Places to Visit in Annapolis

Annapolis is popularly known as the “Sailing Capital of America” is truly the crown jewel of the Chesapeake Bay. Annapolis is also home to charming, bricked streets lined with one-of-a-kind houses, shops and restaurants. Below are a few places to visit 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 on the picture to go to the restaurant's website 

Address: 910 Kentmorr Rd, Stevensville, MD 

Sam's on the Waterfront

Address: 2020 Chesapeake Harbour Dr E, 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. 





Overnight Bed & Breakfast

Looking for a private getaway to offer family & friends an escape from their daily routine? Want a unique and romantic experience that you'll talk about the rest of your life? Offering a remarkably different vacation experience, an Island Chill Overnight Boat & Breakfast cruise is the perfect solution. Perhaps staying on land is.........

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 fleet.

Help raise the sails, steer the boat, or simply sit back & relax as Island Chill cruises from Londontowne marina, onto the South River and into the Chesapeake Bay. As a family business, we take great pride in making your sailing experience a memorable one. Our captains and crew are engaging, enthusiastic and very entertaining. Choose the wave & lets island chill mon!

Island Chill Catering Menu


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.