So, Do You Want to Buy a Boat?

That was the question I posed to my wife after a long discussion about our long and short-term goals. Living in Washington, DC, so close to the historic Chesapeake Bay (one of the greatest bodies of water for sailing in the world), that was a natural next step. But that seemingly simple question, raised so many more; some far more complex. In general, sailing is more than a sport, it is a way of life. Regardless of whether or not one prefers coastal cruising, racing, on-shore, or off-shore "blue water" sailing, it gets in your blood and commands attention. This demand for attention is magnified, in spades, when one moves from crewing on someone else's boat or renting/chartering to boat ownership. The responsibilities increase by an order of magnitude, and the range of decisions you have to make are amazing. 

This next set of posts will take you through that process, as it unfolded for us. I will cover the initial decision to move forward, and the logic that allowed us to make the decision. I will also cover finding and surveying a boat, decommissioning, commissioning, finding a marina, maiden voyage, boat ownership, hurricane prep, winterizing, and planning for the 2016 sailing season. So, Do You Want to Buy a Boat?

Sailing Knowledge

As our passion for sailing grew, and since buying our own boat still seemed out of the question for the foreseeable future, we continued to arm ourselves with knowledge.  For me, this came in the form of some outstanding sailing podcasts, blogs, YouTube videos/channels and the books.  


One of the first sailing podcasts I listened to, and still one of my favorite is called 59 North Podcast. Hosted by Andy Schell, this podcast is both an interview show (with Andy talking to some of the world's sailing elite), and discussions about Andy and his wife Mia starting their business, and his own sailing background. Andy and Mia are currently sailing Isbjorn (Polar Bear), a classic 1972 S&S Swan 48. I have learned so much about sailing from this podcast, I had to highlight them in this reflection.  Another critical podcast for me has been the Shooting the Breeze Sailing Podcast, hosted by Jeffrey Wettig.  Jeffrey sails a Paceship Yachts PY 26 (which will become a very important part of this fantastic voyage very soon).  While Jeffrey has many fantastic episodes in his sailing podcast, including interviews with Kamau Iandiataiyero, who is building a boat in his Baltimore backyard, the discussion that had the biggest impact on me was the two episode interview with Marcus Asante, Commodore and founder of the Universal Sailing Club (USC).  USC was formed in 2001 "as a way for African Americans to learn and share the sailing arts in an environment conducive to our culture and outlook."  Jeffrey, Marcus, and the USC will all return in important ways as we continue down this Fantastic Voyage.


There are numerous blogs that are helpful for the sailor; new, seasoned, or simply interested. Some of these blogs include:

  • The Boat Galley:
  • Have Wind Will Travel:
  • Distant Shores:

YouTube Channels

Some of the blogs above also have YouTube Channels, but I will highlight some of they channels to which I subscribe below:


Finally, there are a number of books that have been very helpful to me.  I'll list just a few of them here below:

  • This Old Boat
  • The Self Sufficient Sailor
  • The Capable Cruiser
  • Sailing
  • Sailing Fundamentals
  • As Long as Its Fun
  • Cruising the Chesapeake
  • Salt of a Sailor
  • Keys to the Kingdom
  • The Annapolis Book of Seamanship
  • Chapman Piloting & Seamanship
  • Your First Sailboat
  • Sailboat Maintenance
  • Twenty Affordable Sailboats
  • Blue Mind
  • Living Aboard a Boat
  • Sailing - A Metaphor for Life
  • Inspecting the Aging Sailboat
  • Twenty Small Sailboats to Take You Anywhere Sailing Knowledge

First Long Sail

In October 2014, I had a tremendous opportunity, facilitated by my buddy Yaya.  He invited me to serve as crew on a daylong sail on the Bay with Rodney, sailing on a Morgan 36. Rodney is an amazing sailor, who shares a passion for the sea.  After learning to Sail at DC Sail, he worked his way up from sailing his 27' O'Day out of Rock Hall to the 36-foot Morgan out of Baltimore.  What an incredible day.  We left Baltimore harbor very early in the morning, and the crisp, cool air made for a spectacular departure.  I've been to Baltimore many times, and absolutely love the Inner Harbor.  However, I had never experienced it from the water, and sailing out of the harbor and down the Patapsco River, past Fort McHenry, and then past many of the sights I had seen on the television show, The Wire.  We sailed out into Chesapeake Bay, and down to the beautiful Magothy River. This was my first docking, as we found a restaurant for lunch.  It ended up being too crowded to eat there, and there were no empty transient slips.  Afterwards, we headed back to Baltimore on a more relaxed pace, listening to music and arrived at Ft McHenry right as the sun was starting to set behind it.  Seeing downtown Baltimore, and the Inner Harbor bathed in golden sunset light was magical.  Again, if I wasn't hooked on sailing before, there was no question about it afterwards.  I also learned so much from this sail, including some of the challenges of docking against the forces of wind and current, and the logistics of managing a sail with both knowledgable crew and passengers. Thanks again Yaya and Rodney! First Long Sail

