Title: Things to Do in Southold in 2026 | Expedia.com [Southold Travel Guide](https://expedia.com/Southold.dx183719)[Hotels in Southold](https://expedia.com/Southold-Hotels.d183719.Travel-Guide-Hotels)[Flights to Southold](https://expedia.com/Cheap-Flights-To-Southold.d183719.Travel-Guide-Flights)[Car Rentals in Southold](https://expedia.com/Car-Rentals-In-Southold.d183719.Car-Rental-Guide)[Southold Vacation Packages](https://expedia.com/Southold.d183719.Destination-Travel-Guides) # Things to do in Southold ## Find and book activities, attractions and tours ## Visit Southold Types of activities [Southold Travel Guide](https://expedia.com/Southold.dx183719) ![Tranquil evening seascape on Truman's Beach Marsh in Southold, Long Island, New York, USA](https://images.trvl-media.com/place/183719/763c5957-1d09-4b50-be9f-256173572489.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![Tranquil evening seascape on Truman's Beach Marsh in Southold, Long Island, New York, USA](https://images.trvl-media.com/place/183719/763c5957-1d09-4b50-be9f-256173572489.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![Tranquil sunset seascape on Truman's Beach Marsh in Southold, Long Island, New York, USA](https://images.trvl-media.com/place/183719/2f5d59dd-9baa-4fe4-96b8-839361de94bb.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![Tranquil seascape on Truman's Beach Marsh in Southold, Long Island, New York, USA](https://images.trvl-media.com/place/183719/31ba309a-453e-45eb-ba2b-eccf35423a5b.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![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. ](https://images.trvl-media.com/place/183719/81468873-e891-4a92-aa0d-1938572ea198.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) --- - ![find price illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__find_price.svg) ### Explore activities Explore thousands of experiences from activities and attractions to day tours and transfer. - ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Book with ease Skip the line- book tickets online in minutes to top attractions with free cancellation on many activities. - ![trophy illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__trophy.svg) ### Treat yourself One Key members save % or more on select activities, hotels, cars and vacation rentals. [Learn about One Key](https://www.expedia.com/welcome-one-key) --- ## Recommended things to do in Southold | Number of things to do | 6 | | ------------------------------- | --------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------- | | Cheapest thing to do on Expedia | [Private Luxury Wine Tours of Long Island Pindar Winery](/things-to-do/private-luxury-wine-tours-of-long-island-pindar-winery.a50790562.activity-details): $180 | | Top 5 things to do | [Half-Day Private Long Island Wine Tour Experience](/things-to-do/half-day-private-long-island-wine-tour-experience.a47265708.activity-details)[Private Luxury Wine Tours of Long Island Pindar Winery](/things-to-do/private-luxury-wine-tours-of-long-island-pindar-winery.a50790562.activity-details)[The Hamptons Coastal Escape from NYC](/things-to-do/the-hamptons-coastal-escape-from-nyc.a50590738.activity-details)[Long Island Wine Tour North Fork Sights Bites Flights Half Day PM](/things-to-do/long-island-north-fork-sights-bites-flights-half-day-tour-pm.a50223091.activity-details)[Long Island Wine Tour North Fork Sights Bites Flights Half Day AM](/things-to-do/north-fork-sights-bites-and-flights-private-tour.a49153679.activity-details) | | Under $25 | | | With kids | | ## What to do in Southold --- Looking for sports, concerts, or theater events in Southold? [Search event tickets](https://www.expedia.com/event-tickets/) to see what's happening today, or to plan what to do this weekend! --- --- ### Discover the most popular places to visit in Southold ![Cleanest, prettiest winery on the east end of Long Island! Try the Cuvee' Rose!](https://images.trvl-media.com/place/183719/1c666367-92bc-4b18-b16d-e60341a06481.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### 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. [](https://expedia.com/Sparkling-Pointe-Southold.d6327589.Vacation-Attraction) #### 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. [](https://expedia.com/Horton-Lane-Beach-Southold.d553248635983992604.Vacation-Attraction) #### 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. [](https://expedia.com/Sanninos-Bella-Vita-Vineyard-Southold.d6327435.Vacation-Attraction) #### 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. [](https://expedia.com/Croteaux-Vineyards-Southold.d6326852.Vacation-Attraction) #### 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. [](https://expedia.com/The-Old-Field-Vineyards-Southold.d6327777.Vacation-Attraction) #### 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. [](https://expedia.com/Ospreys-Dominion-Southold.d6326243.Vacation-Attraction) #### 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. [](https://expedia.com/Corey-Creek-Winery-Southold.d6326844.Vacation-Attraction) #### 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. [](https://expedia.com/Horton-Point-Park-Southold.d6064489.Vacation-Attraction) #### 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. [](https://expedia.com/McCabes-Beach-Southold.d950890248278548480.Vacation-Attraction) --- Looking for fun things to do nearby? Check [things to do near me](https://www.expedia.com/things-to-do-near-me) to find and book the best things to do, fun activities, and top attractions wherever you happen to be. --- ## Popular day trips from Southold ![The one of best destinations for summer vacation!#Trove#Summer](https://images.trvl-media.com/place/110728/bf7f0ae9-ecfe-4ab0-b34c-f44de31622e4.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Greenport ![Sunset along the beach at Towd Point in Southampton, Long Island, New York.](https://images.trvl-media.com/place/144477/d8201a6e-8861-410b-8d02-9fda68bbf3f3.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Peconic ![Central Park summer](https://images.trvl-media.com/place/157359/6c674470-f02c-495a-ad05-e592d3be267f.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Shelter Island ![coastal landscape at Greenport at the islands of shelter islands heights, county New York](https://images.trvl-media.com/place/183716/7e82dc91-d6c1-40f0-b4ce-69678c9bd599.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Shelter Island Heights ![A summer paradise ](https://images.trvl-media.com/place/6217344/1112a8ef-40db-42b8-808d-0eb80b7db396.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Noyack ## Frequently asked questions ### Is Southold worth visiting? ### How do I spend a day in Southold? ### What is the top tourist attraction in Southold? ### Is three days enough to stay in Southold? ### What are some activities to do in Southold with kids? ### What to do in Southold for adults? ### Are there free things to do in Southold? ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save even more - get up to 20% on select hotels when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. 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