The Ultimate Boston & Salem Travel Guide

By The Backseat View

All Americans deserve the pleasure of meeting Boston. Strolling the cobblestone streets and preserved villages where the Founding Fathers plotted and planned for our nation brings emotional waves of patriotism. Walking the Freedom Trail with the ghost of Paul Revere as your guide to the Boston Massacre, Faneuil Hall (where the American Revolution was plotted), and Bunker Hill (where Britain attacked) brings a new understanding of Paul Revere’s Ride. Old Ironsides, launched in 1797, is still floating in the beautiful harbor.

“Give me liberty or give me death!” Patrick Henry

Historic towns surround Boston, so let’s explore Salem and the mansions of Newport. Salem is bewitching with its spellbinding beauty, blood-chilling history, and seaside charm. There is nowhere I would rather be than New England in the fall. I am thrilled to have you join me on this trip through American history!

BOSTON & SALEM Travel Guide

Boston

No amount of planning prepared me for LOVING BOSTON immediately. For every American in Boston, day one is arriving, and day two is the Freedom Trail. Parking in Boston is insanity. We finally found a parking garage and made it to our first stop on the Freedom Trail, the Old State House built in 1713 and the site of the Boston Massacre.

Freedom Trail

Freedom Trail

Boston knew we were coming, so the red brick line embedded into the sidewalk leads you to all 16 historic trail sites. Following the red-bricked line is the easiest 2.5-mile tourist walk ever. The trail winds through historic neighborhoods, including Downtown, the North End, and Charlestown. Over 4 million people walk the line yearly, so plan on plenty of company.

Faneuil Hall

The second stop is Faneuil Hall, where the American Revolution was plotted. Over 40 vendors, restaurants, and street performers will distract you for hours. The famous 1980s TV Cheers Bar, Bull & Finch, is here. The New England Holocaust Memorial and The Boston Public Market are also on this street. We had lunch at Boston Chowder in the Quincy Market and wandered the shops until we were a little lost, then found our way back to the red-brick line.

Union Street

The street where Boston was established in 1630 still stands, with the oldest bar and restaurant in America on Union Street. The Bell in Hand Tavern opened in 1795 and is filled with history and original architecture. The Union Oyster House is a National Landmark, and reservations are required for clam chowder in the oldest restaurant. The patriotic decorations, cobblestone streets, and stunning buildings make you fall in love with Boston.

North End

As I stumbled into the North End of Boston, I needed to sit down to absorb the beauty of the 1700s architecture, the small European town feeling, and the mouth-watering smells drifting through the Italian restaurant windows. It’s also easier to eat the famous Mike’s Pastry Cannoli sitting down. I wasn’t exactly sure where I was, but I wish I lived here. Having a meal in Little Italy is a requirement for visiting Boston.

Paul Revere

The North End has the Paul Revere House, the Paul Revere Statue, and the Old North Church. The Paul Revere House sells $6 tickets to glimpse inside the 1680s home. We walked through and took pictures of the statue and church. The Old North Church is the oldest in Boston, built in 1723, and is a National Historic Landmark. It brings Paul Revere’s Ride and Warning to life.

“The British ARE COMING!”

Take a Step Back in Time

Bunker Hill

Around the corner and down streets lined with historic homes, you will find the Bunker Hill Monument. The first major battle of the American Revolutionary War was fought here. You can buy a ticket, walk the 294 steps to the top, or soak in the view from a park bench.

Copp’s Hill

Copp’s Hill Burying Ground is Boston’s largest colonial cemetery. I enjoy looking at the messages carved in the old tombstones.

The TD Garden is nearby and home to the Celtics and Bruins for basketball and hockey events.

The Museum of Science in Boston is more focused on the Northwest area. It offers interactive exhibits and dinosaurs for family entertainment.

Old Ironside

USS Constitution “Old Ironsides” launched in 1797 and fought in the War of 1812. The WORLD’S OLDEST WARSHIP ship is docked at the Charlestown Navy Yard. Tours are free, but you must show a valid federal or state-issued photo I.D. USS Constitution Museum is here for more information on the ships. The USS Cassin Young, a WWII Destroyer, is also available for tours. This is the last stop on the Freedom Trail.

