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Stopped in Tolchester Marina and the famous Shanty Bar for the afternoonBeautiful sunset cruiseEnjoying the foredeck in the sunEver see the Bay Bridges from this vantage point?

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

With Captain

100% refund within 3 days of your trip
  • Rare Discovery!

    This date is popular and usually gets booked early.

Guests describe a peaceful, scenic Chesapeake Bay sail with a calm, relaxing vibe, easy last-minute hosting, and time to simply unwind on the water.
Well-kept sailboat praised as pristine and comfortable, offering a smooth, quiet ride that lets you focus on views, conversation, and time on the bay.
Reviews highlight an excellent captain and welcoming co-host who communicate clearly, share sailing knowledge, and create a warm, attentive experience.
Renters say this listing is great for:
RelaxationSightseeingFamiliesCouples
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AI Overview

Owner's Description

Make a memory with your friends and family! The Boat- Optimytic is a Hunter 41 AC with a spacious cockpit and salon down below. A full galley and two heads (bathrooms for the land lubbers) On board will be a cooler full of ice with bottled water. Bring your own refreshing beverage, snacks or meals. 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. You may choose to randomly sail the bay, or for longer cruises choose from the follow destinations; 1, Land Point Winery, Worton Creek. Sail across the Bay to pull up dockside to the winery. A beautiful setting overlooking the harbor while tasting the best wines from the Eastern shore https://www.landspointwinery.com/ 2, Shanty Bar, Tolchester. A great waterfront bar with cool drinks and great food, live music and beach to take a dip. https://www.facebook.com/theshantybeachbar/ 3, Carson’s Creekside Restaurant. Savor their great fare and drinks while sitting on the deck at the waters edge. https://www.facebook.com/CarsonsCreekside For the adventurous, take the wheel and let the Captain grade you on your ability to keep a course, do a tack, or ‘heave to’. The Owner/Captain is ready to discuss with you and special request or ideas you may have to make your charter a memory everyone will cherish. 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. Special RATES Midweek Let Captain Charles help you make a long lasting memory!

Charles

Charles

10 total bookings
Capacity
6 guests
Sailing
Cruising Monohull

Reviews

5.0 (5 reviews)
  • Listing Accuracy

    Awesome
  • Departure & Return

    Awesome
  • Vessel & Equipment

    Awesome
  • Communication

    Awesome
  • Value

    Awesome
  • Itinerary & Experience

    Awesome
  1. Welcome Aboard Optimystic! Create a beautiful memory on the water.
  2. Welcome Aboard Optimystic! Create a beautiful memory on the water.
  3. Welcome Aboard Optimystic! Create a beautiful memory on the water.
  4. Welcome Aboard Optimystic! Create a beautiful memory on the water.
  5. Welcome Aboard Optimystic! Create a beautiful memory on the water.
  6. Welcome Aboard Optimystic! Create a beautiful memory on the water.
  7. Welcome Aboard Optimystic! Create a beautiful memory on the water.
  8. Welcome Aboard Optimystic! Create a beautiful memory on the water.
  9. Welcome Aboard Optimystic! Create a beautiful memory on the water.
  10. Welcome Aboard Optimystic! Create a beautiful memory on the water.
  11. Welcome Aboard Optimystic! Create a beautiful memory on the water.
11 photos have been added by reviewers who booked this listing.
  1. LM

    Liz

    Charles was an outstanding guide. Before the outing (which was a birthday gift for my fiancé) he even offered to pick up a cake so that it could be a surprise. He and his wife made us feel at home right away as if we were out just sailing with friends. It was a gorgeous late afternoon / sunset sail with the option of swimming and cooking on the boat. We didn't rush back. Riding on the bow was so relaxing. He took time explaining sailing tips to my fiancé and let him drive the boat for awhile. Communication was clear. We'd love to book again with Charles and Renee!

  2. DL

    Dylan

    Had the best time. Great boat and experience. Communication,knowledge, and time was phenomenal. A+

  3. 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) ⚓️⚓️⚓️

  4. 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!

  5. AM

    Amber
Charles

Charles

10 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

Departure Location

The boat's approximate location on a map

You’ll get helpful information for your departure after your booking is confirmed.

Street Address For Arrival

Street Address For Arrival

1900 Old Eastern Avenue
Essex, Maryland, 21221
United States
Departure Location

Departure Location

Same as Street Address

Cancellation Policy

Free cancellation up to 3 days before your trip.

Additional Terms & Information

We offer a generous reschedule policy should there be inclement weather not conducive to an enjoyable day/evening sail

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