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    Browse Chesapeake Bay Boat Rentals.

    Average of 1,237 reviews in this area.
    1 - 18 of 136 listings
    38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA
    hour$150
    Super Owner6 guests

    38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

    Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland
    hour$150
    Super Owner6 guests

    Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland

    Charter a Motor Yacht in Washington, District of Columbia
    hour$350
    Super Owner6 guests

    Charter a Motor Yacht in Washington, District of Columbia

    Charter 29ft Crownline Bowrider In Wildwood, NJ / Cape May, NJ
    hour$250
    Super Owner6 guests

    Charter 29ft Crownline Bowrider In Wildwood, NJ / Cape May, NJ

    Jet ski - Jet Boat - 4 People - Sportster- SeaDoo - 16ft Be the Captain!
    hour$150
    Super Owner4 guests

    Jet ski - Jet Boat - 4 People - Sportster- SeaDoo - 16ft Be the Captain!

    Bayliner Yacht for $160/hour Weekdays - $200/hour Weekends - Up to 6 people
    hour$160
    Super Owner6 guests

    Bayliner Yacht for $160/hour Weekdays - $200/hour Weekends - Up to 6 people

    Sea Ray 300 Yacht Charter for $250/hr Weekend- $200/hr weekday- 8 people
    hour$250
    Super Owner8 guests

    Sea Ray 300 Yacht Charter for $250/hr Weekend- $200/hr weekday- 8 people

    "1001 Nites" Mainship Sedan Bridge
    hour$440
    Super Owner12 guests

    "1001 Nites" Mainship Sedan Bridge

    "Imi Ola" Seawind 1260
    hour$716
    Super Owner12 guests

    "Imi Ola" Seawind 1260

    "No Regrets" Regal Sport Coupe
    hour$562
    Super Owner6 guests

    "No Regrets" Regal Sport Coupe

    "3 BuOYS" Regal 38 SAV
    hour$575
    Super Owner10 guests

    "3 BuOYS" Regal 38 SAV

    J70 Daysailer rental in Hampton
    hour$100
    Super Owner4 guests

    J70 Daysailer rental in Hampton

    "Arabella" Meridian 341
    hour$671
    Super Owner6 guests

    "Arabella" Meridian 341

    "Sea Quenched" Hurricane SunDeck Sport 231
    hour$254
    Super Owner6 guests

    "Sea Quenched" Hurricane SunDeck Sport 231

    "Stress Free" Four Winns Vista 348
    hour$599
    Super Owner8 guests

    "Stress Free" Four Winns Vista 348

    "S.S. CamJoy II" Chaparral Signature 270
    hour$570
    Super Owner6 guests

    "S.S. CamJoy II" Chaparral Signature 270

    100+ results

    Boating Guide - Chesapeake Bay

    Chesapeake Bay Boat Rentals

    One of the best experiences you can have on the east coast of the United States is a boat rental on the Chesapeake Bay. Book a sailboat charter for an all-encompassing tour of the bay and see the stunning shoreline from the water. Boat tours and fishing on the Chesapeake Bay are not only great for tourists but are also fabulous experiences for life-long locals to enjoy in the summer. There are many water tours and types of boating experiences you can have on the Chesapeake Bay. Choose from pontoon rentals, sailboat rentals, bareboat rentals, yacht charters and even houseboat rentals.

    GetMyBoat customer reviews for boat rentals in Chesapeake Bay.

    1. rc
      raymond
      38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

      I cannot speak highly enough about Capt. Alberto. He and his ‘first mate’ gave us a great morning on the bay. A chilly but sunny morning with good wind kept us thoroughly engaged in the sailing. The Capt and his wife were easy to spend time with. Their love and knowledge of sailing and their warmth made for good conversation and a relaxing day. The boat is comfortable and well maintained. Even with some stiff breezes we stayed dry. When my wife got chilly, they provided a blanket to keep her warm. Very thoughtful and appreciated. Capt. Alberto gave me the helm for a time and allowed me to sail a beautiful boat. It topped off a perfect day. Thanks Cap! We’ll be back.

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

      We had the best time with Captain Alberto! He was so nice and professional. His many years of experience is obvious and he shared so much of his knowledge with us. Our time together gave us such a huge appreciation and love of sailing! We can’t wait to go again!

    3. DS
      Dan
      38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

      Capt Alberto and his wife Grace are amazing hosts and people! This was our families first trip on the Getty oat site and we’re happy to choose this one. The boat was in pristine condition and even though there wasn’t much wind the day we went out, the Capt searched and found some! The kids were able to steer and learn about sailing. All in all a perfect morning and would definitely recommend to anyone!

    4. AM
      Amy
      38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

      Captain Alberto was such an amazing host and captain! He and his wife were wonderful hosts, and made our trip even more amazing. We had such a great time and can not wait to go back again for another "girls weekend" or with our family and friends. We will be recommending Captain Alberto to everyone we know!

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

      Captain Alberto and Grace are fantastic! It was fascinating to hear about their backgrounds and what lead them to sailing. They were very accommodating, and the boat was exactly as described. It was such a fun day for everyone. We would absolutely book with them again!

    6. SF
      Sarah
      38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

      Had a wonderful time with Alberto and Grace. They were kind, friendly, and extremely knowledgeable. My husband and brother in law loved learning some sailing basics. Grace also brought a variety of life jackets for our 2.5 year old daughter. All in all an incredible, relaxing, trip and we look forward to returning in the future!

    GetMyBoat has 136 listings for boating experiences in Chesapeake Bay with 1,237 reviews.

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