Top Long Island Private Sightseeing Tours

Discover the legendary Hamptons on this self-guided tour through the oceanfront villages along the South Fork of Long Island. For centuries, these shores have drawn artists, writers, and presidents, yet the Hamptons remain rooted in a quieter history of Shinnecock native peoples, settlers, and whalers. Begin in Southampton, where white-columned estates line lanes, then drive east through farm stands and vineyards between the glamorous towns. Explore Sag Harbor's whaling heritage, stroll the tree-canopied main street of East Hampton where windmills from the 1600s still stand, and continue to wild Montauk, where a lighthouse has guarded the Atlantic since George Washington authorized its construction in 1796. Along the way, encounter world-class beaches, art museums, and nature preserves that make the Hamptons far more than a celebrity playground. This tour reveals the authentic character beneath the glitz — a place shaped by the sea, the land, and 4 centuries of American stories.

Sip on Long Island wine or cider while visiting the area’s renowned vineyards, including Osprey's Dominion Vineyards and Duck Walk Vineyards, all in one indulgent, private tour. With round-trip transit from your preferred Long Island location and included tastings (with a lunch upgrade option available), enjoy simplified logistics and an enjoyment-focused experience.

Welcome to the ultimate East End Long Island Wine Adventure! Prepare to immerse yourself in a journey through the region's lush vineyards, picturesque landscapes, and a symphony of exquisite flavors awaiting at every turn. Our escapade 1st stop is at the Bridge Lane Tasting Room, nestled snugly in the heart of Long Island's esteemed wine country. Bridge Lane's award-winning wines awaits your discerning palate. From crisp whites to robust reds, each sip is a testament to the unwavering dedication and passion of the esteemed winemakers. But hold on to your glasses, for our adventure is far from over! Our next stop is the illustrious Pindar Winery, a veritable jewel of the East End. The Pindar estate emanates an aura of elegance and charm, offering a delightful selection of meticulously crafted wines awaits your exploration. Join us on this unforgettable wine tastings through the captivating landscapes of Long Island's East End.

As local experts, we take the guesswork out of planning your visit to the North Fork of Long Island. We know which venues are the most memorable and which wines are most enjoyable. As a team of passionate locals, we have scoured the area to handpick the best vineyards, restaurants, and hidden gems that you won't find on your average tourist map or group tour. Our expert guides will accompany you every step of the way, providing insider knowledge and fascinating stories about the rich history of the North Fork. Our private slow tour is 100% customizable and is tailored to you and/or your group's interests. Our all-inclusive fee covers all activities, food/wine, gratuities, and transportation for a seamless and memorable experience. Rain or shine.

As local experts, we take the guesswork out of planning your visit to the North Fork of Long Island. We know which venues are the most memorable and which wines are most enjoyable. As a team of passionate locals, we have scoured the area to handpick the best vineyards, restaurants, and hidden gems that you won't find on your average tourist map or group tour. Our expert guides will accompany you every step of the way, providing insider knowledge and fascinating stories about the rich history of the North Fork. Our private slow tour is 100% customizable and is tailored to you and/or your group's interests. Our all-inclusive fee covers all activities, food/wine, gratuities, and transportation for a seamless and memorable experience. Rain or shine.

Traverse the ‘Big Apple’ on foot and discover some of the city’s best architecture on this 4-hour private tour with hotel pickup. Learn about New York City's history as you visit landmarks like Rockefeller Center, the New York Public Library, Grand Central Station, and the Flatiron Building. Admire architecture from the 1700s to present day, featuring styles from Beaux Arts to Art Deco.

Embark on this Half-Day Private Long Island Wine Tour Experience and indulge your senses in the heart of USA's renowned wine country! Your day begins with a personalized, chauffeur-driven journey through the stunning Long Island landscapes, setting the scene for an unforgettable adventure. As you traverse the picturesque landscape, you'll have the opportunity to visit two beautiful wineries - Osprey's Dominion Vineyards and Duck Walk Vineyards North - each with its own unique charm and distinctive wines. Expert sommeliers and winemakers will guide you through the tastings of exceptional wines, sharing their deep knowledge and passion for winemaking. Don't miss the opportunity to create lasting memories on this Half-Day Private Long Island Wine Tour Experience, escaping the hustle for a day of indulgence, relaxation, and appreciation of Long Island's vinicultural heritage.

As local experts, we take the guess work out of planning your visit to the North Fork of Long Island. We know which venues are the most memorable and which wines are most enjoyable. As a team of passionate locals, we have scoured the area to handpick the best vineyards, restaurants, and hidden gems that you won't find on your average tourist map or group tour. Our expert guides will accompany you every step of the way, providing insider knowledge and fascinating stories about the rich history of the North Fork. Our private slow tour is 100% customizable and is tailored to you and/or your group's interests. Our all inclusive fee covers all activities, food/wine, gratuities, and transportation for a seamless and memorable experience. Rain or shine.

Create your own itinerary and explore the destinations that interest you most. Spend the day at the beach, visit shopping outlets, amusement parks, scenic attractions, local neighborhoods, restaurants, or other popular destinations—it’s your trip, your schedule. Complimentary bottled water and light snacks are included to help make your journey even more enjoyable. This private experience is perfect for travelers looking for a stress-free, customizable day of sightseeing and exploration with the flexibility to go where they want, when they want.

Nature Abounds on this 3 Hour Tour - Excellent way to See the Best of Long Island's Wine Country here on the North Fork. Take in beautiful views on this relaxing guided 2.5-hour tour cruising through the charming north fork. On this backroads ride nature abounds as seasoned guides lead you on winding roads up close to the Peconic Bay. Stops may range from 14-19 miles …your preference. Bike riding is mostly flat but with a couple of rolling hills. Pass lush green vineyards, osprey nests, wind mills as we cycle winding roads alongside the Peconic Bay Break at a small charming beach (hidden treasure that the locals try to keep to themselves) for herb infused oil & fine vinegar tastings overlooking the Peconic bay. Unique farm stand stop w/ hand woven clothing, & fresh baked goods, veggies, charcuteries etc. Love Lane Shopping Experience for trinkets & souvenirs to commemorate your day (after the tour). Shops located around the corner from our shop. 21-Speed Hybrid Bikes