United StatesChesapeake Bay

Awesome cruising monohull rentals in Chesapeake Bay, United States.

Average of 42 reviews in this area.
16 listings

Rent a cruising monohull boat for a fun day exploring on the water in Chesapeake Bay.

Chesapeake Bay is a great place to rent or charter a cruising monohull. Sailing on a cruising monohull is always a good time - the boats have a sleek design and a single hull, making it easy to cruise through the waves. Whether you're sailing for leisure or looking for some friendly competition, cruising monohulls are the perfect choice. Choose from a range of sizes depending on the size of your group and desired event. A captain and crew can help you sort out the perfect itinerary for your boat day in Chesapeake Bay.

Using GetMyBoat to rent your next cruising monohull.

Experiencing the water has never been easier thanks to GetMyBoat. GetMyBoat allows you to quickly search, compare prices, submit rental inquiries, and pay for your rental or charter from the convenience of your phone or computer. We offer a secure platform for renters to facilitate a seamless rental transaction. For boat owners, we connect millions of renters to their boat and provide the security and safe checks on each rental transaction.

Search for the perfect experience now and book your dream day out on the water.

GetMyBoat customer reviews for Cruising Monohull in Chesapeake Bay.

  1. JW
    Jen
    Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland

    We had the most amazing sail even though we didn’t have the most ideal weather. Capitan Joe motored is out to “find the wind” and we were able to enjoy both tranquility and the blissful breeze of a non-thunder cloud. The brownies and fresh raspberries were a nice indulgence as we glided peacefully back to the marina. We can’t wait to go out again!

  2. SC
    Shelby
    38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

    Captain Alberto and his wife were an absolute delight! He is incredibly knowledgeable in sailing and he made us feel welcome and at home on his sailboat. My entire family had such an amazing time, and I would recommend to anyone! If you have an opportunity and want a wonderful, safe, and fun experience, choose this charter!

  3. NS
    Nihar
    38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

    Rented for 7 hours with 3 kids and my wife. The boat was clean. It seems Captain had just washed it before our arrival. Captain Alberto is very knowledgeable and really enjoyed the conversation. He took us to a great restaurant on a creek. Overall, I would rent this boat again.

  4. DB
    Daniel
    Charter the Beneteau Oceanis 440 Sailing Yacht in Tracys Landing

    We booked this trip last minute and no expectations or plans of what we wanted to do and Richard was able to provide us with options and ensured we had a great trip. Boat was very comfortable with plenty of room for more people. Really enjoyed the relaxed atmosphere and flexibility to change plans depending on which way the winds were blowing.

  5. sm
    sydney
    38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

    A lovely captain and comfortable vessel to explore the Chesapeake. Highly recommend Alberto for anyone looking for a relaxing day trip and sailing lesson! A hands on adventure and perfect escape with family or friends.

  6. Bp
    Bill
    Charter the Beneteau Oceanis 440 Sailing Yacht in Tracys Landing

    It was a great day on the bay. No clock watching with this charter. The day was ours and we had a great time. Capt. Rick made it easy and fun.