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    Browse Chesapeake Bay Boat Rentals.

    Average of 1,423 reviews in this area.
    1 - 18 of 176 listings
    53' Luxury Yacht for Charter in Washington, District of Columbia
    hour$475
    Super Owner12 guests

    53' Luxury Yacht for Charter in Washington, District of Columbia

    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 29ft Crownline Bowrider In Wildwood, NJ / Cape May, NJ
    hour$250
    Super Owner8 guests

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

    💎🛥1️⃣of a Kind Luxury Cruisers Sports Yacht‼️🍹☀️
    hour$500
    Super Owner6 guests

    💎🛥1️⃣of a Kind Luxury Cruisers Sports Yacht‼️🍹☀️

    Yacht $275/hour - 9 people
    hour$275
    Super Owner9 guests

    Yacht $275/hour - 9 people

    SeaRay $250/hr - 9 people + Water Activities
    hour$250
    Super Owner9 guests

    SeaRay $250/hr - 9 people + Water Activities

    $400hr Weekdays / $450hr Weekends Private Luxury Yachting
    hour$400
    Super Owner12 guests

    $400hr Weekdays / $450hr Weekends Private Luxury Yachting

    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!

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

    "3 BuOYS" Regal 38 SAV

    "Allon-Z" Jeanneau MC11
    hour$398
    Super Owner8 guests

    "Allon-Z" Jeanneau MC11

    "Arabella" Meridian 341
    hour$671
    Super Owner6 guests

    "Arabella" Meridian 341

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

    "Stress Free" Four Winns Vista 348

    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. KG
      Kathleen
      38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

      Absolutely wonderful experience!! Captain Alberto and his wife, Grace, are lovely hosts on their sailboat. We were worried about rain and they offered for us to leave the dock early. They were incredibly kind and interesting—we learned a bit about sailing, we even got to drive the boat once we were in open space! We toured Back Creek, downtown past Ego Alley and the Naval Academy then crossed the Chesapeake. The boat itself is large and beautiful. We enjoyed the seating area in the back and also sat on the bow and enjoyed the view. Highly recommend a trip with Captain Alberto and Grace if you’re looking for a fun ride around Annapolis!

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

      Alberto and Grace were terrific! we had a great afternoon on the water. sailed across the bay, and also dropped anchor in quiet water for wine and snacks. Alberto will teach you about sailing if you like, and let us try steering the boat. it was a great value. we will book with them again.

    3. MP
      Michelle
      ☀️🛥🔺No Extra Fees🔺$250hr Weekdays / $350hr Weekends Premium Private Yachting🍹🏝

      Shane arrived early and let us know where we could park at and instructions for getting down there in enough time. The trip was nothing short of amazing, the music, the vibe, the conversation, and the photos he took of us were icing on the cake. Highly recommend, worth the trip, bring your friends, tell everyone and book immediately.

    4. AD
      Ananda
      BEST DAY EVER! CLEAN BOAT! VERY EXPERIENCED CAPTAIN! $325/hr WEEKENDS $275 WEEKDAYS

      I can’t say enough about the great evening my friends and I had on this boat. John is a great captain, very laid back and really came through for me with clutch response and communication, when another booking cancelled on me last minute. Next time I will just book with John from the beginning! The boat was beautiful and my friend enjoyed her birthday surprise. Book him with confidence!

    5. AM
      Angela
      ☀️🛥🔺No Extra Fees🔺$250hr Weekdays / $350hr Weekends Premium Private Yachting🍹🏝

      Last night, my friends and I celebrated my fiancé’s birthday with a late night boat ride. It was one of the best experiences we’ve ever had! I’ve never rented a yacht before so I was a bit nervous. I knew I made the right decision before we even got on the boat. Captain Shane’s professionalism and communication were A1! He was very responsive to all inquiries and kept in touch with me throughout the days leading up to our charter. We arrived at the dock a few minutes early as Captain Shane was pulling in. The boat was beautiful! It was very clean and looked exactly as pictured on the booking site. We sailed the Anacostia river for 2 hours. The views of the city at night from the water are beautiful! Captain Shane’s personality and DJ skills just enhanced our experience. I definitely plan to use S&S Charters again and HIGHLY recommend them to anyone looking for yacht rentals in DC.

    6. ES
      Emily
      38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

      10/10 recommend! Alberto was an amazing guide for our sail. The boat was in great condition and he was very conscientious in planning a route and tour throughout Severn River and Buck Creek. We had a fantastic time and great conversation!

    GetMyBoat has 176 listings for boating experiences in Chesapeake Bay with 1,423 reviews.

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