Faneuil Hall
Spend the day at Faneuil Hall to shop, eat, and watch street performers. There are over 30 food vendors inside Quincy Market at which you can use a pre-purchased food voucher ($5-$9) if you're trying not to splurge. If you visit in the evening, there are plenty of restaurants and bars (like Cheers) in the area to spend a fun-filled night with your date. Stores also close around 8 pm.
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[Photo via @lakeumbagog]