I love being able to share cool travel ideas for road trips. I'm a road trippin' kinda gal. I do a lot of it and exploring America is a deeply satisfying pleasure. I know a lot of baby boomers are in situations in life where there is more free time to do these things. I will suggest some wild and crazy treks for novelty and making crazy memories, and peaceful quiet introspective ones, like the Southern Chesapeake, for photography and sea air. This is one of my favorite finds on the Chesapeake where my family used to have our summer home.
I'd highly recommend you book a room or cottage at the Inn at Tabbs Creek in Port Haywood, Virginia.
From the dock, you can book Chesapeake Deadrise a 38-foot classic wooden boat for a tour of the water including a trek around the abandoned lighthouse, my childhood haunt, New Point-Comfort Lighthouse.
This was our summer home (below) in New Point, Virginia. It was on a quiet inlet called Doctor's Creek.
This was our summer home when I was growing up (above). It was on Doctor's Creek with a dock, a cabin cruiser and lots of crab traps. Father used to wake us kids up at 4 am when there was low tide and have us hike down the sandy road to the dock to jump into an outboard motor boat. He would put a lantern on the bow and we would go way out into the dark bay and jump overboard into waist high water where we would dive for clams and oysters. We would ride back at sunrise. My times here and the ghostly hauntings in the area are found in my 5-star book "Vacationing With Ghosts."
I recommend riding over to nearby Gloucester to the abandoned historic plantation, Rosewell.
There is a lot of gorgeous swamp land and seaside land to photograph as well as abandoned buildings everywhere on the quiet inlets, beautiful cemeteries and churches, and historic buildings. I highly recommend Haven Beach in Diggs because it's very private and gorgeous and has some local legends about pirate ghosts.
I also suggest The Courthouse Restaurant in Gloucester. The food is great, the people friendly, good location, great local find. The Doug Bowl is an especially yummy breakfast.
Be ready to put toes in sand, catch lightning bugs, walk along the marshes, take boats out onto the bay (which now has dolphins chasing the boats!), listening to tree frogs and crickets at night, and breathing the sea air.
It's very slow-paced, relaxing, and not the usual crowded beach side. This is where people live on the water, not vacation on it. Everyone is so friendly and hospitable. It's not the usual find for a vacation destination which is why it's absolutely ideal for us baby boomers who want more an experience than a happening.