The North Fork of Long Island is chock full of hidden gems and having visited Greenport twice, once in the Fall and recently this summer, I am obsessed. This quaint, historic beach town has so much to offer for couples, families, and for a girl’s getaway. Below I will share all of my top tips for going to Greenport with girlfriends, most of which I also did with my husband on our anniversary trip in October.

One thing to know about Greenport is that many of the restaurants and shops are closed Monday-Wednesday and reopen on Thursday, even in the summer. This was something we were shocked about but honestly, it made the whole town very laid back and quiet while we were there. If you are looking for more of a party vibe, you should definitely check Greenport out on the weekends.

Soundview, Greenport: I recently stayed at Soundview and it was the best of both worlds for a stay in Greenport. Every room has an ocean view and a balcony and with the beach right outside your door and a pool, you are all set to enjoy the summer sun. This hotel offers more outdoor amenities than others but is a little further out of town. This didn’t stop us from using the complimentary bikes from the hotel and making the 20-minute ride into town. This is a perfect amenity, instead of driving or Ubering back and forth. The hotel room was spacious for me and my two friends and the service was excellent. I have eaten at their restaurant, The Halyard, before and the views are breathtaking. The complimentary breakfast, pool bar, and piano bar make this hotel an all-around perfect stay for a weekend retreat to the North Fork!

American Beech Hotel: This hotel offers suite options that are great for crowds. We stayed in the two-bedroom suite in the middle of the hotel’s courtyard. The beds were comfy and the common area was perfect for hanging out and getting ready. The room also includes a free breakfast picnic basket at your door each morning with coffee, bagels, yogurt, and granola. What’s great about American Beech is its location right in the center of town and access to all of its restaurants and bars including the Black Llama Bar and 1943 Pizza Bar on the property. There is also a boutique attached to the hotel that sells amazing dresses, jewelry, candles, and even baby clothes. The one thing to know before you go to American Beech is that many of the rooms are right above the lively restaurants and bars. We were there mid-week so it was very quiet but if you plan to go on the weekend, especially in the summer, just be aware that it might be loud until about 11 pm.

The Gallery Hotel: My husband and I stayed at this eclectic boutique hotel, right across the street from American Beech, in October. The whole vibe of the hotel is very 1960s-mod and “Mad Men”. There are multiple rooms where the attention to design detail is incredible and you find hidden, vintage gems at every turn. There is a coffee bar and outdoor garden to relax and enjoy in the mornings. The room we stayed in had a kitchenette and a seating area as well as a balcony with ample outside seating. The only drawback of this room was the bathroom. It was a little awkward with a huge jacuzzi tub and just a handheld shower, which made showering a little tricky. Overall, our stay here was amazing and the location once again, in the middle of town, was great.

 Crazy Beans Diner: If you’re looking for a retro-ish, laid-back breakfast or lunch spot, you have to check out Crazy Beans in the heart of downtown Greenport. You may notice a line around the corner, especially for breakfast, but trust me, it’s worth the wait. The menu is large and offers both breakfast and a variety of lunch options including salads and sandwiches. They also have an extensive ice cream selection. Its cozy inside and no frills, but the perfect spot for brunch or lunch.

The Frisky Oyster: This is a must-try when you are in Greenport. It’s on the main road but without a clear sign, it’s a little hidden. The food at Frisky Oyster is impeccable. So far I’ve been twice and both times they knocked it out of the park. My favorite dishes are the Montauk tuna spring rolls, the chopped vegetable salad, which is so well seasoned and the addition of pesto makes it so special, the grilled halibut with zucchini noodles, and the cauliflower quinoa cakes with truffle are out of this world! What makes this restaurant so special is that they take simple flavors and just make them pop. All of my friends enjoyed their meals including the pomegranate beef short ribs and lobster pasta. You will not have a bad dish at The Frisky Oyster and must stop in while in Greenport, make sure to have reservations.

Bruce and Son: When we were in Greenport in October, my husband and I went to Bruce and Son and we both agreed it was one of the top 5 brunch meals we have ever had. When I went again with my friends, I would have to move it to the number 2 or 3 spot. Bruce and Son has a small menu of breakfast and lunch choices that seem to be pretty simple, but the way they mix ingredients together is what makes you go, “Wow” after each bite. The bacon egg and cheese on brioche with sugar bacon is one of the best sandwiches I have ever tasted! This time we also tried the turmeric granola which had such surprising pops of tastiness from the gooseberries, the hotcake which was a delectable pancake that had been soaked in syrup and doused with fresh berries, and the savory steel-cut oats with mushrooms and goat cheese. Bruce and Son also offer a wide selection of coffee and tea including matcha and mushroom lattes, while also serving a pretty spectacular Bloody Mary and other brunch cocktails. I would go back to Greenport again and again just to eat here. You have to try it!

