Cookies!

We use cookies to improve your browsing experience. By continuing to browse or closing this banner, you agree to our use of cookies. Find out more about our cookies policy here.

Stopped in Tolchester Marina and the famous Shanty Bar for the afternoonReady for 2023 sailing season??? Come join usCaptain, his mate and familyBeautiful sunset cruise

Charter a Hunter 41 AC Sailboat for a Memorable Middle River Sailing Experience

With Captain

Hunter 41 AC Sailboat is a fractional rig, 41’ monohull with in mast furling Hourly rate - 2 hour minimum $155 Friday thru Sunday; $125 Weekdays Other packages available Come sail with a USCG licensed Captain/owner with years of boating and sailing experience. He’ll make you feel comfortable as you embark on a day’s sail (or evening sunset cruises as well) You’ll begin by enjoying a complimentary Orange Crush as we make way passing the beautiful homes along the middle river till we reach Hart Miller Island and beyond. Relax as the wind takes us for experience that you will remember  The vessel shows a nice spacious cockpit with raised stern seats. For those more adventurous, settle up on the bow and listen to the hull cut through the water. Inside the salon there is ample seating for a nice meal or meeting if it’s a corporate team building event. Heads (bathroom) are both forward and midship. Should anyone take a splash, a stern shower is there to rinse off. Additional photos of interior will be coming soon. If you have any questions, we can answer those through GetMyBoat’s messaging platform before you pay. Just hit, “Send Booking Inquiry” and send us an inquiry for a custom offer.

Charles

Charles

6 total bookings
Capacity
6 guests
Sailing
Cruising Monohull

Reviews

5.0 (3 reviews)
  • Listing Accuracy

    Awesome
  • Departure & Return

    Awesome
  • Vessel & Equipment

    Awesome
  • Communication

    Awesome
  • Value

    Awesome
  • Itinerary & Experience

    Awesome
  1. Come Aboard and Sail Optimystic-Experience the breeze w/Lunch, Wine and Cheese
  2. Come Aboard and Sail Optimystic-Experience the breeze w/Lunch, Wine and Cheese
  3. Come Aboard and Sail Optimystic-Experience the breeze w/Lunch, Wine and Cheese
  4. Come Aboard and Sail Optimystic-Experience the breeze w/Lunch, Wine and Cheese
  5. Come Aboard and Sail Optimystic-Experience the breeze w/Lunch, Wine and Cheese
5 photos have been added by reviewers who booked this listing.
  1. Elisabeth
    Elisabeth

    Charles & Renee were amazing! We booked last minute and enjoyed an awesome afternoon on The Optimystic in Chesapeake Bay!! We can’t wait to sail again!! Charles is an excellent Captain and host. A good teacher as well! Have an awesome winter!! See you in the Spring!! Charlie, Beth and Sam (Class of 2026) ⚓️⚓️⚓️

  2. Cindy
    Cindy

    Our sailboat outing was absolutely perfect - peaceful, scenic and incredibly relaxing. The boat was pristine. Captain Charles and his wife were perfect hosts. Highly recommend!

  3. AM

    Amber
Charles

Charles

6 total bookings

The Chesapeake Bay is an impressive body of water. I've sailed from Hampton to the C&D; Canal for years. Whether you want a relaxing day or evening on the water, or more interested in learning how to handle a larger vessel, Optimystic is the sailboat you would want experience. Friendly, and wanting you and your guests to have a great time aboard, reach out to me to learn more and should you have any questions.

Features & Details

  • Hunter
  • 44 AC
  • Capacity: 6 people max

Approximate Location

You’ll get directions to the departure location when you make a booking.

The boat's approximate location on a map
Approximate Location

Cancellation Policy

Free cancellation up to 3 days before your trip.

  • Other people are asking about this date.Act now to secure your booking.
With Captain
  • Hourly Only
  • With Captain Only