Skip to main content

Kent Island to Kent Island Itinerary

This Kent Island itinerary is a yacht lover’s dream vacation. Cruise on a body of water where fresh and saltwater mix, known as the ‘Bay.’ The Bay is the largest of more than 100 estuaries in the United States and the third-largest worldwide. 

Kent Island itinerary
Annapolis, Maryland

Stretching from Havre de Grace, Maryland, to Virginia Beach, Virginia, the ‘Bay’ is also known to be 200 miles of prime cruising ground filled with small towns and numerous anchorages.

Day 1 | Kent Island to St Michaels

Also known for its history, Kent Island is the most significant Island in the Chesapeake Bay. Beautifully centered between the narrow channels of Kent and the Delmarva Peninsula, Kent Island covers 31 miles and is considered the gateway to Maryland. Enjoy the beauty this charming Island has to offer! 

St. Michaels is a picturesque harbor on Maryland’s Eastern Shore. It was also named one of America’s Top 10 Best Small Coastal Towns. Its harbor and some homes date back to the mid-1600s. Here you will find perfect outdoor activities, including

  • kayaking
  • golfing
  • bicycling
  • shopping

Day 2 | St Michaels to Cambridge

Cambridge is a charming historic town on the Choptank River, perfect for those who enjoy outdoor recreation and exploring small towns. Discover the historic district, which features brick-paved streets with parks, a marina, museums, and a lighthouse on the water. The area attracts nature lovers, birders, photographers, cyclists, and paddlers to the Blackwater National Wildlife Refuge.

Day 3 | Cambridge to Solomon Island

Solomon Island is located between the Patuxent River and the Chesapeake Bay and draws travelers with its natural beauty and family-friendly atmosphere. Visit the Calvert Marine Museum, which exhibits the maritime history of the Chesapeake Bay. The Drum Point Lighthouse is part of the museum experience. If you have kids, take them to the Discovery Room. There are dress-up clothes and a place to look for sharks’ teeth.

Day 4 | Solomon to Annapolis

With more surviving 18th-century buildings than any other city in the United States, visiting Annapolis is like stepping back to the days when the city was a colonial seaport. Known as America’s Sailing Capital, the city is located on the shores of the Chesapeake Bay. It is a paradise for water lovers, famous for its crab cakes, lighthouses, and 500 miles of gorgeous shoreline. Tour the campus of the US Naval Academy, or the Maryland State House, the oldest state capitol still in use.

Day 5 | Annapolis to Baltimore

There is a buzz about Baltimore, as it makes people who visit fall in love with its vibe. Explore the world-famous inner harbor, renowned museums, attractions, award-winning restaurants, locally loved music scene, and hip and historic neighborhoods. This is a truly authentic American city.

Day 6 | Baltimore to Kent Island

Head back to Kent Island, located in the nest of the Chesapeake Bay Bridge. End this Kent Island itinerary until next time.