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22 Nov 2025
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7 best places for weekend getaways from Islip, NY

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

  • Trip Point Pin1

    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.
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  • Trip Point Pin2

    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.
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  • Trip Point Pin3

    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.
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    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.
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    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.
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  • Trip Point Pin6

    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.
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  • Trip Point Pin7

    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.
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Restaurants

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    Lucharitos

    4.5
    $$$$

    Lucharitos

    A lively spot in Greenport known for creative tacos and margaritas in a relaxed, colorful atmosphere.
    4.5
    $$$$
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    Duryea's Lobster Deck

    3.9
    $$$$

    Duryea's Lobster Deck

    This Montauk favorite offers stunning waterfront views and some of Long Island’s best lobster rolls.
    3.9
    $$$$
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    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.
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    The Shed Restaurant

    4.6

    The Shed Restaurant

    A local Hamptons staple serving contemporary American comfort food in a stylish yet casual setting.
    4.6
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    Baron's Cove

    3.3

    Baron's Cove

    Baron’s Cove in Sag Harbor blends local flavors and classic cuisine in a charming waterside setting.
    3.3
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Hotels

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    Gurney’s Montauk Resort & Seawater Spa

    4.1

    Gurney’s Montauk Resort & Seawater Spa

    A luxurious beachfront resort in Montauk known for its ocean views, upscale spa, and beautiful private beach.
    4.1
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    Baron's Cove

    3.3

    Baron's Cove

    A classic Sag Harbor hotel offering elegant rooms, a waterfront pool, and easy access to local attractions.
    3.3
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    The Garden City Hotel

    4.4

    The Garden City Hotel

    A legendary Long Island hotel with refined accommodations, an award-winning restaurant, and convenient location.
    4.4
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    The Inn at Fox Hollow Hotel

    4

    The Inn at Fox Hollow Hotel

    An all-suite boutique hotel featuring spacious rooms, complimentary gourmet breakfast, and a tranquil suburban setting.
    4
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    Topping Rose House

    4.3
    $$$$

    Topping Rose House

    A luxury Hamptons hotel that combines classic charm with modern amenities, farm-to-table dining, and serene surroundings.
    4.3
    $$$$
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Local Events & Happenings

  • Event Icon

    Sherri Shepherd

    Sherri Shepherd

    The event will take place at Patchogue Theater in Patchogue.
    Map IconPatchogue Theater in Patchogue (7.36 mi)
    Calendar Icon1 Feb 2026
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    Billy Gibbons

    Billy Gibbons

    The event will take place at Patchogue Theater in Patchogue.
    Map IconPatchogue Theater in Patchogue (7.36 mi)
    Calendar Icon15 Feb 2026
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    THANKSGIVING EVE La Casita edition

    THANKSGIVING EVE La Casita edition

    The event will take place at Stereo Garden in Patchogue.
    Map IconStereo Garden in Patchogue (7.5 mi)
    Calendar Icon27 Nov 2025
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    LONG ISLAND COMEDY JAM & After-Party

    LONG ISLAND COMEDY JAM & After-Party

    Suffolk/ Nassau County get ready for LONG ISLAND COMEDY JAM & After-Party @Stereogardenli Saturday November 29th [Thanksgiving Weekend] Hosted by funny man @RobStapleton @SmokeySuarez @Joclownz @IamBlackRoseNYC and more!!! Doors 7:00pm Showtime: 8:30...
    Map IconStereo Garden in Patchogue (7.5 mi)
    Calendar Icon30 Nov 2025
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    The Au BLACK affair

    The Au BLACK affair

    The event will take place at Stereo Garden in Patchogue.
    Map IconStereo Garden in Patchogue (7.5 mi)
    Calendar Icon13 Dec 2025
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    MACH 8 DADDY Pasame la Botella

    MACH 8 DADDY Pasame la Botella

    The event will take place at Stereo Garden in Patchogue.
    Map IconStereo Garden in Patchogue (7.5 mi)
    Calendar Icon14 Dec 2025
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  • Event Icon

    THE NAUGHTY LIST

    THE NAUGHTY LIST

    The event will take place at Stereo Garden in Patchogue.
    Map IconStereo Garden in Patchogue (7.5 mi)
    Calendar Icon20 Dec 2025
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Travel Gems from Reddit

  • Reddit Icon

    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...

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

    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...

    /r/longisland
  • Reddit Icon

    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...

    Weekend getaway

    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...

    /r/longisland
  • Reddit Icon

    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 ...

    Recommendation for planning a trip to Long Island?

    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 ...

    /r/longisland
  • Reddit Icon

    Years back we spent a nice weekend in Sag Harbor.

    Best Place for A Mini Vacation in Long Island?

    Years back we spent a nice weekend in Sag Harbor.

    /r/longisland

Music for Your Journey

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    Coldplay - Viva La Vida

    Coldplay - Viva La Vida

    An uplifting anthem perfect for scenic drives and inspiring exploration.
    Listen on Spotify
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    Rusted Root - Send Me on My Way

    Rusted Root - Send Me on My Way

    A feel-good, adventurous tune that sets a positive mood for travel.
    Listen on Spotify
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    Rascal Flatts - Life is a Highway

    Rascal Flatts - Life is a Highway

    A classic road trip song that energizes any journey.
    Listen on Spotify
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    Fleetwood Mac - Go Your Own Way - 2004 Remaster

    Fleetwood Mac - Go Your Own Way - 2004 Remaster

    Encourages freedom and spontaneity during a getaway.
    Listen on Spotify
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    Edward Sharpe & The Magnetic Zeros - Home

    Edward Sharpe & The Magnetic Zeros - Home

    A warm, acoustic song to remind you of comfort and discovery.
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    Billy Joel - New York State of Mind

    Billy Joel - New York State of Mind

    Perfect for traveling around New York and feeling connected to the state.
    Listen on Spotify
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    Katrina & The Waves - Walking On Sunshine

    Katrina & The Waves - Walking On Sunshine

    A bright, optimistic tune that matches the joy of exploring new places.
    Listen on Spotify
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    WALK THE MOON - Shut Up and Dance

    WALK THE MOON - Shut Up and Dance

    An energetic, fun song to keep spirits high during your trip.
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    Ed Sheeran - Castle on the Hill

    Ed Sheeran - Castle on the Hill

    Captures nostalgia and the beauty of drive-through landscapes.
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  • Music Icon

    The Chicks - Wide Open Spaces

    The Chicks - Wide Open Spaces

    Invites you to embrace adventure and the freedom of the open road.
    Listen on Spotify
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