Southold

Day Trips

Start your day with a visit to the Southold Historical Society, where you can delve into the rich maritime history of the area. Enjoy a leisurely stroll through the charming streets of the historic district, taking in the colonial architecture and local boutiques. Don’t forget to grab a fresh pastry at a local café to fuel your exploration.

After lunch at a cozy bistro, head to the Southold Town Beach for some relaxation and stunning ocean views. Engage in some beachcombing or simply lay back and soak up the sun while listening to the gentle waves. As the afternoon progresses, consider renting a kayak to explore the nearby marshes and waterways.

As the sun begins to set, make your way to a waterfront restaurant for a delicious seafood dinner with a view. Savor the local flavors of Long Island, perhaps sampling fresh clams or a lobster roll. End your evening with a peaceful walk along the beach, watching the stars emerge in the clear night sky.

Kick off your day with a hearty breakfast at a local diner known for its delicious pancakes and fresh coffee. Afterwards, set out on a scenic drive through the North Fork Wine Country, where vineyards stretch as far as the eye can see. The morning is perfect for visiting a couple of local wineries for tastings and tours.

Continue your wine adventure with a picnic lunch at one of the vineyards, surrounded by lush grapevines. After lunch, take part in guided tours that often include insights into the wine-making process and the chance to sample unique blends. Enjoy the relaxed atmosphere as you sip on a glass of wine while taking in the picturesque landscape.

As the day winds down, visit a winery that offers sunset tastings on their patio. Bask in the warm glow of the setting sun while enjoying a flight of wines paired with artisanal cheeses. Wrap up the evening with a seasonal dessert and perhaps a nightcap before heading back to your accommodations.

Begin your day with a visit to the Southold Town Park, where you can immerse yourself in nature on a peaceful walking trail. The morning light is perfect for spotting local wildlife, so bring your binoculars for some birdwatching. Enjoy the tranquility of the park as you listen to the sounds of chirping birds and rustling leaves.

After a morning of exploration, enjoy a packed lunch while overlooking the beautiful Peconic Bay. Spend the afternoon walking along the shoreline, collecting shells, or simply relaxing on the beach. If you're feeling adventurous, consider taking a boat tour to explore the surrounding waters and spot more wildlife.

As dusk approaches, return to your lodging to freshen up before dinner. Head to a local seafood shack for a casual meal featuring the catch of the day, enjoying the relaxed ambiance. End your day with a bonfire on the beach, roasting marshmallows and sharing stories under the stars.

Start your culinary adventure with breakfast at a farm-to-table café that sources its ingredients locally. Enjoy a fresh omelet or a smoothie bowl made with seasonal fruits. After breakfast, visit the Southold Farmers Market to browse fresh produce and artisanal goods.

Join a cooking class at a local culinary school where you can learn to prepare traditional Long Island dishes, guided by a professional chef. Enjoy the meal you prepare for lunch, tasting the delicious flavors of the local cuisine. Spend the afternoon visiting nearby farms to learn about sustainable practices and perhaps pick your own fruits or veggies.

After your culinary experiences, head to a quaint restaurant known for its seasonal menu that changes frequently. Savor a multi-course dinner featuring locally sourced ingredients, each dish paired with a carefully selected wine. Conclude your evening with a dessert made from local berries, celebrating the flavors of Southold.

Begin your day at a local art gallery showcasing the works of regional artists, where you can appreciate various styles and mediums. Spend time discussing the pieces and the inspiration behind them with the gallery staff. Afterward, take a walk through the charming streets to admire local murals and public art installations.

After lunch at a nearby café, visit the Southold Arts Center to participate in a workshop or art class that piques your interest. Whether it's painting, pottery, or photography, indulge your creative side and learn something new. Take some time to explore the gift shop, where you can purchase unique handmade items.

For the evening, attend a local theater performance or concert, enjoying the vibrant cultural scene of Southold. Immerse yourself in the local talent and enjoy a night of entertainment. After the show, grab a late-night coffee or dessert at a nearby café to reflect on your artistic day.

Kick off your beach day with an early swim at Southold Town Beach, where the soft sands and gentle waves await. Spend some time sunbathing or playing beach volleyball with friends or family. Grab a light lunch from a beachside vendor to keep your energy up for the afternoon ahead.

Engage in various water sports like paddleboarding or windsurfing, taking advantage of the summer breeze and warm waters. If you prefer a more relaxed vibe, rent a beach chair and read a book while enjoying the view. As the afternoon progresses, participate in a beach scavenger hunt or join a group for a fun game of frisbee.

As the sun sets, head to a local seafood restaurant where you can relish the day’s fresh catch. Enjoy your meal outside on the patio, soaking in the beautiful twilight view. Conclude your beach adventure with a leisurely stroll along the shore, reflecting on the day's fun and laughter.

Begin your day with a visit to the Horton Point Lighthouse, where you can learn about its history and take in breathtaking views of the Long Island Sound. Climb to the top of the lighthouse for a panoramic view of the coastline and surrounding waters. Enjoy a picnic breakfast on the grounds, surrounded by blooming gardens.

After your visit to the lighthouse, head towards the nearby village for a leisurely lunch at a charming café. Spend the afternoon exploring the quaint shops and galleries, picking up unique souvenirs and local crafts. Take your time to appreciate the historical significance of the area as you stroll through its streets.

As evening falls, dine at a restaurant that offers a view of the lighthouse, allowing you to watch the sunset as you enjoy your meal. Savor a delicious dinner paired with local wines while reminiscing about your day’s adventures. Conclude your evening with a nighttime visit to the lighthouse for a different perspective of the iconic structure illuminated against the night sky.

Start your day with a hearty breakfast before heading to a local park for some outdoor fun. Engage in hiking or biking along scenic trails that wind through Southold’s beautiful landscapes. Enjoy the fresh air and the sights of nature as you explore the area’s natural beauty.

After your morning activities, have a picnic lunch in the park, surrounded by the sounds of nature. Spend the afternoon playing frisbee, soccer, or taking part in organized sports activities available in the park. If you prefer a quieter afternoon, find a cozy spot to read or relax with a friend.

As the day comes to a close, gather with friends for a barbecue at a local park or beach. Share delicious food and laughter as you cook together and enjoy the beautiful weather. Wrap up your outdoor day by stargazing, perhaps with a bonfire to keep warm.

Treat yourself to a restful morning at a local spa, where you can indulge in a rejuvenating massage or facial. Take your time to unwind and enjoy the tranquil environment, sipping herbal tea and relaxing in a sauna. After your spa treatment, enjoy a healthy breakfast at a nearby café known for its organic options.

Spend the afternoon at a nearby wellness center participating in yoga or meditation sessions designed to refresh your mind and body. Enjoy a light lunch incorporating fresh and local ingredients, keeping the relaxation theme going. Take a leisurely stroll in a nearby garden or park, appreciating the calming beauty of nature.

As the sun begins to set, treat yourself to a gourmet dinner at a fine dining restaurant, where you can savor beautifully crafted dishes. Enjoy the ambiance and perhaps indulge in a glass of wine to complement your meal. End your relaxing day with a quiet evening walk along the beach, reflecting on your tranquil experiences.