Cruise the Chesapeake Bay from the South River - located 5 miles south of the 'Sailing Capital' of Annapolis Maryland. We offer private and exclusive cruises, endless water activities and serve as your entertainment venues. We're your 'One-Stop-Shop' for cruise, food and entertainment!
Charter bare boats or allow our crew to take you on a journey to remember.
Whether for personal use, business engagements, or a beautiful private overnight bed and breakfast or sunset cruise,  this Jamaican-style boat charter is the perfect getaway on the Chesapeake Bay.
The Relaxing Excitement of the Islands - on the Chesapeake!
Please tag us in your photos; we would love to share! #islandchillmd #islandchillyachtcharters

Special Offer for Island Chill Guests

Enjoy $50 OFF your next cruise with us, call and mention discount code: Cruise18
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Choose The Wave!