Start your day off right: with snacks from the Pennsylvania Dutch Farmer's Market.
Known locally as the "Amish Market," this giant market has everything you could need for your road trip. All the products come from Pennsylvania's Lancaster County, and the recipes here have been handed down by the Amish through the generations.
There will be a fair amount of walking on this trip, so get some light snacks you can carry with you in case you get hungry later in the day. Stock up on produce, desserts, cheese, candy, or whatever else your heart desires. Many people rave about the fresh-baked pretzels in particular.

You'll be driving across the Chesapeake Bay to get to Kent Island. Make sure to have your camera ready—the photos will be worth it.

This 276-acre nature park isn't as crowded as it should be given all that it offers.
There is a 3.25-mile oyster chaff walking trail, which takes you through marshlands, woodlands, and sandy beaches. You can also bike or kayak here, if you want something a bit more active.
Thanks to the diversity of habitats here, this park is great for bird-watching. It is the top hotspot in Queen Anne’s County in terms of the number of bird species reported.
This park doesn't have a public beach for swimming. If that's what you're looking for, try the Matapeake Clubhouse and Beach nearby.

Maryland is known for crab and crab cakes, and this is the place to try both.
This waterfront restaurant faces the Chesapeake Bay, so you can enjoy the view while you eat. In the spring and summer, Dirty Dave's Tiki Bar serves up cold beer and frozen drinks right on the beach.
If crab isn't for you, you can try one of the brick oven pizzas, steamed shrimp, or any of the fish entrees.

Watermark offers seven different cruises in Annapolis, with different lengths and destinations.
If you're not sure what you're looking for, try the Annapolis Harbor and U.S. Naval Academy cruise. This narrated cruise will leave you with a better understanding of Annapolis’ role as a historic seaport and the history of the Naval Academy. You'll also catch another glimpse of the Bay Bridge, this time from a different angle.
If it's later in the day, you should do the Annapolis Sunset Cruise. This 60-minute cruise through the harbor will be beautiful.
Watermark is closed on Saturdays, but you should be able to find another cruise option as you explore Annapolis.
You can book a tour in advance.
After the cruise, leave your car here and explore the city on foot.

Alex Haley was a prominent Black writer, most famous for his best selling novel Roots, which won national acclaim. The story follows Kunta Kinte, an 18th-century captured from Gambia as a child, sold into slavery in Africa, and later transported to North America. It details Kinte's life as well as his descendants—all the way to Haley himself.
In the story, the slave ship on which Kinte is entrapped lands in Annapolis, Maryland—hence the location of this memorial.
Like many other monuments to Black leaders and Black history in America, the Kunta Kinte-Alex Haley Memorial has faced an uphill battle. A group of Annapolis residents initially proposed the idea of a memorial to city council in 1979, but were met with opposition from Annapolis' mayor. Two years later, with a new mayor in office, a plaque was set up at the City Dock in commemoration of Kinte's arrival in 1767. But according to the Kunta Kinte-Alex Haley Foundation, the plaque was stolen just two days later.
The memorial in downtown Annapolis today was not completed until 2002, nearly 30 years after Roots was published. Haley did not live long enough to see this memorial.

In 1965, Annapolis became one of the first cities to become a National Historic Landmark District. This status covers most of the colonial historic district as well as the waterfront.
Many 18th-century buildings still stand here, including historic residences, townhouses, and the Maryland State House, which is nearby. The State House is the oldest state capitol in continuous legislative use and the only one ever used as the nation's Capitol.
This is also a great area to just explore, with many restaurants and shops you can spend your afternoon getting lost in.

Return to pick up your car and head to the dinner restaurant.

This seafood restaurant has everything you could want: crab, crab cakes, crab soup, oysters, shrimp, mussels, fish of the day, and more.
This restaurant is small, further away from the crowded Main Street, and always packed because of how great the food is. If you ate crab for lunch, it doesn't matter—order it again here. It's delicious.