Everything took more time than I planned as we strolled the day away. As the sun set, the restaurants and streets came alive with FANS covered in Celtic gear and a sense of community spirit as windows opened and everyone cheered for their team. Their excitement was contagious, and I couldn’t resist grabbing a pizza at Regina Pizzeria to be a part of the community and cheer on the Celtics.

South Boston

On Day 3, the goal is Downtown Boston.

Granary Burying Grounds is the first stop for American Patriots like Paul Revere, John Hancock, Sam Adams, and Mother Goose. After paying respects, walk a few steps to the Boston Common and Public Gardens.

Boston Common

The Boston Common is a park that leads into the Boston Public Gardens. While the park is beautiful, this area is sketchy at night with homeless people.

Boston Public Gardens

It’s America’s first Public Garden, and the variety of trees and flowers is breathtaking. The Garden is famous for its Swan Boats, but they close around Labor Day. The statues, benches, and views are peaceful and refreshing. It feels more like a park than a garden to me. The Gardens have Beacon Hill on one side and Chinatown on the other.

Acorn Street

Beautiful homes, gas-lamp-lined streets, and historic cobblestone streets surround Boston Common Park, the definition of classic New England Charm. The most famous is narrow Acorn Street, the most photographed street in Boston. It’s hard to capture. It’s more of a feeling of walking through preserved history.

Beacon Hill

I could wander these quaint streets with boutiques, antique shops, cafes, and restaurants all day. Louisburg Square, Mt. Vernon Street, Charles Street, and Chestnut are wealthy and historic addresses. The State House, with its iconic gold dome, is nearby. Honestly, I spent an hour gawking at all the lavish homes and buildings. The Boston Athenaeum, at 10 1/2 Beacon Street, is an independent library with five floors of rare books I wanted to visit.

Newbury Street

We strolled Newbury Street for an hour and could have spent the day in the trendy, high-end boutiques. With all the outdoor cafe dining, I could pretend I was in Paris. The tree-lined residential streets are perfect for a stroll to the Charles River. You can continue down the street a few blocks to tour the Boston Public Library, which opened in 1852 and is on the National Register of Historic Places. We ran out of time before visiting the Prudential Center, with over 75 shops. After all the shopping, I’m out of money, so it’s time to head to Fenway.

Fenway Park

The Fenway Park atmosphere is hallowed ground for Boston Red Sox Fans. America’s oldest and most beloved ballpark is a legend, and a tour must be on any itinerary. The tour includes a stop at the iconic Green Moster wall, the Lone Red Seat, the press box, and their food garden. The Fenway Park Living Museum has over 200,000 artifacts, photographs, and historical displays.

We allotted two hours for our one-hour $25 tour that starts on the hour. Everyone visiting Boston tours Fenway, so buy those tickets in advance. “America’s Most Beloved Ballpark” does not disappoint with an education in baseball history. Since there wasn’t a game, I didn’t realize the stadium rules about purses applied to tours. So, leave everything in the car since they will not hold your purse, and you will miss part of the tour returning to the car. We headed to our next stop after touring the shops and statues outside the stadium.

Fine Arts

The Museum of Fine Arts is near Fenway. It costs almost $30 a person and takes 3-6 hours to see the museum. I didn’t travel with “museum-loving” people, so we skipped.

The Isabella Stewart Gardner Museum is near the Fine Arts Museum, where you can tour a Venetian palace with sculptures, paintings, and art displays. The tickets are timed entrance and $20 for an hour-long self-guided tour.

House of Blues is an iconic music venue.

JFK Museum

The John F. Kennedy Presidential Library and Museum recreates the Kennedy era. Honestly, I voted to come to see Jackie O’s clothes. We spent an hour watching movies and learning about the Civil Rights, Peace Corps, and NASA programs. The museum’s setting is stunning, overlooking the water with the Boston skyline. Honestly, I would not bring children here. The time-entrance tickets are almost $20/ person. The JFK Museum brings a close to our day.

