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Southold

Welcome to Southold, NY 11971, a charming slice of Long Island paradise! With its picturesque vineyards, sandy beaches, and quaint historic charm, this coastal gem invites you to sip local wines, stroll through lush orchards, and enjoy stunning sunsets. Don’t miss the Southold Lighthouse or the delicious seafood restaurants—perfect for an unforgettable getaway! 🌊🍷

From the Community

matthewaperrone

Recommendations

Outdoor5/5

Southold Bay

Welcome to Southold Bay, where coastal charm meets serene beauty! This picturesque spot in Southold, NY, offers stunning views, tranquil waters, and lovely sandy beaches perfect for sunbathing or picnicking. Explore quaint local shops, savor fresh seafood, and don’t miss the breathtaking sunsets. Whether you’re boating or just basking, Southold Bay is a slice of paradise waiting to be discovered!

Cafe4.2/5

Minnow At The Galley Ho

Located in New Suffolk, Minnow At The Galley Ho offers a unique blend of fresh, locally sourced seafood and stunning waterfront views, creating an unforgettable dining experience that captures the charm of the East End.

Drink$$$4.8/5

Brix & Rye

Nestled in Greenport, NY, Brix & Rye is an iconic destination for craft cocktails and artisanal bites, renowned for its vibrant atmosphere and expertly curated spirits, making it a must-visit for locals and travelers alike.

Eat4.7/5

Southold Fish Market

Cafe$$$4.4/5

Stone Street Cafe

Stone Street Cafe offers a charming blend of local flavors and a cozy atmosphere, making it a must-visit destination for delicious brunch and unforgettable coffee in the heart of Southold.

Eat4.6/5

Greenport Harbor Brewing Company

Eat$$$$4.6/5

Southold Social

Nestled in the charming town of Southold, Southold Social is your go-to spot for laid-back vibes and delicious bites! With a menu boasting fresh farm-to-table dishes and a creative craft cocktail list, it’s a foodie’s paradise. Swing by for a game of bocce outside or enjoy live music—perfect for making memories on the North Fork!

Stays

Stay$$4.4/5

The Harbor Front Inn

Offering a seasonal outdoor swimming pool and a fitness center, The Harbor Front Inn is centrally located near the shops and restaurants in Greenport. Free WiFi access is available. Beach access is 1.9 km away. A flat-screen cable TV and refrigerator are included in each guest room. The private bathrooms are equipped with a hairdryer and a bathrobe. A balcony is available for certain room types. A front desk is available at the Harbor Front Inn. North Ferry Terminal is just 3 minutes’ walk from the property. Kontokosta Winery is 3 minutes’ drive.

Stay$$$$4.1/5

Sound View Greenport

Set on the North Fork in Greenport, 157 km from New York City, Sound View Greenport features a seasonal outdoor pool and views of the Long Island Sound. Guests can enjoy a drink at the bar. Some units include a seating area where you can relax. The rooms have a private bathroom fitted with a shower. For your comfort, you will find free toiletries and a hair dryer. There is a shared lounge at the property. There is a private beach area and bike hire is available. You can play tennis at the property. Montauk is 38 km from Sound View Greenport, while East Hampton is 23 km away.

Stay4.9/5

The Harvest Inn

Nestled in the heart of the North Fork, The Harvest Inn boasts charming accommodations and delightful farm-to-table cuisine, making it a perfect retreat for those seeking a unique blend of relaxation and local flavor.

Stay4.3/5

The Blue Inn at North Fork

Nestled in the picturesque North Fork, The Blue Inn offers charming coastal accommodations, breathtaking views, and easy access to local vineyards, making it an iconic retreat for relaxation and exploration in East Marion.

Stay4.3/5

The Pridwin Hotel & Cottages

Get ready to sail into an island paradise at The Pridwin! Located at 81 Shore Rd, Shelter Island, NY, this seaside gem will have you grinning from ear to ear. With stunning views, cozy beachside rooms, and delicious seafood galore, you'll never want to leave. So come on over and let The Pridwin make your vacation dreams come true!

Stay4.2/5

Greenporter Hotel

Nestled in the heart of Greenport, New York, the Greenporter Hotel captivates with its charming coastal vibe, inviting amenities, and easy access to local vineyards and stunning waterfront views, making it an iconic getaway.

