The Adventure Begins - well in a couple of years

When is the appropriate time to start a trip blog? I doubt too many people would begin 26 months before departure like I am doing now. However, when you consider that I have already been planning this trip for about 7 years, perhaps it's not so bad. First, some background.

For at least the last 15 years, I have been obsessed with boating. I don’t know why. I didn’t grow up boating, and had very little exposure to it as a child in mostly land-locked Tennessee. Ann and I lived in New Jersey in 2002, when I decided to move to academia from an industry research job at AT&T and an adjunct teaching appointment at NYU. I had several faculty offers in different locations, but the one in Baltimore, with its access to the Chesapeake Bay was most attractive to me, given the boating opportunities. In 2008, we purchased our first boat, a 40’ 2003 sailboat that I named Prime Factor and obsessed over for 8 years. 

Prime Factor: A 40 foot 2003 Catalina MK II sailboat

We had a lot of fun sailing around the Bay with the kids, taking several week-long trips, sleeping on the boat, and exploring places like Oxford, Cambridge, St. Michaels, and Solomons Island. But then the kids got old enough to revolt, and I decided to buy a powerboat and sell Prime Factor. In June, 2016, we purchased Lucky Break, an ironic name we chose based on the circumstances that led to our purchase where we mistakenly thought the stars had aligned for us. The boat was a brand new 47’ Sea Ray Sundancer. Much easier to handle than our sailboat had been, but much less fuel efficient. Honestly, not the greatest boat ever. But we enjoyed it for a year.

Lucky Break: The ironically named 2016 Sea Ray Sundancer

Ready to embark upon a serious boating adventure, I planned a 3-week boat trip from Baltimore to Boston to visit Tamara on visitors day at her camp in New Hampshire and to check out the major waterfront attractions on the way (See my blog of that trip). Shortly before the trip, we came across a Prestige 560 Fly for sale, a significantly nicer, bigger and more comfortable boat for such a trip, and decided to buy it and sell Lucky Break. The opportunity to take our upcoming trip on a new, bigger, boat was a big factor in our calculation. We named the boat Sababa, which is a way of expressing that something is beyond fantastic in Hebrew and Arabic.

Sababa: a 2017 Prestige 560 Fly. Fantastic boat!

Some time in the early 2010s, I became aware of a popular boating adventure around an area called the Great Loop which spans 15 US states and two Canadian provinces and over 6,000 miles.  Many Loopers extend the trip in the Winter to include the Bahamas and other Caribbean destinations.

As I learned more about The Loop, I set my sights on some day completing this boat trip with Ann on our own boat. At first it was a vague, hypothetical notion. Several events would be required to make this a reality. One, our kids would have to grow up and leave home. Two, we would need a proper boat that could travel 350-400 miles without fueling, would have a draft of maximum five feet, but preferably four, would have an air draft (height from waterline to top) of 19’ 6” or less, and could comfortably accommodate us as well as any guests we would want to bring. 

Over time, as Ann will attest to, I became increasingly obsessed with doing The Great Loop. I started researching boats and reading everything I could find about the trip. I followed several blogs of active loopers and attended Webinars as well as seminars at boat shows. 

To give myself confidence to do the Loop, I decided to study for my Captain’s License. I worked on my own with a self-study kit for about a year, and ended up getting a 100 Ton Masters Captain’s license from the Coast Guard. Probably overkill, but now I have a backup career if I need it. When the twins approached the end of high school, I got a lot more serious about planning the loop. I targeted my next Sabbatical from Hopkins, the 2024-2025 academic year, and started searching for an appropriate boat.

I went to every boat show possible. In February, 2020, a month before Covid hit, I went to the Miami boat show to scope out Loop boats, and while I had a tough time finding a boat the met all the required specs, including our budget and our taste, I did manage to fall in love with a center console, an Everglades 295cc, which I had also been researching as a day boat to get around the Bay quickly and for water sports with the kids. So, I did not come back from Miami empty handed, and we purchased River Bet. Ann also decided she was going to be more careful about letting me go to boat shows by myself.

Our Fleet:  River Bet, a 2020 Everglades 295cc, next to Sababa

Over the next several years, I learned more and more about the Great Loop, and I began planning some of the details of our trip in earnest. A start date, arrival dates in key cities, and how we would prepare a boat and provision it. When we were three years out from our planned departure, I realized that it was time to get even more serious about finding a loop-capable boat. As I increased my number of boating magazines subscriptions and spoke to some experienced loopers, I finally had a revelation. I was not going to find an appropriate Loop boat that I would be excited about. It hit me like a ton of bricks. After years of planning this trip and telling many friends and family members about it, I decided I would prioritize the choice of boat over a particular itinerary. We’d pick the boat we wanted more than any other, and then we would figure out good places to go with that boat. This changed everything!

