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#GLAMTravelDiary: Our Greenport, New York Long Weekend Itinerary

Tularosa Jumpsuit

Hi, friends.  It’s been a hot minute.

I’ve been working on putting this post together all week — it’s been ONE OF THOSE WEEKS.  You know that feeling after a long-weekend away with your college friends when you’re now in your 30’s?  That’s me this week.  I can barely keep it together and am still recovering from the most fun I’ve had in a while.  We had been planning for this trip for most of the summer and Raja and I have actually had Greenport, New York on our local bucket list for years.  We try to make it out to The Hamptons at least once a summer and have rented a house with friends there for the last 4 or 5 years.  We’ve done everything from Montauk to Southampton in past years… and on our way from the ferry in Orient Point, we always pass by Greenport on the North Fork.  We were able to roundup some of my very best friends + our spouses/significant others for a fun weekend on Long Island, and rented one of the most beautiful houses I’ve ever been to!

I’m sharing our full itinerary (we did an extra long weekend, Wednesday-Sunday) and rounding up the best spots we were able to check out in the few days we were in town.  I’m also going to share a list of other spots we didn’t get to, since I had a list about a mile long of recommendations from all of YOU!  We will be SURE adding these to our itinerary next time!  Hoping to plan a trip back this fall!

Travel Guide Greenport, New York
Orient Point Ferry

Sunset Beach Shelter Island
Sunset Beach Shelter Island

Sunset Beach Shelter Island

Mattebella Vineyard
Mattebella Vineyard

Mattebella Vineyard

Mattebella Vineyard Long Island
Mattebella Vineyard Wine Tasting



Ferry: New London, CT —> Orient Point, NY.  I had a lot of questions on how we initially got to Long Island from Connecticut, and it’s much easier than you initially might think!  We were planning to bring our cat Mischa along with us and were renting a house, so we wanted to make sure we had all of her stuff (#catmomproblems) and some groceries with us to stock the house — so, bringing the car on the ferry was the best option for us.  You can totally get away without the car if you’re coming into Orient Point — the drive from there to Greenport is under 15 minutes and you could easily arrange for a cab from the ferry into town without the car!  The ferry is about an hour from us in West Hartford, and the ferry ride is about an hour and 20 minutes — so door-to-door, it’s not a bad ride, considering half of the time, you’re not even driving.  There are SO many different departure times for the ferry, which makes it super easy to plan.  You just need to book in advance — especially if you plan to take the car over.  The summer fills up FAST, so I had to book 2 weeks in advance to get optimal travel times.

Explored downtown Greenport and lunch at Crabby Jerry’s.  After we got ourselves situated in our house rental, Raj and I popped around the little downtown area for a few hours before the rest of our friends arrived.  Our location on Bay Avenue was so ideal and right in the center of everything — an IGA grocery store was a few blocks away and all the best restaurants were within minutes of us.  We ended up eating a delicious niçoise salad at Crabby Jerry’s outside at the bar and then popped in and out of a few local shops!

Dinner at Lucharitos.  I knew I was about to go on a full seafood binge for the next few days, so I was excited for a little bit of Mexican food!  This place is absolutely ADORABLE and has such a fun atmosphere, and it was absolutely packed any hour of the day we walked by.  The food was delicious — I got the veggie burrito, and the margs were on point!


Ferry: Greenport, NY –> Shelter Island, NY.  A few of my readers made this recommendation loud and clear, and I’m SO glad we took you up on it.  We wanted a straight up beach day, and while there are a few public beaches right in Greenport, this 10 minute ferry to Shelter Island was WELL WORTH IT.  We ended up walking over to the ferry from our house, hopped on for $2 each, and grabbed a cab to Sunset Beach — a gorgeous hotel that looks like it’s straight out of the South of France or Amalfi Coast in Italy.  The beach was public, and there were umbrella and chair rentals, massages on the beach, paddle boards and kayaks, and a delicious restaurant right across from the beach.  We ended up staying here the entire day, ate lunch at the hotel, and had one of the best days I remember having in a loooong time.

Dinner at Noah’s.  Another dinner spot that came highly recommended from a bunch of you guys!  We ended up happy overall, but there was a slight hiccup: we ended up sitting outside because the inside smelled terrible.  Not a clue what was going on… or if it was a one night sort of thing, but it almost made us turn around.  As a group of 8, we knew we would have a hard time finding another spot, so we sucked it up and ate outside because the place was packed.  I’m glad we did, because we all loved our meal + the drink menu was great!  I would recommend this spot only outside… it seemed like there was a filtration problem on the inside and bad filtration + seafood… you get the picture.


