I admit that making this itinerary feels a bit like cheating since we've lived in the city for a few years now, but it's ultimately a good thing for people visiting Boston to get recommendations from those who have been there for a while. So here's an itinerary that has great views, amazing food and a taste of the rich culture and history that make Boston such an amazing city.
Day 1
- Arrived in Boston. Cabs to the city range from $30-40 or you can take the Blue line for $2.50 which now runs until 2:30am!
- Check-in. If you're looking for character, stay in the South End neighborhood. If you want to be near the touristy stuff, stay near Copley or Faneuil Hall. My friend regards Allston as the armpit of Boston, which is generally true. It's also far away from the city but cheaper and near great ethnic food.
- Dinner @ Giacomo's. Get any of the linguine dishes and the butternut squash ravioli. The South End location takes reservations (make them if you can)- I recommend that you go that route and if you still have to wait, you can hangout next door @ Anchovies for amazing truffle fries.
- Walk along Tremont St.
- Drinks @ Beehive. A bar with great aesthetics and a cozy feel- you'll probably hear live jazz performances.
- Brunch on Newbury St. We recommend Trident Booksellers & Cafe, Joe’s American Bar & Grill, or Papa Razzi.
- Shop along Newbury St. There's no sales tax (on non-luxury items) so enjoy!
- Explore Copley Square. Some tour attractions include the Boston Public Library, Trinity Church, Prudential Mall, Also, if you're looking for good coffee around the area, Thinking Cup has great pour overs.
- Hip Hop Yoga @ Back Bay Yoga. They have afternoon drop in classes during the week for $5. Trust me, it's a non-judgmental, yet challenging experience for all ranges. You may want to bring a change of clothing. Mat rentals are $3.
- Walk to the Boston Common and Public Gardens. This is where they filmed one of my favorite scenes of Good Will Hunting. Some activities include the swan boat ride and ice skating on theFrog Pond (winter). It's also a great place to enjoy a mid-afternoon picnic.
- Walk the Esplanade, Boston's most scenic jogging route. If you're in a rush, just walk across the Mass Ave bridge. In the summer you'll see many sail boats coasting on the Charles- beautiful!
- Oysters @ Marliave. Thien's fave- Happy Hour Oysters starting 4-6pm and 9-10pm. Best oysters and clams in the city.
- Dinner @ Parish. Each sandwich is specially crafted by one of Boston's best chefs.
- Drinks @ Top of the Hub. Personally, I like going during the day more because the city view is prettier with sunlight, but at night they sometimes have live jazz music.
- Haymarket opens on Friday and Saturday mornings starting around 9 am. Definitely go if you have a chance, it's a really fun experience! Super cheap souvenir t-shirts near T stop by Bell in Hand Tavern.
- Pizza @ Regina Pizzeria, but really, you can't go wrong with any of the Italian restaurants in the area
- Cannolis @ Mike's Pastry. If you're not too full, also try Modern Pastry Shop.
- Explore the streets of the North End. Visit Paul Revere's house.
- Faneuil Hall- The meeting hall where some of the most important reformation policies were drafted by the nation's brightest minds. There's shopping and street entertainment in the area and food in the Quincy Market building. This is also a good place to pick up souvenirs.
- Dinner @ Gourmet Dumpling House. Get the Szechuan fish. Trust me.
- Drinks @ JM Curley or HighBall
- Lobster roll, clam chowder, etc @ Yankee Lobster
- Harpoon Brewery Tour
- Institute of Contemporary Art -only if it's a Thursday (free admission) as it is a mediocre museum- or drinks @ Whisky Priest. The food isn't great but it does have a great upper deck for night views of the harbor.
- Dinner @ No Name Restaurant or Menton (since Thien raves about it)
- Cocktails @ Drink
Don't forget! If it's a...
Sunday, check out SOWA: vintage shopping+ food trucks. Worth a visit!
Wednesday, go to the Museum of Fine Arts! Free after 5pm (technically by donation) & though it's smaller than MOMA and LACMA, it has very interesting exhibits. They also have a free sketching program if you're in an artsy mood.
If you're a glutton for punishment, consider doing the Freedom Trail. Be forewarned, it's a 2.5 mile trek and it's not fun to move let alone walk outdoors during the summer (or winter). But if you're a history buff, you'll love it.

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