Eat$$$$4.1/5

The Halyard Restaurant

Things To Do
Provided by

5/5

5 h

Private Guided Wine Country Bike Tour in Mattituck

Nature Abounds on this 4.5-Hour Wine Country Bike Tour. An excellent way to see Long Island's Wine Country here on the North Fork. Take in beautiful views on this relaxing guided 4.5 Hour Tour cruise thru the scenic backroads of the charming north fork. On this backroads ride, nature abounds as seasoned guides lead you on winding roads up close to the tranquil Peconic Bay. Choose between 12, 14.5, 16, or 19 Mile routes...your preference. This tour has the ability to customize your experience. Different routes will offer different vineyard stops. After booking we will contact you via phone to craft the perfect experience that YOU are looking for! Bike riding is mostly flat with a few rolling hills.

$249.00

5/5

2 h

Sunday Brunch Sail in Greenport

You haven't truly visited the North Fork if you haven't been on the water! A sailing trip is hands down the best ways to see the East End of Long Island, and sailing aboard our unique schooner makes the experience extra special. Unlike private charters that are widely offered in the area, this ticketed sail allows you to get on the water at a more affordable price.

$175.00

5/5

Half Day(AM) North Fork Private Wine & Food Tour by Local Expert

As local experts, we take the guesswork out of planning your visit to the North Fork of Long Island. We know which venues are the most memorable and which wines are most enjoyable. As a team of passionate locals, we have scoured the area to handpick the best vineyards, restaurants, and hidden gems that you won't find on your average tourist map or group tour. Our expert guides will accompany you every step of the way, providing insider knowledge and fascinating stories about the rich history of the North Fork. Our private slow tour is 100% customizable and is tailored to you and/or your group's interests. Our all-inclusive fee covers all activities, food/wine, gratuities, and transportation for a seamless and memorable experience. Rain or shine.

$439.00

5/5

Private Luxury Wine Tours of Long Island Pindar Winery

Discover the beauty and flavor of Long Island's wine country on this private tour tailored for wine enthusiasts and nature lovers. Begin your day with a comfortable transfer from Hicksville LIRR Station to the picturesque East End, where the charming Pindar Vineyards awaits. Enjoy a guided tasting of handcrafted wines amidst a scenic backdrop, complemented by casual music and insights into the local winemaking heritage. An optional lunch at one of the wineries allows for relaxation and enjoyment of the stunning views & Visit to Raphael Vineyards & Lenz Winery . - Private tour perfect for wine enthusiasts and nature lovers - Guided tour & tastings at Pindar Vineyards - Visit to Raphael Vineyards & Lenz Winery for Photoshop - Comfortable transport provided from Hicksville LIRR Station

$198.00

5/5

North Fork Full Day Private Wine & Food Tour by Local Expert

As local experts, we take the guess work out of planning your visit to the North Fork of Long Island. We know which venues are the most memorable and which wines are most enjoyable. As a team of passionate locals, we have scoured the area to handpick the best vineyards, restaurants, and hidden gems that you won't find on your average tourist map or group tour. Our expert guides will accompany you every step of the way, providing insider knowledge and fascinating stories about the rich history of the North Fork. Our private slow tour is 100% customizable and is tailored to you and/or your group's interests. Our all inclusive fee covers all activities, food/wine, gratuities, and transportation for a seamless and memorable experience. Rain or shine.

$579.00

5/5

4 h 30 mins

Private Guided Wine Country Bike Tour For Two (Mattituck)

Nature Abounds on this 4.5 Hour Wine Country Bike Tour. An excellent way to see Long Island's Wine Country here on the North Fork. Take in beautiful views on this relaxing guided 4.5 Hour Tour cruise thru scenic backroads of the charming north fork. On this backroads ride, nature abounds as seasoned guides lead you on winding roads up close to the tranquil Peconic Bay. Choose between 12, 14.5, 16, or 19 Mile routes...your preference. This tour has the ability to customize your experience. Different routes will offer different vineyard stops. After booking we will contact you via phone to craft the perfect experience that YOU are looking for! Bike riding is mostly flat with a few rolling hills.

