Block, Watch Hill, Shelter Island, Milford Ct

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Block Island to New London

We left Block in mostly clear conditions and were hit by fog the whole way to the Thames River. We tied up at IP Dealer Hellier Yachts dock in New London – what a great bunch of people. They made us feel very welcome. Congrats to Vin on his retirement. This was a whirlwind tour with a rental car (upgraded to a Cadillac!) for 24 hours. We shopped Defender and West Marine, where Radeen got a cute red folding bike and got the usual groceries. We saw the Coast Guard Academy museum and toured the beautiful campus by car.

New London to Watch Hill

The anchorage and ocean beach at Watch Hill are so great! The little town is charming, too. We enjoyed seeing the antique carousel and walking out to the Coast Guard Station. Sunday we had fun with Jim and Vanessa from IP-420 Windrunner. They met us for lunch at the Olympia Tea Room where Marilyn Monroe worked as a teenager. The St. Claire Annex has been in business for over 100 years and is fun for breakfast and made on the spot ice cream.

Watch Hill to Block Island

Let a new adventure begin! Radeen has not ridden a bike solo since she was 11, so Payne’s dock early on a weekday morning was a good place to get started. By day four, she rode the rough and hilly road to the Coast Guard Station and the next day we rode into busy Old Harbor and had breakfast at Aldo’s to celebrate. Another celebration was dinner with Craig and Debbie on IP440 Charmed in honor of the start of their southbound cruising adventures.

Fun on Block Island

Friends we met at the public library, Norm and Shelley, invited us to dinner at their beautiful home off Corn Neck Road and then took us to a concert sponsored by the Block Island Residents Association called “Blues on the Beach.” We are starting to feel like locals now! A restored Army vessel named “The General” flying a 4 star flag ,had a ceremony each nite at sunset, complete with 3 progressively louder cannons, a fly-by from some sort of fast airplane, a bugler playing “Taps” and a properly lowered flag. We “dressed” the dinghy in bunting and participated in the air horn salute.

Block Island to Dering Harbor, Long Island

A neighboring local boat shared his freshly caught clams with us and we made New England style chowder which seemed so appropriate for our last night in Block. What a dream to be here from July 4th to August 7th with just a few side trips. We departed on a favorable tide with the new Hylas 49 Black Diamond on her shakedown cruise. She is the beautiful new boat of former IP45 Time Bandit owners, Rich, Bonnie and daughter Alex. The sun turned to fog which made for a somewhat stressful trip across Block Island Sound. It lifted as arrived in Gardiner’s Bay and took a mooring ball in Dering Harbor. Jack’s Marine is a fascinating old hardware store with an amazing toy department – worth a tour!

Dering Harbor to Greenport

After a stormy morning, we crossed to Greenport and took a mooring ball in Stirling Basin. What a charming town! The BLISS Rendezvous will be held here next July and we look forward to exploring it more. Highlights included pizza with Black Diamond, a fascinating old department stored called The Arcade, a visit to a convenient and clean Laundromat and a tour of one of 6 wooden Yard Patrol training vessels on summer cruise with cadets from the Naval Academy in Annapolis.

Greenport to Sag Harbor

We had a fabulous sail around the western side of Shelter Island to Sag Harbor. A sudden change in the forecast dictated a mooring ball and then we dashed ashore for the Thursday nite Summer Concert series. When we were here in 2004, the local band played patriotic songs; this year “The Cascades” played 50’s and early 60’s. We admired the mega-mega-yachts “Bad Girl” and “ My Iris. ”The really dreadful weather didn’t arrive until Friday, but that didn’t stop us from sharing a lively hot lunch with Al from IP32 Half Moon aboard Black Diamond.

Sag Harbor to North Cove on the Connecticut River

We had a leisurely sail out of Gardiner’s Bay and enjoyed shooting some beautiful photos of IP 32 Half Moon before exiting at Plum Gut. We were looking forward to meeting our Rock Hall friends, Bob and Kathy of IP380 Drake’s Passage. They are amazing – so much energy! They got to their boat in Oyster Bay, Long Island, at midnite on Friday nite. Till they loaded everything and the 2 girls and the 7 month old baby aboard in the pouring rain and high winds, it was 1:30 a.m. They got up at 6:00, left at 7:00 and sailed against a foul tide for 10. 5 hours to meet us for dinner and mini-golf. We were ashore by 6:00 p.m., seated at 6:30 and dinner didn’t arrive till after 8:00. The children were soooo good! Kathy Ann read a book and Alley drew a nautical chart with grass, water, docks and boats. The round yellow object in the corner we all assumed was the sun, till she informed us that it was the compass rose on her chart! After we ate, we played mini-golf till 10:00 and THEN went for ice cream!! Unbelievable day!

North Cove to Milford, CT

We anchored in the Gulf south of Milford behind a curving, mile long sand bar that is bare at low tide and then covered 6 hours later by a 7 foot tide. It was a great place for a swim, a walk on the bar and a chat with the park ranger who drives out to Charles Island. The long harbor was tight with boats moored on floats in the middle, a fast current and lots of boat traffic on a sunny Sunday afternoon.

Milford, CT to Port Jefferson, NY

Another great sailing day, this one across the Sound. Port Jefferson is not a very cruiser-friendly place unless you take a mooring ball and use the launch. The fuel dock claimed to have no water, till we found a faucet and used our own hose. The door to the Harbormaster’s two story office is impossible to find. There is no sign to indicated that you are supposed to enter through the electrical closet! The town dock has no dinghy landing and we nearly got a ticket for tying up there since we couldn’t talk to anyone in the harbormaster’s office. Danford’s marina charges $7, not per day, but every time you come ashore. The best part of Port Jeff was meeting Kiwis, Roy and Doon, aboard Bold Endeavour. See their adventures at

Port Jefferson to Oyster Bay, NY

The best sail of the entire summer! The videos show it all! Now we are In Oyster Bay for several days.

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0 Replies to “Block, Watch Hill, Shelter Island, Milford Ct”

  1. Milford Earth Day Committee is reaching out to businesses, Civic orgs, residents 5 to 105 to come out on Saturday May 17th and help beautify Milford. Most businesses are creating 5 person Teams with their Logos on jackets or tee shirts. At Eisenhower field all kids will receive a FREE event patch, and all who register will receive Food and drinks. Please contact me if you can help.

    This costs you nothing and you get to give back to this community.

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