About Us

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'To Bring People Together to Create Memories,

 Strengthen Friendships & Family Connections'.

Whether you live in the Annapolis, M.D, D.C, V.A or visitors from out-of-state, we want you to enjoy an unforgettable Chesapeake experience. Our private charters create memorable cruise experience for families, friends and a comfortable venue for corporate events, photoshoots and film productions.

Our Goal: Create 10,000 Lasting Smiles & Memories!

Enjoy sailing the shorelines of the 'Sailing Capital of America', Annapolis, MD aboard any of our comfortable yachts with water sport activities, snacks and beverages and non-stop entertainment all day!

Exclusive captained or bareboat charter company in the Chesapeake Bay supported by professional and fun staff and crew. Choose between Therapy 43' sailboat, Irie Vibes 34' powerboat or Tallawah 20’ bow-rider and relax aboard. Our team of USCG licensed Captain and Cruise Director strives to provide quality service, a great product and a wonderful cruise to our valued guests.
3

Vessels

110

Celebrations

63

Families Aboard

84

Kids

Our History: ISLAND CHILL Yacht Charters operates out of the Londontowne Marina and rents sailboat and powerboats. It began as a venue for photoshoots and music videos in the year 2013 and evolved in 2016 as a boat charter. We aim to continuously give our guests and visitors of Annapolis and the Chesapeake Bay the feeling of an exclusive cruise getaway.

Welcome & Enjoy the WAVE!!! Learn More About Our Team and Our Story!

'All You Have To Worry About Is Having Fun,

We'll Take Care Of Your Memories'

PROUD PARTNERS/MEMBERS: Visit Annapolis (VAAAC), Visit Maryland.org., Maryland Business Connection and Anne Arundel Chamber of Commerce.

 

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OUR FLEET

paddle board & kayak rental

Irie Vibes

34' Formula Cruiser Powerboat - Rates from $150/h

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Therapy

43' Center-Cockpit Sailboat - Rates starting at $125/h

bow-rider-chesapeake-bay-bareboat-yacht-annapolis-south-river-water-skii

Tallawah

20' Wellcraft Bow-Rider - Rates as low as $125/h