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Essex, Maryland Boat Rentals

Page 1 of 12 listings

Come Aboard and Sail Optimystic-Experience the breeze w/Lunch, Wine and Cheese
Sailing in Essex · 6 guests

Come Aboard and Sail Optimystic-Experience the breeze w/Lunch, Wine and Cheese

5.0
$150/hour
Cruise the Chesapeake on Bay Lady
Powerboats in Essex · 5 guests

Cruise the Chesapeake on Bay Lady

New
Snoozed - Active 02 Mar 2026

Essex Reviews

  1. Elisabeth

    Elisabeth

    Come Aboard and Sail Optimystic-Experience the breeze w/Lunch, Wine and Cheese

    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

    Come Aboard and Sail Optimystic-Experience the breeze w/Lunch, Wine and Cheese

    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!