A Weekend On Shelter Island

Last week, John and I made the long journey from Richmond up to Shelter Island, NY where he grew up visiting his Grandpa with his family.  He hadn’t been back in something like 8 years, so experiencing the island with him was really something special.  I have never been anywhere quite like it and it is kind of hard to truly explain it.  Gorgeous coastlines, gorgeous homes and a very unique general ambiance.  So, here I’m rounding up a few highlights, enjoy! 

On our way out to Shelter Island, we made a little pit stop in Greenport and went to Kontokosta Winery.  The tastings + glasses were a little pricier than we might have liked but the view + rose definitely made up for that 🙂  Highly recommend it when you’re traveling on the North Fork!

My traveling + winery gear inspo:

Sunset Beach is a MUST when you’re on Shelter Island.  The beach is an epic experience in and of itself, watching sailboats and yachts come and go. BUT the real experience is at the restaurant. We went for a drink around 4pm and upstairs they had music blasting, rose flowing and people having their fair share of fun.  While at the same time, downstairs diners enjoyed a quiet-ish late lunch or drinks with gorgeous beach views.  Again, a little pricey but definitely worth witnessing yourself.

We were on vacation with John’s parents and his sister, but were able to sneak away for a date night on Saturday evening.  His dad suggested Salt and it was absolutely perfect.  Yummy seafood with views of the marina at night, exactly what we wanted! Definitely recommend the calamari app + fish tacos for dins.

 I picked a vintage DVF wrap dress to wear over a black slip dress with my trusty Stuart Weitzman Clogs.  Shop similar below:

and shop second hand DVF here for majorly awesome deals. 

On Sunday, we hopped on the quick ferry that runs from Shelter Island to Sag Harbor, to spend a day at the beach in East Hampton. It was the perfect quintessential beach day, including long walks down the beach, admiring the gorgeous houses and enjoying some solid snack bar eats. 

John + I are of course rocking our Turkish Towels + even though summer is coming to an end, you can still shop for that perfect black one piece. Who knows when the opportunity to wear one will come up. (The one I’m wearing is only $40!)

Beautiful scenery and boats, everywhere we went! From the Shelter Island Yacht Club, to the many marinas we visited in Sag Harbor, it was always an awe inspiring sight. Visiting Shelter Island soon? Drop me a line – I’ve got much more to share!

xx, Reb


  1. Antel Muça
    August 28, 2017 / 8:56 pm

    love your style =)kisses from Italyhttp://blamod.com

    • Rebecca
      August 29, 2017 / 2:20 pm

      Thanks so much Antel!! xx

  2. Shannon Dwyer
    August 28, 2017 / 11:28 pm

    its so pretty – i keep hearing great things about shelter island so i def need to check it out!!

    • Rebecca
      August 29, 2017 / 2:21 pm

      Yes, definitely! It is amazing. xx

  3. Courtney Bentley || http://www.courtneyvioletbentley.com
    August 29, 2017 / 4:49 am

    looks like a fabulous trip! love every photo you shared!Courtney Bentley || http://www.starsystemz.com

    • Rebecca
      August 29, 2017 / 2:21 pm

      Thanks Courtney, it was! <3

  4. Savvynista
    August 29, 2017 / 7:18 am

    What a great travel diary and love all your looks!

    • Rebecca
      August 29, 2017 / 2:21 pm

      Thanks so much girl! xx

  5. Chloe Joy Makeup Artist
    August 29, 2017 / 2:26 pm

    beautiful photos. I love your outfits, especially that long cardigan you wore to the winery…and your date night dress. Looks like you had a wonderful vacation.Chloe xxwww.abrushwithcolour.com

    • Rebecca
      August 30, 2017 / 5:30 pm

      Thanks so much Chloe!! xx

    • Rebecca
      August 30, 2017 / 5:31 pm

      We really did, you've got to check it out! xx

    • Rebecca
      August 30, 2017 / 5:31 pm

      Thanks Antonia!! xx

    • Rebecca
      August 30, 2017 / 5:31 pm

      It really is! Thanks Jana! xx

  6. Turkish Towel
    October 2, 2018 / 3:53 pm

    You are looking gorgeous in these pictures that you have shared here. Your turkish beach towel and dresses are also very beautiful. I would like to thanks for sharing this interesting article here.

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