We planned the weekend to go, but that was about it. Here’s the pros/cons and lessons learned from a spontaneous trip during the local busy season.

Day 1: Boston

We arrived Friday evening and started off by checking into the hotel. We stayed at the Hilton close to the Downtown/Faneuil Hall area. Once we settled in, it was time to pick a restaurant. My request was a pub since that’s a very local vibe. We ended up at The Black Rose for live music, Shepard’s pie, and whiskey. After dinner, we wondered towards the waterfront and some of the North End bakeries. The parks in this area are gorgeous and we found some swinging benches and arbors to take pictures. We got treats from Modern Pastry, but we heard great things about Mike’s Pastry as well. Be prepared to wait in line for both. It’s a blast just to walk the streets, smell the pasta, and pretend you’re really in Italy.

Day 2: Boston

This was our stereotypical tourist day. We did the Freedom Trail starting at the Boston Commons. We had breakfast sandwiches at Beantown Pub with a lovely view of Granary Cemetery. From there we just followed the trail and walked probably 8 miles total. It’s free to walk the trail and see the historical sites, but several sites offer tours for a fee. We skipped most, but took advantage of the tours in the Old North Church. This is where Paul Revere saw the lanterns hung that began his ride to warn about the coming British. We walked around the church then did the bonus crypt tour to walk around under the church. It was really interesting to hear about how burials were handled back then, but I’m weirdly into that stuff. From there, we continued to Charlestown for the end of the trail – Bunker Hill and USS Constitution. I did the Constitution tour a few years ago so we didn’t do it this time, but I do recommend it. At this point we were tired and sore. We headed back to North End for an Italian dinner. Wait times can be long so go early or book in advance. We ended up at L’Osteria and had an amazing time. It was a little off the main section so it was quieter, but it was across the street from a park and we had street performers singing opera for us. The food itself was amazing. We got an appetizer and two entries and dessert between three of us and it was just the right amount. The house red wine and sangria was good, but I still had to get the classic lemoncello with dessert.

Day 3: Salem

We started with breakfast at the hotel restaurant, Tradesman, before driving to Salem. We got a hotel in Danvers – aka Salem Village and drove into Salem (Town). Parking is a mess, so get there as early as possible. This was our main tourist day and a lot of tours were already sold out for the day, so also plan in advance. We started with the Salem Witch Trials exhibit at the Peabody Essex Art museum. We did the combo bundle for the Pirate museum, Witch History museum, and Witch Dungeon. They were all a little cheesy, but fun and educational. The Witch Dungeon was my favorite of the three and led to several Monty Python quotes. The Witch Museum is a separate building on the square. We didn’t go in so I can’t compare with the other museums. We had lunch on the waterfront which was perfect to get my required seafood meal. We continued exploring with the Hawthorne Hotel and the Witch House (opposite sides of Essex St). We saw the Bewitched statue and window shopped. For dinner, we got an outdoor table at Olde Main Street Pub. I had a blast with fall themed cocktails and more seafood.

Day 4: Salem

We had brunch at the Friendly Toast which is known for their brunch. Then we drove to the House of Seven Gables for our scheduled tour. The house was beautiful and had a cool history that helped inspire Nathaniel Hawthorne’s book. They also relocated Hawthorne’s old house to the property so we toured that as well. We circled back to downtown Salem for more shopping and the local cemetery. We tried to go to Pioneer Village, but turns out it was closed on Mondays (plan in advance). We were able to see Max and Dani’s house from Hocus Pocus which is a private residence, but still cool. After we were all done with spooky sites, we drove out to Wingaersheek Beach to see the ocean and some tide pools.

And that ends the trip. After the beach, we packed up and headed home. If we planned ahead of time, I definitely would have got tickets for the Witch House and the Ghosts & Legends Trolley Tour. But we were still able to see and do a lot despite the no plans and large crowds.