Tips

Cities aren’t my favorite places, so I was surprised when Boston’s Fall stole my heart. Boston deserves a few days at the very minimum on all New England itineraries. I packed in layers and needed a heavy North Face jacket for October. Driving in the city is hard, so use the easy public transportation. “The T” has four lines that drop you by most attractions. Boston is known as America’s Walkable City because it is compact. The city also offers walking tours and Hop-on-Hop-off trolley options.

East Harbor

As with all vacations, there were places I wanted to visit that were cut due to stormy weather and flight delays. On the day we arrived, we planned to tour the Boston Tea Party Museum and ships, which have $35 timed entrance tickets, and the Waterfront Area in East Boston, which includes the New England Aquarium. Castle Island is a hidden gem with a 22-acre “island” and a historic fort.

Franklin Park Zoo

The Franklin Park Zoo is in the South End of Boston, away from the other attractions. It has excellent reviews for its 72-acre park.

Hotel Options

There are endless four- and five-star hotels, so it’s about location. The Hiltons and Courtyards are $400 a night, and the two-star hotels are $300 a night. Let’s review the neighborhoods and dream of luxury.

Back Bay is the ritziest neighborhood with Newbury Street, parks, and shopping.

• Fairmont Copley Plaza is a $500-a-night luxury in Back Bay.
• The Liberty Hotel in Beacon Hill for luxury in Boston’s wealthiest area.
• Hilton Boston Park Plaza is near the Boston Public Garden and costs $400.
• The Revolution Hotel is a budget option at $250/night.

North End is my favorite with Little Italy & Paul Revere. The closest you can get is downtown.

• The Bostonian at $350 a night is perfect near Union Street.

Fenway Area has the House of Blues and museums adjacent to Back Bay.

• The Verb Hotel is a 3* Rock-n-Roll Hotel with rooms starting around $320.

Seaport is southeast downtown with highrises overlooking the harbor.

• Boston Harbor Hotel costs $800 a night for an iconic waterfront sanctuary.

Food

Boston has all the fantastic food options you could imagine. I had food goals for a Lobster Roll, Clam Chowder, visit Little Italy, Boston Creme Pie, and Mike’s Pastry for cannoli. Mamma Mia in Little Italy is romantic and authentic, with an old-world feel. Boston Sail Loft has won awards for the best Clam Chowder in New England. Tatte Bakery & Cafe has 18 locations, which speaks for itself. Santarpio’s Pizza is near the airport, has been in business for 100 years, and is in the Pizza Hall of Fame.

Boston & Salem Travel Guide

Boston is perfect for day trips to Salem and Rhode Island’s Cliff Walk Mansions.

Salem in October

Day 4 begins with pulling out my witch hat and heading to Salem.

Salem is the easiest day to plan. Walking the Salem Heritage Trail, which is three miles long and marked with a yellow line on the sidewalk, takes you to all the attractions in town. There are maps to direct you to the most popular attractions. The only advance planning is buying your House of Seven Gables ticket, a Costume Ball ticket, and making a dinner reservation. I felt like one day in Salem was plenty. Salem in October is crazily crowded, especially with large field trip groups. We arrived before 9 am and pulled into the South Harbor parking garage.

Red’s Sandwich Shop

Red’s Sandwich Shop was our first stop for brunch. Reds was the London Coffee House built in 1698 and the meeting place for patriots planning the American Revolution. There was a wait—there was always a wait—but this is Salem’s most popular restaurant. History lessons are served with sandwiches and French toast.

Emporium 32

Any store with a line to get in is worth the wait. Emporium 32 was my favorite store, with over 100 different artists’ unique works in the store. They opened a second store by the Hawthorne Hotel, called 1925 at the Hawthorne. Salem is made for photos with attention to detail in decorations, the skeletons wearing bowties, and flower boxes. We spent hours exploring the boutiques and the town as we followed the yellow line.

Hocus Pocus

The Hocus Pocus Town Hall is hard to miss at 161 Essex Street.

