Long Island is the perfect balance between city and suburban living! Manhattan is easily accessible, yet parks, oceans, and space to roam free of crowds is at your fingertips (not to mention 24 hour diners, drive-through grocery stores, and one of the biggest malls in the country). The popular Hamptons are only a sliver of what this beautiful island has to offer.
Before You Go
Long Island is at it’s best during the summer time. If you’re just going to spend the weekend, I recommend sticking to one of the destinations I cover below. If you’re going to do a full week, you will be able to fit everything in.
Long Island is shaped like a fish. The fish’s face is closer to Manhattan and the tail leads out into the Atlantic Ocean.
Just so you’re in on the lingo: the top of the fish, located on the Long Island Sound, is known as the North Shore (and the North Fork, as you venture out to the top of the fish’s tail). The fish's belly, located on the Great South Bay, is known as the South Shore (and the South Fork towards the tail).
Long Island is divided into two counties: the Western half is Nassau County and the Eastern half is Suffolk County. Today, we will be focusing on Suffolk County, highlighting Long Island’s best vacation spots: Fire Island, Montauk, The Hamptons, and Wine Country.
Fire Island
Right below the fish’s belly we find Fire Island. Thirty-two miles long and less than one mile wide, this beach community is free from cars and is accessible by ferry. There are three ferry terminals on Long Island's South Shore, depending on which section of Fire Island you’d like to travel to (locals often bring their own boat in lieu of the ferry). Once on the island, water taxis are available to bring you to the 17 different resort communities. Each community comes with it’s own charm and personality (ex. Ocean Beach is a happening place for families or parties to spend the day, Kismet is very laid back, Cherry Grove and The Pines are LGBT-centric communications, etc.).
Rocket Fuel's are the alcoholic drink of choice on Fire Island (it's like a Pina Colada with Amaretto and 151 Rum)! You basically spend your time on the beach or walking to different shops or restaurants. There are hotels, but not many, and they are pricey (which doesn't always mean they are nice). Here is a great article for more information on how the island is broken down: https://www.longislandpress.com/2016/05/21/a-beginners-guide-to-summer-on-fire-island/
Montauk
Also known as "The End," Montauk is located on the end of the Southern tip of Long Island (the lower portion of the fish's tail). A low-key beach community, Montauk is small and quaint with a New York price tag. That doesn't mean you can't find reasonable hotels. Options that are not CrAzY expensive (and you can get a good deal on during the off season) are The Montauk Blue Hotel (right on the beach) and The Montauk Yacht Club (while it’s not in the downtown area, it quietly sits beside Lake Montauk, and is a beautiful hotel).
When in Montauk, plan to be on the beach all day, walking from hotel to hotel along the sand. Sometimes, acoustic guitarists will be playing. Grab a drink and a hotdog and enjoy!
The Hamptons
The area known as The Hamptons is made up of West Hampton, Hampton Bays, Southampton, Bridgehampton, and East Hampton. The Hamptons are very residential but feature some beautiful downtown shopping areas and lovely beaches.
For lodging, renting a huge beachfront house in West Hampton on Dune Road is the way to go. However, this is definitely going to cost you in the 5 digits for a week. If you’re considering the Hamptons for a bachelorette weekend, birthday weekend, or something along those lines, splitting a house with friends a few miles from the water won’t set you back too much financially and will still offer the glimpse of glamour you’re looking for.
When taking time off from your beach days and party nights, be sure to check out some of the local vineyards. Wolffer Estate, in my opinion, is the most beautiful vineyard on Long Island. There are very few vineyards on the South Fork.
The beauty of the Hamptons carries through the trendy and delicious restaurants, like the nautically decadent Dockers, into the charm of local downtown shopping and cultural sites, like the Southampton Historical Museum. While the Hamptons are known for lavishness, residents still cherish life's simple pleasures and use this community to escape the daily hustle and bustle. Relax, unwind, but still wear a Polo, in the Hamptons.
Wine Country
Let me start by saying Long Island is not known for it's wine, HOWEVER, you will still have an amazing time at the wineries. Long Island’s North Fork hosts several sprawling vineyards, many of which are conveniently located on the same road. Each vineyard has it's own unique style. Most provide tables and picnic areas, encouraging you to spend the day sipping wine and eating cheese amongst the vines. Renting a limo and doing a wine tour with a large group is a common activity; for smaller groups, consider utilizing taxis. I would say visiting three vineyards in a day will give you enough time to relax, yet explore Long Island's wine country. You could also just spend the day sitting in an adirondack chair at a single vineyard for HOURS.
Here’s a list of my top ten favorite wineries. I’ve highlighted features each offers based on the season. Also, before planning your trip, make sure you pick at least one vineyard that lets you bring in your own food, so you can have a picnic lunch. And, if you have a group, be sure to make a reservation.
Baiting Hollow Summer: live music Winter: live music & cozy fireplace
Bedell Cellars Winter: chic loft; small but private & comfortable indoor area
Corey Creek Summer: multilevel porch; rustic charm
Kontokosta Summer: ocean view; tons of outdoor space
Marcari Summer: large porch; Cutchogue location has food trucks
Pindar Summer: live music & taco truck
Roanoke Summer: very comfortable; adirondack chairs (members only)
Sherwood House Summer: backyard barn to explore & collection of antiques for sale Winter: acoustic guitarist; fire place
Sparkling Pointe Summer: outdoor couches Winter: large, sunny dining room with ample seating
Wolffer Estate Summer: large porch with beautiful decor
Lastly, when it’s time to eat, check out one of these delicious restaurants: A Mano (Italian food), Claudio's (historical & waterfront), Cooperage Inn (good for brunch and Octoberfest), Love Lane Kitchen (made with love & family owned), Pure (good for picky eaters), Phil's Restaurant (fun). If you have a sweet tooth, top it off with some ice from Magic Fountain. I highly recommend the flavor “Lots of Stuff,” it looks and sounds like it was created by a 5-year-old, but it’s one of the more magical flavors I’ve had.
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From bon fires on the beach to picnics at the vineyards, Long Island has a perfect blend of country charm and city amenities. Once there, you can relax with a laid-back agenda but also, be put to ease knowing you could get a gourmet sandwich at 2am, if need be. A place for families, friends, and couples, Long Island will provide you with the type of vacation you’re looking for: whether it’s chic and trendy, party-central, or comfy-cozy. Thank you for reading! Feel free to ask any questions, and I’ll see you next time on 10-Minute Travel Tips.
See video: https://www.youtube.com/watch?v=gY7knG8hwoc
See video: https://www.youtube.com/watch?v=gY7knG8hwoc
