Both our sailboat and powerboat charters create memorable cruise experiences: ‘togetherness’ and connection with friends and family on a shared experience, with fantastic views, destination opportunities and fun activities – how much and the nature of each are dependent on:
- Your priorities: see also Sail vs Powerboat
- The location of the marina relative to the views and destinations of choice
- The amount of time you have available
- The fun toys carried aboard
- The flexibility and experience of the charter company.
Actually, the challenge of a Chesapeake Bay boat charter is that there are too many possibilities! Maybe you should just think of moving here!
‘Amazing Views’
‘Amazing Views’ are standard on Chesapeake Bay charters: you’ll see them from the moment the boat leaves the dock! The key question is how long is needed for a ‘Goldilocks cruise’ to optimize the experience: not too short, not too long – Just Right!
To cut to the chase, I’d say about 3-hours of cruising total on a powerboat is minimum to see the different types of shoreline along the upper South River, explore at least one creek and experience restful, peaceful anchorage views. A sunset cruise covers the same experiences in about two and a half hours. With a 4-hour charter, you’d also see the lower River and see the open Chesapeake Bay – with views of a lighthouse or two, and a very large Bridge. Same options on a sailboat charter, but without the upper River component.
Longer cruises Island Chill Yacht Charters, say 7-hours, have time to go further distances. On both our powerboat and sailboat charters, we add visiting the lighthouse and Rhode River where there are islands and a sand bar and some larger wild areas to explore. These charters add the experience of cruising on the open Chesapeake Bay too. They give time to get into the rhythm of the Bay and can include the sunset.
‘Fun Activities’
There’s plenty of fun activities to focus on, including swimming, paddleboards, kayaks and fishing. 
Charters would, of course, include ‘Amazing Views’ during the cruise and at anchor, and we’d talk with you about the balance of relative times for each option. Four- and seven-hour cruises work well when there’s emphasis on water sport activities.
‘Specific Destinations’
There are some great places of significance to visit, including the William Brown House and the ferry location where George Washington, Thomas Jefferson and Francis Scott Key took to cross the South River (which is very close) and the Thomas Point Shoal Lighthouse (visited during the 4- and 7-hour charters). We’ve even done overnight charters to St. Michaels.
At Island Chill Yacht Charters, we’re glad to entertain your specific destination requests.