Southold
Day Trips
Make the most of your day with our curated plans, packed with Southold's hidden gems and unique experiences!
Start your day with a visit to the beautiful Southold Town Beach, where you can enjoy a peaceful morning walk along the shore. Make sure to bring your camera to capture the stunning sunrise views.
Visit the Southold Historical Society to learn about the rich history of the area. Afterward, have lunch at a local café and try some fresh seafood dishes.
End your day with a scenic sunset at Moores Beach. Relax with a picnic dinner while taking in the breathtaking colors of the evening sky.
Visit a local vineyard for a morning tour and tasting, where you can learn about the wine-making process. Enjoy the picturesque surroundings of the vineyards at this time.
Take part in a wine and food pairing experience at the vineyard’s restaurant, enjoying delicious local cuisine. This is a fantastic opportunity to appreciate culinary pairings.
Attend a wine tasting event at another vineyard, where you can explore different flavors. Wrap up your day with a relaxing glass of wine in the serene vineyard setting.
Rent a bike and hit the scenic Southold trails. Pedal through beautiful countryside and coastal views, allowing you to soak up the fresh air.
Stop for lunch at a charming eatery in one of the nearby towns, enjoying local specialties. Afterward, continue your biking adventure on more trails.
Find a nice spot at a local park to relax and enjoy a picnic dinner. The peacefulness of the evening will be a perfect conclusion to your day.
Start your day with an early fishing trip, either from a boat or the pier. The tranquility of the water is perfect for a calming morning experience.
Prepare and cook your catch back at your accommodation for lunch. Consider inviting friends or family to join in on the fun.
Enjoy a family-style dinner featuring your fresh catch while sharing stories from the day. Consider heading to a local tavern for some live music to end the evening.
Spend a relaxing morning at the Southold Nature Trail, enjoying a leisurely hike surrounded by nature. Observe the local wildlife and enjoy the tranquility of the area.
Pack a lunch to enjoy at the park, where you can sit back and soak in the surroundings. Bring a book to read as you unwind in the peaceful setting.
Head to a nearby farm for a farm-to-table dining experience, focusing on seasonal ingredients. Your meal will be an excellent way to celebrate the flavors of the region.
Spend your morning soaking up the sun on one of Southold’s picturesque beaches. Bring a beach chair and your favorite book for a relaxing morning.
Grab lunch at a beachside café, enjoying cool drinks and light bites. Afterward, try out some water sports like paddleboarding or beach volleyball.
As the day winds down, enjoy a bonfire on the beach, roasting marshmallows and sharing stories. This casual setup is perfect for winding down after a fun-filled day.
Start with a visit to one of Southold’s parks for a leisurely stroll or a morning workout. The fresh air and greenery are invigorating.
Pack a picnic and relax in the park, enjoying the ambience and nature around you. You can also play frisbee or go for a short hike.
Spend your evening at an outdoor movie or community event in the park. Connecting with locals and enjoying the community vibe will enrich your experience.
Kick off your day with a sunrise photography session at the beach or bayfront. Capture the mesmerizing colors and reflections in the water.
Continue your photo expedition to local landmarks, like lighthouses or historic homes. Have a lunch break at a quaint café to recharge.
Share your best shots at a local art gallery or coffee shop, where you can meet fellow enthusiasts. Wind down the day by reviewing your photos and reflecting on your experiences.
Visit local galleries and craft shops to appreciate the art created by local artists. This is a great way to immerse yourself in Southold's culture.
Sign up for a creative workshop, such as painting or pottery, to tap into your artistic side. Lunch at a nearby café will replenish your energy for the afternoon activities.
Attend a local theater performance or concert for a dose of entertainment and culture. Wrap up your day by mingling with artists and locals at post-event gatherings.