Day 1: Arrival in Boston
We flew direct from Louisville to Boston, and spent our first night wandering the city. After checking into our hotel, we stumbled upon a standout spot for drinks: Yvonne’s in downtown Boston. With chic décor, bold cocktails and a lively vibe, it was the perfect welcome-drink stop.
We relaxed, toasted to our trip, and soaked in the city energy.
Day 2: On the Road — Salem, Gloucester, PORTSMOUTH, PORTLAND
Early the next morning we picked up our rental car and headed north.
- First stop: [Salem, Massachusetts]. We didn’t stay long — just drove through — but the historic town instantly caught our interest and we made a mental note to come back. 
- Next: [Gloucester, Massachusetts], home of the “Wicked Tuna”! We paused for lunch right by the harbor and enjoyed fresh-coastal fare. The view + seafood combo = winner. 
We continued our drive, crossing into New Hampshire and then Maine.
- [Portsmouth, New Hampshire] absolutely charmed us. We nearly stayed the night — it’s the cutest seaside town with cobblestone streets, boutiques, and boats lining the water. We took a fun tour of the USS Albacore! I had never been in a submarine before and that was very interesting to experience! Then we strolled downtown along the waterfront. 
- By evening, we made it to Portland, Maine, where we stayed in the Old Port district. It’s such a walkable area filled with cozy shops, breweries, and restaurants. 
Day 3: Lighthouses, Dinner & Kennebunkport
Morning in Portland was all about coastal exploration: we did a lighthouse boat tour (a must when you’re in Maine!) and also spotted some old Civil War forts.
For dinner, we treated ourselves at ViA VECCHiA in Portland’s Old Port. The Italian-inspired small plates, cocktails and ambiance were next-level. That evening we drove on to [Kennebunkport, Maine] for our final night — a peaceful, coastal town with so much charm. The kindness of the locals and the relaxed vibe felt like the perfect gentle finale to our adventure.
Reflection: The Joy of Unplanned
What made this trip extra-special? We didn’t have much booked in advance. No strict schedule. We simply drove until we felt like stopping, and that spontaneous freedom made every place feel like we discovered it — not just checked it off.
 
             
                 
                 
             
             
             
             
             
             
                