Allison’s house is the stunning Ropes Mansion and Gardens, built in 1727. The mansion at 318 Essex Street is open for weekend tours. The $25 tickets are timed entrance, and they are only $5 if you add them to the Peabody Museum ticket.

Salem Witch Trial Memorial

The Salem Witch Trial Memorial is a park with the names of the 20 people executed carved into benches. In the middle of the hustle and bustle and commercialism of Halloween sits a sobering green park overlooking a graveyard. The injustice of over 200 people standing trial moves you. It’s my second favorite stop in Salem.

The Witch House

The Witch House is the only remaining Salem structure directly related to the 1692 witch trials. It was owned by a witch trial judge, Jonathan Corwin. Tickets for the $12 self-guided tours can be purchased online at 8 a.m. on the day of the tours.

The Bewitched Statue

The Bewitched Statue is in the town center, and there is a line for photos. The famous TV show in which a witch married a mortal in the 1960s was extremely popular.

House of Seven Gables

My favorite part of Salem was the House of Seven Gables, to which I purchased tickets weeks in advance. Built in 1668, it is famous for Nathaniel Hawthorne’s 1851 novel and is one of the oldest surviving homes in North America. The exquisite history tour took an hour filled with secret passageways and beautiful furniture. We spent even more time gazing at the magnificent harbor view and enjoying the garden. It’s a 15-minute delightful walk from the center of Salem for the timed entrance $25 or $30 house tour.

Across the street is America’s Oldest Candy Company, so enjoy a candy snack with a harbor view.

Maritime Historic Site

The Replica of the 1797 Friendship Vessel is in the harbor at the Salem Maritime National Historic Site. It was the first National Historic Site in the U.S., with twelve historic structures on the waterfront. You can tour the buildings and the boat. It’s on the way to the House of Seven Gables, and the Custom House is stunning, so plan a little extra time to enjoy it. It was peaceful, and we enjoyed the break from the crowds.

The Hawthorne Hotel

The Hawthorne Hotel was built in the 1920s and is worth looking around the lobby or making a dinner reservation at The Tavern or Nathaniel’s. The most popular costume ball, the Hawthorne Hotel’s Halloween Ball, put its tickets on sale six months in advance. The historic Hawthorne Hotel is the most famous in Salem.

Chestnut Street

Chestnut Street is considered “the most beautiful street in Salem” and is lined with preserved historic mansions in the heart of Salem.

Haunted Happenings

There are haunted houses, witch museums, a Salem witch village, and endless entertainment shops. Haunted Happenings organizes information on Salem’s costume balls and fall activities.

More Options

• Peabody Essex Museum (PEM) is an art museum that features art and culture worldwide. It also has artifacts from the Salem Witch Trials and Salem’s history. However, they close on Wednesdays, so we couldn’t buy a $25 ticket.
  
• Count Orlok’s Nightmare Gallery is a monster museum with over 60 realistic life-sized monsters. It costs around $25 for all horror fans.
  
• Gallows Hill Museum/Theatre provides ghostly productions of the witch trials in October.
  
• The Witch Dungeon Museum offers a trial reenactment and a tour of a recreated dungeon where the witches were sent. It is not recommended for small children.
  
• Salem Witch Museum with stages and actors recreating the dark time in a story-telling fashion. The reviews aren’t great.
  

Turner’s Seafood Lyceum Hall

Turner’s, with its old-world brick walls, fireplaces, and tin ceilings, offers a delicious dining experience. Turner’s uses a Queue System for tables, so get in the line early.

As night settles on Salem, the mystery doubles as more street-performing ghouls come out to play.

Lodging

Salem Waterfront Hotel and Suites have the best view in the center of town.

Hawthorne Hotel is the most historic hotel in the heart of Salem. To attend their famous costume balls, a two-night minimum stay was required. Verify the policies as they change from year to year.

Arrival

• Pick a parking garage ahead of time, such as South Harbor.
• Train-Commuter Rail from North Station in Boston on the Newburyport/ Rockport line.
• The Boston ferry from Long Wharf takes 50 minutes.
  

