Depending on where you are coming in from will depend on your departure time and arrival method. I have included two options for Day 1 depending on driving in from the NYC area or if you plan to fly into Boston Logan International Airport.

Day 1: Travel Day + Arrival (Driving from North Jersey/NYC)

• Start drive around 9am north toward Boston

• Make a pit stop in Mystic, CT to stretch legs and get lunch at the famous Mystic Pizza!

  • From where we live it takes about 2 hrs. 45 mins to get to Mystic

    • Dayne and I ordered small build your own ($14 before toppings) then walked down by the river to enjoy the weather and views

• If you’re looking for a little coffee pick me up you can check out: Mystic Depot Roasters, Lighthouse Bakery, Sift Bake Shop or for a little spooky witchy vibe visit The Cloak and Wand!

• Get back on the road and continue drive to Boston (1 hr. 30/45 mins.)

• Road Trip Sidebar: If you are a fan of Samuel Adams Beer, you’ll be close to the company’s original brewery in Jamaica Plain!

  • The tours range in price and time - we chose the Sam Signature Experience ($15/45 mins)

    • Note: the parking for this brewery is a little tricky since it’s in the middle of a neighborhood so make sure you have plenty of time to park and walk

• Get to Boston mid/late-afternoon and head to hotel or Airbnb

  • Neighborhoods I recommend:

1. Downtown/Financial District*- Right in the middle of the action, lots of hotels and Airbnb locations to choose from plus close to several public transit stations (the T).

2. North End - Here you’ll experience the hustle and bustle of Boston’s Little Italy while also enjoying all the wonderful smells from the local restaurants and bakeries

3. West End* - Right near Boston’s Little Italy, the West End makes travel easy as you are close by major transit stations, close to the famous Mass Gen Hospital and right on the Charles River. You’re also close to a few bridges that connect you to Charlestown and Cambridge.

4. Beacon Hill - This picturesque historic neighborhood is home to beautiful brownstones, Instagram worthy backdrops, local shops, and close to the Boston Gardens and Common. If you can’t find a place to stay in this area, I still recommend exploring it for a few hours.

5. Back Bay* - Another neighborhood in the middle of the action, Back Bay plays host to Copley Square, Trinity Church, the Boston Public Library, and the Finish Line for the Boston Marathon on Boylston Street.

6. Cambridge* - Located across the Charles River from Downtown Boston, Cambridge is home to MIT and Harvard University. This city is scenic, quiet, and perfect for anyone who wants to escape the large crowds.

*Places I’ve stayed in Boston

• Once you are settled/checked in and refreshed head out to the North End for dinner at one of these amazing restaurants:

  • Carmelina’s

    • If you plan to go here you need to make reservations WELL in advance or be prepared to wait a long time - however it is 100% worth the wait.

  • Ristorante Limoncello

  • La Famiglia Giorgio’s

• After dinner, make sure to get a little treat at one of the many delicious bakeries in the North End! I always opt for a cannoli from Modern Pastry.

  • In case you didn’t know, there’s a longstanding cannoli rivalry between Modern and Mike’s Pastry (right across the street) that locals and tourists go back and forth on. Modern has a traditional feel (ironic considering the same) while Mike’s has a wide selection of cannoli flavors. Amongst my family and friends, we choose Modern but I’ve talked with others who prefer Mike’s - so now it’s up to you!

    • Also make sure to bring CASH when going into North End bakeries. Several of them do not take card at all.

Day 2: Explore the city

• Get up, get ready and make sure to fuel up as it’s going to be a long day exploring the city via the Freedom Trail

  • The Freedom Trail is denoted by a red-brick path that runs 2.5 miles through the whole city with 16 official stops along the way

    • Depending on your pace and interest the Freedom Trail can take anywhere from 2-6 hours

Jordy’s Journal Hot Take: Go backwards on the Freedom Trail (start at Bunker Hill and end in America’s oldest park - Boston Common)

• Why do that? Well, the trail starts in the center of the city, Boston Common, and ends on the other side of the Charles River in Charlestown at the Bunker Hill Monument. If you go backwards, you get your furthest distance out of the way early, then can backtrack into the city which would put you near all the great restaurants close to lunch time! You can follow whichever path is best for you or best for your schedule.

• What you will see along the way: Bunker Hill Monument, USS Constitution, Copp’s Hill Burying Ground, Old North Church, Paul Revere House, Faneuil Hall, Boston Massacre Site, Old State House, Old South Meeting House, Old Corner Bookstore, Boston Latin School Site/Benjamin Franklin Statue, King’s Chapel & King’s Chapel Burying Ground, Granary Burying Ground, Park Street Church, Massachusetts State House, and Boston Common.

• As I mentioned above, you might start feeling a little hungry halfway through your exploration, which should put you right near Quincy Market. If it does, be sure to grab a delicious lobster roll and cup of clam chowder from The Oyster Bar.

  • Many locals will say this is a total tourist trap and while it might be, the lobster rolls are amazing and the combo meal price is decent. Plus the guy who helps seat everyone at the counter top is the sweetest person!

    • A highly recommended spot close by is the Neptune Oyster near the North End. I have never been there but from what others are saying online and the reviews, it seems to be a favorite!

• Once you get your afternoon pick me up, head back onto the Freedom Trail.

• If you chose to go backward and ended up in Boston Common you have a couple options on what to do next:

  • Go visit Beacon Hill (lots of local shops, bookstores, and cafes)

  • Go see the Boston Public Library (5-10 minute walk from Common)

  • Walk 15 minutes and go visit the Boston Tea Party Ships & Museum

  • Go visit another museum in the area (Boston Children’s Museum, Isabella Stewart Gardner or the Museum of Fine Arts, Boston)

• As for nighttime plans, there are a couple options on what to do (depending on when you visit and what’s in season):

  • Go to a Red Sox baseball game at the historic Fenway Park

    • If you are interested in this option:

      • Head to the Bolyston station for the T and take the Green Line toward Kenmore. When you exit just follow the crowd heading toward the stadium

      • I would recommend getting to the area outside Fenway at least 1.5/2 hours ahead of first pitch so you can get onto Jersey Street for food, drinks, and souvenirs.

        • The Italian sausage sandwich with peppers and onions from The Sausage Guy is sublime.

  • Go to TD Garden to catch either a Bruins or Celtics game

    • This stadium is about a 10 minute walk from Boston Common and is where the North Station is located

    • If you are looking for a fun stop for a pre-game drink or app head to Hurricane’s at the Garden

• If sports aren’t your thing or the teams are away/off:

  • Pop into the Samuel Adams Taproom right near Faneuil Hall (if it’s fall they have a fall beer flight that is amazing!)

  • Post up at a restaurant nearby and enjoy happy hour:

    • Bostonia Public House

    • Union Oyster House

    • Boston Sail Loft

    • State Street Provisions

• Finish the night with a drink at the oldest, continuously operating tavern, in America - Bell in Hand Tavern

Day 3: Cambridge