I have been to Portland twice and have had different experiences each time. My first trip to Portland was during a road trip I took with friends that started out in Boston and ended in Portland. Since we had many stops during that trip we didn’t have the time to properly explore Portland. On this trip we explored some of the local shops in Old Port.
Here are a lot of local shops in converted warehouses. We found some great local specialities like maple candy and stopped to enjoy some ice cream at Captain Sam’s Ice Cream shop. We also hit some touristy spots like Longfellow’s childhood home and took a trolley tour around to see the sights such as Victorian homes, Portland City Hall, and Portland Observatory.
The second time I stopped in Portland was on a cruise with Royal Caribbean. Since we had a specific amount of time to explore the city we booked a best of Portland and Kennebunkport excursion through Royal Caribbean. This tour took us through Portland where we saw the same sights I saw on my last visit to Portland. This time I was able to make a stop at the Portland Head Light. Even though this visit to Portland was in early June the weather was still on the chilly side. The Northeast had an unusually cool start to the summer so we had a stiff breeze coming off the ocean. The grounds around the lighthouse give nice views of the ocean, there is a museum and gift shop but you are not able to climb to the top of the lighthouse. I highly recommend making this a stop when you are in Portland, especially if you like lighthouses.
Another stop that is common while in Portland or going to or from Portland is Kennebunkport. The first time I went to Kennebunkport we stopped on our way from York to Portland. We spent a few hours that time walking around town, going in and out of shops which have local art, jewelry, and ceramics just to name a few. We also took in the million dollar beach front homes! Unfortunately the day was rainy so we didn’t have a chance to spend any time on the beach. The second time I was in Kennebunkport we only had enjoy time to stop for lunch. We decided to eat at a small local bar which was a good idea. We ate at the Pilot house and had fried clams – delicious! This go around we did drive around and spot the Bush compound as well as the gingerbread house which is a local home that is at times open for tours.