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Chesapeake Beach Tours
Chesapeake Bay Private Cruise
5
LIKELY TO SELL OUT*

Chesapeake Bay Private Cruise

By Chesapeake Windsail Cruises Corporation
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Lowest price guaranteeReserve now & pay laterFree cancellation

Ages 0-120
Duration: 2h 30m
Start time: Check availability
Mobile ticket
Live guide: English
More


  • water and snacks
  • USCG Captain and a First Mate
What's not included
  • Food


Start:
  • 4160 Mears Ave, Chesapeake Beach, MD 20732, USA
    Rod N Reel Resort 4160 Mears Avenue, Dock X, slip 15
End:This activity ends back at the meeting point.

    • Not wheelchair accessible
    • Infants must sit on laps
    If you have questions about accessibility, we’d be happy to help. Just call the number below and reference the product code: 107044P3

    • Confirmation will be received at time of booking
    • Not recommended for travellers with back problems
    • Not recommended for pregnant travellers
    • No heart problems or other serious medical conditions
    • Travellers should have a moderate physical fitness level
    • Life jackets are available
    • No Smoking
    • This experience requires good weather. If it’s cancelled due to poor weather, you’ll be offered a different date or a full refund
    • This is a private tour/activity. Only your group will participate

    • For a full refund, cancel at least 24 hours in advance of the start date of the experience.

    If you have questions about this tour or need help making your booking, we’d be happy to help. Just call the number below and reference the product code: 107044P3

    From
    £543.09
    per group (up to 6)
    Select date and travellers
    Revenue impacts the experiences featured on this page, learn more.

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    About the operator
    Don’t take it from us – here’s what people have to say about this operator:
    • Chesapeake Windsail Cruises Corporation
      65
      United States
      Joined in April 2019
    • 428adelynf
      0 contributions
      1.0 of 5 bubbles
      Poor communication & disappointing experience
      Our trip was canceled twenty minutes before we were supposed to set sail, even after we had already received confirmation earlier that day that everything looked good. We booked far in advance and arranged our day around it, and we drove a long distance to get there. This was a frustrating and disappointing experience and I wish that there had been better communication.
      Written 9 September 2024
    • catheriner730
      0 contributions
      4.0 of 5 bubbles
      Hot day but relaxing on the water
      The trip was relaxing. Unfortunately the weather was a little uncomfortable, obviously something that can't be controlled.
      Written 30 August 2024
    • T3604XKchelseag
      0 contributions
      5.0 of 5 bubbles
      love it
      I had a lot of fun. It was rainy and windy on my tour, but it was still a lot of fun. This was my first time on a sail boat and the skipper and first mate were awesome.
      Written 18 August 2024
    • Jpell64
      0 contributions
      5.0 of 5 bubbles
      Relaxing trip with great guides
      Kevin and Lloyd were great tour guides. Fun stories, lively conversation. The bay was calm, it was sunny. We had a great time.
      Written 12 August 2024
    • ingridt938
      0 contributions
      5.0 of 5 bubbles
      A Beautiful Day Sailing the Chesapeake on the Eternal Hope
      We went out to celebrate a birthday. What a beautiful experience. The forecast called for rain, but it was nice and sunny the entire time! The sailing was smooth, the boat is beautiful, the captain and crew were kind, funny, and so knowledgeable. We look forward to doing this again soon.
      Written 16 July 2024
    • Explore05028253564
      0 contributions
      5.0 of 5 bubbles
      Fantastic experience on our first sailboat cruise!
      Our experience was so amazing and relaxing. Floyd and Nate were an absolute pleasure to talk to and interact with. If we ever vacation in North Beach again, we will book another one of these cruises.
      Written 9 July 2024
    • Lightning362
      0 contributions
      5.0 of 5 bubbles
      Awesome Experience!
      We had a great time sailing with Chesapeake Windsail. The crew was personable, considerate and friendly. First mate worked his butt off and he and the captain went out of their way to make it a pleasant experience for all of us. They were both very knowledgeable and pleasant and regaled us with tales from their experiences. We truly enjoyed our trip and would highly recommend this trip to anyone.
      Written 4 July 2024
    • 621neldac
      0 contributions
      5.0 of 5 bubbles
      A BEAUTIFUL DAY ON THE BAY
      We thoroughly enjoyed our Windsail Cruise. LLoyd and Nate are personable, knowledgeable, and good conversationalists. We sailed at noon; the weather was beautiful. Because there wasn't much wind, we didn't have the experience of racing through the water. Instead we had a relaxing sail and would definitely do it again.
      Written 21 June 2024
    • Passport29490144564
      0 contributions
      5.0 of 5 bubbles
      Friday Afternoon Sail
      The crew was amazing and Scott shared a lot of the local history. Watching the team manage the sails and sharing their sailing experiences was very special. My Mom is 83 and she really enjoyed this cruise.
      Written 19 June 2024
    • karendC3318EE
      0 contributions
      5.0 of 5 bubbles
      A lovely stroll along the Chesapeake Bay
      Jana led a wonderful and scenic tour along the long elevated boardwalk. The water views were stunning that led to the beach and cliffs. She provided an interesting facts and historical narrative.
      Written 27 May 2024
    • B2160KTscottb
      0 contributions
      5.0 of 5 bubbles
      Enjoyable
      Beautiful views. Great history provided by the guide. Spent time exploring North Beach and surrounding area based upon our guide's recommendation.
      Written 29 October 2023
    • Fearless68483471767
      0 contributions
      5.0 of 5 bubbles
      Morieda
      The view was amazing. Breath taking. I recommend anyone to go there. Its nice going as a couple. You can see all the beautiful things together
      Written 26 October 2023
    • Explorer35629460954
      0 contributions
      5.0 of 5 bubbles
      Great sail!
      Great crew - nice boat! Beautiful area of Maryland and famous restaurant for over 50 years. New facilities Being built.
      Written 5 October 2023
    • 11suzieh
      0 contributions
      5.0 of 5 bubbles
      Great excursion!
      The captain and first mate were so nice and shared some great stories. They made sure to keep checking on my seasick son and went out of their way to help make him as comfortable as possible. We enjoyed the beautiful breeze and would recommend it!
      Written 27 August 2023
    • ima2thbrushr
      0 contributions
      5.0 of 5 bubbles
      Chesapeake Beach Walk
      Very nice walk with great information about the area. Jana was knowledgeable and was very familiar with the walk. Nice day.
      Written 13 August 2023
    See all 65 reviews
    These reviews are the subjective opinions of Tripadvisor members and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

