Cruising With The Chilbergs: Teddy Roosevelt's Stomping Ground (BLOG)

I first cruised here in around 1958 with my parents and later returned with my own kids in 1986. Many of the boats are now bigger and homes more luxurious, but the charm of harbors is still the same.
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“It is not the critic who counts. … The credit belongs to the man who is actually in the arena; whose face is marred by the dust and sweat and blood; who strives valiantly … who, at worst, if he fails, at least fails while daring greatly; so that his place shall never be with those cold and timid souls who know neither victory nor defeat… Far better it is to dare mighty things, to win glorious triumphs even though checkered by failure, than to rank with those poor spirits who neither enjoy nor suffer much because they live in that gray twilight that knows neither victory nor defeat.”

—Teddy Roosevelt

August 14, 2016:

After passing under the Throgs Neck Bridge, we entered Long Island Sound which is about 80 miles long and about 20 miles at the widest. We headed along the South Shore, which is Long Island itself. One place we stopped was Oyster Bay, which was where one of my three favorite presidents lived: Teddy Roosevelt. I must confess that I had forgotten how wonderful Long Island Sound is as a cruising destination. I love it. The homes are beyond magnificent and the bays and harbors are beautiful.

I first cruised here in around 1958 with my parents and later returned with my own kids in 1986. Many of the boats are now bigger and homes more luxurious, but the charm of harbors is still the same.

Orient Point Lighthouse.

Orient Point Lighthouse.

Watermen tong for oysters just as they did 100 years ago and family fishing is still prevalent. I am not sure which were crab traps and which were lobster traps, but I did manage to avoid both types! To see sailboats actually sailing was refreshing as countless sails crossed the Sound and skirted the shores. The Sound was alive with boating enthusiasts from jet skis to megayachts. Again, I love it!

The Sound has a plethora of lighthouses that are scattered on the many points up and down the waterway. I don’t know what it is, but like sunsets and dolphin, I can’t resist taking pictures of lighthouses. They represent what is best and classic while traveling along America’s Coastlines.

As I pause and reflect on the first half of this cruise, I am so grateful to have traveled thru some of the greatest cruising grounds. The Florida Keys have that laid back charm of bygone years in America. The Exumas and Abacos have that pristine water with fabulous snorkeling reefs of which I never tire.

Trying on some Oyster boots at the St. Michaels Museum.

Trying on some Oyster boots at the St. Michaels Museum.

The Chesapeake Bay with its unique assortment of anchorages, lighthouses, and towns that take me back centuries is fascinating.

Now on Long Island Sound, I begin a journey thru America’s roots and a whaling industry that will take us to Mystic, Connecticut, Block Island, Rhode Island, and of course Martha’s Vineyard and Nantucket in Massachusetts. Herman Melville’s Moby Dick and Robert Lewis Stevenson’s Treasure Island are the literary bookends of this cruise. I feel so grateful that I followed Teddy Roosevelt’s challenge.

Yes, it would be safer to stay tied up at a dock in St. Petersburg and to avoid the stress of new passes, new anchorages, thunder squalls, and reefs.

But to sit on the flybridge upon getting anchored in a new cove and celebrate with a glass of wine as the osprey, gulls, herons, pelicans, or eagles fly overhead, is both priceless and worth it.

Long Beach Point Lighthouse.

Long Beach Point Lighthouse.

Thomas Point Light.

Thomas Point Light.

Read more of Joe's blog here.

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