Sailing on the Chesapeake

For our fifth anniversary, my big surprise for Dave was a private sunset sail on the Chesapeake Bay. He has recently become really interested in sailing (must be all the time on his hands since finishing the BAR!) and I thought a chance to get out on a real sailboat would be both romantic and help him decide if this would be a hobby he’d like to pursue. 
I googled and searched and talked to friends and didn’t seem to have any luck finding a private charter that fit into my price range. Finally, a call to the Belle Haven Marina got me a couple websites, and one of them ended up leading me to Captain Bill and Dream Catcher.
The arrangements were simple, the captain was easy to communicate with, and when I told him Dave was considering learning to sail, he said he’d be happy to let us help out with the operation of the boat during our cruise! 

I kept the sailing adventure a secret until the night before, when I invited Dave to join me. We left the boys with our dear neighbors, packed up a simple, delicious picnic for the boat, and headed to Holiday Hill Marina.
I was so excited to see Bill standing up on the bow of a huge, beautiful boat in a Hawaiian shirt, Bermudas and Sperry Topsiders. He looked the part! We climbed on board, got a safety run-down (there are about 20 fire extinguishers on that thing!) and then set sail. 
The first half-hour we were “on motor” and Dave had the ship’s wheel to navigate the little inlet that would lead us out to the Bay. The scenery was breathtaking, and I tried to figure out where exactly we were on the map, but enjoyed looking at the boats, and boat houses more. 
Once past into the main channel, Bill gave us the okay to hoist the sails!! It was fantastic! Dave pulled and pulled as the giant white sheet zipped up the mast over fifty feet! The jib (front sail) unwound by pulley, and then we learned to “trim” them both just right to maximize the wind power. Then the motor went to idle, and we were sailing!
Luckily, there was a little bit of wind, and we were able to cruise along quite nicely (slowly, but nicely!) Both Dave and I switched off steering, and we had to keep an eye on those sails to make sure they were nice and full. 
The cruise became quite peaceful, and we simply soaked up the autumn air, the setting sun, and the energy of being out on the water. I had some time to enjoy the fun details of the boat. Like this old compass, rarely referred to with all of the GPS technology, but a cool reminder of the good old (pirate, arr!) days.
Here’s Captain Bill, making sure we kept the sails trimmed nicely, and were headed the right direction:) He did a fantastic job explaining everything as we did it, and teaching some of the theory behind the actions as well. It was like a mini lesson and cruise in one.
I might be developing a thing for rope. Which will work out perfectly if Dave maintains his thing for sailing, because there are ropes all over the place on a sailboat!
How cool is this little safety ring? I think Dream Catcher is a great sailboat name. I wonder what we would name a boat, if we ever have one?
Of course, we let Bill take the wheel for a little while, so we could sit together on the bow and enjoy the wind through our hair. Sailing was a fun, new experience for both of us (though I grew up sailing on a catamaran, this was quite different!)
And then the sun began to set. There might not be anything quite as beautiful as watching the sun go down over the water, from the water.
We took back the wheel, and Dave steered us into the setting sun, back toward the marina. He was pretty happy with the experience, and as we cruised towards the dock, we got all sorts of advice about what to look for in a sailboat. Turns out a Catalina 27′ would be perfect for our little family…someday!
The dropping of the mainsail was almost as cool as it’s hoisting! It fell quickly and we bustled to get it strapped into place.
Peach-colored light from the setting sun created a warm feeling, even though it was getting pretty brisk out. I think October is a perfect time to sail.
And as it was ending, I was simply happy. We had enjoyed every moment of our time, and are excited for what future sailing experiences we may have in store.
I steered the boat until we were a couple hundred yards from the dock, when Captain Bill took over to guide us expertly in between the pilings. We said “Thank you” and “See you again, soon!” and then spent the drive home talking about all of the fun we will have on the water next summer, with the boys.
Celebrating our past five years with a new experience left us thinking excitedly about the future. And it will be great! 


  1. Aline Kaehler
    Posted October 20, 2011 at 7:21 pm | Permalink

    that´s so cool! it sounds like fun and you guys sound like an amazing family 🙂 It was great to put pictures to book because one of my favorite novels happens in Chesapeake Bay. 🙂

  2. Melissa
    Posted October 27, 2011 at 11:53 am | Permalink

    so glad you found a sailing adventure! looks like a great time. brought back fun memories of sailing..

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  • By Tie The Knot - The Dating Divas on October 20, 2014 at 1:40 pm

    […] Tuesday though Saturday (five years, five days) and finished the week of celebration with a sunset sailboat charter on the Chesapeake Bay (though you could also go fishing, rock climbing, or to a nice dinner and […]

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