Chesapeake’s Famous Landmarks

There are many wonderful places to explore along the Chesapeake Bay!

Located in the heart of the Chesapeake Bay, Annapolis is “America’s Sailing Capital.” Island Chill Yacht Charters cruises from Londontowne Marina onto the beautiful Chesapeake Bay and South River and the historic Annapolis shoreline. Sailing past lighthouses, bridges and wild-life tributaries. As a family business, we take great pride in making your sailing experience a truly memorable one. Our captains and crew are chill, engaging and enthusiastic. Choose the Wave - Cruise with us!


Chesapeake Bay has some of the most desiring anchorages and creeks, which offers diversity of high quality shore activities. 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 like.

  • Harness Creek
  • River Farms State Park,
  • Crab Creek
  • Broad Creek
  • Beards Creek
  • Rhode River,
  • West-River
  •  Annapolis-Severn River
  • Learn more about marinas & anchorages on the Chesapeake that would be great for stay while on the water.

Island Chill Guests partying in Harness Creek


Food looks & tastes better when you dine on the water and 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!

  • Mike's Crab House
  • Oyster Bar & Grill
  •  Yellow Fin
  • Kentmorr
  • Pussers
  • Learn more about our water taxi service and enjoy delicious meals by the water.


Our crewed charter takes you on the beautiful and mesmerizing views of the  Chesapeake Bay. We tour secluded wild life tributaries, cruise along the Severn River, explore untouched beaches, scenic vistas and some of the neighboring islands. During our sightseeing tours,  our entertaining crew who will gladly show you the highlights of the Chesapeake Bay. Some of our favorite historic landmarks are:

  • Thomas Point Shoal Lighthouse
  • Chesapeake Bay Bridge
  • Bloody Point Lighthouse

Join us for a specially designed Chesapeake Lighthouse Tour to capture each of these lighthouses and significant markers around Annapolis. Learn more about our Chesapeake Lighthouse Tour.

Island Chill Yacht Charters offers Florida sailing adventures on Therapy, our sailing yacht.

For cruises in Florida, feel free to contact us. (desired date, city)

Dec - April