Breakfast at Crazy Beans.  We actually ended up just picking up from the location and eating back at the house, but this place looks straight out of the 50’s and is so quaint and cute.  Think: the diner from Grease.  Their menu was expansive and they had a ton of both breakfast and lunch options, which was great for a large group!

Vineyard hopping.  We ordered a few Uber’s and headed off a little ways down Long Island to two beautiful vineyards for some wine tastings.  Since it was super hot and muggy that day, we did these starting at 3pm, so we wouldn’t be in the heat all day.  It ended up working out perfectly!  We started with a wine tasting at Mattebella’s which was absolutely gorgeous and the wine was incredible — all of the grapes for the wine were from Long Island!  We then moved to Bedell for another tasting and had the most amazing view of the rolling hills and multiple vineyards.  If you don’t want to do a tasting, they are both just great spots to grab a glass (or bottle) of wine and order some apps!

Dinner at 1943 Pizza.  We actually didn’t have reservations this night and were planning to just feel it out after a day of wine touring.  We ended up walking here after it came highly recommended from a bartender!  It was pretty busy and we had to wait a bit for a table, but well worth every second!  I’m always a pizza snob — I’m a born and raised CT gal and LIVE for New Haven style pizza.  This totally hit the spot.

Late night at Claudio’s.  I will preface and say that Raj and I opted out of going out late… and I’m mixed between regretting missing the action and being thankful we took the night off.  Your girl can’t hang anymore.  Raj and I stayed in with Mischa, and the rest of the gang went out for drinks at Claudio’s, which is probably one of the most famous spots in all of Greenport.


Slow start to the day/mixed it up.  After a late night, and cooking breakfast at the house, half of the crew ended up at the private beach our house had access to and we spent a few hours paddle boarding and hanging out by the water.  The over half popped around town a bit to explore and ended up checking out the Greenport Brewery and getting some oysters for happy hour!

Dinner at American Beech.  We ended up doing the pre-fixed menu here due to our group size, but the food was AMAZING.  We all ate SO MUCH and were so full — we ended up having to bring back dessert to the house.  I think the ambiance at American Beech is better than anything.  It’s the most gorgeous restaurant and really has a Montauk-vibe to it.  Super trendy yet beachy, lots of lights and outdoor dining, and is the perfect mix of cool yet casual.  I could have spent an hour taking pictures of the place!

Karaoke at Lucharitos.  Yup, we came back.  We are big fans of karaoke and always seem to end up singing our hearts out after multiple rounds of liquid courage.  As if this place wasn’t busy enough, it turns into a SCENE after dinner… the tables get moved out of the way, a projector comes out, and people start lining up to belt out some tunes.  Pretty sure I’m still recovering from this night and my Dr. Dre and Eminem “Forgot About Dre” performance I killed with my forever duet partner and best friend, Amanda, but it’s been well worth the pain.


Hitting all the spots we missed before heading home.  On our last day, Raj and I set out to hit a few spots before we left that were still lingering on our list (we didn’t make it through all of them, sadly).  I grabbed a delicious blueberry iced-tea at the most adorable spa (I know, weird, right?!) that is also a tea house called Special Effects.  After walking around town a bit and popping in and out of some local shops, and visiting the famous antique carousel, we grabbed a drink at Brix & Rye — a speakeasy spot with an insane drink menu that came highly recommended.  I stepped out of my usual boring drink comfort zone and got a refreshing drink made with gin and mint.

Dinner at Frisky Oyster.  So glad we were able to squeeze this spot in before we left!  Our meal was beyond delicious!  It was just Raj and I at this point, so we split the scallops and the octopus entrees.

Privacy Please Linen Button Dress
Greenport, New York Pier

Special Effects Salon Greenport, NY

Paddle Board Greenport, NY
Greenport, NY Itinerary Long Weekend

American Beech Greenport, NY

There were a bunch of other spots we just didn’t have time to visit that you guys recommended and I wanted to include on this post!  We’re seriously already trying to plan a quick trip back there in the fall to visit another winery (or two), so I’ll be referring back to this list!

  • Other wineries including: Kontakosta, Sparkling Point, Ospreys Dominion, Lieb Cellars, and Martha Clara that are part of the North Fork wine trail.
  • Lavender By The Bay.  We have actually made this stop a few times on our way to The Hamptons.  It’s a gorgeous lavender farm where you can pick your own, or buy a bunch of local lavender gifts!
  • Little Creek Oysters
  • Love Lane Kitchen
  • Bruce & Son
  • Sweet Indulgences

Did I miss anything?!  Let me know in a comment below!  & make sure to check out SO MANY of my other #GLAMTravelDiary posts on the TRAVEL tab!

& if you would like a link to the house rental we stayed at, feel free to email me!

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