Fall Foliage and Frights: Exploring Salem and Boston

Arrive at Logan International Airport around midday and hop onto the free bus that will take you directly to the Boston subway system, known as The T. After navigating the efficient transit system, head to your hotel for check-in. Once settled, make your way to the vibrant Back Bay district for some delightful shopping and a leisurely lunch.

Be sure to stop by the Boston Public Library to marvel at its stunning architecture and explore the exquisite artwork adorning its walls. For dinner, treat yourself to an iconic lobster roll at Luke's Lobster — served warm or cold, it's delicious either way!

As the evening unfolds, you have two options: wind down for the night or kick off the festivities at the Bull & Finch Pub, famously known as the inspiration for the beloved TV show "Cheers." This lively bar features great music, an impressive selection of beers and ciders and an atmosphere that feels like stepping right into an episode of the show. What a way to kick off your first night in Boston!

Boston's Freedom Trail (First Half)

What better way to experience Boston than by following the iconic brick trail that weaves through the tapestry of American history? While many visitors walk the trail to see all 16 historic stops, the true magic lies in stepping inside each site to uncover the stories that shaped the nation. To fully immerse yourself without feeling rushed, I recommend splitting this adventure into two enjoyable days.

Start your mornings bright and early by indulging in an iconic breakfast sandwich at a local café, then head to the picturesque Boston Public Garden to savor your meal with a stunning view. Once you’ve finished, make your way to Boston Common, where you’ll find a visitor center at the park's corner offering free maps to kickstart your journey.

As you embark on your adventure, take your time exploring each stop. Learn about the historical significance of sites like the Massachusetts State House and the Boston Massacre site, where the seeds of revolution were sown. You’ll end your day at Faneuil Hall, perfectly timed for lunch. Enjoy a variety of culinary offerings at Quincy Market, where you can explore a variety of shops and local delights. I recommend getting the New England clam chowder. It truly is the best!

As the sun sets, you have two thrilling options to wrap up your day: embark on an iconic pub crawl that takes you through some of the oldest bars in the United States, or join a haunting ghost tour led by a colonial guide through historic graveyards, revealing Boston’s eerie past.

When you book your trip with me, I’ll provide a custom guide. Including details of the history and significance of each location. This ensures you don’t miss any fascinating stories. I’ll also help in securing your tickets to attractions and museums while offering tips for visiting during off-peak times. Plus, I’ll delve into the haunting histories that linger in the shadows of this storied city.

Boston's Freedom Trail (Second Half)

Take the T to the Faneuil Hall stop, and pick up where you left off from yesterday’s adventure. Today, you’ll head into the North End, Boston’s charming Italian district, as you finish the Freedom Trail. While there are fewer stops today, be prepared for more snack opportunities and some hills—so make sure to wear your best walking shoes and stretchy pants!

Your journey begins with a visit to the iconic Paul Revere’s House, where you’ll glimpse life in colonial times. Next, explore the historic Old North Church, famous for signaling the arrival of the British. If given enough notice, I can arrange access to the church's underground crypts for a bit of spooky fun!

Afterward, cross the bridge over Boston Harbor to visit the USS Constitution. Walk through the ship's many decks and learn about its significant role in naval history and other iconic vessels of the time. Your final stop on the trail will be Bunker Hill, a site steeped in revolutionary significance.

What better way to celebrate the conclusion of this colonial journey than by visiting one of the oldest pubs in the United States? This hidden gem is considered one of the most authentic establishments from the 1700s. I’ll share this secret location with you when you book!

Depending on when you finish the trail, you can either continue the fun or wrap up for the night. If you choose to extend your adventure, why not explore the North End further with an Italian food tour?

Throughout my tours, you’ll never have to worry about going hungry or wondering where to eat. As I plan your trip, I gather personalized food recommendations from my own experiences in New England, as well as places that come highly recommended. I can also accommodate any dietary restrictions or allergies so you can enjoy the best of New England without worry or breaking the bank.

Getting Spooky in Salem

Wake up and pack your bags — it's time to head to Witch City for an unforgettable overnight stay! Check out of your hotel early and make your way to North Station to catch the train to Salem. The ride takes about 30 minutes, offering a leisurely journey through the stunning fall colors of Boston.

Upon your arrival in Salem, you'll check into one of the most haunted hotels in America, where the eerie atmosphere adds to the excitement. Once you’re settled in, feel free to explore the Haunted Happenings taking place throughout the town.

To ensure you make the most of your time, I’ll schedule all your museum visits and stops based on your interests. Salem can get quite busy this time of year, and waiting in lines can eat up a significant portion of your day. Let me handle the timings and stress so you can fully enjoy the frights!

After seeing the sights, immerse yourself in the vibrant festivals that Salem hosts each night. There’s always a special event happening, and we can coordinate your visit to ensure you catch any specific festivities you’re eager to experience.

Finish your day with one of the best seafood dinners in New England before returning to your haunted hotel for the night. I hope you don’t lose too much sleep, because the next morning is packed with even more spooky fun!

Wake up to the crisp fall air and the satisfying crunch of leaves underfoot. Today, we’ll take a step back in time to experience what Salem looked like in the 1600s by visiting Salem Village. This immersive experience features blacksmiths, farm animals, and more, plus it served as one of the filming locations for the iconic movie Hocus Pocus.

After exploring the village, we’ll wrap up our Salem adventure by stopping at one of the oldest candy shops in the United States. You can’t leave without indulging in their mouthwatering fudge or delicious maple treats!

Once you’ve gathered your goodies, freshen up and pack your bags, as our enchanting Salem trip continues back in Boston. We’ll take the train back to North Station, where you’ll check into your hotel.

To end your night on a high note, you can choose to dine at one of Boston’s best and most historic restaurants, or I can arrange for you to catch a show in the vibrant theater district. The evening is yours to enjoy!

Up to You!

Feel free to sleep in after all those early mornings and late-night frights! If you’re a sports fan, I can arrange a stadium tour of the iconic Fenway Park, where you can immerse yourself in the rich history of one of baseball's legendary venues. If you're in the mood for a little academic adventure, you can explore the historic Harvard campus and channel your inner Elle Woods.

Alternatively, we can keep the thrill alive by visiting more hidden, spooky locations and intriguing museums throughout Boston.

This day also offers the flexibility to revisit any of your favorite spots from the previous days. Feel free to tailor your adventure to your preferences!