Chesapeake Bay

Chesapeake Bay is a fantastic destination for families, with its beautiful scenery, rich history, and plenty of activities to keep everyone entertained. Here’s a fun and family-friendly 3-day itinerary that will help you make the most of your time in this beautiful area!

Day 1: Explore Annapolis

Morning:

• Breakfast at Chick & Ruth’s Delly: Start your day with a hearty breakfast at this local favorite. Don’t forget to try their famous milkshakes!
• Visit the U.S. Naval Academy: After breakfast, take a guided tour of the Naval Academy. The kids will love seeing the impressive buildings and learning about naval history. The grounds are beautiful, and there’s plenty of space for the kids to roam.

Afternoon:

• Lunch at the City Dock: Grab a casual lunch at one of the many eateries along the waterfront. You can find everything from seafood to sandwiches.
• Explore the Maryland State House: After lunch, head to the Maryland State House, the oldest state capitol still in continuous legislative use. The kids will enjoy the history, and the grounds are perfect for a little exploration.

Evening:

• Dinner at Cantler’s Riverside Inn: Enjoy a family-friendly dinner at this iconic crab house. Try the crab cakes or steamed crabs for a true Chesapeake experience!
• Sunset at the Waterfront: After dinner, take a stroll along the waterfront. The sunset views over the bay are simply stunning!

Day 2: Outdoor Adventures

Morning:

• Breakfast at your hotel or a local café: Fuel up for a day of adventure!
• Visit Sandy Point State Park: Spend the morning at this beautiful park. You can hike, bike, or just relax on the beach. There are picnic areas, so pack a snack or lunch to enjoy by the water.

Afternoon:

• Lunch at the park: Enjoy your packed lunch or head to a nearby eatery.
• Kayaking or Paddleboarding: Rent kayaks or paddleboards for some fun on the water. Many places offer rentals right at the park, and it’s a great way to explore the bay!

Evening:

• Dinner at The Boatyard Bar & Grill: This family-friendly spot has a great menu with something for everyone. The atmosphere is casual and fun!
• Evening Stroll in Downtown Annapolis: After dinner, take a leisurely walk through the charming streets of downtown Annapolis. The shops and historic buildings are lovely to explore, and you might even catch some live music!

Day 3: Discover the Eastern Shore

Morning:

• Breakfast at a local diner: Try a classic diner for a hearty breakfast before heading out.
• Drive to St. Michaels: It’s about a 30-minute drive from Annapolis. This quaint town is perfect for a family day trip!

Afternoon:

• Visit the Chesapeake Bay Maritime Museum: This museum is a hit with families! Kids can learn about the bay’s history, see historic boats, and even climb aboard some vessels.
• Lunch in St. Michaels: There are several family-friendly restaurants in town. Try the crab soup or a classic burger!

Evening:

• Explore the Town: After lunch, take some time to wander around St. Michaels. Check out the shops, and don’t forget to stop by the local ice cream shop for a sweet treat!
• Dinner at The Crab Claw: End your trip with a delicious seafood dinner overlooking the water. The kids will love the casual vibe, and you can indulge in some more crab dishes!

Tips for Your Trip:

• Pack Sunscreen: The sun can be strong, especially if you’re spending time outdoors.
• Bring Snacks: Having snacks on hand can keep the kids happy during outings.
• Check Local Events: Depending on when you visit, there may be local festivals or events happening that could be fun to attend!

I hope this itinerary helps you have a fantastic family adventure in Chesapeake Bay! Enjoy the beautiful scenery, delicious food, and quality time together! 🌊🦀🏖️