“Twenty years from now you will be more disappointed by the things that you didn't do than by the ones you did do. So throw off the bowlines. Sail away from the safe harbor. Catch the trade winds in your sails. Explore. Dream. Discover.” – Mark Twain

Why would you Travel North to Go South?


We planned our trip down the East Coast of the U.S. with minimal exposure to overnight passages and open water passages. In order to do this, we would transit North up the Delaware Bay/River, West across the C&D Canal (Chesapeake-Delaware Canal) and then South down the Chesapeake Bay.

I admit, the mouth of the Delaware is much larger then I had envisioned. In my mind I was comparing it to Buzzards Bay which is 8 miles wide and 28 miles long, but, the Delaware is more then twice as large at 17 miles wide from the southern most point of New Jersey (Cape May) to Lewes, Delaware and is 52 miles long.

We stopped in Lewes, Delaware in order to tour the Dogfish Head Brewery. I would say this is one of my top three favorite ports I have been to on the East Coast (so far). The historic district and city dock is so quaint with lots of nature trails and cute little restaurants and the people are so incredibly nice. The entrance to this town is a narrow channel and canal with not-so-deep water (about 10 feet at most with many more shallow spots and we like to have at least 6 feet), but it was worth the trip in. Especially when you get to watch dolphins on the way.

Lewes, Delaware:  The lighthouse marking the Harbor of Refuge, the Historical district, and Cheers! at Dogfish Head

Lewes, Delaware

After a couple of days in Lewes, we headed North up the Delaware with neither the current or wind in our favor. Unfortunately, we would have had to wait several more days in Lewes if we wanted more favorable current (I mean, I love Lewes but I really wanted to get moving, it is October, and, as we all know – Winter is Coming). So, we picked out an anchorage that looked to be sheltered from most wind directions. What we did not consider was the amount of crab pots that we would have to maneuver around in order to get to the anchorage we wanted. I cannot begin to adequately describe how many there were – I am just happy that we came in with enough daylight left to see them. For those of you that have not dealt with crab or lobster pots before: the basket that catches these delicious critters sits on the water’s bottom, then there is a long line that is pulled to the top of the water’s surface with a float. If we were to hit one of these, we can potentially wrap the line around the propeller on our boat. Jesse would then have to dive into the water and try to untangle us or cut the line (the water is freezing cold – thus why Jesse would be doing this).

Based on our experience with the Cape Cod Canal (CCC) we planned our transit of the C&D Canal to have the current in our favor. A go-slow boat, like our Smitty, will always try to transit the canal with the current because the current can be quite strong . To go against the current would be a very slow, long day since we normally only average 5-6 knots (about 5.8 – 6.8 mph). Often when we transit the Cape Cod Canal we can almost double our hull speed (so move about 9 knots) when traveling with the current…the C&D Canal – not so much. Unfortunately, we never really experienced the “turbo boost” from the current that we were expecting. The other difference with the C&D compared to CCC is the width and commercial traffic. The C&D is maybe about 1/2 has wide of the CCC – which was very interesting when we were passed by “Terminator” – one of the largest ships that I had ever seen (not it’s real name – this is what Jesse and I were referring to it as we were hoping it would not make the turn into the canal behind, but then it did – yikes! – we really did not have fun dealing with sharing the canal when it passed us). Once we were through the canal, we were back on track heading south.

Delaware Bay/River, C&D Canal, Bohemia River

DE MD VA-002

Next stop – Annapolis! We had planned the timing of our departure and the first month of our trip around arriving in Annapolis between October 8 – 12 in order to go to the Annapolis Boat Show. We arrived in Annapolis on…ready…wait for it…drum roll… October 13 – one day late of the boat show..wah-wah. 😦 ’Tis the sailors life. Waiting out the potential arrival of Hurricane Joaquin and for seas to calm off the coast of New Jersey, cost us too much time and we missed the boat show. However, Annapolis itself is a really cool destination. We anchored in Weems Creek and were once again in good company with Ron and Jackie on s/v Hullabaloo (blog: Skelton Crew) and Chris and Jim on s/v Radio Wave (blog: Mangoes, Marley, and Mermaids). We then made new friends: Vicky and Ed on s/v Elara (blog: Catch the Horizon), and Lauren and Brian on s/v Nightingale Tune (blog: Sea Biscuit). While here, we toured the Naval Academy, historic downtown Annapolis and had some beverages with a fellow Bostonian also making the journey south (also in a 2001 Catalina 310) at the infamous Davis Pub.

