Our drive to Maine was great – it was not overly rainy and it was full of shopping stops. We took Route 1 from Kittery to Portland and enjoyed driving through numerous small seaside towns. We found our way to Southport Island amongst the late afternoon rainfall and navigated ourselves to Brett’s grandparents’ summer cottage. Brett’s grandparents have been summering on the island for 55 years. It was a tradition in the family to spend the summers up here and to learn how to sail at the Southport Yacht Club; a tradition that Brett was lucky enough to partake in while growing up.

It is a cute island with an amazing atmosphere that makes you want to stay forever. It has an impressive library for its size and is very close to shopping and entertainment in nearby Boothbay Harbor.

We have a great experience in Southport each time we visit. Our last visit was in early June of 2004 on a roadtrip that Brett and I took the summer before we got married.

During this visit we were able to see not only Brett’s grandparents but also his Uncle Bill and Aunt Peggy. It was great hearing about their recent whale sightings. We were also lucky enough to see a musical at the renowned Boothbay Playhouse. The trip would not be complete without shopping in Boothbay Harbor, however. So we braved the rain and had a great time.

Our day on Wednesday was a washout with possibly three or four hours all day without pouring rains falling from the sky but Thursday was shaping up to be a good day, so Brett and I got on the road right after breakfast to make our way up to Bar Harbor.