A Five-Day Love Letter to New England

My guide to spending five days in Boston!

There’s something about New England that feels timeless. Cobblestone streets, salty air, historic facades, and an abundance of coffee shops. Our five-day trip packed in shopping, costal drives, and the best food spots.

Day One: Arrival in Boston

Our trip began in Boston, checking into The Boxer, a boutique hotel tucked into the city with just the right balance of classic charm and modern comfort. Day one was intentionally slow — a travel day meant for settling in and unpacking.

Day Two: Gardens, Fenway & North End

We started the morning at BON Coffee, before wandering through the Boston Public Garden and Boston Common. I made my fiance walk through it each morning we were there because I simply could not get over the beauty of it right in the middle of the city! We even found the viral tik tok newspaper stand, which I was beyond excited about.

From there, we toured Fenway Park, a must-see even if you’re not a die-hard baseball fan. The history alone is worth it. We spent the afternoon shopping along Newbury Street, popping into boutiques and stopping for lunch at a small pub before walking along the Charles River.

Later, we returned to the A Five-Day Love Letter to New England for something incredibly special: our engagement photos. We wanted a unique photo session and couldn't think of anything better than doing it in our favorite city!

That evening, we headed to the North End for dinner at Carmelina’s. It was such a cozy, romantic resturant/wine bar. Ordering a pizza and the Vodka sauce pasta is a must. We ended the night at Mike’s Pastry, where the tiramisu and cannolis were truly to die for. No notes. Perfection.

Day Three: Beacon Hill to the Maine Coast

Morning coffee came courtesy of Blank Street in Beacon Hill, followed by a stop at Beacon Hill Books & Café — easily one of the cutest bookstores I’ve ever seen. If you love cozy corners and beautifully curated shelves, this place is magic.

From there, we picked up our rental car and drove north to Portland, Maine. The drive alone was worth it — winding roads, ocean views, and that unmistakable New England charm.

We visited Portland Head Light, then headed into town to explore. Soleil quickly became a favorite, especially for its adorable little art prints. And of course, no Maine stop is complete without donuts from The Holy Donut.

After Portland, we followed the coastline down to Cape Cod, stopping in Chatham to see Chatham Light, run along the beach, and shop Main Street. The Black Dog, Chatham Collections, and Chatham Candy Manor were the kind of shops you wander into “just to look” and leave with bags in hand.

We made our way back to Boston for dinner at Saltie Girl. The lobster roll? A 10/10, best in Boston. And the Hugo Spritz? Instantly transported me back to Cape summers by the sea.

Day Four: History, Libraries & A Taste of Ireland

Our final full day began at Tatte Bakery — so, so good — before visiting Acorn Street, one of the most photographed streets in the city for good reason. We spent the morning walking the Freedom Trail, soaking in the history woven through the city. Afterward, lunch at Quincy Market was another one of my favorite parts. The pizza and chocolate-covered strawberries were good enough to make me fly back just for the food.

The afternoon was reserved for the Boston Public Library. I couldn't tell if I was in France or if I was Elle Woods. We ended our last night at The Dubliner, where the Guinness and fun pub atmosphere made it feel like we’d somehow crossed the Atlantic and landed in Ireland.

New England gave us everything: romance, history, coastal beauty, and moments that felt both fleeting and unforgettable 🤍