Here are 11 date nights for two in Boston that come in around $50 or less, with prices pulled from each venue's own site. The single best move this fall: grab free tickets for an ICA Thursday night, then walk the Seaport waterfront after. All prices are as of Sept. 2026, and none include dinner, because you know yourselves better than we do.
One heads-up before you plan: the MBTA says there are no Green Line trains in the central tunnel through Oct. 4 for signal work, with shuttles and fare-free buses instead. Budget extra time, or pick a date on the Red or Blue Line this week.
Museum nights that cost nothing (or $10)
ICA Free Thursday Nights
The Institute of Contemporary Art is free for everyone every Thursday from 5 to 9 p.m., though you need advance tickets. The museum sits right on the harbor, so the view out the glass does half the flirting for you. Current shows include Caroline Monnet and Cynthia Daignault, per the ICA homepage.
About $0 for two · Silver Line Waterfront to World Trade Center or Courthouse, per the ICA · Thursdays, 5 to 9 p.m.
MFA $5 Third Thursdays
The Museum of Fine Arts runs pay-what-you-wish admission, $5 minimum, after 5 p.m. on the third Thursday of each month. The next one is Oct. 15. Regular adult admission is $30, so this is the rare Boston bargain that's actually a bargain.
About $10 for two · Green Line E to Museum of Fine Arts, or Orange Line to Ruggles, per the MFA · Oct. 15, after 5 p.m.
Movie dates at the indie theaters
The Brattle
Harvard Square's nonprofit arthouse and classics theater charges $15.50 general admission and $13.50 for shows before 5 p.m. Double features are $19.50 each, which is the best dollars-per-hour-of-hand-holding ratio in the city.
About $27 to $39 for two · Red Line to Harvard, one block away via the Brattle Street exit, per the theater · Any night; matinees save a few bucks
Coolidge Corner Theatre
The Coolidge in Brookline lists adult tickets at $17, matinees before 3 p.m. at $15, and students at $14 Sunday through Thursday. Skip the 70mm screenings if you're counting pennies: those run $24.75.
About $28 to $34 for two · Green Line C to Coolidge Corner, per the Coolidge · Weeknights, especially if you're both students
Date nights on the water
The Charlestown ferry, aka the $2.40 harbor cruise
The MBTA's inner harbor ferries cost $2.40 one way, same as the subway. The Charlestown Ferry runs between Long Wharf and the Navy Yard in about 10 minutes, with skyline views that tour boats charge a lot more for. Note that CharlieCards aren't accepted on ferries; use the mTicket app or contactless payment.
About $10 round trip for two · Long Wharf, a short walk from Aquarium (Blue Line) · Before dark; check the timetable for the last boat
The long way: Hingham ferry
Want more boat for your buck? The Hingham/Hull ferry is $9.75 each way, so a round trip for two lands right around $39. It's a real ride across the harbor, not a 10-minute hop. Check the MBTA schedule before you go, since evening and weekend service varies.
About $39 for two · Rowes Wharf or Long Wharf · A clear afternoon
Sorry, no Swan Boats until spring
The Public Garden's Swan Boats closed for the season on Sept. 7, 2026 and reopen in April 2027. Adults paid $4.75 this year, so bookmark it for a cheap spring date.
Free dates outside (bring a jacket)
Sunset at Castle Island
Castle Island and Pleasure Bay in South Boston are run by the state's DCR, open sunrise to sunset with free parking, so time your walk to finish as the sky goes orange. For a daytime date, volunteers run free Fort Independence tours from noon to 3 p.m. on Oct. 4, Oct. 10 to 12, and Oct. 24 to 25, weather permitting.
About $0 plus T fare for two · Red Line to Broadway, then a City Point bus (routes 9 or 11) and a walk; use the MBTA trip planner · Late afternoon
A picnic in the Public Garden
Pack sandwiches, a blanket and a thermos of cider, and claim a spot by the lagoon at 4 Charles Street. Leave the wine at home: city rules prohibit alcohol in Boston parks, and parks close from 11:30 p.m. to 6 a.m.
