Frequently Asked Questions

How do I reserve a boat?

Discounts & Special Offers

Island Chill Yacht Charters is accepting bookings for the 2019 SEASON and offers a variety of affordable ways for you to cruise the Chesapeake Bay. Sign up for Deals and Special Offers


We are located 5 miles South of Annapolis, MD and

How many boats do we have?

Island Chill Yacht Charters currently has three (3) boats in our fleet. Irie Vibes (34-foot powerboat) Therapy (43-foot sailboat) and Tallawah (20' Bow-rider). See our fleet.

What are the most popular cruise package?

Our Sunset and 4hr cruises the beautiful Chesapeake Bay, wild-life tributaries, lighthouses and bridges. Our guests enjoys anchoring, swimming and non-stop Watersport fun with their party. Our Birthdays & Anniversary packages are also customer's favorite. View our cruise packages.

Will I need a Kayak or paddle board?

Free Watersport equipment for charterers who book cruises 4h or over aboard any of our sail or powerboat. For guests and couples that love a little adventure in their vacations, a kayaking & paddle board tour may be the perfect getaway. See Watersports.

What equipment is on board?

All required USCG Safety Equipment/Life jacket, Navigation Chart, Cruising Guide, Nav Tools,  Binoculars, Traveling set of Dock Lines, Basic Tool Kit s and first-aid kit are provided. Pots, pans & plastic utensils are provided aboard, feel free to bring your own.

How many guests can I bring?

For bare-boat rentals, each boat is required to bring the maximum weight, stated on specific boat page. For our crewed charters we take up to a total of 6 guests aboard.

Can I bring my pet?

Because of  safety & health reasons, we do not allow pets aboard.

Are food and beverages available?

Enjoy free finger food aboard your charter. From succulent appetizers to scrumptious buffet meals, your Island Chill sales agent will help you choose the perfect accompaniment to your private cruise. All food selections are served either chilled or room temperature during your charter.

What is your cancellation policy?

Reservation is  fully refundable up to 7 days before charter.

Customers will receive a full refund or credit with 72 hours notice of cancellation. Customers will also receive a full refund or credit in case of operator cancellation due to weather or other unforeseen circumstances. Contact us by phone to cancel or inquire about a cancellation. No-shows will be charged the full price.

Weather Policy.

Unlike other cruise charters, we do not have a ‘Cruise Rain or Shine – No Refund’ policy. If the weather forecast is for ‘Continuous’ or ‘100 % Chance of Rain’ or ‘Thunderstorms’, or if the U.S. Coast Guard issues a ‘Small Craft Warning’ for the Chesapeake Bay, for the day of the cruise, the date of your cruise can simply be rescheduled for any un-booked timeslot. If the weather forecast is simply for ‘Chance of Showers or Rain’, or ‘Showers” or ‘Scattered Thunderstorms’ or ‘Isolated Thunderstorms’ or ‘Chance of Thunderstorms’, we will discuss the best fun and water activities and cruise routes with you prior to departure. Generally, we shelter for passing thunderstorms and stay closer to post. If the U.S. Coast Guard issues a ‘Small Craft Advisory’ for the Chesapeake Bay, we will restrict our cruise destinations to the South River.

$100 deposit is required to reserve your charter booking, this is fully refundable up to 7 days prior to your charter. We do not refund deposits after this time period.

Are utensils, plates and dishes available?

We have aboard plastic plates. While you may bring your own, glasses are not allowed for safety reasons.

If I damage, the boat, what am I responsible for?

If the boat is damaged during your scheduled charter, you are responsible for up to the full deductible amount of the insurance.

How do we compare?

We create the authentic  ‘Island Chill’ atmosphere and hospitality while enjoying our private cruises. You have the opportunity to be featured on Island Chill MagaZeen & seen by our 7,000+ viewers. Our guests are our main priority!

Contact Info.

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 activities. Call us (410) 212 4476 or request information, availability and quotes online here.