Boston · For couples
Things to Do in Boston for Couples
A flowering courtyard museum, sunset on the harbor, a rooftop dinner over the Public Garden and a jazz club that plays every night: Boston is a very good city for two.
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Dinner for two
Contessa
The Newbury Boston, 3 Newbury St
A Northern Italian rooftop restaurant on top of The Newbury hotel, looking over the Public Garden: carpaccio, antipasti, tortellini en brodo and bistecca Fiorentina. Dinner from 5 p.m., until 10 p.m. Sunday to Wednesday and 11 p.m. Thursday to Saturday.
Tip: Book on Resy well ahead for a weekend table.
Oleana
134 Hampshire St, Cambridge (Central Square)
A Cambridge favorite for the cooking of Turkey and the Eastern Mediterranean: vivid spices and fresh local produce. Open daily from 5 p.m. Reservations open 30 days ahead, and space is held every evening for walk-ins.
Row 34
383 Congress St, Fort Point
A buzzy oyster bar and seafood restaurant in the Fort Point warehouses, with a raw bar, lobster rolls and responsibly sourced local fish. Open Monday to Saturday 11:30 a.m. to 10 p.m. (drinks until 11) and Sunday until 9 p.m.
Neptune Oyster
63 Salem St, North End
A tiny North End oyster bar known for its lobster roll, raw bar, fried clams and North End cioppino. Open daily from 11 a.m.; the kitchen runs to 9:30 p.m. on weekdays and 10:30 p.m. at weekends. No reservations: walk-ins only.
Tip: Go at opening or mid-afternoon to avoid the longest wait.
After dark
Boston Harbor sunset cruise
Boston Harbor City Cruises, downtown waterfront
Boston Harbor City Cruises runs a sunset sightseeing cruise past the skyline, plus dinner cruises on the Odyssey and the Spirit of Boston with table service. Boats leave from several piers, so check the one on your ticket.
Tip: Book the sunset sightseeing cruise for views; save the dinner cruise for a special occasion.
View Boston observation deck
Prudential Tower, 800 Boylston St
A 360-degree observation deck at the top of the Prudential Tower, with indoor and outdoor decks and the Stratus rooftop bar. Open daily 10 a.m. to 10 p.m. (last entry 9:15 p.m.); tickets from $32 plus a $3 booking fee.
Tip: Time it for sunset, then stay for a drink at Stratus as the lights come on.
The Hawthorne
Hotel Commonwealth, 500A Commonwealth Ave, Kenmore Square
A grown-up craft cocktail bar in the Hotel Commonwealth, with fine wines and a living-room feel. Open nightly from 4 p.m. to 1 a.m. Reservations are taken for up to 10 guests until 9 p.m.; walk-ins are welcome, with a wait list at busy times.
Tip: Book a table for a pre- or post-concert drink; Symphony Hall is a short ride away.
Wally's Café Jazz Club
427 Massachusetts Ave, South End
A family-run jazz club with live music every night of the year since 1947. Students from the local conservatories sit in with veterans at the jam sessions (Tuesday to Saturday, 7 to 9 p.m.), then the night sets run until midnight. Doors open at 7 p.m. Tuesday to Saturday and 9 p.m. Sunday and Monday.
Tip: It is a small room; arrive early for a seat.
Boston Symphony Orchestra at Symphony Hall
Symphony Hall, 301 Massachusetts Ave
The BSO's 2026-27 season at Symphony Hall began at the end of September. The orchestra spends its summers at Tanglewood in the Berkshires, and the Boston Pops cover jazz, film music, Broadway and the great American songbook.
Tip: Check the concert calendar before you fix your dates.
By day
Isabella Stewart Gardner Museum
25 Evans Way, Fenway
A Venetian-style palace around a flowering courtyard, hung with Isabella Stewart Gardner's collection. Open 11 a.m. to 5 p.m. every day except Tuesday, and until 9 p.m. on Thursdays. Adults $25, seniors $22.
Tip: Book a timed ticket ahead; popular entry times sell out. Thursday evening is the calmest visit.
Museum of Fine Arts, Boston
465 Huntington Ave, Fenway
One of the country's great encyclopedic art museums, a short walk from the Gardner. Open 10 a.m. to 5 p.m., and until 10 p.m. on Thursdays and Fridays; closed Tuesdays. Adult admission is $30.
Tip: Pair it with the Gardner on the same day, or save it for a late Friday evening.
Harvard Art Museums
32 Quincy St, Cambridge
Harvard's art collections under one roof, by Harvard Yard. Open Tuesday to Sunday 10 a.m. to 5 p.m., closed Mondays, and free to everyone every day.
Salem and the Peabody Essex Museum
161 Essex St, Salem
Heads-up: The Salem Ferry runs mid-May through October only.
Salem's great museum of art and culture, open Thursday to Monday 10 a.m. to 5 p.m. (adults $25). Get there on the Commuter Rail (Newburyport/Rockport line) and walk half a mile, or take the 50-minute Salem Ferry from Long Wharf, which runs mid-May through October.
Tip: October is Salem's busiest month; go on a weekday, and book PEM's extras early (October Ropes Mansion tours sold out).
Our advice
- Visit the Gardner on a Thursday, when it stays open until 9 p.m., then walk to dinner.
- Watch the sunset from the harbor or from View Boston, then have dinner on the Contessa rooftop.
- End a night at Wally's: sets run until midnight and the room is small, so arrive early.
Everything here was checked in September 2026. Museum hours, tour times and seasonal ferries change, so confirm before you go.
Questions people ask
What is the most romantic thing to do in Boston?
Take a sunset cruise on the harbor, then have dinner on the Contessa rooftop at The Newbury, overlooking the Public Garden.
Where should couples eat in Boston?
Contessa for a rooftop Northern Italian dinner, Oleana in Cambridge for Turkish and Eastern Mediterranean cooking, and Row 34 or Neptune Oyster for oysters and lobster rolls.
What do couples do in Boston at night?
A Boston Symphony Orchestra concert at Symphony Hall, cocktails at The Hawthorne, late jazz at Wally's, or a drink at the Stratus bar on top of the Prudential Tower.