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East Hampton & Sunset Beach, Shelter Island

The Maidstone

From the moment we set foot on the grounds of The Maidstone in East Hampton, New York we knew this was a very unique and magical place.

The makers of hotel magic

We would be spending three nights at the hotel as guests of the owners, good friends Jonathan and Jenny Baker (See our previous post to learn more about our journey to get here). Hailing from Sweden, Jenny was raised in the hotel business. She has brought a chic combination of Scandinavian culture and vintage charm to The Maidstone, complete with imported Swedish Army bicycles for guests to explore and rotating art exhibits throughout the intimate on-site bar and lounge.

For our friends, this time was a working vacation as they were recovering from the effects of last year's tourism slump and were planning a soft re-opening for the following week. We would have plenty of free time to ourselves and evenings with them to catch up. Just perfect!

Biking around East Hampton

One of the first things we did was set off on bikes to explore the area. We passed an old cemetery that the hotel overlooks and so many beautiful homes with lush gardens. The home pictured below was one of my favorites.

The village of East Hampton offers high-end shopping, an excellent gourmet market, and many eateries. But beware...there is an emphasis on viewing the night sky here, and the building codes limit lighting so as to not obstruct the ability to stargaze. The result is, the town has no street lighting and closes down early. The locals seem to like it this way!

Main Beach

Main Beach is the daily hang-out for families and friends from New York and New Jersey who own or rent summer homes to vacation in Southampton Village. We found it was very different from west coast beaches. Here, families can rent cabañas for changing and eat at a beach cafe, which offers a wide variety of yummy and healthy noshes and good coffee for the early and active bunch. A team of lifeguards are on duty making this beach very family friendly.

We enjoyed a long walk on the sand toward Southampton and marveled at the expansive homes built on the bluffs with stunning ocean views. Some of them looked like they've been there for generations, while others were newly renovated. We imagined the storms these homes have seen, many of which have small windows for protection.

The second evening here, we joined Jonathan, Jenny, and their kids for the Tuesdays Main Beach Music Series, which brings together the whole community. The band Inner Roots was great, taking requests from the audience at the end of the evening. The balmy air mixed with the sunset sky made this a highlight during our stay.

A glimpse of our magical evening


Introducing our friends to Relentless

Jonathan and Jenny took an afternoon off from their work for a sailing adventure. Jonathan suggested we sail to Sunset Beach, a trendy waterfront restaurant on nearby Shelter Island. It was a spectacular day for sailing on our Code 0 with wind from the east at 7-10 knots. Jenny decompressed on the trampoline, while Jonathan and Steve enjoyed hoisting sails together and discussing the similarities and differences between our boats.

We arrived after a couple of hours, taking the long and most scenic route. This was our first time sailing to and dropping a lunch-hook – it was quite thrilling to see our boat out there from the restaurant.

Spontaneous Christening of Relentless

What a perfect afternoon it was! Back on our mooring in Sag Harbor, we thought to finally christen our boat. It was spontaneous and goofy, with no forethought to prepare. And, although we are fully aware it is our precious Lord Jesus Christ who hears our prayers and keeps us safe, we had some fun doing a traditional sailor's toast, offering some bubbly to the ocean as is customary.

Thanks to our niece Tami for the champagne and to Director Jonathan for capturing the silliness on video and making a cameo appearance at the end.

Thank you, Jonathan, Jenny, and The Maidstone staff for making our stay so enjoyable. What a treat it was! Great friends enjoying sailing adventures together.


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