10 Best Places for Romantic Weekend Getaway from Brookhaven, NY

10 Jun 2026Updated last time

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

  • Montauk offers stunning ocean views, romantic beaches, charming lighthouses, and a relaxing coastal atmosphere ideal for couples seeking tranquility and scenic beauty.
  • 2

    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.
  • 3

    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.
  • 4

    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.
  • Newport offers romantic cliff walks, grand historic mansions, oceanfront dining, and a lively harbor, perfect for couples who appreciate culture, history, and seaside beauty.
  • Mystic combines maritime history with small-town charm, featuring an enchanting seaport, picturesque waterfront, unique shops, and cozy inns ideal for cozy weekends.
  • 7

    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.
  • 8

    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.
  • Hudson features a vibrant arts scene, antique shops, gourmet restaurants, and stunning river views, making it ideal for couples who enjoy culture and exploration.
  • 10

    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.

Restaurants

  • Picture for The Frisky Oyster

    The Frisky Oyster

    27 Front St, Greenport, NY 11944, USA
    Known for its creative seafood dishes and chic ambiance, this Greenport spot offers a unique and romantic dining experience.
    4.3
    $$$$
  • Picture for The Surf Lodge

    The Surf Lodge

    183 Edgemere St, Montauk, NY 11954, USA
    Set by the water in Montauk, this trendy venue blends fresh cuisine, live music, and breathtaking sunset views for an unforgettable evening.
    5
  • Picture for The Maidstone

    The Maidstone

    207 Main St, East Hampton, NY 11937, ארצות הברית
    Located in East Hampton, this eclectic restaurant features Scandinavian-inspired fare in a boutique hotel setting, complete with garden dining.
    4.2
  • Picture for The 1770 House

    The 1770 House

    143 Main St, East Hampton, NY 11937, USA
    A historic inn and restaurant in East Hampton, offering romantic candlelit dinners and gourmet cuisine in an intimate, centuries-old setting.
    4.7
    $$$$
  • Picture for Dopo La Spiaggia

    Dopo La Spiaggia

    6 Bay St, Sag Harbor, NY 11963, USA
    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
    $$$$

Hotels

  • The Surf Lodge

    183 Edgemere St, Montauk, NY 11954, USA

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

    209 Front St, Greenport, NY 11944, USA

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

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

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

    207 Main St, East Hampton, NY 11937, ארצות הברית

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

    11 Stearns Point Rd, Shelter Island Heights, NY 11965, USA

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

Local Events & Happenings

  • Picture for 5 Seconds of Summer: EVERYONE'S A STAR! World Tour

    5 Seconds of Summer: EVERYONE'S A STAR! World Tour

    Mohegan Sun Arena in Uncasville (27.04 mi)30 May 2026
    The event will take place at Mohegan Sun Arena in Uncasville.
  • Picture for Air Supply 50th Anniversary Celebration

    Air Supply 50th Anniversary Celebration

    Mohegan Sun Arena in Uncasville (27.04 mi)31 May 2026
    The event will take place at Mohegan Sun Arena in Uncasville.
  • Picture for Teddy Swims - Summer 2026 Tour

    Teddy Swims - Summer 2026 Tour

    Mohegan Sun Arena in Uncasville (27.04 mi)5 Jun 2026
    The event will take place at Mohegan Sun Arena in Uncasville.
  • Picture for Carin Leon - De Sonora Para El Mundo Tour 2026

    Carin Leon - De Sonora Para El Mundo Tour 2026

    Mohegan Sun Arena in Uncasville (27.04 mi)7 Jun 2026
    The event will take place at Mohegan Sun Arena in Uncasville.
  • Picture for Wet Leg

    Wet Leg

    Mohegan Sun Arena in Uncasville (27.04 mi)14 Jun 2026
    The event will take place at Mohegan Sun Arena in Uncasville.
  • Picture for Lauren Daigle

    Lauren Daigle

    Mohegan Sun Arena in Uncasville (27.04 mi)18 Jun 2026
    The event will take place at Mohegan Sun Arena in Uncasville.
  • Picture for Tucker Wetmore: The Brunette World Tour

    Tucker Wetmore: The Brunette World Tour

    Mohegan Sun Arena in Uncasville (27.04 mi)21 Jun 2026
    The event will take place at Mohegan Sun Arena in Uncasville.

Travel Gems from Reddit

  • Romantic Weekend Getaway Upstate NY

    /r/upstate_new_york

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

  • Couples getaway

    /r/upstate_new_york

    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

  • Retreat for a couple within 2 hours drive of NYC?

    /r/NYCbitcheswithtaste

    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

  • Cute affordable weekend getaway from the city?

    /r/AskNYC

    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

  • Weekend getaway with boyfriend

    /r/upstate_new_york

    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