and Ann Hampton Callaway.
9. Live music at The Beehive
The Beehive, in the Boston Center for the Arts on Tremont Street, has live music every night, from jazz and blues to cabaret, with no cover charge, plus a live-music brunch on weekend mornings. It is a dinner that turns into a late night without changing venues.
Dinner dates
10. Harbor-view dinner at Woods Hill Pier 4
If you came here for Meritage, which closed in 2020, the harbor-view dinner to book now is Woods Hill Pier 4, a farm-to-table restaurant at the end of Pier 4 in the Seaport, overlooking Boston Harbor. The kitchen cooks with meat, eggs and produce from the owners' farm in New Hampshire and from small suppliers. Reservations are through Resy.
11. Rooftop Italian at Contessa
Contessa is a glass-enclosed Northern Italian restaurant on the top floor of The Newbury Boston, looking across the Public Garden and Back Bay. Dinner runs until 10 or 11 p.m. and cocktails later, so it works for a late second stop as well as a full meal.
12. A North End dinner at Mamma Maria
Mamma Maria fills a brick townhouse on North Square, where Paul Revere lived, with five separate dining rooms over two floors; the smallest holds a single table. The seasonal menu cooks New England produce as regional Italian dishes. After dinner, the Paul Revere House and the Old North Church are a short walk away through the North End.
13. Oysters at Row 34
For something less formal, Row 34 in a 1908 Fort Point warehouse is a lively raw bar named for a row of oysters grown in Duxbury Bay. Sit at the bar for oysters and a lobster roll; it serves from late morning until late evening every day.
Drinks and a sweet stop
14. The speakeasy at Carrie Nation
Carrie Nation Cocktail Club, on Beacon Street near the State House, hides a windowless back lounge behind a red velvet curtain, with leather seats, a pool table and its own bar. The dining room takes reservations, but the bar and the speakeasy are first come, first served.
15. Charles Street and Beacon Hill Chocolates
A daytime walk along Charles Street at the foot of Beacon Hill ends well at Beacon Hill Chocolates, which has sold small-batch chocolates here since 2006 and keeps more than 100 kinds of truffle. Charles/MGH on the Red Line is at the Cambridge Street end. A guided Back Bay chocolate and art galleries tour is also bookable on Viator.
Planning tips for a Boston date
Check the season before you plan: the Swan Boats, Harbor Islands ferries and many rooftops close between fall and spring, while museums and jazz clubs run all year. The T stops running around 1 a.m. and last call is 2 a.m., so plan the ride home for a late jazz set. For more ideas, read our date night guide to Boston, romantic things to do for couples and things to do in Boston at night.