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06 Sep 2025
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10 Best Places for Romantic Weekend Getaway from Brookhaven, NY

Romantic Weekend Getaways from Brookhaven, NY: Itinerary Overview

Escape the ordinary and embark on a journey to some of the most enchanting destinations just a short drive from Brookhaven, NY. Whether you seek the calming sounds of ocean waves, charming historic towns, or tranquil wine country landscapes, this selection of romantic weekend getaways has something for every couple. Relax on the sandy shores of Montauk, stroll hand in hand through the sophisticated streets of The Hamptons, or savor a cozy dinner overlooking the water in Greenport. Discover the untouched beauty of Fire Island's car-free communities, the grandeur of Newport's legendary mansions, and the maritime charm of Mystic, CT. Delight your senses in North Fork’s vineyards, find seclusion on the peaceful Shelter Island, or get inspired by Hudson’s vibrant arts scene. Don’t miss Sag Harbor, where historic allure meets coastal elegance. Each destination is selected for its romantic ambiance, unique attractions, and unforgettable experiences, ensuring a perfect weekend retreat for you and your loved one.


Recommended Activities

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    Montauk, NY

    Montauk offers stunning ocean views, romantic beaches, charming lighthouses, and a relaxing coastal atmosphere ideal for couples seeking tranquility and scenic beauty.
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    The Hamptons, NY

    The Hamptons are known for luxurious resorts, fine dining, art galleries, and beautiful sandy beaches, making it a favorite romantic escape for couples looking to enjoy sophistication and leisure.
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    Greenport, NY

    Greenport provides a quaint and picturesque village feel with waterfront dining, boutique shops, local wineries, and opportunities for romantic strolls along the harbor.
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  • Trip Point Pin4

    Fire Island, NY

    Fire Island is renowned for its pristine beaches, car-free environment, charming coastal villages, and stunning sunsets, creating an intimate and peaceful getaway for couples.
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    Newport, RI

    Newport offers romantic cliff walks, grand historic mansions, oceanfront dining, and a lively harbor, perfect for couples who appreciate culture, history, and seaside beauty.
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  • Mystic combines maritime history with small-town charm, featuring an enchanting seaport, picturesque waterfront, unique shops, and cozy inns ideal for cozy weekends.
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    North Fork, NY

    North Fork is known for its serene vineyards, scenic countryside, farm-to-table dining, and romantic wine tastings, providing a relaxing escape for couples.
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    Shelter Island, NY

    Shelter Island offers peaceful nature preserves, quiet beaches, charming inns, and a laid-back atmosphere perfect for couples seeking privacy and natural beauty.
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  • Hudson features a vibrant arts scene, antique shops, gourmet restaurants, and stunning river views, making it ideal for couples who enjoy culture and exploration.
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    Sag Harbor, NY

    Sag Harbor is a historic waterfront village with charming streets, boutique shops, fine dining, and scenic harbor views, offering couples a romantic and culturally rich getaway.
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Restaurants

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    The Frisky Oyster

    7.8
    $$$$

    The Frisky Oyster

    Known for its creative seafood dishes and chic ambiance, this Greenport spot offers a unique and romantic dining experience.
    7.8
    $$$$
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    The Surf Lodge

    3.9

    The Surf Lodge

    Set by the water in Montauk, this trendy venue blends fresh cuisine, live music, and breathtaking sunset views for an unforgettable evening.
    3.9
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    The Maidstone

    3.8

    The Maidstone

    Located in East Hampton, this eclectic restaurant features Scandinavian-inspired fare in a boutique hotel setting, complete with garden dining.
    3.8
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    The 1770 House

    4.3
    $$$$

    The 1770 House

    A historic inn and restaurant in East Hampton, offering romantic candlelit dinners and gourmet cuisine in an intimate, centuries-old setting.
    4.3
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    Dopo La Spiaggia

    4.3
    $$$$

    Dopo La Spiaggia

    Tucked away in Sag Harbor, this cozy Italian spot is celebrated for its authentic dishes and charming waterside views, perfect for a romantic meal.
    4.3
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Hotels

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    The Surf Lodge

    3.9

    The Surf Lodge

    A vibrant hotel in Montauk known for its boho-chic design, waterfront setting, live music, and lively summer atmosphere.
    3.9
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    The Harborfront Inn

    7.3

    The Harborfront Inn

    Nestled in Greenport, this boutique inn offers modern amenities, nautical charm, and stunning views of the Peconic Bay.
    7.3
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    Gurney’s Montauk Resort & Seawater Spa

    4.1

    Gurney’s Montauk Resort & Seawater Spa

    Famed for its private beach, oceanfront rooms, and luxurious spa services, it's perfect for couples seeking relaxation and pampering.
    4.1
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    The Maidstone Hotel

    3.8

    The Maidstone Hotel

    A boutique hotel in East Hampton with Scandinavian-inspired rooms, eclectic decor, and a dog-friendly, artsy vibe.
    3.8
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    Shelter Island House

    4.5

    Shelter Island House

    Located on Shelter Island, this charming boutique hotel offers beautiful gardens, cozy rooms, and an intimate, peaceful escape.
    4.5
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Local Events & Happenings

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    PITBULL

    PITBULL

    The event will take place at Mohegan Sun Arena in Uncasville.
    Map IconMohegan Sun Arena in Uncasville (25.23 mi)
    Calendar Icon30 Dec 2024
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    TEST

