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Book In Advance
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US$ 40.00*
and up
History of Chesapeake Bay Sailing Tour
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US$ 50.00*
and up
Wine and Cheese Sail in Chesapeake Bay
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US$ 375.00*
and up
2 Hour Chesapeake Private Boat Cruise
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  • Excellent60%
  • Very good35%
  • Average0%
  • Poor0%
  • Terrible5%
25 Feb 2016
“The bay spans a distance and a rating...from scary as heck to bilssfull”
31 Aug 2015
“Chesapeake Yacht Charters-Captain Bob Bell”
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Reviews (17)
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1 - 10 of 17 reviews

Reviewed 26 February 2016

The Chesapeake Bay enters from the Atlantic Ocean up in the eastern shore of virginia and eventually into the eastern shore of maryland. Many miles,many attractions. It ends near the End of the Susquehanna River up in northern Maryland at a charming little village called...More

3  Thank ocshaffer
Reviewed 31 August 2015

For our 40th anniversary we rented a beautiful 40 foot sailboat for a day out on the bay from Chesapeake Yacht Charters (www.chesapeake-charters.com ) Captain Bob Bell was very friendly and knowledgeable as he guided us through the bay. He even gave good advice to...More

1  Thank Mary R
Reviewed 26 April 2015

I use to take many trips to Rock Hall and I recommend that you take a trip here as well. The marinas are so fun to walk around and see, and the beautiful scenery and shops and the food is superb, obvilously especially the seafood....More

3  Thank antoinettel434
Reviewed 20 April 2015

A favorite destination for boaters from the nearby rivers and the Chesapeake Bay, Chesapeake City is a place worth visiting. With five bed and breakfasts, fine restaurants and shops the entire City can be walked in under an hour. Download the Walking Tour Map from...More

5  Thank JeremyPF
Reviewed 15 October 2014

Trolling for striped bass. I've catch several, only three the permitted size. Good boat, good people, nice trip, not enough emotion (because of the size of the fish)

1  Thank MarioIsra
Reviewed 7 September 2014

The bridges do drive are amazing. We drove from Norfolk back to MD over the bay and it was just stunning especially early in the morning when the sun is riding and the sky seems to be one with the sea, have to go back....More

3  Thank Jesjoe13
Reviewed 5 August 2014

We took this ride on a sailboat from Annapolis in Maryland and sailed into the sea for two hrs.The weather was extremely good and the thirty odd persons on board were entertained to some good commentary and beverages and chips.The Annapolis area is beautiful with...More

2  Thank 1948ashok
Reviewed 30 June 2014

Found a guy down here who has an air boat and does trips around the bay,he is a local and know his way very well.we were very impressed with his knowledge of area.and enjoyed the trip.

Reviewed 2 August 2013

This was our first time in this area. We absolutely loved it. Quaint and romantic,full of history and charm.We stayed on the North Shore. The homes were so well kept,and the coastal sections were very clean and appealing.There was a beach area available for swimming...More

10  Thank Revele
Reviewed 25 July 2013

On a lovely evening when we had just planned to look at shells and wander, we all waded out and had a great time. Lovely sand feels great on the feet. Not very salty here with the confluence of the Susquehena River and the ocean,...More

1  Thank eliana23
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