Destinations on the Chesapeake
The Chesapeake Bay is the largest estuary in the United States and offers an enormous and varied cruising ground for sailors and power boaters alike. The Chesapeake Boating Club is located where the Severn river meets the Bay and is ideally situated for conveniently sailing or motoring to all the best the Chesapake has to offer.
We've put together details on some of the most popular Chesapeake destinations to help make your adventure even more enjoyable. In the pages linked below we've included mileage, trip times, local amenities, and more. Pick the destination that interests you most and plan your next adventure with the Chesapeake Boating Club at J/Port.
With over 2,500 square miles of water to explore, there's always somewhere to go, an event to attend, and something to see here on the Chesapeake. So whether you cruise to one of the highlighted destinations below or create your own cruise, it's time to stop dreaming and get out on the water with the Chesapeake Boating Club.
Be sure to check out the latest destinations guide from Chesapeake Bay Magazine...
Club Member Testimonials
"I day-sail (and single hand) quite a bit. My wife comes with me on two longer trips (spring and fall) when we take a J32 for the week end. There is plenty of opportunity for overnight outings, especially during the week." Hey Paul! As so often happens after a great J/80 sail, I feel a swell of gratitude to you and the entire J/Port group for making it possible. The enthusiasm and integrity of everyone is a pleasure to be a part of... "How can you beat it --- more sailing, more places and fewer hassles and we haven't even talked about the racing program." "... Ellen is by nature very cautious. Your concern over safety and the condition of the boat contributed to her enjoyment of the day. As I have mentioned, I think the sailing club is the greatest thing since sliced bread. A J/80 Fan!" "During the April-November season I try to get out once or twice a week for a day sail. Winter is a little tougher but there are nice days and the J80s and J105s are ready all year around." The H20 is a blast. Thank you for bringing it on and making the introduction simple and fun. It keeps things interesting! Proof is in the pudding. She sailed us out of the creek and didn' t let go of the tiller til we got back into the creek about 1hour 20 minutes later. Bravo! "This will be my third year with J/Port. Originally, I had planned to sail with you for a year and then look into getting my own boat. Now that I've experience all that you have to offer I am more than content to continue my membership. It's better than owning a boat. " "At the end of the day, I can hop off and not worry about dealing with the Marina or maintenance. Better yet because I have a selection of boats I can choose a specific boat for the type of sailing I want to do. The J105s with their speed can not be beat for day sailing on the bay. Eileen and I have enjoyed the J32s when we've wanted to spend a few nights on the boat and do a little cruising. " "Given the amount of use they get, the JPort boats are in amazing shape. If you owned your own boat and maintained it yourself, I'll bet it would't be in as good condition as the JPort fleet. Full time professional staff are going over the boats every day to make sure that when you get there all the stuff works like it should." "In the last two years, I've sailed more than 40 days and only used about a quarter of my reserve days. With that experience, we plan to bareboat in the British Virgin Islands [ BVI ] in late fall. The classes we took with the sailing school have helped to make our trips out on the bay more enjoyable and allowed us to plan on more adventures. I think if you total the cost of the BVI trip and J/Port it would still be less than if I owned my own boat. " "...one thing you didn't ask about is the club's members. They are the really unique resource and one of the things that make the club so special. If you need a sailing partner to show you the ropes or just to keep you company while you are sailing someone will be there...." I joined the Jport Sailing Club last year because I wanted to have access to sailing on weekends. The boats were great and so were the people, and soon I found myself crewing in races and commuting to Annapolis from my home in Arlington every chance I could. Paul and Nan, Lynn and I did our summer cruise last week and I wanted to let you know what a great time we had. The J/32 was in perfect shape, every component worked exactly like it should and we had no problems or drama whatsoever. "Not having to maintain, haul out in the winter, worry about storms, etc cetera, more than makes up for [not owning]. It's a no-brainer!" Thanks for your help in planning my trip. Having someone who has actually sailed there and knows the best places to go is a real help. I don't normally write thank you letters because good service should be expected but my experience with Chesapeake Boating Club has been so far above what I expected that I wanted to let you know how much I appreciated it. "For literally the same price as a yearly slip fee in Annapolis, I not only get to sail out of a prime location in Annapolis, but I don't have to purchase a boat! It's like renting a slip and getting the boat for free!" "Had to pack a few personal things, get some ice, buy a few groceries and take off on a 3 day adventure less than an hour after stepping foot aboard. That's what a sailing time share is all about: for busy folks who don't have the time to own their own boat but love to sail a good boat." This is sailing heaven if you like your boats, fast, fun, easily accessible and you simply want to just go sailing with the minimum of fuss. I mean literally pack the Jeep with a picnic, your family/friends, collect some ice and be skimming across the Bay in no time. Our usual time from leaving the house in Arlington Va to puttering out of the slip is right on one hour. Your infinite willingness to find ways to make the club so much more than an offer of inexpensive sailing is deeply appreciated. Thank you, thank you, thank you. "...the real hidden equation here is in the time factor. Time becomes an even rarer commodity than anything else within our busy lives. With this concept you are going to maximize your hours spent under canvass surrounded by your family and friends with a whole team behind you to worry about the watering and feeding." "You won't find a more economical, less stressed and more convenient way to go sailing. The club takes care of everything. All you do is make a reservation, show up and go sailing. There are no hassles or hidden costs."