“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 – Sailing Town USA


With a slight breeze from the south-southwest, we decided this weekend was a great opportunity to check out Marblehead.  We had yet to visit this harbor and it was time we corrected that.  Marblehead has a reputation of being one of the best coastal towns and is often up there in discussion of the best sailboat harbors in America.

We had a nice sail from just past our home harbor, sailing threw the Hull Gut, taking the Narrows to clear out of Boston Harbor and then a down wind run all the way to Marblehead.  We spent most of the day sailing wing and wing in 8-10 knots of wind.


Sailing wing and wing has me thinking about adding a whisker pole to our cruising upgrades.  I already plan to add a good preventer system but the pole might be a nice add as well.

Our calm sail continued with a couple of singlehanded wing and wing jibes.  The pouch and my Bride had plenty of time to relax and check my navigation.

IMG_0756 IMG_0753

We had some friends pass us on their way south and swung by to say hi and take a photo of us under sail.


Thanks for the photo Dan and Kerry.


After striking out with getting a mooring from all of the yacht clubs except the Dolphin, who’s moorings were at the mouth of the harbor and looked uncomfortable, we hailed the harbormaster.  Wouldn’t you know it, they had one more mooring right up next to the dinghy dock.  It was a great spot and only $25 for the night.

Once we got settled on the mooring, we launched the dinghy and went exploring this cool coastal town.  It was great but the highlight for me was Crocker Park.  Lots of park benches dedicated to loved ones that overlook the harbor.

All 3 of my girls in one photo (you can see Smitty just over the bench, to the left of my Bride)

All 3 of my girls in one photo (you can see Smitty just over the bench, to the left of my Bride)

There is also a stairway down to a floating dock set up just for swimming in the beautifully clear water of the harbor.  You can see down a good 15-20 feet in the crystal clear water.

We had a great dinner at the Landing that night.  They feature grass fed beef and fresh, local veggies.  Perfect for someone doing the Paleo thing (like me for the last 5 weeks, love the results so far).  After dinner, we walked up to Maddie’s Sail Loft where I had a few too many of their stiff drinks.

Following my night at Maddie’s, I turned the helm over to my Bride.  She expertly took us back to our home port as I slept most of the trip.

It was a great spur of the moment trip to a great harbor.  We will definitely return here in the future for another (more sober) visit.


3 thoughts on “Marblehead – Sailing Town USA

  1. Don’t ya just love it when a last minute weekend getaway works out? Well, except for the hangover 😉 Sounds like a great time!

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

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