Long Island truly offers something for every traveler. From rolling green hills and local wineries to lush wildlife, charming campgrounds, upscale coastal escapes, pristine beaches, and family‑friendly boardwalks, the region is rich with experiences worth exploring. No matter how long your stay (or what draws you here), there’s a perfect place to match your travel style. Read on to discover the town or region that best fits your vision of a Long Island summer.
Summer Getaways for a Day or a Long Island Weekend
If you’re a local looking for a day away or a visitor hoping to make the most of a long weekend, these towns and regions are perfect for a day trip or a short stay.
With enough to fill several days by the water, South Shore or Fire Island are ideal choices for an extended beach stay. The South Shore features miles of white-sand beaches connecting seaside communities where you can enjoy boardwalks, waterfront trails, a thriving nightlife, and thrilling water excursions. Stay in Babylon to get the most out of the beaches, with easy access to Gilgo Beach, perfect for those looking for tranquility and fishing spots, or Robert Moses State Park, whose 875 acres offer beaches, trails, a golf course, and more to explore. On Field 5, you have the option of taking a day trip to Kismet on the iconic Fire Island and enjoy its unique, pedestrian-only beachside lifestyle.
For those looking to get into the local flavors or to take in the serene, rolling hills of the countryside, explore the North Fork. For the weekend, take advantage of the North Fork’s exclusive winery hotels and cozy B&Bs nestled in the East End region. If you’re just there for the day, head over to Greenport. Just off the Long Island Rail Road, the walkable waterfront village offers a quaint and historic downtown with restaurants, shops, a theater, scenic waterfront views, and fresh, farm-to-table flavors. Not far from Greenport, you can catch a few rays on the beach at Crescent/Sunset Beach.
Romantic Coastal Getaways for Couples
Celebrate your love by falling in love with Long Island’s breathtaking beachfronts, quaint villages, and sprawling countryside. Whether you’re looking for the ideal honeymoon or a spontaneous romantic weekend trip, the region will have you swooning.
Known as the Gold Coast, the North Shore offers charming colonial and New England-style charm on the waterfront. Filled with history, art, and culture, you can tour the North Shore’s historic mansions or pursue the artwork of The Heckscher Museum of Art.
Explore the world together through your taste buds with the variety of cuisine, ranging from authentic Mexican or Indian food to steakhouses and bagel shops! Unwind on its breathtaking beaches, such as the Sunken Meadow State Park, where three miles of pristine beach are paired with tall, glacier-formed bluffs, picturesque hiking trails, and picnicking spots for a stunning afternoon on the water.
North Fork’s winery hotels, nestled in the countryside, are the perfect romantic escape for lovers on the weekend. It is an ideal place to take in the local scenery and flavors while indulging with your special person over some perfectly selected wine. Rose Hill Vineyards & Inn offers a historic farmhouse setting within a natural hideaway built for relaxation and indulgence. An escape from the city, the Inn boasts spacious and sustainable bedrooms, a vineyard at your front steps, and an easy driving distance to the luxurious Hamptons.
Family-Friendly Beach Towns & Summer Spots
Montauk offers an easy-going yet adventurous atmosphere that will appeal to children’s wonder and adults’ need for reprieve. Its rugged coastline and iconic Montauk Point Lighthouse offer a striking backdrop for memorable family photos. Ditch Plains invites relaxed beach strolls and water sports like surfing, while Hither Hills State Park adds to the experience with approachable hikes, easygoing moments spent storytelling around picnic tables or outdoor fireplaces, and sunny afternoons on its sandy beach or playground. In addition to beaches, Montauk features guided tours, charming local businesses, sunset cruises, and more to round out your vacation!
Fair Harbor on Fire Island is great for a day trip with the whole family. After taking the ferry to the island, visitors can explore the lively central harbor, where local ice cream shops delight kids, and eclectic boutiques appeal to adults, all just steps from a lifeguarded beach and playground. Another great day trip for the whole crew is Adventureland in Farmingdale. The amusement park features over 30 adult and kiddie rides, a state-of-the-art arcade, classic fair food, a gift shop, and even more exciting rides coming out this summer!