Tips

• Arrive EARLY to enjoy the town and take photos before crowds arrive. Over half a million people visit Salem in October.
  
• The public bathrooms are nonexistent and hard to find at the Essex Museum and the House of Seven Gables.
  
• Costume ball tickets are in high demand and have expensive strings attached, like two-night hotel stays. You need to plan at least seven months in advance to have a chance.
  
• It’s a lot of walking, so wear comfortable shoes.
  
• House of Seven Gables Tickets are purchased months out.
  
• Dinner reservations are recommended, or get in the queue line for Turner’s.
  
• The Witch City Mall is considered dangerous, so skip it.
  
• If Salem gets too crowded, the neighboring towns of Beverly and Manchester-by-the-Sea are equally impressive. The creative Spirits haunt the towns through Halloween yard decorations.
  

Hammond’s Castle

By 2 p.m., after five hours of walking, we were done with the crowds. So, we drove 30 minutes north to Hammond’s Castle, took the last $20 tour at 3 p.m., and then returned to Salem for our 6 p.m. dinner reservations.

A Medieval castle filled with fascinating artifacts and a millionaire inventor with a life of crazy stories is perfect for a tour. I loved this Renaissance castle by the sea, with its rooms locked from the outside, opulent decorations, and the most beautiful courtyard. We enjoyed exploring the area, and the tour was worth our hour.

The Breakers

Day five opens with a two-hour drive to Rhode Island for The Breakers, The Cliff Walk, and Newport. Vanderbilt’s Summer Cottage is a palace built in 1895 that was on my bucket list. The mansion has 70 rooms, including 48 bedrooms.

The Grand Hall has 50-foot high ceilings. Y’all, I can’t even begin to grasp the Vanderbilt wealth during the Gilded Age that built this summer home. The house is iconic and the most impressive palace I have ever seen. The tickets were $30, and we parked in their parking lot and walked to the other cottages.

The Cliff Walks

The view of the mansions by the sea is breathtaking. We strolled along for an hour. We toured Marble House, but I didn’t even take any pictures. Then, it was after lunchtime, so we headed to downtown Newport’s Thames Street along the waterfront.

Newport

Newport is one of the most charming seaside towns in America. We had a late lunch at The Red Parrot Restaurant and strolled through the cutest high-end boutiques on Thames Street. The place feels old with its cobblestone streets and historic buildings. Some people claim it’s a classy tourist trap, but I loved it. I wished I had spent a night here.

Mystic, CT

With Mystic, CT, only an hour away, we checked that state off our list for dinner at Mystic Pizza. Mystic is adorable, and I plan to visit again when I have more time.

With a long drive back to Boston and a plane to catch on Day 6, our New England vacation ends. Add as many days as possible to Boston, but I must be home for those Fall Friday Night Lights to cheer on my guys. Thank you for reading my Boston & Salem Travel Guide. Check out a few other family adventures at the bottom.

For more history, every American should have the opportunity to experience a walk through American history exploring Washington, DC. From museums and monuments to Arlington then Old Town Alexandria and Georgetown, the city is filled with endless adventures. Explore America’s most visited city in my Ultimate Guide to New York City the bright lights and chaos is waiting.

Itinerary Recap

Day 1: Arrive at Boston Logan Airport and pick up our car rental. Tour the waterfront area with the Tea Party Museum and Aquarium.

Day 2- Freedom Trail with extra hours at the Faneuil Hall Marketplace & Quincy Market, exploring the shops in North End, Paul Revere, Bunker Hill, Old Ironside

Day 3- Boston Public Gardens, Acorn Street area, Newbury Street, Fenway, JFK Museum

Day 4- Salem Heritage Trail, Red’s Sandwich Shop, Salem Witch Trial Memorial, House of Seven Gables, Emporium 23, Hocus Pocus, Witch House, Bewitched Statue

Hammond Castle & explore surrounding towns.

Day 5- Rhode Island with The Breakers, The Cliff Walk and Newport

Day 6 Home