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 1 Alternative: Travel Day + Arrival (Flying into Boston Logan International)

• Fly into Boston Logan International Airport

  • If you can make it happen, fly in earlier so you can maximize your day.

  • Also, if you are only planning to be in Boston and the surrounding cities during your trip, there’s no need to rent a car! The transit system is easy to use, cheap, and very clean.

• Once you get all your luggage head for Ground Transportation/shuttles and look for the free to ride Massport Route 22, 33, or 55 shuttle that will take you to Airport Station

  • Once at the Airport Station, take the inbound Blue Line (toward Bowdoin) into Downtown Boston.

  • Depending on where you are staying will depend on which stop you get off on but usually it’s convenient to get off at the Government Center as that puts you right in the middle of the city.

    • My go-to app when using any sort of public transportation is Google Maps! Just put in your origin then destination and it will pull up the different lines and times you can choose from.

  • Also the T has tap-n-go turnstyles so just have your card ready!

  • If any of this is confusing or overwhelming do not worry someone will help you out. Look for an official transportation employee or ask a fellow traveler!

  • The trip from the airport into the heart of Boston usually takes 20 minutes

• Once you get off at your stop and get your bearings, head toward your 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

• Get up, get ready and head out to Beacon Hill (if you didn’t have a chance to explore it yet)

  • Stop into Beacon Hill Books & Cafe (aesthetic, adorable, but can be cramped)

  • Head over to Acorn Street and snap a photo of the famous road

  • If you’re a fan of the show Cheers, the bar is located right near Beacon Hill/Public Garden

• Walk over to the Park Street station in Boston Common to catch the Red Line out to Cambridge/Harvard (10 mins)

• Once there, find your way to Harvard University and take in the sites of the beautiful Ivy League school

• Stroll Brattle Street and Massachusetts Ave that are lined with plenty of stores, boutiques, cafes, and bookstores - which leads me to my next bullet point

• A must check out for anyone who is a fan of romance books is Lovestruck Books & Cafe

  • This shop has every romance novel you can think of plus adorable merch, a coffee bar and a wine/cocktail bar! I could definitely get lost in here for a few hours.

• Looking for something to eat? Or a little mid-afternoon beverage? Head over to Source Restaurants (right up the street from Lovestruck)

  • Make sure to get the Cast Iron Country Rolls - they are incredible

• Same spiel as the day before, depending on where you are staying and what season it is, there are a couple of options for the late-afternoon/evening:

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

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

  • Check out a museum nearby (Harvard Art Museum, Museum of Science)

Day 4: Salem

• Get up, get ready and eat breakfast

  • Make sure to wear comfortable shoes since there will be a lot of walking again

• Head to the North Station to catch the train toward Salem

  • Tickets are about $8-$10 one-way and it’s about a 30-40 minute train ride

  • The trains also run pretty regularly but you will want to check a few days before to make sure you don’t miss the one you want!

    • More information about tickets and purchasing options can be found here

• Once you get to Salem start walking down Washington Street to the center of town

• Here are the top things to check out:

  • The House of the Seven Gables

  • Nathaniel Hawthorne’s Birthplace

  • Ropes Mansion and Garden (aka Hocus Pocus House)

  • Witch Trials Memorial

  • Bewitched Sculpture

  • The Witch House at Salem

  • The Burying Point

  • Old Town Hall

  • Peabody Essex Museum

• If you need a caffeine break stop into Jaho Artisan Coffee (they have delicious lattes)

• Take a stroll toward the water and see the Historic Derby Wharf as well as the Derby Wharf Light Station

  • Also in the area is a historic candy shop: Ye Olde Pepper Company (hailed as America’s oldest candy company)

• After all your walking, you might have built up an appetite. Here are my top-two spots in Salem!

  • Boston Burger Company

  • Rockafellas

• Now what better way to round out your trip to Salem than with a ghost tour? Make sure to book tickets ahead of time since they can fill up quickly! Most tours are also decently priced.

  • Salem Ghosts

  • History and Hauntings of Salem Guided Walking Tour

  • Salem's Best Ghost Tour

Museums & Attractions to check out:

If you are interested in art, history, politics, or animals here are some more top-rated attractions in Boston

• Isabella Stewart Gardner Museum

• Museum of Fine Arts, Boston

• Museum of Science

• Boston Children’s Museum

• John F. Kennedy Presidential Library

• Institute of Contemporary Art

• New England Aquarium