    Most Recent: Reviews ordered by most recent publish date in descending order.

    Detailed Reviews: Reviews ordered by recency and descriptiveness of user-identified themes such as waiting time, length of visit, general tips, and location information.

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    5.0
    5.0 of 5 bubbles3 reviews
    Excellent
    3
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    0
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    0
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    0

    Janna T
    1 contribution
    5.0 of 5 bubbles
    Oct 2023 • Family
    An absolutely amazing experience. The first mate and captain were friendly and incredibly knowledgeable. They answered all our questions and told so many fascinating stories. Highly recommend to everyone wanting to spend a couple of hours out on the water.
    Written 5 October 2023
    This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

    Anastasia D
    Bethesda, MD2 contributions
    5.0 of 5 bubbles
    Aug 2022 • Family
    Fantastic afternoon sailing cruise from CB, beautiful vessel, skilled and wonderful captain and first mate. Great getting to know them and the area, we recently moved into nearby neighborhood and had endless questions - they were exceptionally generous with their knowledge! Looking forward to future charters!
    Written 14 August 2022
    This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
    Thanks 611ana for your review. We are happy to hear that you enjoyed your cruise with us. We look forward to having your back with us. Thanks for your business and thank you for booking your private cruise with us!
    Written 17 August 2022
    This response is the subjective opinion of the management representative and not of Tripadvisor LLC.

    Diane H
    1 contribution
    5.0 of 5 bubbles
    Sept 2020 • Couples
    Captain Ken and First Mate Nate were fantastic! Wonderful relaxing sail with loads of good information shared.
    Written 7 September 2020
    This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
    Ms. DianeH, Thank you for your review and compliment. We enjoyed having your aboard and enjoyed your conversation. I hope you had a pleasant trip back to Pittsburg and we look forward to seeing you again next year. Once again, thank you for your review and your business.
    Written 8 September 2020
    This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
    *Likely to sell out: Based on Viator’s booking data and information from the provider from the past 30 days, it seems likely this experience will sell out through Viator, a Tripadvisor company.

    Chesapeake Bay Private Cruise provided by Chesapeake Windsail Cruises Corporation

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