Bareboat Rentals

For qualified sailors, chartering any of our yacht bareboat (rent without captain) for a day on the bay, overnight boat & breakfast, and weekly charter 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. All bareboat charters incur a MD sales tax-6% Plus, Fully refundable Damage and Security Deposit of $1000, paid at the beginning of the charter.
  3. Fill out bareboat charter inquiry 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.
  4. Learn more about our Rates, Insurance, Waivers, Damage & Security Deposit here.
paddle board & kayak rental

Irie Vibes

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



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: N/A

Overnight Boat & Breakfast: Available with captain

Sleeps 6 guests comfortably.

Therapy Pricing

1/2 day: N/A

Full day: N/A

Overnight Boat & Breakfast: contact us

Weekly: contact us

Plus 6% MD sales tax and boat insurance of approximately 10% of rental rate. Details here.

Sleeps 8 guests comfortably. 

(Bareboat cruises unavailable April-Sept season, call for more info)

Tallawah Pricing

1/2 day: $450

Full day: $950

Sunset Cruise: $450

Overnight: unavailable

Plus 6% MD sales tax and boat insurance of $50. Details here.

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

Select from our fleet of spacious sail and powerboats. Custom yacht choices and top Chesapeake, South River and Annapolis destinations come together to create the ideal trip just right for you and your party!

See Top 10 Places to Visit in Annapolis

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.

Opens 7 Days A Week 1/2 day, Full Day & Overnight Rentals

The staff at Island Chill Yacht Charters operate all year round, even when the tourist season for maritime services has ended. In this way, you can keep up to date on our activity rates, cheap prices on our South River, Chesapeake Bay, Annapolis and Florida tours, cruises and special offers. Contact Us.

Frequently Asked Questions