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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
  • Looks Good

    This date is available.

Relaxed, friendly sails on Chesapeake Bay with time to lounge on the bow, swim, cook onboard, and linger through a scenic late afternoon into sunset.
Spacious cockpit and salon with full galley and two bathrooms create a comfortable setting for swimming stops, casual meals, and easy moving around on deck.
Warm, attentive hosts who feel like old friends, communicate clearly, teach sailing, and often add thoughtful touches to make celebrations feel special.
Renters say this listing is great for:
Sunset CruisingCelebrationsFamiliesRelaxation
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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. Captain’ Suggestion! Midweek Special- ditch work with a few friends to enjoy a fall day on the water sailing that would include a meal aboard with the captain putting on a chef’s hat as he grills for you and your guests at anchor or allow him to approach and dock and Loon A Sea or Carson’s Creekside restaurant 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 glass of wine as we make way passing the beautiful homes along the middle river till we reach Hart Miller Island and beyond. 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

13 total bookings
Capacity
6 guests
Sailing
Cruising Monohull

Reviews

5.0 (9 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.
  12. Welcome Aboard Optimystic! Create a beautiful memory on the water.
24 photos have been added by reviewers who booked this listing.
  1. Rudolf
    Rudolf

    Charles and his wife are amazing people who went above and beyond to offer us an amazing sailing experience all while teaching us about the various aspects of boating life. Book them for your next adventure, you won’t be disappointed.

  2. BF

    Barb

    Highly recommend sailing with Captain Charles on the Optimystic! Was like hanging out with an old friend. Beautiful boat and fun time!

  3. EB

    Elias

    Charles is fantastic, he and his wife went above and beyond to make everything go flawlessly, and the boat is gorgeous

  4. SF

    Serlena

    A great host!

  5. 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!

Charles

Charles

13 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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