This realization was so liberating. Now I could boat shop with no constraints! And as my friend Matt told me, boat shopping is at least as much fun as boating. I was thrilled! Ann was on board before I finished explaining.

I started planning a new itinerary. Annapolis, Baltimore, Philly, Cape May, Atlantic City, NYC, Cape Cod, Block Island, Newport, Boston, Maine, Nova Scotia, and then back to Annapolis in the Fall, hitting all the places we missed on the way North. After a short stay in Annapolis, when it starts getting cold we go down to the Florida Keys, the Bahamas, Turks and Caicos, Dominican Republic, Puerto Rico, Barbados, and then in the Spring back to Florida, Georgia, South Carolina, North Carolina, Virginia and then home in late April or early May. Yes, not too shabby. The Great Loop can wait!

So, I began researching boats with a different set of constraints: sea worthiness, electronics, comfort at sea, comfort at rest, and ultimately I ended up with the question: What is the most sea-worthy, largest and nicest boat that Ann and I can handle as a couple and feel safe and secure in different sea and docking conditions? After several months of research, I came up with a short list.

At the top of my list was a Fleming 65. This is hands-down I think the best possible boat in the owner-operated size, the most beautiful, and the most desirable. But, there are three problems with the Fleming. The first is that the number of used Fleming 65s for sale in the entire world right now is zero, and the backlog to build new is 3 years. There was an older one that popped up in Florida a few months ago, and it sold in a day. The second problem, just as serious, is that for some reason I cannot fathom, Ann does not like the look of the Fleming. That should be grounds for divorce. But, I guess it’s harder to find a wife like Ann than even a Fleming, so I’ll keep her. Finally, the Fleming is super expensive. Boats in the size range we want are not cheap, but you pay a serious premium for the Fleming brand, and in the scheme of things, without unlimited funds, it is not nearly as good a value as my next favorite boats.

Fleming 65 - my favorite boat. Backlog for building is 3 years, and there are no used ones for sale.

Second on my list, after all my research, is the Hampton Endurance. After that, at a close third is a tie between the Outer Reef and the Marlow Yachts. Truly, I would be ecstatic with any of these. Over this past Winter Break, a 72’ Outer Reef that was one year old came on the market in Ft Myers, FL. Ann and I were driving to Florida anyway, so we went down to see it. We loved everything about the boat except the layout. It was a closed design where the main salon was a separate room from the kitchen. Grudgingly, we decided to pass and continue our search. That layout was a fatal flaw.

One year old Outer Reef 720 in Ft Myers, FL with closed layout

A few weeks ago, a 2017 Endurance 720 with length overall of 74’ came on the market in Seattle. Ann and I jumped on a plane to see it. We liked the Endurance even more than the Outer Reef. But, again, a fatal flaw. This boat had been neglected for over 2 years. There were no service records beyond 2019, and that was too risky for us. But the trip was not a total loss, as we learned a ton about the Endurance. The following week was the Miami boat show, and of course, Ann was not going to let me go alone! We spent five days at the show. We looked at Marlow and Endurance boats and frankly could have probably gone either way, but we both liked the Endurance better. 

2017 Hampton 720 Endurance LRC that we flew to Seattle to see 

When we got home from the Miami boat show, we decided to pull the trigger and put a deposit on an Endurance 658L. Overall length is 71’, draft is 5’3”, and beam is 19’2”. Exactly what we were looking for. As I write this, we are in the process of customizing everything about the boat. We opted for the deluxe sky lounge feature where the flybridge is completely finished like indoor space with the boat’s only helm. This lets us use the entire main deck level for living space, and we are going to put a country kitchen in the forward area of the main deck. There are so many features that we love about the boat, that I could fill several pages writing about them, and perhaps I will at some point.

The boat will be completed in early December, in China. Covid permitting, Ann and I are planning on going there to perform our inspection and see the boat come off the line. It will then be shipped to us for delivery in late Dec or early January. We’ll keep the new boat in Florida until mid March when we can bring it home to Annapolis. We’ll then have one year to plan our trip on our new boat, which we are naming —  EMPTY NEST.

Initial sketch of Empty Nest in March, 2022

I expect that my blog postings will be few and far between over the next couple of years. When we have major developments relating to our trip, such as taking delivery of Empty Nest or finalizing a portion of the itinerary, I may post something. But, the majority of the posts on this blog will come when we are actually on the trip.