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Planning a Long Island Vacation

Think ahead to a Fantastic Summer On Long Island

This year, whether you’re in New York city or anywhere that you’ve been cooped up all winter by yourself or with family, a visit to somewhere you can breathe in the fresh air is in order. Somewhere you can enjoy beachfront dining, and take in charming sites and enjoy fun attractions, perhaps aboard a Private Boat Charter that will make the past year quickly sink behind the valley of an exquisite horizon.

Imagine a Private Yacht in Long Island

If you’re thinking that we’re thinking about travel to The Hamptons, chartering a Yacht Hampton Boat Rental yacht; seeing images of Montauk Harbor, mansions along the Gold Coast, gorgeous vineyards, and dining after a long beach day at one of the many fabulous Long Island New York restaurants, you’re right. Did we mention roasting marshmallows over a bonfire in Fire Island or say anything about a trip to Long Island if only to sink into a hotel bed again, made by someone else? Paradise, here you come

Start your Long Island Summer plans with a Hamptons boat charter

Start your Long Island Summer plans with a Hamptons boat charter

Consider This Your Free Long Island Travel Guide

Your long awaited Long Island travel guide, that is. Search no further, we’ve got the inside scoop on every Long Island location to plan your trip anytime from Mar to Sept. We’re abbreviating to save time getting to the point of getting you off on your Long Island summer vacation.

It Takes a New York Minute to Pack

For those of you who may not know the expression, a New York minute is like everyone else’s second—twice as fast—so open the suitcase and start your clock.

If you’re coming to Long Island from anywhere outside of New York City—whatever your location or language—you don’t have to search any further for vacation ideas. Follow us; just pack up the car and the family, or alert your friends that it’s time to travel, email the job, and post an “adios, miss ya, I’m going on a trip “sign on your Instagram site and make way to Long Island.

It’s time to plan your trip for the summer or even a weekend. Head north and don’t park until you see a sign for the hotel where you’ve booked your accommodations.

Hotel Reservations — The First Item To Check Off Your Getaway List

The last thing you want to hear after a long day in the car or plane trip is “I’m sorry but all our rooms are reserved”. Unless, of course one of those reserved rooms happens to be reserved for you. So when you’re in the planning stage, searching hotel sites and booking online, make sure you get a confirmation email, and if you don’t, then make sure you email the hotels to ask for a reply email before you make the trip to anywhere in Long Island. After traveling many miles, you don’t want to go knocking on local folks’ doors pretending to be a long lost relative coming for a surprise visit. Bottom line: take a page out of our travel plan book—and book ahead.

Confirmation emails make for a stress-free trip

Confirmation emails make for a stress-free trip

Do Not “Drop in” to any Long Island Destinations

The summer (Don’ forget, late Mar thru Sept) is season all across Long Island, so plan your Fire Island or Montauk getaway way in advance. Of course, you can always get lucky, but we do not recommend that approach. Just one of our many valuable Long Island travel tips: book hotels early and get confirmation emails from those you’ve reserved. This will save you a whole lot of aggravation and a need to search for last minute places to stay.

Hotels by the Beach, on an Island, or Right in Town

Whether you’re taking a few days or have put aside an entire summer to explore the gold coast, there are always choices to make, so here’s just a few ideas out of our Long Island guidebook of amazing places you can stay—and eat—during your trip:



    • Gurney’s Montauk Resort and Seawater Spa – The view is beautiful at this beachfront hotel where the room and cocktail prices are (like many places) north of average. But Gurney’s is a Long Island institution and though it has hills and valleys when it comes to reviews, we suggest you make your own assessment
    • Ruschmeyers – With its own restaurant and bar, Ruschmeyers is a Hamptons hotspot. Great place to stay, and play


  • Scarpetta – Located at Gurney’s, this beautiful and delicious Italian/seafood indoor and outdoor eatery is worth the experience whether or not you’re a guest
  • Gosman’s Dock – Worth a trip here for lunch or dinner, the lobster rolls are as good as any on the Long Island Beaches. Casual, fun shopping
  • Duryea’s – Whole Lobster, yachts, sunset, people-watching. Need we say more?