The United States Sailboat Show

On 9 October, we made a wonderful discovery that began one of our more important recent traditions, the United States Sailboat Show in Annapolis, Maryland.  There is a smaller show in the spring, the Annapolis Spring Sailboat Show, and while both are great, the fall Sailboat Show (as it is known) is the largest in-water boat show in the United States, and one of the largest in the world. The show also has a wide variety of vendors, selling everything from sails and biminis, to winches and engines, and also aggressively marketing marinas and sailing schools.

The show lasts four days (the VIP day is on Thursday, and while tickets for this first day of the show cost more, the crowds are far less and it is definitely worth the price of admission).  At this show, we started thinking seriously about buying a boat. Thinking; just thinking, because while the Sailboat Show gives attendees a tremendous overview of the wide range of boats available, and the various manufacturers, it is also dissuasive because of the prices.  These boats are the newest boats on the market, and the floating docks for the Sailboat Show are their showroom.  You can climb aboard all the boats, stand at the helm, go down below to the cabin, or relax on deck.  Essentially, you are "kicking the tires" of these new vessels.  The show also gives participants an opportunity to explore the differences between catamarans (and other "multihulls") and monohulls (the more traditional form of sailing vessel, with one hull vs. the two hulls of a catamaran or the three of a trimaran).  While we love the space, and luxurious functionality of multihulls (my son SMC sat on the flybridge of one with his feet up, kicked back against the cushions and exclaimed, "I like this" (he hasn't repeated this sentiment so vociferously since - smile), we are traditionalist.  We love the clean classic lines, stability, and maneuverability of monohulls. 

Unfortunately, the prices of these new boats are overwhelming, especially the multihulls (yes, that is another reason we see ourselves as monohull people - smile).  When people see these prices, it fosters the idea that sailing is super expensive, and only for the wealthy.  Even in the "Brokerage Cove," where the Sailboat Show offers used boats for sail, boats are very expensive.  The boat above, was a beautiful 1980 Sabre 28 MK II.  It was described as "A Gentleman's little Yacht."  This stunning boat really caught our eye, but at $27,000 we knew this would be a long way off for us.

In addition to the show, there are workshops, both free and relatively expensive.  The free seminars are hosted by a variety of groups, including the magazines Spin Sheet, Chesapeake Bay, and Cruising world; along with the Annapolis School of Seamanship.  The paid seminars are part of what is called "Cruisers University" and requires advance registration, and usually sell out.

While at the show, we met a wonderful couple, Tim and Julie, relative newlyweds who were also contemplating the cruising life.  We were all standing at the dinghy dock for "Ego Alley" as the long strip of water at City Dock in Annapolis is known, looking out over huge catamarans and monohull sailboats.  Tim and Julie have become our closest sailing couple, as they invited us to sail on their Seidelman 30, and we have spent wonderful time together off the water as well, golfing and enjoying good food. The United States Sailboat Show

Time to Train - Annapolis Sailing School

After my experience on the Woodwind, I was hooked, and started reading as much as I could get my hands on about sailing. I couldn't think of much else except gaining formal sailing training. I was able book a weekend training course for Noemi and me at the Annapolis Sailing School, in Annapolis, Maryland. The Sailing School, as we refer to her, is one of the oldest schools for teaching sailing to the public in the world and offers a wide variety of courses at beginning, intermediate and advanced skill levels. We took their Basic Keelboat course on one weekend, which included four sessions of classroom training and theory, and four on-the-water sessions sailing on the gorgeous Chesapeake Bay with an eccentric instructor using Rainbow 24 keelboats (the same boats used at one point to train Midshipmen at the U.S. Naval Academy).  Another couple started the course with us, but they bailed out after the first day on the water, so Noemi and I essentially had private lessons on the second day.  On that second day, Noemí and I met Yaya, an alumnus of the School taking advantage of an opportunity offered by the School called the Keelboat Club.  Membership in the Keelboat Club offers free, unlimited use of a Rainbow for a full year. Yaya has become one of our closest sailing friends, and we look forward to many future adventures with him and his family.

Another wonderful aspect of the Annapolis Sailing School is for the first week after successfully completing a course with them, students may take out a Rainbiw for free to practice. Thereafter, alumni of their program receive a lifetime discount on full-day or half-day rentals.  We took advantage of this feature, and tried to get as much practice as we could, sailing on the Chesapeake Bay as a family (introducing our six-year old son to the sport) and sailing with Yaya. Time to Train - Annapolis Sailing School