Day 1. The North Fork – Begin your trip by spending a slow day in Riverhead, where you can explore the downtown and main street or shop around for deals at the Tanger Outlets. Take in the spectacles of the Long Island Aquarium and Exhibition Center, or relax in a seat with a show at the Suffolk Theater. A good day of rest will have you energized for the activities ahead.

Day 2. Scenic Bicycle Tour – Head off the beaten path for a bicycle ride through the scenic North Fork. With help from local tour guides at LI Bicycle Tours you’ll take a casual tour of Long Island Wine Country, pedaling along scenic roads at a leisurely pace. Stop at small tasting rooms, local farms and take in all there is to offer along the country roads; have a special reserve tasting, with a fresh fruit/cheese & cracker platter. Indulge in a gourmet picnic lunch and explore the historic village of Mattituck and its ‘Love Lane’. The route is mostly flat with some small rolling hills and is perfect for healthy and active people to enjoy. The total riding distance is 12 miles and most tours finish by 4pm.

Day 3. Quaint Villages and Local Cuisine – Make your way toward Greenport, but be sure to pick out a bottle to accompany dinner before you arrive. Spend the afternoon in the village, antiquing or browsing other quaint shops. If you’re done with wine you are welcome to try some local Greenport brew. Learn about the seafaring heritage of Suffolk County at the Maritime Museum and take in a historic experience at the carousel. Finish up at any number of truly amazing local restaurants, where you’ll find farm-to-table local produce, seafood, wines and brews.

Day 4. Sun, Water and Wine – End your stay on the North Fork at Orient Point State Park beach and put your feet in the water all the way at the tip of the island, to mark the furthest point you reached. Head back to Greenport to catch the ferry heading to Shelter Island. From here you can find a waterfront B&B if you’d like to extend your vacation, or just take in the sights of Long Island’s hidden gem before crossing over to the South Fork at Sag Harbor.

Day 5. The South Fork – While in Sag Harbor stop by the Whaling Museum where you’ll find poignant displays revealing a long-ago chapter in Long Island’s history. Discover the offerings of the South Fork, with wineries in East Hampton and Southampton and villages to explore. Window shop or spend time at the most beautiful ocean beaches in the country, and make sure to stroll along the sand as the sun sets.