We checked 56 real places in Boston, MA from OpenStreetMap, including 8 places to eat, 8 bars and nightlife spots (21+) and 8 sights. Squad Plan's three day plans below draw on these places, and your group can vote on the one you like best.
Last updated 2026-10-14
We found 8 places to eat, 8 bars and nightlife spots (21+), 8 sights, 8 parks and outdoor spots, 8 game spots, 8 sports venues and 8 places to shop in Boston, from OpenStreetMap map data.
Three ready-made day plans
Costs are rough estimates per person in US dollars. Check hours and prices before you go.
Plan A
The Battle of Bunker Hill Museum to Monument Charlestown Restaurant & Tavern
Slow pace, good food, plenty of time to talk. Group of 4 for friends hangout.
Estimated total per person: $69–210
10:00Visit The Battle of Bunker Hill Museum
43 Monument Square, Boston, MA 02129
Free to $25 (estimate)
11:00Explore Rainsford Island
Harbor Islands, Boston, Massachusetts
Free
12:30Lunch at Spectacle Georges Concessions
Moon Island Road, Quincy, MA 02171
$12–20 (estimate)
14:00Play at Central Park Lanes Bowling Center
8;10 Saratoga Street, Boston, MA 02128
$15–30 (estimate)
15:00Get active at Olsen Pool
Turtle Pond Parkway, Boston, MA 02136
$10–25 (estimate)
16:00Browse Saratoga Market
Trident Street, Boston, MA 02128
Free to $40 (estimate)
18:30Dinner at Pueblo Viejo
307 Bennington Street, Boston, MA 02128
$20–40 (estimate)
20:30Drinks at Monument Charlestown Restaurant & Tavern
224 Main Street, Boston, MA 02129
$12–30 (estimate)
Plan B
Bay State Model Railroad Museum to Medallo Bar
A fuller day of sights and new places. Group of 4 for friends hangout.
Estimated total per person: $69–210
10:00Visit Bay State Model Railroad Museum
760 South Street, Boston, MA 02131
Free to $25 (estimate)
11:00Explore Georges Island
Harbor Islands, Boston, Massachusetts
Free
12:30Lunch at Napoles
1233 Bennington Street, Boston, MA 02152
$12–20 (estimate)
14:00Play at Lucky Strike Social Boston
145 Ipswich Street, Boston, MA 02215
$15–30 (estimate)
15:00Get active at YMCA
Saint Botolph Street, Boston, MA 02115
$10–25 (estimate)
16:00Browse Jamaica Plain Farmer's Market
Park Place, Boston, MA 02130
Free to $40 (estimate)
18:30Dinner at Bohemio's
16-30 Bennington Street, Boston, MA 02128
$20–40 (estimate)
20:30Drinks at Medallo Bar
411,413 Chelsea Street, Boston, MA 02128
$12–30 (estimate)
Plan C
The Institute of Contemporary Art to Bilares
High energy from start to finish. Group of 4 for friends hangout.
Estimated total per person: $69–210
10:00Visit The Institute of Contemporary Art
25 Harbor Shore Drive, Boston, MA 02210
Free to $25 (estimate)
11:00Explore Lovells Island
Harbor Islands, Boston, Massachusetts
Free
12:30Lunch at La Gran Manzana
William C. Kelley Square, Boston, MA 02128
$12–20 (estimate)
14:00Get active at Conte Forum
2599;2601 Beacon Street, Boston, MA 02135
$10–25 (estimate)
15:00Browse Prudential Center
800 Boylston Street, Boston, MA 02199
Free to $40 (estimate)
16:00Catch a show at Mugar Omni Theater
Science Park, Boston, MA 02214
$15–30 (estimate)
18:30Dinner at Angela's Cafe
131 Lexington Street, Boston, MA 02128
$20–40 (estimate)
20:30Drinks at Bilares
16-30 Bennington Street, Boston, MA 02128
$12–30 (estimate)
Family friendly things to do in Boston
Real places in Boston for a day out with kids.
Visit Joseph A. Bonito Square
Free to visit, with room to run around. Bring snacks and water.
FreeEast Boston, Boston, Massachusetts
Eat at Cabana Grill
A sit-down meal for the whole family. Call ahead for a big group.
$12–20 (estimate)254;256 Bennington Street, Boston, MA 02128
Go to Central Park Lanes Bowling Center
Mini golf, bowling and arcades are easy for kids. Check the hours before you go.