About $15 to $25 for groceries · Green Line to Arlington, at Arlington and Boylston streets · Warm fall afternoons
Stargazing at BU's Coit Observatory
Boston University opens its rooftop observatory for Public Open Nights on most Wednesdays. Tickets are free but required, released on Eventbrite Thursday mornings around 11. From October to March the program starts promptly at 7:30 p.m., and nobody gets in once it begins. It's stairs only, and it gets canceled for bad weather, so call 617-353-2630 the day of.
About $0 for two · 725 Commonwealth Ave., near BU Central on the Green Line B · Clear Wednesdays
Games and live music
Candlepin at Sacco's Bowl Haven
Candlepin is New England's gloriously frustrating version of bowling: tiny balls, skinny pins, humbling scores. Sacco's in Davis Square charges $39 per lane per hour plus $4 shoe rental. An hour for two with shoes comes to about $47. Some lanes are held for walk-ins each day, and there's a two-hour max.
About $47 for two · Red Line to Davis · Weeknights, when walk-in lanes are easier to grab
Open mic night at Club Passim
Passim is a basement listening room just off Harvard Square, and it's a cozy one. Its Sunday and Monday open mics run 7 to 9 p.m., and the current listing shows $13 a ticket. Expect music plus some poetry, storytelling and comedy. Next ones: Oct. 4 and 5.
About $26 for two · Red Line to Harvard, then one block to 47 Palmer St. · Sunday or Monday, 7 p.m.
A note on comedy
Improv Asylum's free Wednesday shows in the North End ran only in summer 2026, July 1 to Aug. 26. The theater says ticket cost depends on the day and show, so check its calendar before promising anyone a cheap laugh.
What works right now (and what to save)
Fall-friendly this week and next: the ICA on Thursday, the Brattle or Coolidge any night, candlepin, Passim's Oct. 4 and 5 open mics, and BU's Wednesday stargazing. The MFA's $5 night lands Oct. 15.
Do the outdoor ones soon. Castle Island at sunset and a Public Garden picnic are great in early October and less great when the wind off the harbor starts feeling personal. Save Swan Boats for April.
The short version
- Free: ICA Thursdays (5 to 9 p.m., reserve ahead), BU stargazing (Wednesdays), Castle Island at sunset.
- About $10: MFA Third Thursday on Oct. 15, or a round trip on the Charlestown ferry.
- About $26 to $39: Passim open mic, a Brattle or Coolidge movie, the Hingham ferry.
- Splurge-ish at about $47: an hour of candlepin at Sacco's.
- Closed till spring: Swan Boats.
- This week: avoid the Green Line tunnel through Oct. 4.
Sources
- ICA Boston: Visit
- ICA Boston: Home
- ICA Boston: Directions and parking
- MFA Boston: Visit
- MFA Boston: Free and discounted admission
- MFA Boston: Getting here
- The Brattle: Policies
- The Brattle: Location
- Coolidge Corner Theatre: Ticket prices
- Coolidge Corner Theatre: Directions and parking
- MBTA: Ferry fares
- MBTA: Charlestown Ferry timetable
- MBTA: Green Line alerts
- MBTA: Arlington station
- Swan Boats: Plan your visit
- Mass.gov: Castle Island, Pleasure Bay, M Street Beach and Carson Beach
- Castle Island Association: Fort Independence tours and activities 2026
- Boston.gov: Public Garden
- Boston.gov: Parks rules and regulations
- Boston University: Public Open Night at the Observatory
- Sacco's Bowling by American Flatbread: Bowling reservations
- Passim: Open mic guidelines
- Passim: Open mic event listing
- Passim: Directions and parking
- Improv Asylum: Free Wednesday comedy shows
- Improv Asylum: General FAQs
Prices, hours and schedules change. Tap through to the official source before you go, and if we got something wrong, tell us. We log every fix on our corrections page.
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