$405.00

5/5

8 h

Full Day Private Long Island Wine Tours from New York City

Welcome to the ultimate East End Long Island Wine Adventure! Prepare to immerse yourself in a journey through the region's lush vineyards, picturesque landscapes, and a symphony of exquisite flavors awaiting at every turn. Our escapade 1st stop is at the Bridge Lane Tasting Room, nestled snugly in the heart of Long Island's esteemed wine country. Bridge Lane's award-winning wines awaits your discerning palate. From crisp whites to robust reds, each sip is a testament to the unwavering dedication and passion of the esteemed winemakers. But hold on to your glasses, for our adventure is far from over! Our next stop is the illustrious Pindar Winery, a veritable jewel of the East End. The Pindar estate emanates an aura of elegance and charm, offering a delightful selection of meticulously crafted wines awaits your exploration. Join us on this unforgettable wine tastings through the captivating landscapes of Long Island's East End.

$189.00

5/5

Half Day(PM) North Fork Private Wine & Food Tour by Local Expert

$439.00

4.9/5

6 h

NYC Bus Tour of Brooklyn, Bronx, Queens: Art, Food & Sports

This bus tour spans four of New York City’s boroughs, covering everything you need to see in one day with convenient and comfortable transportation. With your local guide, learn about Harlem’s African-American history at the Apollo Theater and the Hasidic Jewish community in Williamsburg. Elsewhere in the Bronx and Brooklyn, admire colorful street art. We’ll also stop by an empanada shop that locals swear by, worth adding to your NYC bucket list. We’ll stop at Flushing Meadow-Corona Park to see Citi Field and the giant Unisphere. And there's a stop for lunch in a popular foodie destination surrounded by street art. And don't forget the photo ops of the Manhattan skyline and Brooklyn Bridge as you learn what makes DUMBO special. Our tour winds down with a visit to Chinatown and Little Italy. If you want to explore more here, your guide has tips on where to eat and shop!

$84.00

4.9/5

12 h

Hamptons Private Day Trip from New York City

Visit the Hamptons on this private, full-day trip from New York City with a chauffeured minivan that accommodates up to six passengers. Enjoy the ride in comfort and style, then spend the day seeing some of the most expensive and luxurious residential properties in the USA, with beautiful mansions and estates that slope down to the ocean's edge. Explore the streets of small villages, quaint shops, boutiques, art galleries, cafes and of course visit a winery. Highlights of the trip include lunch by the ocean's edge.

$1,299.00

4.4/5

Long Island Winery Tour

Relax with family and friends, enjoy live music on weekends, and sip on famous Long Island local wine while looking over the gorgeous vineyards at Osprey and Duck Walk! Private pickup with tastings included at the wineries. You can bring your own lunch to enjoy at the vineyards, or buy a light lunch at Osprey. We pickup from any address on Long Island. Locations further west (Nassau County) will require additional travel time.

$335.00

4.3/5

12 h

The Hamptons and Long Island Wineries Private Tour

On this private tour from New York City, your morning will be spent visiting the quintessential Hamptons Village of Southampton with its lovely shops, cafes, pristine beaches and ocean front mansions. Then on to Sag Harbor with its 18th Century New England-style homes, infamous yacht club, wind mill and Long Wharf. Following a harbor-side lunch of locally harvested seafood, you will take a ferry to Shelter Island. After a relaxing drive across the Island, a second ferry will be taken to the North Fork of Long Island - the third largest wine making region in North America with 29 wineries. You will enjoy tastings at several different wineries, with a return to New York City early in the evening. This will be a day to remember!

$1,299.00

4.3/5

10 h

Long Island Winery Tour with Lunch from Manhattan (#1 Rated!)

First it was California, now it’s Long Island. For a number of years now, the North Fork of Long Island has been gaining respect for producing fine wines. Join this day tour to sample the finest vintages at three carefully picked vineyards on the North Fork. You’ll enjoy round trip transportation from Manhattan, a hearty picnic lunch and a friendly guide to walk you through the day.

$179.00

2 h

Southampton Shuffle Scavenger Hunt

Our very unique, immersive adventures are the only ones of their kind. We, unlike other companies, provide your very own remote, interactive, live host to assist and encourage you along through your phone. We are an Austin, TX-based global custom event design company offering scavenger hunts and other events in 300+ cities in North America and beyond. Our specially hand-crafted adventures are equal parts tour, creative challenge, detective hunt, and social experiment! Guests get to discover in an alternate reality our favorite hidden gems off the beaten trail and creatively interpret fun art, history, and culture clues - for points! They get to enjoy fame and glory while appearing on our website’s international leaderboard, no matter what their score. They get to essentially race other teams in other cities, even if they don’t have competitors who have signed up in their city that day. Get ready to discover unusual oddities, laugh out loud, and make the experience your own!