Sag Harbor


    • Baron’s Cove – Charming village and water-facing getaway. Clean, comfortable beds, friendly service, close to all, and a fine restaurant and bar
    • Sag harbor Inn – Luxury Boutique Hotel on the harbor. Complimentary breakfast, quiet, walking distance to center of town


  • The Beacon – Thought to be the best food, and surely the best Marina view, especially at sunset. Close to local theater
  • Lulu Kitchen and Bar – Open kitchen, wood fired-foods . Fun for foodie theater

Shelter Island


    • Dering Harbor Inn – Luxury hotel of suites and villas overlooking Dering Harbor
    • Pridwin Beach Hotel and Cottages – Full amenities, rooms with views and cottages with fireplaces available. On the water, excellent restaurant, worth the short ferry trip


  • Salt – Fabulous fresh seafood and view, frozen drinks and live music at Shipwreck Bar
  • Maria’s Kitchen – Authentic Mexican cuisine, great juice bar, and veggies from their own garden, a Shelter Island gem

East Hampton


    • East Hampton Point – The perfect Hamptons Cottage inn, short drive to LongHouse Reserve and Amagansett Square. Waterfront
    • Mill House Inn – Quiet B & B walking distance to town with lovely garden and comfy beds, nice rooms. Delicious included breakfast


  • Dopo La Spiaggia – Upscale Italian and unique seafood dishes, wonderful ambience and outdoor seating area
  • The Palm – The famous palm can always be counted on for great steaks and lobster and this location stands up to its reputation

Fire Island


    • Fire Island Beach House – 40 room newly renovated hotel across from the most beautiful white island beach for easy access. Basic, family trip-friendly
    • Fire Island Pines – Beautiful rooms and views. Close access to ferry, beaches, harbor, Sunken Forest and Ocean Beach


  • CJ’s Cafe and Bar – Fabulous seafood, upscale bar food, ocean view and Fire Island cocktails. Try the famous Rocket Fuel cocktail
  • Butera’s – Family style Italian, great location for special occasion. Bourbon list and an espresso martini worthy of a trip highlight post
Millhouse Inn B & B, East Hampton

Millhouse Inn B & B, East Hampton

Long Island Vacation Rental Options

Besides hotels, there are plenty of nice motels, private homes and condos on beaches, as well as mansions for rent throughout The Hamptons. Search local listing sites. This route gives you more flexibility if you’re looking to save money or have a set vacation budget. Long Island isn’t known for being an inexpensive destination, but New York has always been full of surprises so it doesn’t hurt to explore air bnb world for owners looking to attract Long Island guests.

Your Private Charter is Way More than a Shuttle Between Attractions

In fact, a Yacht Hamptons Boat Rental is considered by many to be among the main attractions of a Trip to Long Island. This is the number one way to travel between the best beaches, to park and play amazing water sports, or take a trip to see the historic lighthouse in Montauk while enjoying the most beautiful (and always free) event in all of Long Island: sunset on the ocean, or beach, or any place you pause in the water for this signature Long Island attraction that has had visitors planning their getaway since before there even was a Long Island New York and beaches in The Hamptons became the popular destination of celebrities, artists, writers and beach bums alike that it is today.

The look and language here is trendy, artsy, and always beach-chic

The look and language here is trendy, artsy, and always beach-chic

Your Epic Visit to Long Island

The Hamptons is filled with historic places that look like a page torn right out of an American history book. It is also a place of unforgettable beaches and vineyards, and Long Island signature hotspots “You simply must visit”. But the most historic part of a trip to this amazing ocean paradise will be the memories you make that won’t fade in a New York City minute— but will last a good Long Island lifetime.

Copyright 2021