Lounge on the Beach and Explore the Boardwalk

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 of 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. A lot of 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.

Chesapeake & Maine is a casual seafood restaurant with a raw bar.
As the name suggests, the seafood here is exclusively sourced from the Chesapeake and Maine regions. Here, you know the seafood you're eating is fresh.
The raw bar serves a selection of oysters, clams, and other seafood. The "Smoke in the Water" oyster is unique to Chesapeake & Maine. These oysters were raised in water infused with wood-smoked-salt, giving them a natural smoky flavor.
Chesapeake & Maine's bar was also a James Beard Award semi-finalist nominee, so if you want a drink, this is definitely the place to get one. Chesapeake & Maine is the brainchild of the founder of Dogfish Head Brewery, a local Delaware brewing company. You can find many of their beers and spirits on the menu at Chesapeake & Maine.

Spend some time at the beach. This is why you drove all this way, after all.
Whenever you're done soaking in the sun, spend some time exploring the milk-long boardwalk. There are many eclectic shops, restaurants, and family amusements and attractions.
You can also stop at Thrasher's French Fries, the boardwalk fry chain that started in Ocean City, Maryland. These are perhaps the best boardwalk fries you'll ever try. Get a giant bucket and douse it in salt and vinegar.
National Geographic once named the Rehoboth Beach Boardwalk among the top 10 boardwalks in the country.

Big Fish Grill Rehoboth is a staple in the area.
Here, you can get heaping platters of seafood, the freshest fish, and even sushi. If you're not sure what to get, try the "Flash Fried" Seafood Combo, which gives you a little bit of everything. The portions here are huge, so you can share with friends or take the leftovers back to the hotel for a late night snack.
For those who don't love seafood, there are other options on the menu for you as well.

Have a nice rest before continuing your adventure tomorrow.