Annapolis:  Weems Creek, Ego Alley, US Naval Academy Sailing Team, Military Blimp, Chesapeake Bay Bridge

Annapolis: Weems Creek, Ego Alley, US Naval Academy Sailing Team, Military Blimp

Annapolis:  United States Naval Academy

DE MD VA-004

Continuing on South down the Chesapeake Bay, we headed to Saint Michaels. The Chesapeake is an amazing body of water – it’s so large that at times I felt like we were in the middle of the ocean. There are so many large rivers and and creeks and harbors on the Chesapeake that you could spend a lifetime here and never see them all. Just about every house that we saw had a boat and a fixed dock (the tidal range here is only about 2 feet). Also, everyone has a boat lift that holds their boat out of the water, at the dock, when not in use – even for sail boats! Unfortunately, this means that most of the waterfront is private with little or no dinghy access to get to shore – which proved challenging when looking for a good spot where we could bring Summer to shore. Sailing the Chesapeake was challenging as well, the Marine Weather indicated a “small craft adversary” every day – I am still not sure why because the waves and the winds were never as forecast.  Due to these challenges, we were pretty disappointed with the Chesapeake area.

Saint Michael is a cute little town. We checked out the local craft brewery (this is really starting to become a theme) and Blue Heron Coffee – a really good, inexpensive coffee shop. We toured the Maritime Museum that was complete with a lighthouse that has log books dating back to the 1800’s. We also went to Foxy’s – anyone that has been to the British Virgin Islands is most likely familiar with the famous Foxy’s there.

Saint Michael, Maryland:  Foxy’s, Maritime Museum, Historic Downtown, San Domingo Creek, Eastern Shore Brewery


Our final stop in Maryland: Solomon Islands. Friends advised us that this was one of their favorite stops; I was really looking forward to staying here a few days. Unfortunately, it did not live up to my expectations. We stayed at a marina here (super cheap at $1/foot and had a complimentary loaner car) – but that’s all that was around – marinas. There were not any nice parks or anchorages and there really wasn’t much around at all. We borrowed the marina’s Mercedes to check out the town and get provisions – this thing was the biggest piece of crap – I had to drive because the seats no longer could be repositioned and I could fit more easily then Jesse – but the car looked good from the outside – and hey – it was free. While here, both Smitty and Summer got long overdue baths.

At this point it was starting to get pretty cold and I was more then ready to be in warmer weather – so we have decide to really kick it in gear and get south. We had actually bought a heater while in Annapolis that we were now using;  it was so cold that I even wore my ski gear on one of our sails. We flew through Virginia with a stop over in Deltaville. It was fun to again catch up with the Annapolis-Weems Creek crews and I got my first grounding under my belt – yup – that happened while I was at the helm – but Jesse still has more then me. 😉

New boating friends that we have met along our journey (and stalked on FB and their blogs). ;)

New boating friends that we have met along our journey (and stalked on FB and their blogs). 😉

Our last stop before we officially start the InterCoastal Waterway (ICW) and head into the Dismal Swamp was Portsmouth, VA. We had dinner at a great little German Restaurant, Bier Garden. Jesse’s Umi would have put the stamp of approval on this place – very tasty. As for our dock – I do not understand why the south insists on fixed docks…when I got up in the morning to take Summer for a jog, the dock was almost a foot under water! So, back into the boat I went to put on rain boots and then had to figure out how to get on and off the boat with Summer (since there was a large gap between the boat and fixed piles and dock…needless to say, it was projecty and I do not care for projecty, especially in the morning pre-coffee. Oh well, this was just yet another random learning experience as we continue on our adventure. 🙂

DE MD VA-005


3 thoughts on “Why would you Travel North to Go South?

  1. The difference between an ordeal and an adventure is attitude. The admiral always reminds me of this.

  2. Hi Jesse and Stacey,
    We are enjoying reading of your adventures. Glad you’re getting into the warmer waters. We’re planning a whaler ride up the North River and that will probably end our boating for this year. The weather had been fabulous here and the colors beautiful.

    • That sounds fun! We are making our way further down the ICW. Today we are heading from Oriental, NC to Beaufort, NC. The days are getting shorter but at least they are also getting warmer – I am pretty excited to be wearing shorts in November! 🙂

Leave a Reply

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out / Change )

Twitter picture

You are commenting using your Twitter account. Log Out / Change )

Facebook photo

You are commenting using your Facebook account. Log Out / Change )

Google+ photo

You are commenting using your Google+ account. Log Out / Change )

Connecting to %s