“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

Marblehead Revisted…..Maddie’s Sail Loft gets the Best of Me, Again!

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This past weekend we were hanging out with some friends at the dock and I was reminded of this post that I never finished.  So it’s a little late but thought it was worth sharing.

For Labor Day weekend of 2014 we headed back to Marblehead with our friends Pam and Chris for Friday Night prior to continuing onto to Gloucester for the 4th year in a row with a large group from our home dock.  Pam and Chris were in their Catalina 30, Windchaser, and we were of course on Smitty.  We had an uneventful trip up to Marblehead with light winds that were mostly on the our noses.  So motor sailing for us.  No biggie.  We made it up to Marblehead by early afternoon.

Our favorite spot in the very large mooring field is the Marblehead Harbormaster moorings right opposite the Landing Restaurant.  We were able to get two of these moorings near each other.  After securing the boats we spent some time walking around Marblehead and checking out some local spots.


Pam: “The sun is hot!”

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We headed back to the boat prior to having a great meal at the Landing.  After our meal we headed for Maddie’s Sail Loft to meet up with Pam’s sister-in-law.  After my epic hangover from drinking too much at Maddie’s last year, I put myself on a strict two drink limit.  Yeah, that didn’t happen.  I quickly drank my two drinks.  Then two more.  Then some more.  Then we left and went back to the Landing where I decided it was a good idea to switch from vodka and soda water to Scotch.  I also felt the need to declare that “you don’t get hangovers from good Scotch!”  Yeah, that may be true if you only have one or two good glasses of Scotch, it is certainly not the case when you have 3 (or 4 I don’t really remember) after too many tall, stiff vodka and soda waters.

Needless to say I was hungover the next day. I got up and took the dinghy to shore.  I walked a couple of blocks to the nice coffee shop we had seen the previous day and got some coffees and egg sandwiches for the group.  I stumbled my way back to the dinghy and delivered the breakfast to Windchaser just before I passed out in the cockpit of Smitty.  Eventually we got underway but I was in no condition to handle the boat.  Once I got the boat past the mooring field I passed the helm over to my Bride.  She got to watch Pam and Chris have a great, single tack sail all the way into Gloucester Harbor.  I say watch because every time she asked if we should be sailing I said no because I was too hungover to move. (Jesse should have added here that The Bride has banned him from Marblehead trips – no stop over on the way to Gloucester this year!)

We made it into Gloucester where we met up with the rest of our group from our home dock.  This year there were about 18 boats that made the trip.  There are so many of us that now they have taken to rafting us up to make enough space.   After docking, I went up to the pool to have something to eat and a little hair-of-the-dog.  Feeling a little better but really tired I went back to the boat to sleep.  I was woken up around 8PM my our friends Jenn and Jeff (Jenn is from Gloucester and meets up with us whenever we stop here).  Everyone was pretty drunk and the parade of lights was about to start (boats all light up like Christmas Trees going down the canal and out into the harbor) and fireworks were to follow.


Smitty and Windchaser rafted up at Cape Ann Marina

We love this annual trip to Gloucester.  It is one of our favorite local harbors.  We will typically stay at Cape Ann Marina and enjoy their indoor pool with a bar.  They have a cool Caribbean vibe restaurant that has a $1 raw bar happy hour.  The highlight of the weekend is the dinghy trip up the Annisquam River.  We all hop in our dinghies and head up the Annisquam to Wingaersheek Beach.  Great spot with fine white sands that looks like a Caribbean beach (the water is a little colder but still really warm for Massachusetts). (The photos below are a mix of a couple of years.  I need to start taking more pictures. And not putting my thumb over the lens.)


On Monday we sailed back south.  We had a nice sail, not too much wind so we ended motor sailing part of the day.  But it was a great way to finish the weekend.


Don’t know what I am going to do about Summer. She just can’t seem to get comfortable on the boat. 😉



One thought on “Marblehead Revisted…..Maddie’s Sail Loft gets the Best of Me, Again!

  1. Pingback: Departure Dates, Corporate Life and To-Do Lists |

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