7 best places for weekend getaways from Islip, NY

08 Jun 2026Updated last time

Weekend Getaway Itinerary from Islip, NY

Embark on an unforgettable weekend adventure starting from Islip, NY, and explore some of Long Island’s finest attractions. Begin your journey with a scenic drive to the historic Montauk Point Lighthouse, where sweeping ocean views and maritime history await. For nature lovers, the Fire Island National Seashore offers tranquil beaches, wildlife spotting, and memorable walks along the sand dunes and boardwalks. Dive into the world of art, science, and exploration at the Vanderbilt Museum and Planetarium, which captivates visitors with its impressive estate and engaging exhibits.

Later, delve into maritime history at the Sag Harbor Whaling Museum, set in a charming historic village, and immerse yourself in the beauty of Old Westbury Gardens, where grand architecture meets lush formal gardens. Stroll through the magnificent landscapes of Planting Fields Arboretum State Historic Park, home to rare and exotic plant species. Finally, indulge in the elegance of Oheka Castle, a grand chateau offering a taste of old-world luxury and romance. This carefully curated weekend itinerary promises a blend of history, culture, natural beauty, and relaxation for every traveler.


Recommended Activities

  • 1

    Montauk Point Lighthouse

    The Montauk Point Lighthouse is the oldest lighthouse in New York State, offering breathtaking ocean views, a historic museum inside, and scenic walking trails surrounding the landmark.
  • 2

    Fire Island National Seashore

    Fire Island National Seashore features pristine beaches, a preserved wilderness area, picturesque boardwalks, and the iconic Fire Island Lighthouse, making it ideal for relaxation, nature walks, and wildlife spotting.
  • 3

    The Vanderbilt Museum and Planetarium

    The Vanderbilt Museum and Planetarium combines beautiful Gold Coast-era architecture, engaging exhibits on maritime history and exploration, and a modern planetarium with star shows, all set on scenic grounds overlooking the Long Island Sound.
  • 4

    Sag Harbor Whaling Museum

    The Sag Harbor Whaling Museum offers fascinating exhibits about the region's rich maritime and whaling history, housed in a historic 1845 mansion with striking architecture and close access to charming Sag Harbor Village.
  • 5

    Old Westbury Gardens

    Old Westbury Gardens showcases a grand Charles II-style mansion and 200 acres of exquisite formal gardens, woodlands, and lakes, perfect for leisurely strolls and photography in a setting steeped in history.
  • 6

    Planting Fields Arboretum State Historic Park

    Planting Fields Arboretum State Historic Park boasts beautifully landscaped gardens, historic greenhouses, and the grand Coe Hall mansion, making it an ideal destination for garden enthusiasts and those seeking outdoor serenity.
  • 7

    Oheka Castle

    Oheka Castle is a stunning French-style chateau that offers elegant architecture, beautifully manicured gardens, and a rich history as one of America’s largest private estates, making it perfect for history lovers, architecture enthusiasts, and romantic getaways.

Restaurants

  • Picture for Lucharitos
    119 Main St, Greenport, NY 11944, USA
    A lively spot in Greenport known for creative tacos and margaritas in a relaxed, colorful atmosphere.
    4.5
    $$$$
  • Picture for Duryea's Lobster Deck

    Duryea's Lobster Deck

    65 Tuthill Rd, Montauk, NY 11954, ארצות הברית
    This Montauk favorite offers stunning waterfront views and some of Long Island’s best lobster rolls.
    3.9
    $$$$
  • Picture for Ella’s Oyster Bar

    Ella’s Oyster Bar

    Renowned for fresh seafood and a welcoming vibe, Ella’s Oyster Bar is a must-try along the coast.
  • Picture for The Shed Restaurant

    The Shed Restaurant

    46 Front St, South Jamesport, NY 11970, USA
    A local Hamptons staple serving contemporary American comfort food in a stylish yet casual setting.
    4.6
  • Picture for Baron's Cove
    31 W Water St, Sag Harbor, NY 11963, USA
    Baron’s Cove in Sag Harbor blends local flavors and classic cuisine in a charming waterside setting.
    3.3

Hotels

  • Gurney’s Montauk Resort & Seawater Spa

    290 Old Montauk Hwy, Montauk, NY 11954, ארצות הברית

    A luxurious beachfront resort in Montauk known for its ocean views, upscale spa, and beautiful private beach.
  • Baron's Cove

    31 W Water St, Sag Harbor, NY 11963, USA

    A classic Sag Harbor hotel offering elegant rooms, a waterfront pool, and easy access to local attractions.
  • The Garden City Hotel

    45 7th St, Garden City, NY 11530, США

    A legendary Long Island hotel with refined accommodations, an award-winning restaurant, and convenient location.
  • The Inn at Fox Hollow Hotel

    7755 Jericho Tpke, Woodbury, NY 11797, USA

    An all-suite boutique hotel featuring spacious rooms, complimentary gourmet breakfast, and a tranquil suburban setting.
  • Topping Rose House

    1 Bridgehampton-Sag Harbor Turnpike, Bridgehampton, NY 11932, United States

    A luxury Hamptons hotel that combines classic charm with modern amenities, farm-to-table dining, and serene surroundings.

Local Events & Happenings

  • Picture for Freedom Fest 2026

    Freedom Fest 2026

    Catholic Health Amphitheater at Bald Hill in Farmingville (2.29 mi)3 Jul 2026
    Please note that all tickets to this event are free. You are purchasing a special limited VIP ticket which includes a guaranteed seat in the orchestra behind an enclosed standing area, access to the Jake's 58 pit and access to the VIP chalet. On site...
  • Picture for Freestyle Feast 2026

    Freestyle Feast 2026

    Catholic Health Amphitheater at Bald Hill in Farmingville (2.29 mi)25 Jul 2026
    The event will take place at Catholic Health Amphitheater at Bald Hill in Farmingville.
  • Picture for Young Frankenstein

    Young Frankenstein

    Theatre Three - NY in Port Jefferson (5.5 mi)31 May 2026
    The event will take place at Theatre Three - NY in Port Jefferson.
  • Picture for Cabaret

    Cabaret

    Theatre Three - NY in Port Jefferson (5.5 mi)20 Sep 2026
    The event will take place at Theatre Three - NY in Port Jefferson.

Travel Gems from Reddit

  • Need a peaceful weekend getaway not further than maybe a 2-3 ...

    /r/longisland

    Consider Rhode Island, specifically Newport or Providence. Best way is to take the Orient Pt Ferry to New London, from there its only an hours drive. Newport has a lot of hist...

  • Weekend getaway

    /r/longisland

    Weekend getaway . Hiiii!! Looking for a little weekend getaway with my partner, 3 hours max drive, any recommendations? Looking for a relaxing, fall type of trip, any help wou...

  • Recommendation for planning a trip to Long Island?

    /r/longisland

    When I lived in the city many years ago, my BF (now husband) and I went to Montauk in the dead of winter for a weekend and loved it. You can take a direct train and the place ...

  • Best Place for A Mini Vacation in Long Island?

    /r/longisland

    Years back we spent a nice weekend in Sag Harbor.