Places to Visit in Annapolis

Places to Visit in Annapolis

Annapolis is popularly known as the “Sailing Capital of America” is truly the crown jewel of the Chesapeake Bay. It is also home to charming, bricked streets lined with one-of-a-kind houses, shops, restaurants, bed and breakfasts and inns. Below are a few places and friends we  recommend checking out when you visit Annapolis.

Restaurants & Bars

Sailing with us means you have the choice of our catered delicious menu and BBQ on your yacht, but don’t forget we have really nice restaurants and bars on the Chesapeake Bay, South River and Annapolis region you have to try out as well!

Click below to visit restaurant's website.

Address: 910 Kentmorr Rd, Stevensville, MD 

Sam's on the Waterfront

Address: 2020 Chesapeake Harbour Dr E, Annapolis


Bed & Breakfast / Inn 

Click to Visit Bed & Breakfast & Inns Located in Annapolis. 


Marinas + Anchorages 

Island Chill cruises from Londontowne Marina onto the beautiful Chesapeake which as one of the most desiring anchorages and creeks and offers diversity of high quality shore activities. Perhaps renting bareboat on land is marinas that we recommend

Click on the link to view marinas & anchorages that would be great for stay while on the water. 




Lets take You On A True Chesapeake Experience !

Allow our crew to take you and your party on a private cruise to remember on any of our boats. See our Cruise Packages. 


Contact an Island Chill Sales Agent

Learn more about sailing with us.

Call 410-212-4476, or fill out an inquiry form by clicking this link.