$15–30 (estimate)8;10 Saratoga Street, Boston, MA 02128
Go to ArcLight Cinema
Movies, games or bowling for a rainy or hot afternoon. Check showtimes and hours first.
$15–30 (estimate)60 Causeway Street, Boston, MA 02114
Snack stop at Zume's Coffee House
A quick stop for drinks and a snack between activities.
Central Park Lanes Bowling Center8;10 Saratoga Street, Boston, MA 02128
ArcLight Cinema60 Causeway Street, Boston, MA 02114
Lucky Strike Social Boston145 Ipswich Street, Boston, MA 02215
MassArt Film Society621 Huntington Avenue, Boston, MA 02115
South Boston Candlepin543 East Broadway, Boston, MA 02127
Mugar Omni TheaterScience Park, Boston, MA 02214
Kings Boston - Back Bay50 Dalton Street, Boston, MA 02115
Simons Theatre95 Boston HarborWalk, Boston, MA 02110
Sports venues
Olsen PoolTurtle Pond Parkway, Boston, MA 02136
Parkway Community YMCA15 Bellevue Street, Boston, MA 02132
YMCASaint Botolph Street, Boston, MA 02115
Palmer Dixon Indoor Tennis Courts780 Soldiers Field Road, Boston, MA 02163
Beren Tennis CenterSoldiers Field Road, Boston, MA 02163
Conte Forum2599;2601 Beacon Street, Boston, MA 02135
Auerbach Center40 Guest Street, Boston, MA 02135
YMCA of Greater Boston615 Washington Street, Boston, MA 02135
Places to shop
Saratoga MarketTrident Street, Boston, MA 02128
Brighton Farmers Market30 Chestnut Hill Avenue, Boston, MA 02135
Jamaica Plain Farmer's MarketPark Place, Boston, MA 02130
Boston Public Market100 Hanover Street, Boston, MA 02201
Quincy MarketNorth Market Street, Boston, MA 02109
Prudential Center800 Boylston Street, Boston, MA 02199
Copley Place100 Huntington Avenue, Boston, MA 02116
Lambert's Marketplace140 Tremont Street, Boston, MA 02111
How much does a day out with friends cost in Boston?
Across the three day plans above, a day out with friends in Boston costs about $69 to $210 per person, from the lowest plan to the highest. Each total adds up the typical price of its stops, so treat it as a rough estimate and check prices before you go.
Frequently asked questions
What can a group do in Boston for free?
Free places on our list include Rainsford Island, Joseph A. Bonito Square and Georges Island. Plans also leave time to wander around town at no cost.
Where can friends eat in Boston?
Good places to start are Spectacle Georges Concessions, Pueblo Viejo and Napoles. The day plans above include food stops from this list.
What is there to see in Boston?
Sights on our list include The Battle of Bunker Hill Museum, Boston Marine Society Museum and Bay State Model Railroad Museum. The full list is in the places section below.
What are good things to do with kids in Boston?
Try visit Joseph A. Bonito Square, eat at Cabana Grill and go to Central Park Lanes Bowling Center. Every idea here is a real mapped place, with a rough cost per person.
What are good date night ideas in Boston?
Try coffee at Zume's Coffee House, walk through Deer Island Park and look around Boston Marine Society Museum. Start small with coffee or a walk, and save dinner for when it is going well.
What are good things to do with a large group in Boston?
Try bowling at Central Park Lanes Bowling Center, play at MassArt Film Society and racket sports at Palmer Dixon Indoor Tennis Courts. Book ahead for a group this size, and send the link so everyone can vote on the plan.
What can friends do on a weekend in Boston?
Try saturday morning: Warren Anatomical Museum, saturday lunch: Spectacle Georges Concessions and saturday afternoon: Spectacle Island. Every stop is a real mapped place, with a rough cost per person.
What are good birthday ideas for adults in Boston?
Try birthday dinner at Spectacle Georges Concessions, play at Kings Boston - Back Bay and drinks at Pockets Billiard Club (21+). Every idea here is a real mapped place, with a rough cost per person.
What can friends under 21 do together in Boston?
Try play at Central Park Lanes Bowling Center, see a movie at Simons Theatre and get active at Parkway Community YMCA. Every idea here is a real mapped place. Costs are rough estimates.
Can Squad Plan make a custom plan for Boston?
Yes. Pick the city, your group and the vibe, and Squad Plan gives you three plans your friends can vote on. It is free for 5 plans a week.