Boston is a special place to both of us! If you're able, plan to come for a few extra days to experience some of what this great city has to offer. From historic places tied to the Revolution, to Fenway Park, and to some of the best breweries in the country, we're a little bias in saying Boston is the best. Here's a perfect day in Boston through the eyes of Tyler and Ashlan, as well as some must do's for your visit.
Tyler's Perfect Day in Boston: Wake up bright and early to head to The Thinking Cup on the Boston Common. Get off at the Park Street T stop and take the long way to the shop...strolling through the Common and the Public Garden. Upon entering order a medium black coffee (specify "black"...a "regular" here means cream and sugar) and a B.A.L.T. (bacon, avocado, lettuce, tomato) sandwich with no tomato. Having a good book in hand (noting the coffee shop doesn't have wifi) hang out and read for an hour or so. Afterwards, go to the Brattle Book Shop and peruse all the books and impulsively buy a few. Next, walk down the Commonwealth Avenue Mall toward Copley Square. Taking a left on Dartmouth Street, hang out at Bates Hall in the Public Library and read for another 3o minutes. Head back home, change clothes, and go on a nice run along the Charles River Esplanade. Clean up, eat lunch, and go take some pictures around Beacon Hill. Come evening head to the Bell in Hand Tavern to have a beer at the oldest tavern in America. After your beer, walk to the North End to have a nice Italian Dinner. Next head over to Trillium's pop up beer garden on the Rose Kennedy Greenway (or go to their brewery in the Seaport...an equally cool spot!). Wrap up the night with a stroll around the Harborwalk, making sure to stop by Christopher Columbus Park.
Ashlan's Perfect Day in Boston: Wake up and meet up with friends for a run along the Charles River. Head home, get ready, and have breakfast in Union Square in Somerville at the Neighborhood Restaurant (try their cream of wheat!) or Union Square Donuts (any of their donuts or Ashlan's favorite: their breakfast sandwich)! Travel downtown to the Rose Kennedy Greenway to check out the vendors at the Greenway Open Market, an open-air artisan market. Grab a quick lunch at either Boston Public Market or Quincy Market then catch a ferry to one of the Harbor Islands. Spend a couple hours exploring the island and enjoying the view of the city from the Islands. Upon returning downtown, head to the North End to try another new Italian restaurant. After dinner, grab a cannoli or gelato and hang out on the swings on the Greenway before heading home.
Must Do's:
1. The Freedom Trail: This starts in front of the Visitors’ Center in the Boston Common and ends by climbing the Bunker Hill monument in Charlestown. (Hints: You can also start the Freedom Trail early at Bunker Hill to possibly avoid crowds and start climbing while you’re fresh rather than after you’ve walked the rest of the trail! Also note that the USS Constitution is closed on Mondays if you happen to visit on this day!)
2. Visit the North End (Boston’s Italian district) for dinner: If going for dinner, we recommend making reservations. Also grab a cannoli at either Mike’s Pastry or Modern Pastry while you’re there!
3. Fenway Park Tour (or game!): The tour is $21 for an adult. See www.mlb.com/redsox/ballpark/tours.
4. Visit the Central Boston Public Library in Copley Square: Enter from Dartmouth St. to see the historic side of the building and make sure to check out both the outdoor courtyard on the first floor and the Bates Hall Reading Room on the second floor.
5. Skywalk Observatory ($20/person): See some views of the city from up here! For more information, visit www.skywalkboston.com/tickets/.
6. Visit one of the Boston Harbor Islands: Check out which island you want to go to as well as the ferry schedule over to the islands. For more information, visit www.bostonharborcruises.com/harbor-islands/.
We recommend using Boston's public transit system for the duration of your stay. This is much easier and cheaper than renting a car.
The Subway/Train is your best option.
You can only buy a T Pass/Charlie Card at certain stations. On the green line anything heading into the city, Kenmore and beyond, is where you can purchase these.
We highly recommend you avoid driving. Parking overnight in Boston/Brookline is difficult and often expensive. Public transportation is decent here, and you can always Uber/take a cab. If you do choose to rent a car, be sure to make your reservations are at a place with parking included.