What to do in Southold, NY

Activities, attractions and tours

Tranquil evening seascape on Truman's Beach Marsh in Southold, Long Island, New York, USA
Tranquil evening seascape on Truman's Beach Marsh in Southold, Long Island, New York, USA
Tranquil sunset seascape on Truman's Beach Marsh in Southold, Long Island, New York, USA
Tranquil seascape on Truman's Beach Marsh in Southold, Long Island, New York, USA
Day trip to North Fork wineries. Stopped at this beach for a break before driving back to the city. #sunset #nature #wanderlust #waterlust #beach #colorful #citylife #NikonD7100 #Manfratto tripod.

Southold Attractions

Let Expedia help you experience the best that Southold has to offer! If you’re looking for fun itinerary ideas, we can provide you with a list of the top sightseeing attractions, as well as helping you to find unmissable activities. Whether you’re travelling with your family, planning a romantic trip with your loved one, or visiting on business, we’ll make it easy to plan an unforgettable holiday that checks all the boxes.

Activities and Tours

Southold is crammed with must-see places to visit and things to do. We can help you decide where to stay, and make it a breeze to explore the surrounding areas with our guides on where to go, what to see and when to see it. No matter how long your stay, it’s easy to find places of interest in Southold to make sure that you enjoy your experience to the fullest and don’t miss a thing. Leave the local knowledge to us and leave the hassle behind.

If you’re planning a visit, why not check out our handy guides to places of interest in the area? You can browse lists of things to do, learn about the most popular attractions, and get help with planning the details of your trip. Expedia makes it easy for you to check out all the top sights.

Southold Attractions

Expedia has something for everyone, so whether you’re planning to get active on a summer holiday, put a spring in your step with a romantic rendezvous, or pamper yourself with a leisurely winter trip, you’ll find plenty of attractions to keep you entertained. In addition to scheduling local tours, booking reservations and scoring advance event tickets, Expedia makes it easy to book your flight, hotel and rental car in advance, all on one consolidated travel itinerary, making for hassle-free travel and freeing you up to explore the sights of Southold.

Looking for things to do can be time consuming, but we can take the hassle out of planning your holiday. Whether you’re looking to get active in the great outdoors, sample the cuisine or catch up with the vibrant local culture, our guides to Southold attractions ensure that you’ll have a successful trip, whatever the season.

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What to do in Southold

Discover the most popular places to visit in Southold

Cleanest, prettiest winery on the east end of Long Island! Try the Cuvee' Rose!

Sparkling Pointe

You can enjoy a tasting or tour at Sparkling Pointe during your travels to Southold. Discover the sunsets and wineries in this family-friendly area.

Sparkling Pointe

Horton Lane Beach

Why not spend a lazy afternoon at Horton Lane Beach during your trip to Southold? Stroll along the beaches or discover the area's sunsets.

Horton Lane Beach

Sannino's Bella Vita Vineyard

You can enjoy a tasting or tour at Sannino's Bella Vita Vineyard during your travels to Southold. Wander the beaches or discover the sunsets in this family-friendly area.

Sannino's Bella Vita Vineyard

Croteaux Vineyards

You can enjoy a tasting or tour at Croteaux Vineyards during your travels to Southold. Wander the beautiful beaches in this family-friendly area.

Croteaux Vineyards

The Old Field Vineyards

You can enjoy a tasting or tour at The Old Field Vineyards during your travels to Southold. Stroll along the beaches or discover the sunsets in this family-friendly area.

The Old Field Vineyards

Osprey's Dominion

You can enjoy a tasting or tour at Osprey's Dominion during your travels to Southold. Wander the beautiful beaches in this family-friendly area.

Osprey's Dominion

Corey Creek Winery

You can enjoy a tasting or tour at Corey Creek Winery during your travels to Southold. Wander the beautiful beaches in this family-friendly area.

Corey Creek Winery

Horton Point Park

Explore the great outdoors at Horton Point Park, a lovely green space in Southold. Wander the beaches or discover the sunsets in this family-friendly area.

Horton Point Park

McCabe's Beach

Why not spend a lazy afternoon at McCabe's Beach during your trip to Southold? Stroll along the beaches or discover the area's sunsets.

McCabe's Beach

 

Looking for fun things to do nearby? Check things to do near me to find and book the best things to do, fun activities, and top attractions wherever you happen to be.

 

 

Day trip destinations from Southold

Central Park summer

Shelter Island

Beautiful spot on the #longisland sound surfing

Greenport West

Frequently asked questions

Is Southold worth visiting?
Southold has a unique blend of culture, attractions and local charm. Whether you're into outdoor activities, history or regional cuisine, there's a lot to enjoy here.
How do I spend a day in Southold?
Once you've visited popular attractions like 67 Steps Beach and Truman's Beach, spend the rest of your day enjoying the retail and food options in Southold.
What is the top tourist attraction in Southold?
The top tourist attraction in Southold is 67 Steps Beach, so be sure to include it on your sightseeing list.
Is three days enough to stay in Southold?
Book an escape in Southold for three days and you'll have enough time to explore its key sights and get a taste for the local vibe. For the chance to see highlights in nearby areas and venture off the beaten path, consider hanging around for a week or longer.
What are some activities to do in Southold with kids?
If you are after sights and activities for all of your group, take a look at these terrific ideas for what to do in Southold with kids.
What to do in Southold for adults?
Peconic Bay Winery and Sparkling Pointe are just a couple of the things to do in Southold. With lots of activities available, there's something here for everyone.
Are there free things to do in Southold?
In Southold, 67 Steps Beach is a top spot for anyone wishing to see the city without opening their wallet. Also, wander around the green spaces and other neighbourhoods, and ask a local tour guide for tips. It's a top way to find out about the best free things to do in Southold.