Little Creek Oyster Farm and Market: If you are craving oysters, chowder, and beer, you must stop by Little Creek. Situated right on the water in a hiddle back alley, you can sit at a picnic table watching the boats and just enjoy the seaside scene. There is a very laid-back vibe here and it’s a great place to stop in for lunch or just for a quick bite in the afternoon. Dogs and kids are welcome as most of the tables are outside, but since its a small space, there may be a wait if you go during a busy time. Just walk along the docks and enjoy the water while you wait!

Greenport has some beautiful beaches and seaside dining options, but the North Fork of Long Island also has some of the best wineries in the area and Greenport is known for its little shops and quaint town. Here are some of my faves:

 Kontokosta Winery Set back after a long drive down through the vineyards and a five-minute drive from Soundview, is this beautiful winery. The views are incredible, not only of the vineyards but also of the Long Island Sound, which you can see from the tables on their patio. The tasting room is equally as gorgeous with high ceilings and plenty of tables. The award-winning Sauvignon Blanc was our favorite and they offered a very nice cheese and cracker spread, no skimping, we even took some home! This is a great place to visit with or without kids and don’t forget to check out their merch on your way out. A friend of mine bought the cozy PJ pants and said they were so comfy!

Croteaux Vineyard: If Rose is your favorite wine of the summer, get yourself to this beautiful vineyard ASAP. With its Instagram-worthy aesthetic and breathtaking views of the vineyard, you will not be disappointed to spend a day at Croteaux. Settle into a picnic table in their Garden tasting area right next to old barns that have been revamped in the style of a modern lounge. Check out their “bottle wall” installation and make sure to check out the food trucks there when you visit. This is a great place to hang with your girlfriends or just sit back and relax with a loved one. Don’t forget to take some of their Rose home with you!

Sparkling Pointe Vineyard: Another beautiful vineyard option for anyone who loves a good sparkling wine, is Sparkling Pointe. Their large tasting room with high ceilings and sweeping chandeliers is beautiful for any occasion. Sitting outside on their patio overlooking the vineyards is just as breathtaking and you will not be disappointed with their menu options, including a very extensive cheese board with many bread options and even a caviar menu. My friends and I enjoyed an afternoon here and went back on our way home to pick up some of their sparkling Brut.

Lavender By The Bay: If you’re looking for a cool experience, stop at Lavender by the Bay on your way into Greenport. Right off the main road, you’ll see a small shop and when you park in the back you will be overwhelmed by the scent of lavender from the fields of purple in front of you. In the high season (summer) they charge $14 per person to visit the grounds. This is a great spot for photos or just to relax or have a little downtime. They have a shop on the premises where you can buy all kinds of lavender-infused goodies. Be sure to check this place out during the summer months. My husband and I made the mistake of going in October and everything was dead! It was still nice to walk around and we weren’t charged, but just know when that the lavender season tends to be May-August, so to get the full experience check it out then!

The Times Vintage: Greenport has an array of cute little shops with home goods, clothing, and accessories but if you’re looking for something out of the ordinary, then this Vintage store is not to be missed. With everything from jackets, dresses, hats, and earrings to old-school house goods and a wide selection of records, The Times Vintage is not only a store but an experience. The back of the store is set up to resemble a 1950s kitchen and another side of the store looks like my basement in the 1980s, complete with a Nintendo and a typewriter! There are so many hidden gems to find in this store, plan to spend some time in here.

Ferry to Shelter Island: One thing I have always wanted to do when I visit Greenport is take a day trip to nearby Shelter Island. I finally had the chance and it was so much fun, I can’t wait to go back. The Ferry leaves Greenport every 10 minutes and is a quick 7-10 minute ride, most people take their cars. Once on Shelter Island, you can go straight to the beach or shop in town or grab some ice cream or just drive around and marvel at the island’s beauty. My friends and I were lucky enough to rent a room at the Sunset Beach Club for the day, which gave us access to their beach, chairs, umbrellas, and other amenities that the hotel offers. This place transports you to Italy or the South of France. The vibes are very European and the beach setup was comfortable and convenient. One thing we were not too impressed with was the lunch at Sunset Beach’s restaurant. The prices were insanely high for sub-par food. You’re basically paying for the atmosphere, which you can get just by walking around the grounds or lounging at the beach. Overall, our day at Sunset Beach was great and we all loved the laid-back vibes of Shelter Island.