Our Boats

paddle board & kayak rental

Irie Vibes

34' Formula Cruiser Motor Yacht - Rates from $150/h

sailboat Chesapeake bay Annapolis md rental south river boat

Therapy

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

Tallawah

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

Chesapeake Bay Charters

Serving MD / V.A. / D.C region

We hosts Exclusive Private crewed charters with our USCG captain & Cruise Director and bareboat rentals, sail & powerboat on the Chesapeake Bay. We cater to guests seeking a private cruise adventure for w. Cruise with us and enjoy the warmth and hospitality of Jamaica, ensuring a truly memorable charter!

Services

Crewed Charters

Allow our USCG captain & crew to take you on a cruise of your lifetime!

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Cruise Packages

Celebrating birthdays, anniversaries, make your day extra special!  

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Bareboat Rentals

Be your own captain, go where you want...

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EXCLUSIVE PRIVATE CRUISE:

  • Celebrate With Us! Birthdays, Anniversary, Bachelorette Party...
  • Family Outings
  • Specialty Cruises
  • FREE Island Chill meal (view menu)
  • Visit Annapolis Historic Landmarks (bridges & lighthouses...) (see destinations)
  • Fuel included in package.
  • Fun watersport activities: Kayaking, waterskiing & paddleboarding...
  • Endless onboard entertainment: anchor, swim, BBQ, fishing...
  • Overnight Boat & Breakfast
  • Corporate Events: Team Building, Business meetings, Client's reward, Team bonding... learn more
  • Venue: Music Video, Photoshoots, Commercials... learn more
  • And more...

Client satisfaction

Customers experience is very important to us. Check out what our recent customers say.

"Happy spouse! tremendous feeling when I proposed to my fiancé on her birthday on Island Chill.  They really treated us to a great experience and were very accommodating. We can't complain, my fiancé and soon to be wife said 'best time she had in a long time'. Been to Jamaica once for vacation in Montego Bay and this is how I remembered the hospitality.

"Island Chill was awesome and extremely accommodating! rented the Sailboat and went on the Bay with my hubby and some friends. So much fun! Everything about the sail was amazing & great customer service! Thanks for such a fun day!!!"

I have never been on a yacht and Island Chill makes me feel so comfortable. Great relaxing settings for me and the kids. Great hospitality will definitely come again next year!

"Island Chill Yacht Charters is a little mini-vacation cruise right in our own backyard here in Annapolis. Stacii & Sheree, are lovely crew that made it extra special with hospitality!"

See Island Chill in Action