Bareboat Rentals

For qualified sailors, chartering any of our yacht bareboat (no captain) for a day on the bay or overnight boat & breakfast, offers you the ultimate freedom with the option to sail-it-yourself or hire a licensed captain. Go where you want, do what you want, explore, snap moments, join in the festivities ashore or slip away from everything on a remote beach on the Chesapeake Bay, South River and Annapolis shoreline…
To get you started:

  1. Choose the boat below that best suits your voyage. View our fleet…
  2. Fill out the form below and one of Island Chill friendly staff will get back to you as quickly as possible and get you sailing in no time.
paddle board & kayak rental

Irie Vibes

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

sailboat Chesapeake bay Annapolis md rental south river boat


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


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

Irie Vibes Pricing

1/2 day: N/A

Full day: contact us

Overnight Boat & Breakfast

Sleeps 4 guests comfortably.

Therapy Pricing

1/2 day: $600

Full day: $800

Overnight Boat & Breakfast

Sleeps 6 guests comfortably. 

Tallawah Pricing

1/2 day: $550

Full day: $950

*Fits 6 guests.  Only 4 allow/tubing...

(overnight unavailable)

Select from an extensive custom-built fleet of spacious sail and powerboat, Custom yacht choices and top Chesapeake, South River and Annapolis destinations come together to create the ideal trip just right for you!

Bareboat Charter Inquiry Form

Please complete the following form to indicate your interest in a bare boat/overnight charter, our sales team will follow all your requirements in detail aiming to find the best solution for your needs and we can then give you a detailed quote.