Incredible sailboat rentals in Chesapeake Bay, United States.
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Rent or charter a sailboat for a memorable experience in Chesapeake Bay.
Are you ready for a fun adventure out on the open water onboard a sailboat in Chesapeake Bay? Rent or charter a sailboat with or without a captain and experience the joy of exploring the water by wind power. From hourly, half-day, full-day or multi-day sailing excursions, you are sure to create memories that will last a lifetime. Chesapeake Bay is a wonderful sailboat rental destination.
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Search for the perfect experience now and book your dream day out on the water.
GetMyBoat customer reviews for Sailing in Chesapeake Bay.
Capt Alberto and his wife, Grace, were amazing! We were running a bit late waiting on the rest of our guests and they accommodated us time wise by adding time to our excursion at the end. Alberto allowed my boyfriend to sail the whole time and he was thrilled. We will definitely be back!
A great thank you to the captain and his wife! This has been one of the most memorable birthdays for my daughter. Thank you so much for accommodating us at the last minute and for making this occasion that much more special. You both were such a amazing spirits and great company! Our friends and family adore you both. Once again, thank you so so much for making this a memorable time in our lives! We will definitely be back and we will definitely recommend you to our friends and family!
Captain Alberto is a very experienced sailor. Went with friends on a half day and we had a great time. I also learned a lot that I will be able to use when I sail alone with friends. If you are thinking of hiring him for a day, you should.
Mom, Dad, & three GROWN children went out on a wonderful outing with Captain Bill. He was a gracious host & his beautiful sailboat was spectacular! Enjoyed the experience immensely & seriously considering sailing lessons next spring. His boat was not only in immaculate condition but very comfortable for all five adults (plus the amiable captain). We were thrilled to see dolphins and hear about the area's history. We sailed 14.9 memorable miles. I gave a 5 star rating because the ratings don't go to 10. Honestly, how does one rate a great memory that lasts a lifetime? We weren't sure if the weather was going to be a wash out for a few days out, but Captain Bill kept in contact via email with weather updates and was extremely accommodating to what would work best for us. The weather wasn't what one would call picture perfect but I thought it was awesome having so much of the water to ourselves. We only saw one other sailboat. This was an exhilarating experience with a knowledgeable captain and I can't recommend him enough!
I had my four children with me ages 5 to 12 the captain was very kind and understanding to them teaching them new things my son it was comfortable taking the helm and the captain enjoy teaching him the other kids not so much but that was okay however not to be prejudiced because they are my children but they are exceptionally good kids my youngest commented that she was upset she would not be seeing Captain bill the next day and on how much she liked him. we will be back to sail in August we learned about the wind the ocean and how to read it wheeler and practical knowledge and history of the area The boat was beautiful the captain was awesome it was a great day my kids will remember forever I am not one to give A+ review without truly meaning it
Capt. Alberto is an extremely knowledgeable sailor who can make sailing fun for both the experienced and inexperienced sailor. He has a great deal of technical knowledge and can explain it very well. Our sail was delightful even though the weather was not 'ideal'. We're sure others will enjoy their time sailing as we did.