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Choose the Wave!

Welcome aboard on for an exclusive private charter to remember! Cruise the heart of 'America’s Sailing Capital' - Annapolis MD. Enjoy breathtaking views of the Chesapeake Bay on Irie Vibes (34-foot powerboat) or Therapy (43-foot sailboat). If you like, help raise and trim Therapy's sails... Set course and feel the exhilaration and power of taking the helm... Set the anchor... Or simply sit back and relax!

Island Chill Yacht Charters cruise from Londontowne Marina onto the gorgeous South River, past the Thomas Point Lighthouse and onwards into the magnificent Chesapeake Bay. We know the best anchorages, sand bars, historic sites, great dock bars and restaurants, and views. We can bring watersport equipment for even more fun. Our captains and crew are engaging and enthusiastic too. You bring summer clothes, swimsuits and a 'Chill' way of letting loose.  As a family business, we take great pride in making your sailing experience truly memorable.

Our cruises are a perfect venue for birthday, anniversaries, and all your celebrations. Daylight, Sunset, Moonlight and all night parties. Anytime! We love our specialty cruises for adventure, yoga and seeing our lighthouses. Our boats are a great venue for Corporate Retreats and celebrating our National Holidays. Let's Chill mon! 

What's Included

♦  USCG licensed Captain & Crew for your safety & comfort!  ♦  Lightfare food & beverage  ♦  All Fuel  ♦  BBQ grill available (make request)  ♦  Alcohol allowed  ♦  We can welcome up to 6 guests comfortably ♦  Enjoy Free Kayaks and Paddle Board Fun on any cruise (make request) ♦  Even Fishing! (make request)  ♦  Anchor in secluded creeks & tributaries, or choose one of the more popular party spots to mingle  ♦  Catered full meals on selected cruises - View our Island Chill Menu  ♦  Specialty Cruises  ♦


Listed below are our Yachts, Crewed Charters, Specialty Cruises and Corporate Events

Check out our Watersport Activities and Menu too!

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Our Yachts

Irie Vibes rates start at: $650

Therapy rates start at: $550

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Cruises for Families, Friends and Couples

Birthday-Anniversaries  -  Start at $550

Night Owl Party

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National Holidays and Events

Blue Angels - Call

Blue-Angels-2018-annapolis-boatrental-memorialday-chesapeakebay-powerboat-southriver-islandchillyachtcharters

July 4th - Call

fireworks Chesapeake bay July 4th boat rental

Memorial Day / Labor Day - Call

fireworks Chesapeake bay July 4th boat rental

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Specialty Cruises

South River Tour - Start at $220

Adventure - Start at $550

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Lighthouse Tour - Start at $550

Water Taxi - Start at $550

Sam's-on-the-Waterfront

Reggae Day / Jamaica Day - Call

Fall Cruise - Start at $550

Yoga Cruise - Start at $550

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Corporate Events

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Commercial Venue

Photoshoot Venue - Call

Music Video - Call

TV - Internet Venue - Call

10 % Off Special Offer!!! 

Returning guests, Serving Military households, Business Organizations Members(Maryland Business Exchange, Anne Arundel Chamber of Commerce, Visit Annapolis and Anne Arundel County) and  Non-Profit Organizations.

Register for our deals and special offers, and help make it easy to join us for an unforgettable Chesapeake cruise experience.

Menu - Call

See Watersport Equipment