My Trip to Boston: Best Food, Scenic Fall Drives, and Must-Do Waterfront Experiences

Planning a trip to Boston? Let me share my experience visiting this historic New England city—because Boston absolutely exceeded my expectations. From incredible seafood to a breathtaking day trip to Portland, Maine, my adventure was filled with great food, beautiful views, and unforgettable moments.

If you’re looking for tips on where to eat in Boston, what to do in Boston, or fall travel ideas in New England, this guide is for you.

Why Boston Is a Fantastic Travel Destination

Boston blends old-world charm with modern energy. Whether you love food, history, or scenic coastal views, this city delivers. I found myself constantly surprised by how much there was to explore—both in and outside the city.

Where to Eat in Boston: Seafood, Chinese Food & Pizza

Boston has an incredible food scene, especially if you love seafood. One of my favorite stops was the iconic Legal Sea Foods, known for its ultra-fresh fish and classic New England dishes. If you want authentic Boston clam chowder or perfectly prepared lobster, this is the spot.

Other Food Highlights

• Chinese food in Boston’s Chinatown — flavorful, authentic, and packed with options

• Boston-style pizza — yes, it exists, and yes, it’s delicious

If you’re a foodie, Boston will not let you down.

Day Trip From Boston: Driving to Portland, Maine

One of the best decisions I made was renting a car and taking a day trip to Portland, Maine. The drive alone is worth it.

Why Portland, Maine Is a Great Day Trip

• Only about 2 hours from Boston

• Scenic highways and charming small towns

• A vibrant downtown and gorgeous ocean views

I visited in October, which made the experience unforgettable. The fall foliage was transitioning—trees glowing with color, some fading, some fiery bright. If you’re a fan of New England fall road trips, this drive should be on your bucket list.

What to Know About Driving in Boston

Let me be honest: driving in Boston is not for the faint of heart. Because the city is old, the streets were built before modern planning. That means:

• Unpredictable street layouts

• Tight turns

• Confusing intersections

My advice? Be patient, rely on your GPS, and don’t be afraid to take your time. Once you get outside the city, the roads open up beautifully.

Take a Boston Harbor Boat Ride for the Best Views

One of the highlights of my trip was taking a boat ride on Boston Harbor. Seeing the skyline from the water gives you a completely different perspective—peaceful, expansive, and absolutely stunning.

Whether you do a harbor cruise, water taxi, or whale-watching tour, being on the water is a must-do activity.

Why Stay Near the Waterfront

Staying by the water adds an extra layer of magic. At night, the harbor lights sparkle and create the perfect backdrop for an evening walk, dinner, or simply relaxing after a busy day.

Final Thoughts: Why You Should Visit Boston

Boston is the perfect blend of:

• Delicious food

• Historic charm

• Beautiful waterfront views

• Easy access to New England’s best fall scenery

If you’re planning a Boston vacation, consider adding a day trip to Portland, trying as much seafood as possible, and getting out on the water. This city has something special, and it definitely left a lasting impression on me.