    TEST

    The event will take place at Mohegan Sun Arena in Uncasville.
    Map IconMohegan Sun Arena in Uncasville (25.23 mi)
    Calendar Icon31 Dec 2024
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    NEW YEAR'S EVE DINNER GALA

    NEW YEAR'S EVE DINNER GALA

    The event will take place at Mohegan Sun Uncas Ballroom in Uncasville.
    Map IconMohegan Sun Uncas Ballroom in Uncasville (25.23 mi)
    Calendar Icon31 Dec 2024
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    Elvis Spectacular

    Elvis Spectacular

    The event will take place at Mohegan Sun Arena in Uncasville.
    Map IconMohegan Sun Arena in Uncasville (25.23 mi)
    Calendar Icon1 Jan 2025
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    Connecticut Sun vs Phoenix Mercury

    Connecticut Sun vs Phoenix Mercury

    The event will take place at Mohegan Sun Arena in Uncasville.
    Map IconMohegan Sun Arena in Uncasville (25.23 mi)
    Calendar Icon6 Sep 2025
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    September 6,2025 Source Member Guest

    September 6,2025 Source Member Guest

    The event will take place at Mohegan Sun Arena in Uncasville.
    Map IconMohegan Sun Arena in Uncasville (25.23 mi)
    Calendar Icon6 Sep 2025
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  • Event Icon

    Connecticut Sun vs Atlanta Dream

    Connecticut Sun vs Atlanta Dream

    The event will take place at Mohegan Sun Arena in Uncasville.
    Map IconMohegan Sun Arena in Uncasville (25.23 mi)
    Calendar Icon10 Sep 2025
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Travel Gems from Reddit

  • Reddit Icon

    New Yorkers from NYC requesting for any suggestions for a weekend getaway (upstate)? Were contemplating either Wildflower Farms or the Bradstan

    Romantic Weekend Getaway Upstate NY

    New Yorkers from NYC requesting for any suggestions for a weekend getaway (upstate)? Were contemplating either Wildflower Farms or the Bradstan

    /r/upstate_new_york
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    22 votes, 45 comments. Husband and I want to getaway for 2 days during the week for our babymoon. Want to visit a place that is calm and relaxing but

    Couples getaway

    22 votes, 45 comments. Husband and I want to getaway for 2 days during the week for our babymoon. Want to visit a place that is calm and relaxing but

    /r/upstate_new_york
  • Reddit Icon

    21 votes, 34 comments. I want to treat my partner to a stay (1 or 2 nights depending on price) at a retreat/spa within 2 hours drive of NYC

    Retreat for a couple within 2 hours drive of NYC?

    21 votes, 34 comments. I want to treat my partner to a stay (1 or 2 nights depending on price) at a retreat/spa within 2 hours drive of NYC

    /r/NYCbitcheswithtaste
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    18 votes, 35 comments. hi! I'm looking to surprise my partner with a weekend getaway anywhere within 5 hours from the city, not looking for anything

    Cute affordable weekend getaway from the city?

    18 votes, 35 comments. hi! I'm looking to surprise my partner with a weekend getaway anywhere within 5 hours from the city, not looking for anything

    /r/AskNYC
  • Reddit Icon

    12 votes, 46 comments. After supporting me through a tough time Id love to treat my boyfriend (were both 27) to a weekend upstate! Does anyone have

    Weekend getaway with boyfriend

    12 votes, 46 comments. After supporting me through a tough time Id love to treat my boyfriend (were both 27) to a weekend upstate! Does anyone have

    /r/upstate_new_york

Music for Your Journey

  • Music Icon

    Leon Bridges - Beyond

    Leon Bridges - Beyond

    A soulful romantic anthem that perfectly captures the spirit of an adventurous journey together.
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    Maroon 5 - Sunday Morning

    Maroon 5 - Sunday Morning

    A warm, mellow track that sets a comforting and leisurely weekend mood.
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    Edward Sharpe & The Magnetic Zeros - Home

    Edward Sharpe & The Magnetic Zeros - Home

    Its hopeful lyrics and bright melody evoke feelings of adventure and togetherness.
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    George Ezra - Budapest

    George Ezra - Budapest

    A whimsical and catchy tune, ideal for road trips and exploring new places.
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    Billie Eilish - ocean eyes

    Billie Eilish - ocean eyes

    The dreamy soundscape fits perfectly with scenic coastal drives and waterfront views.
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    Jack Johnson - Better Together

    Jack Johnson - Better Together

    A heartfelt ode to love, making it a perfect choice for romantic escapes.
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    MGMT - Electric Feel

    MGMT - Electric Feel

    Upbeat and energetic, it brings a sense of fun and excitement to any trip.
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    Coldplay - Yellow

    Coldplay - Yellow

    An uplifting song that matches the awe of discovering breathtaking landscapes.
    Listen on Spotify
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    The Lumineers - Ho Hey

    The Lumineers - Ho Hey

    Folk-inspired and spirited, great for singing along as you drive through charming towns.
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    Fleetwood Mac - Dreams - 2004 Remaster

    Fleetwood Mac - Dreams - 2004 Remaster

    A classic road trip song with a breezy vibe, perfect for unwinding together.
    Listen on Spotify
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