Bob's Page


Bob’s Observations

My observations fall into 2 categories: The Experience and the Boat

The Experience – So far this has been an amazing journey – but very different from what I anticipated:

  1. SAILING - Despite hearing from others who have undertaken similar journeys, I am surprised at how little we have been able to sail (sometimes I think we hear what we want to hear). We left Cleveland on July 23rd and traveled to Buffalo, down the Erie Canal, down the Hudson River, up the East River to Long Island Sound (and back to NY Harbor), down the Jersey Coast, up the Delaware Bay, through the C&D Canal and 1/3 of the way down the Chesapeake (to Annapolis). In the approximately 1,150 nautical miles we have covered, we have sailed approximately 80 miles, motor-sailed approximately 200 miles and motored approximately 870 miles. Hopefully this ratio will change when we (hopefully) shift from “we have to cover ground to get South before winter comes” to “we have arrived in our desired cruising area and can decide on any given day/week if we want to move or sit tight. Stay tuned

  2. REPAIRS - Our friend Ken undertook a similar trip around 12 years ago. His blog was filled with detailed entries on the things that broke on the boat, how they fixed them and the wonderful food they ate in the locations they visited. His daughter fondly named the blog “We Broke The Boat – We Fixed The Boat – We Ate”. I laughed at the time – but again had no idea how much wear and tear the boat experiences when living aboard/traveling long distances. I worked really hard over the past winter to get the boat in as good condition as possible for a 26 year old boat. I’m surprised at the number of items we have already had to repair – and the amount of time spent doing those repairs. If you plan to undertake a journey of this type you need to be handy, know the inner workings of your boat systems and have a significant “repairs” line-item in your cruising budget.

  3. ANTICIPATED RELAXATION – I’m still waiting. I had a fantasy before setting out that I would have time to read, write (I’m supposed to be doing an article for Good Old Boat on our refit), and practicing my rope work. So far, all I have been reading is manuals on the new equipment we installed over the winter, doing repairs and finishing up items from the work list that I didn’t get to over the winter (annual varnishing of deck trim, making racks to store our shoes, installing a shore power outlet in the vee berth…). The other big time user is learning and navigation. While we have had a couple of extended stays (Baltimore for a week, Cape May for a week – sitting out Maria, and Annapolis – for boat show and 14 days of repairs, we have essentially been on the move every day or every other day for 3 months. Because we are traveling in new waters every day, a lot of time goes into route planning and studying the weather. This is further complicated by the learning curve. The 3 big learning items are tides, currents and salt water. Tides and currents speak for themselves. The salt water seems to want to attack every metal part on the boat, dinghy and engines. Much preventive action is required in this battle. Challenges aside – on balance this has been an amazing trip to date – and memories of the history, cute towns, big cities, sunsets and peaceful anchorages we have encountered will be with us for the rest of our lives.

  4. THE EMOTIONAL SIDE – So far the emotional response to the trip has been highly varied – as follows:

  • Being with Sheila day in and day out has been wonderful - harkens back to our days on Har Odem in the Golan in 1980

  • The joy of catching the first glimpse of Lady Liberty as we came down the Hudson River

  • The exhilaration of seeing the knot meter register 11 knots while careening down the East River at Hell Gate with a 5 knot following current

  • The despair and self-castigation after hitting a rock coming out of Mamaroneck Harbor on a falling tide (lessons – study the tides before throwing off the dock lines, stay in marked channel and go in reverse of you drift out of it – NO U-turns).

  • Frustration at catching a crab trap line on our prop and shaft coming out of a marked channel behind Hart-Miller Island. Stalled the engine and did some transmission damage – already repaired as I write.

  • Beautiful anchorage after beautiful anchorage – such serenity!!!






Well, we’re finally throwing off the dock lines and heading out on our sailing adventure. This trip has been a dream of mine for over 30 years, and in planning for the past 20 years. This past January, I retired from a 42 year career in non-profit management. Since that time, I have been devoting all available hours to refitting and upgrading Her Diamond, our Freedom 38 sailboat – more about the boat on her page.


I’ve always been drawn to the water as a swimmer, water safety instructor, canoe tripper and ultimately a sailor. My sailing life began in 8th grade, when I was invited out for a day of sailing on a friend’s father’s Dragon sailboat. She was a beauty – lapstreak construction and brightly varnished. Back in the day, many of us groomed our hair with a bit of (alcohol based) “greasy kids stuff”. There I was, standing at the bridge deck, taking in the scenery and the fresh breeze, when a wave washed over the bow and hit me squarely in the face. The greasy kid’s stuff ran down into my eyes – stinging sharply. It was at that moment that I had to make a choice – sailing or my 1950’s hair style. I decided to forgo the greasy kid’s stuff and here we are 54 years later embarking on our retirement journey.

Along the way we have owned, chartered and sailed boats from 11’ to 43’, taken numerous sailing summer vacations and sailed in conditions from dead calm to hurricane strength squalls. Our early summer trips with our girls included diapers, bottles and infant formula – yes, they started sailing at 4 months of age – no greasy kid’s stuff. Anticipating the trip and considering the possibility that we might want to do some chartering or boat deliveries in the future, I earned my 50 ton Coast Guard Master’s (captain’s) License.

One final note on my many blessings. I’ve spent 33 years at marinas and yacht clubs and have had a chance to observe numerous men sailing or working on their boats by themselves or with a few buddies. Only a small number appeared to be sharing their boating lives with a spouse or children. In addition to my Sheila (the Admiral) being the love of my life and an amazing human being, she grew up sailing with her family and shares my passion for the water. How lucky can a guy get!

Sheila and Bob at Kettle Creek Marina at Port Stanley, Canada 2016.