$20.00

8 h

Hamptons Insider Tour with Private Helicopter from Manhattan

Experience the magic of the Hamptons—long known as a playground for the rich and famous—with a private helicopter flight from Manhattan to East Hampton Airport. Upon arrival, meet your local concierge and enjoy a full day with a climate-controlled luxury vehicle at your disposal. Begin with a guided tour of Sag Harbor, exploring hidden gems and centuries of history, or opt for shopping in East Hampton and visits to local art galleries. Take in the coastal lifestyle with seaside dining, award-winning wines, and glimpses of iconic celebrity homes. Enjoy a gourmet lunch with champagne at an elegant restaurant, followed by a private wine tasting in Bridgehampton. The experience can also include a visit to a classic Hamptons estate and time at pristine Atlantic beaches stretching for miles. Return to East Hampton Airport for your helicopter flight back to Manhattan. Availability: year-round. Flight time: ~1 hour each way. Total duration: ~8 hours.

$28,900.00

5 h

Hamptons Beach Picnic with Private Helicopter from Manhattan

Escape the city with a private helicopter journey from Manhattan to East Hampton for a curated Hamptons luxury picnic experience. Enjoy scenic aerial views of Long Island’s coastline before landing at East Hampton Airport, where a private chauffeur will escort you to an exclusive beachside location. A beautifully styled picnic awaits, set against the Atlantic Ocean with elegant blankets, plush pillows, fresh flowers, and curated décor. Savor a fully catered gourmet spread with your preferred food and beverages, served on real china and glassware, while a dedicated attendant ensures every detail is flawless. After two hours of oceanside relaxation, return to the airport for your helicopter flight back to Manhattan, complete with a breathtaking NYC skyline tour. Availability: May–September. Flight time: ~1 hour each way. Total duration: ~4 hours.

$23,200.00

3 h

Half Day Private North Fork Bike Tour Thru Wine Cntry in Matituck

Nature Abounds on this 3 Hour Tour - Excellent way to See the Best of Long Island's Wine Country here on the North Fork. Take in beautiful views on this relaxing guided 2.5-hour tour cruising through the charming north fork. On this backroads ride nature abounds as seasoned guides lead you on winding roads up close to the Peconic Bay. Stops may range from 14-19 miles …your preference. Bike riding is mostly flat but with a couple of rolling hills. Pass lush green vineyards, osprey nests, wind mills as we cycle winding roads alongside the Peconic Bay Break at a small charming beach (hidden treasure that the locals try to keep to themselves) for herb infused oil & fine vinegar tastings overlooking the Peconic bay. Unique farm stand stop w/ hand woven clothing, & fresh baked goods, veggies, charcuteries etc. Love Lane Shopping Experience for trinkets & souvenirs to commemorate your day (after the tour). Shops located around the corner from our shop. 21-Speed Hybrid Bikes

$834.00

2 h

Bridgehampton Bash, NY Scavenger Hunt

$29.00

5 h

Half-Day Private Long Island Wine Tour Experience

Embark on this Half-Day Private Long Island Wine Tour Experience and indulge your senses in the heart of USA's renowned wine country! Your day begins with a personalized, chauffeur-driven journey through the stunning Long Island landscapes, setting the scene for an unforgettable adventure. As you traverse the picturesque landscape, you'll have the opportunity to visit two beautiful wineries - Osprey's Dominion Vineyards and Duck Walk Vineyards North - each with its own unique charm and distinctive wines. Expert sommeliers and winemakers will guide you through the tastings of exceptional wines, sharing their deep knowledge and passion for winemaking. Don't miss the opportunity to create lasting memories on this Half-Day Private Long Island Wine Tour Experience, escaping the hustle for a day of indulgence, relaxation, and appreciation of Long Island's vinicultural heritage.

$598.64

10 h

Private Tour Hamptons from New York City

Experience our Private Excursion tailored exclusively for you! Embark on a serene journey through the picturesque landscapes of USA as you make your way to the heart of the city. Upon your arrival, meet your seasoned tour guide, ready to lead you on an enchanting tour of New York City. Discover the awe-inspiring allure of Southampton, marvel at the grandeur of Sag Harbor, and capture iconic moments at landmarks like Wolffer Estate Vineyard, East Hampton, Montauk, and many more. Our excursions are meticulously designed schedule. We'll greet you directly at the hotel and ensure you return with ample time to relax and relish your day.