10am: Take a jog around Jamaica Pond
Laps are boring, unless you’re lapping a picturesque body of water right in the city proper. Also? Jake Gyllenhaal has been spotted working out here ahead of the next Boston Marathon movie. No harm in checking out his routine, right?
11:30am: Indulge your two favorite pastimes at Tres Gatos
Those pastimes, of course, being tapas and secondhand records. This Centre Street restaurant is all small-plates business in front (morning-time deviled eggs and chicken liver toast, together at last) with a small used music and bookstore in back. View on Map
1pm: Gallery hop on Centre/South Streets
Take a long stroll down JP’s main thoroughfare to hit up three indie art galleries: Aviary, The Hallway, and UForge, all open on weekends, all displaying locally spun artworks. You might even luck into an art class. You could be next!
10am: Replicate the Harvard Stadium November Project workout
Did you know that the November Project began in Boston? Alas, its most venerated workout takes place on this stadium’s steps … at 5:30am and 6:30am. Go to the website and then recreate the WoD at a slightly more reasonable morning hour. View on Map
11am: Have a pre-noon beer at SoWa Market
The May opening of the SoWa Market is the official kickoff to summer. After chatting with local farmers, testing samples of organic ice cream, and snooping around the vintage market, you can beat a retreat into the new beer and wine garden for a regionally brewed Tall Boy. View on Map
12pm: Splash some cash on Tremont Street
The South End is that rare bird that boasts an equal number of male- and female-centric clothing boutiques, plus funky gift and accessories shops like Niche, and Olives & Grace. Everybody wins!
1:30pm: Savor oysters and some rosé at Select Oyster Bar
Just around the corner is one of the neighborhood’s most exciting restaurant openings in years, and your best bet for expertly prepared New England seafood. Cross your fingers for a back patio table and ask for wine recommendations -- they pour specials both by the bottle and the carafe. View on Map
3:30pm: Thrift shop on Newbury Street
There’s a special joy in hitting up secondhand shops on a famed boulevard that also houses Versace, Chanel, and Giorgio Armani. Relish beating the system at the just-opened men’s consignment shop from 2nd Time Around.
Fort Point/Seaport/Innovation District
4pm: Grab a growler at Trillium Tasting Room
It’s not a tasting room per se, but rather a lilliputian window (well, door) into one of the great local brewing hive minds. Chat with the beermakers and then carry out your favorite IPA in an economy size. View on Map
5pm: Drift off Carson Beach
Somehow even us locals forget about the watersports right here. Boating in Boston sets you up to kayak or paddleboard right off the beach into Dorchester Bay.
7pm: Split a lobster roll and some soft serve at Sullivan’s
Sully’s is as Southie as it gets (i.e. Whitey Bulger was once a regular patron). Yeah, the lines might be out the door, but the lobster roll is actually one of the city’s great deals, and who can resist a vanilla-chocolate twist? View on Map
7pm: Spring for a same-day seat to a Red Sox game
Yes, they’re some of the most elusive tickets in town, but that doesn’t meant they’re impossible. Ninety minutes before gametime, the box office releases a limited number of seats at E Gate. And if you’re still out of luck, let’s just say that scalped tickets are *not* hard to come by. View on Map
11pm: Stick a straw in a classy scorpion bowl at Hojoko
High-end izakayas are totally a thing, and this one can be found inside a cool hotel. You and your compadres are best served going for the “large-format” cocktails, be it a Blue Hawaiian (plantation rum, pineapple, mizu sochu, lemon, blue Curacao) or the Surfer on Acid (Appleton rum, clément coconut, pineapple, Peychaud’s, absinthe). View on Map
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1. SELECT Oyster Bar50 Gloucester St, Boston
2. Trillium Brewing Company369 Congress St, Boston
3. Legal Sea Foods Harborside270 Northern Ave, Boston
4. The Gallows1395 Washington St, Boston
5. Aeronaut Brewing Co.14 Tyler St, Somerville
6. Union Square Donuts16 Bow St, Somerville
7. Loco Taqueria & Oyster Bar412 West Broadway, Boston
8. Daedalus45 Mount Auburn St, Cambridge
9. The Sinclair Kitchen52 Church St, Cambridge
10. Hojoko1271 Boylston St, Boston
11. Trina's Starlite Lounge3 Beacon St, Somerville
12. BISq1071 Cambridge Street, Cambridge
13. Tres Gatos470 Centre St, Jamaica Plain
14. Lulu's421 Cambridge St, Boston
15. Boston Public Library700 Boylston St, Boston
16. SoWa Market460 Harrison Ave, Boston
17. Lawn On D420 D St, Boston
18. Brooklyn Boulders12A Tyler St, Somerville
19. Harvard Stadium65 N Harvard St, Boston
20. Orchard Skateshop156 Harvard Ave, Allston
21. Sullivan's Castle Island, South Boston2080 William J Day Blvd, Boston
22. In Your Ear!72A Mt Auburn St (Cambridge)/957 Commonwealth Ave (Boston), Cambridge
23. Fenway Park4 Yawkey Way, Boston
24. Game On82 Lansdowne St, Boston
25. Ryles Jazz Club212 Hampshire St, Cambridge