Jul 18, 2026

Sandwich, MA to Portsmouth, NH - July 8-13


Wednesday, July 8 was a windy morning but finally the sun is shining again!  We pulled out of Sandwich, MA and entered Cap Cod Bay. We traveled 23 miles to Plymouth, MA. Our ride was lumpy but Island Bound handled the swells like a champ. Our slip for the night was at Safe Harbor Plymouth which had a clear view of the Mayflower replica docked nearby. We spent the afternoon scoping out the town shops and sights, including the Plymouth Rock. (boy was that a disappointment - much smaller that we imagined it would be)  That evening, from the back of our boat we enjoyed a concert in the local park next door. 


Thursday morning we woke up only to realize the Mayflower was gone!  Upon investigating we found out it was being towed to Boston for their America’s 250th tall ship celebration.  Before we left, the captain did oil changes on the boat as he was able to dispose of the old oil at this marina.  Shortly after leaving Plymouth Harbor we spotted our 1st whales! So fun! We thought our destination was going to be Gloucester, MA however we ended up swinging into the outer harbor of Boston for the night in order to watch the tall ships arrive. It took awhile for us to find a settled spot, but we finally dropped the anchor in a good location. We watched the Mayflower as well as a few tall ships arrive that afternoon and many more the next morning. Then on to Gloucester. 

Gloucester is known as America’s oldest fishing port dating back to 1642. It is home to the bronze monument named “The Fishermen’s Memorial”  which honors the more than 10,000 Gloucester fisherman who have lost their lives at sea. We anchored out for 2 nights in the inner harbor where we had front row seats to the comings and goings of lobster and fishing boats. A short dinghy ride gave us access to the legendary town. 

On Saturday afternoon we were off for a grand dinghy adventure thru the Blynman Canal. This is a 4 mile canal which leads from the Gloucester outer harbor thru to Ipswich Bay. Upon entering the harbor, one must pass thru a narrow bridge where the currents run strong. Boats line up single file to take their turn gunning it thru the wild tidal currents. It was a wild ride but our dinghy handled it.  We had an interesting ride passing many boats stranded/parked on shore due to the low tide. We had a super afternoon scouting the local low tide beaches where boaters and beach goers spent a hot summer afternoon.

Gloucester has an annual festival where contestants try to conquer “The Greasy Pole”. This is a 45 foot horizontal telephone pole covered with grease, fish guts and lard suspended over the bay where competitors attempt to walk to the end of the pole to grab a flag before falling into the ocean.  We weren’t in town for the festival but we did check out the pole. No thanks! 

On Sunday we cruised 43 miles north to Portsmouth, New Hampshire where we took a slip at Safe Harbor Wentworth by the Sea for 2 nights. This marina is nestled in a pristine setting next to the Wentworth by the Sea Resort. We took advantage of the marina’s courtesy car to load up with provisions and spent the afternoon shopping in downtown Portsmouth. Very neat area. 

This will be our only stop in New Hampshire as they only have 18 miles of coastline and Portsmouth is located on an inlet that borders Maine.  Maine…here we come!


Plymouth gets our “seal” of approval


The Mayflower in Plymouth 


Busy mooring field between us and the Mayflower 


Beauty passing by us


View of Boston from anchorage


No sails up, but still impressive 


Another beauty 

Rocky shoreline 

View of Gloucester from our anchorage


Gloucester harbor


The Fisherman’s Memorial


Haddock Tacos


Staying home till the tide comes up


Relax, it will be floating soon


The famous Greasy Pole. Wanna try it?



Grilling on the dock at Wentworth by the Sea

 

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