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All listings in Chesapeake Bay

Incredible sailboat rentals in Chesapeake Bay, United States.

Page 2 of 233 listings

Sailing Adventures on the Choptank River
Sailing in Cambridge · 6 guests

Sailing Adventures on the Choptank River

New
$100/hour
Romantic Sunset Champagne Cruise on the Chesapeake Bay - 2 Hours
Sailing in Saint Michaels · 6 guests

Romantic Sunset Champagne Cruise on the Chesapeake Bay - 2 Hours

New
$400/hour
Sail on the Potomac in Washington, DC aboard the 28ft Hunter Sailboat
Sailing in Washington · 6 guests

Sail on the Potomac in Washington, DC aboard the 28ft Hunter Sailboat

New
$280/hour
Instant Book
Sail the Chesapeake Bay, Atlantic Coast or the Caribbean Islands in style! Charter this Jeanneau Sun Odyssey 509
Sailing in Deltaville · 8 guests

Sail the Chesapeake Bay, Atlantic Coast or the Caribbean Islands in style! Charter this Jeanneau Sun Odyssey 509

New
$524+/day
 VIKO S 35 Sailboat in Deale
Sailing in Deale · 6 guests

VIKO S 35 Sailboat in Deale

New
$298/hour
41’ Bristol Sailboat Charter in Solomons Island, MD
Sailing in Solomons · 6 guests

41’ Bristol Sailboat Charter in Solomons Island, MD

New
$90/hour
VIKO 30 Premium Sailing Yacht In Deale, MD
Sailing in Deale · 5 guests

VIKO 30 Premium Sailing Yacht In Deale, MD

New
$925/day
34ft Sailing Yacht in Annapolis, Maryland
Sailing in Annapolis · 4 guests

34ft Sailing Yacht in Annapolis, Maryland

New
$250/hour
STARZ -Lagoon 42 Catamaran in Chesapeake Bay
Sailing in Annapolis · 13 guests

STARZ -Lagoon 42 Catamaran in Chesapeake Bay

5.0
Snoozed - Active 02 Oct 2025

Sailing Reviews in Chesapeake Bay

  1. JS

    Jen

    STARZ -Lagoon 42 Catamaran in Chesapeake Bay

    I highly recommend Chronic Sailing! We did a 4 hour charter out of Annapolis as a bachelorette party. Captain Steve and Sarah were so accommodating and made our time so memorable. We are so appreciative. They made everything so easy- from booking to sailing and making memories with us. The STARZ catamaran boat was incredible! It fit our big group comfortably and gave us a little bit of luxury as we lounged and enjoyed on the bay. Again, this was a great experience for all of us and I would love to use them again!

  2. MR

    Matt

    STARZ -Lagoon 42 Catamaran in Chesapeake Bay

    Great experience and our family and friends had a wonderful time. Clean boat and fun crew to help us celebrate a special occasion. Highly recommend!