Long Island travel is a perfect summer escape, offering a mix of scenic beaches, charming villages, historic landmarks, and exquisite vineyards. Whether you’re a first-time visitor or a local looking for a refreshing getaway, this ultimate Long Island travel itinerary will help you make the most of your summer adventure. From beach lounging to wine tasting, this guide covers the must-see spots and hidden gems that define a true Long Island experience.
Day 1: Kick Off Your Long Island Travel with Beaches and Boardwalks
Start your Long Island travel journey in the west with a visit to Jones Beach State Park, one of the most famous beach destinations on the island. Stretch out on the soft sand, take a swim in the Atlantic Ocean, and stroll along the boardwalk. This beach is a staple in every summer Long Island travel plan, thanks to its lively atmosphere and family-friendly amenities.
After the beach, head to Long Beach, another popular seaside destination. Enjoy water sports, grab a bite at the local eateries, or catch the sunset for a perfect end to your first day.
Day 2: Dive into History and Coastal Charm
Your Long Island travel itinerary wouldn’t be complete without exploring the island’s rich history. Start the day in Cold Spring Harbor, a quaint hamlet with maritime roots. Visit the Cold Spring Harbor Whaling Museum to learn about Long Island’s whaling history.
Next, make your way to Sag Harbor, a historic whaling town with charming streets, boutique shops, and the iconic Sag Harbor Whaling and Historical Museum. It’s a key destination in any Long Island travel plan, offering both educational and picturesque experiences.
End the day with dinner in Greenport, a lively village on the North Fork known for its seafood and harbor views.
Day 3: Wine Country Adventures on the North Fork
No Long Island travel itinerary is complete without exploring its famous wine region. Spend the day touring North Fork’s scenic vineyards, such as Bedell Cellars, Paumanok Vineyards, and Macari Vineyards. The North Fork offers a more relaxed vibe compared to the Hamptons, making it ideal for wine tasting and countryside views.
Pack a picnic, take a winery tour, or enjoy live music at one of the outdoor tasting rooms. Long Island travel during summer becomes especially magical when spent among the vines, sipping crisp rosé under the sun.
Day 4: Explore the Hamptons in Style
Dedicate your fourth day to the glamorous South Fork. Start in Southampton with a visit to Cooper’s Beach, one of the top-ranked beaches in the country. Explore the upscale shops and art galleries along Jobs Lane.
Continue to East Hampton, known for its luxurious estates and serene beaches like Main Beach. If time allows, visit Montauk, the easternmost point of Long Island, for iconic lighthouse views at Montauk Point State Park—a bucket list spot for any Long Island travel enthusiast.
Day 5: Nature, Parks, and a Scenic Farewell
Wrap up your Long Island travel experience by reconnecting with nature. Visit the Fire Island National Seashore for pristine beaches and untouched wildlife habitats. You can also hike the trails of Caumsett State Historic Park Preserve or kayak through the salt marshes at Connetquot River State Park.
Finish your journey with a seafood dinner at a waterside restaurant in Port Jefferson or Huntington Village, two towns that beautifully blend charm, nature, and dining.
Final Thoughts
Your ultimate Long Island travel itinerary for summer should balance relaxation, adventure, and cultural discovery. From the stunning beaches of the South Shore to the vineyards of the North Fork, Long Island travel offers something for everyone. With so many unique towns, historical sites, and natural wonders, every moment spent on Long Island promises unforgettable memories.