Boat & Breakfast

Private Exclusive Cruises

Are you searching for the perfect way to stay on the water in historic Annapolis, complete with accommodations aboard the schooner, a 2-hour sunset sail and a gourmet breakfast.

Boat & Breakfast Gift Cards make a perfect gift.

The Schooner Woodwind is a 74-foot sailing and power yacht that departs four times daily for two-hour sails. On Saturday evenings we offer a special Boat & Breakfast package to as many as four couples, from the first weekend in May to the last weekend in September.

Looking for a private getaway to offer family and friends an escape from their daily routine? Want a unique and romantic experience that you'll talk about the rest of your life? Offering a remarkably different vacation experience, an Island Chill cruise is the perfect solution. Your journey starts by giving us a call. 

Benefits of Cruising with Island Chill:

  • Up to 6 guests in an intimate, private setting
  • Thoughtful, personalized service
  • Inclusive of all lite-fate food,
  • Enjoy gourmet dishes, including our famous jerk chicken (see menu)
  • Includes complimentary 'champagne'  Gratuities welcome
  • Comfortable cabins and deck space
  • Customized itinerary calling on small, intimate yachting harbors and water-front restaurants
  • and more…

You Deserve the Best

Luxury Amenities for Your Private Yacht Cruise

After cruising along the South River and into the Chesapeake Bay, we anchor to enjoy food and music - with options to paddle board or kayak to explore secluded areas and sandy islands. You can also dine at one of the Bay's many water-front restaurants. 

But, you are not limited to any of our existing itineraries! Instead, you have the freedom to choose what you want included on your voyage. Our Cruise Director can help develop an personalized itinerary that fits your needs and desires. This way, you are in complete control of the voyage, including special requests for cuisine, on-board entertainment, ports of call, and restaurant. Regardless of how long your voyage lasts or where it takes you, your time aboard an Island Chill yacht is always special. With an array of inclusive options, you can enjoy every moment at sea. Our guests cite us as the best charter on the Chesapeake.



Comfy Overnight Accommodations

Beyond the various cruise options, both Therapy and Irie Vibes feature sleeping staterooms for 6 guests for you to enjoy. These are designed to complement your casually elegant yacht cruise and provide a comfortable and private place to rest your head on overnight charters. Amenities include, rest room and shower, fridge/ice box, and comfortable living space. The cockpit area includes comfortable seating with a cocktail table to really let you unwind. If you prefer the open-air feel, you can always rest on deck!

Irie Vibes - 34' Powerboat

Irie Vibes is a high-performance Formula-34 cruiser pc. Her stern lounge area can be reconfigured for dining to swimming to partying and a comfortable powerboat that makes a wonderful option for a memorable voyage along the Chesapeake Bay. Irie Vibes Features & Amenities

Crewed Charters on the Chesapeake bay birthday party anniversary

Therapy - 43' Sailboat

This resolute & comfortable 43' sailboat – center cockpit C&C Landfall amazingly comfortable and spacious sailing yacht makes a wonderful yacht charter for you and is a wonderful option for a memorable voyage along the Chesapeake Bay.  Therapy Features & Amenities

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Book Your Exclusive Cruise

  Whether for personal & family fun, business engagements, or a beautiful romantic sunset or overnight cruise, Island Chill Yacht Charters is the perfect getaway on the Chesapeake Bay. Whatever your plan, our yacht is yours for the duration of your cruise, which why so many return to book with us.

   When you are ready to embark on the voyage of a lifetime, request to be contacted below and we’ll get you started right away. 



Great Bed-Breakfast Service

      The crew was fabulous, stayed overnight, had breakfast we were treated like kings & queens, very personal, like no other experience we've ever had. See you next year and every year there after. Mr & Mrs Michael Ambm - New York


I'm scared of going boating from a young age. So I reluctantly signed up for a IslandChill and after half hour in our trip, I could not think of one thing that was not done to perfection. The food was great, the staff was spectacular, and love the Jamaican atmosphere created.