The Two Happiest Days

We’ve all heard it: “The two happiest days in a boat owner’s life are the day you buy the boat and the day you sell the boat!”

While the idiom can be overused, it does apply to many sailors. I clearly recall the day we bought our Caliber 28 sailboat and named her Lollipop II. My mother had died in December 1986, and she had loved joining us on our boat, any boat. First it was a Sunfish, then an open Tanzer 16, upgraded to a Catalina 22, good for 12 years. But after settling her estate, we decided it was time to get that bigger sailboat. 

In Hingham, Massachusetts, we discovered a one-year-old Caliber 28, named On Tap II.  This boat was different from the 27s we had viewed; it was bigger and heavier with lots of teak inside. The owners were moving up to a 38 footer and the local marina was happy to take our Catalina 22 in trade. It was a done deal. 

I worked on cleaning the boat and touching up the teak—about the limit of my skills—and then splash day came. Roger Merrill, the pipe-smoking and reserved marina owner, came along for the first sail. Bunky Kehoe made sure I had a suitable mooring and thus began 34 years with Lollipop II.    

First day sails, then sleepovers at World’s End, and eventually visits to the Harbor Islands were all memorable. One Fourth of July on the return from Boston Light, we listened to the Boston Pops broadcast from the Esplanade and viewed multiple fireworks displays along the shoreline. Then came some light cruising to the North Shore, Salem, Marblehead, and south toward the Cape Cod Canal. My longest adventure aboard Lollipop II was nine days with my son David and sailing buddies; we made it to Maine, Biddeford Pool, Isle of Shoals, and many places in between.  

Lollipop II continued to be an important part of our life after the kids moved on. I made some modifications for singlehanded sailing, including running lines led aft to the cockpit. In more recent years, I made short day sails with just the genoa, which was easy to control. Then came the dawning realization that the rituals of spring preparation, rigging, launch and too-soon haulout were becoming a bit much. Help from my friends and son Matt eased the burden, but reality was setting in. Better to move on a year before I had to, rather than a year afterward. We listed the boat, but were secretly happy that it was still ours through the 2020 season.

During the height of winter, and just after one of the few significant snowfalls, our broker called to say that a local couple had inquired and would like to take a look. I shoveled a path for access to the boarding ladder and made sure the shrink wrap door indeed opened. They spent a cold hour on board while I maintained a respectful distance. To my surprise, I heard the next day that the couple wished to make an offer. Negotiations proceeded smoothly with the guidance of the trusted and skilled broker… and then, it was done. 

I wasn’t ready yet to acknowledge that selling Lollipop II was the second happiest day because we’d had so many memories aboard her. But what a good feeling to know that the boat would continue to bring joy and pleasure to another family. I looked forward to assisting new owners Mike and Alisha in getting started and provided a notebook full of entries on maintenance, rigging, hints, and stories.

Launch day at Sunset Marina in Hull was cool and the wind blew from the northwest at 20 to 25 knots. We had a full crew in attendance—the new owners, the broker, a diesel mechanic, and me. The hydraulic trailer was right on time and the driver loaded the boat and backed down the short ramp. Waiting for his sign, I started the engine and let it warm up a few minutes, making sure a sufficient amount of water was being pumped overboard. 

The driver backed the trailer into the water, then I put it in reverse gear and powered off. As required by the sales contract, we motored out for 10 to 15 minutes to confirm the engine’s performance, but the wind and spray were a bit much. Back at the dock, I worked with Mike to get halyards and lines sorted out, the boom installed, and everything set except for the sails and canvas. Mike took us out to the mooring and we packed things away, both of us glad for this key step.  

A couple of days later, I was back to finish the rigging with Mike and Alisha. The genoa went on first, then the mainsail, contending with a balky topping lift and outhaul.  Next, the bimini frame and the canvas, the radar mast, and finally the dodger, leaving the side windows for a warmer day. It was time for their first sail and Mike took the helm. I sat back; it was their turn and time. Mike started the engine, Alisha released the mooring lines, then they raised the mainsail and unfurled the genoa. We sailed at a gentle 1.5 to 3 knots out into Hull Bay and picked up speed as we passed through Hull Gut. Trimmed and heeling slightly, the boat moved along nicely at 5 to 6 knots towards Georges Island. When it was time to come about, the wind had a chill bite. We sailed fast back through the Gut and headed for the marina. They furled the genoa and dropped and packed the mainsail and headed for the mooring. With the boat secure, we called for the launch and each of us was satisfied with the day. I knew the boat was in qualified hands.  

I suspected that I might pass by on our small powerboat, just to see our old friend bobbing at the mooring, ready for the next sail. I shared this final story with the new owners, and they wrote:

Dear Nick, 

We’ve enjoyed all your stories, but especially this one. We are delighted to be part of this happy ending for your time with Lollipop II, and not surprised at all to hear that selling doesn’t come close to your many other happy days as an owner. Of course feel free to motor by, and if you ever happen to catch us at the mooring, please stop to say hello. You’re an honored guest, anytime.  

Best wishes, 

Alisha (May 2021)

Towards the end of their first season, Alisha invited us for a sail. The winds were light that day, but it was wonderful to listen to their first-year adventures and see how much they were enjoying their boat. Maybe this was not the typical seller-buyer transaction and relationship, but what a good feeling all around! Finally, the ‘Second Happiest Day.’