Long Island’s diverse landscape makes it a fantastic destination for bike tours. With scenic vineyards, peaceful beaches, and lively coastal towns, it offers something for every cyclist. Whether you’re pedaling through vineyard backroads, cruising on electric bikes at sunset, or exploring historic lighthouse sights, Long Island provides uniquely memorable riding experiences. Its relatively flat terrain and charming small towns make it easy to cover a lot of ground without exhausting yourself, especially if you opt for an electric bike. Plus, many tours include expert guides and personalized routes, helping you see the best sights without the hassle of navigation.
If you’re planning a trip and want to explore Long Island on two wheels, this guide highlights the three best bike tours—from wine country jaunts to sunset coastal rides—that combine scenic beauty with a touch of local flavor. Each offers something different, whether it’s a private guided experience, an electric sunset ride, or a full-day exploration of Montauk’s rugged coast.
1. Private Guided Wine Country Bike Tour in Mattituck
At number one, the Private Guided Wine Country Bike Tour in Mattituck is a top-rated experience with a perfect 5.0/5 from 15 reviews. This 4.5-hour tour offers a relaxing way to explore Long Island’s North Fork while sampling some of its finest boutique vineyards. The guided ride covers 12, 14.5, 16, or 19 miles, giving you flexibility based on your level of fitness and interest. What makes this tour stand out is how customizable it is—your guides tailor stops and routes to suit your preferences.
The tour begins with a visit to New Suffolk, where you can enjoy herb-infused oils and vinegars overlooking Peconic Bay. Then, you’ll head to a private vineyard, chosen specifically for its quality and character—these are not the big commercial wineries but small, noteworthy vineyards that offer a more intimate tastings experience. The final stop, Wickham’s Fruit Farm, lets you pick up local cheeses, fruits, honey, or jams, adding a farm-to-table flavor to your day. The tour combines scenic backroads with stops that highlight the region’s agricultural heritage and wine craftsmanship.
Bottom Line: This tour is perfect for wine lovers who want a relaxed, personalized experience with stunning views and gourmet tastings. The price of $199 offers excellent value for a private, guided tour with flexible routes.
2. Sagaponack Sunset Electric Bike Tour
If you’re after a shorter but equally memorable ride, the Sagaponack Sunset Electric Bike Tour is a fantastic choice. This 2-hour tour is rated 5.0/5 from just one review, which speaks to its quality. Priced at $165 per person, it offers a small group experience—up to five participants—ensuring an intimate atmosphere.
What sets this tour apart is its focus on the beautiful Sagaponack area. You’ll meet your guide on School Street and hop onto a Royal Dutch Gazelle e-bike, which makes exploring easier and more enjoyable. The ride covers roughly 15 miles, taking you to Sagg Main Beach for a perfect sunset moment. The tour includes helmets, a handlebar zipper bag for your valuables, and plenty of local insights from your guide. The route features historic farm stands, quiet streets, and scenic coastal views—highlighting the bucolic charm of this affluent seaside town.
Bottom Line: Ideal for those who want a shorter, scenic ride that ends with spectacular sunset views. The small group size and electric bikes make it accessible even for occasional cyclists or those who prefer a leisurely pace.
3. Electric Bike Tour at Montauk Point
For those looking to cover more ground and see iconic sights, the Electric Bike Tour at Montauk Point offers a guided adventure that lasts about 3.5 hours. Priced at $240, this tour is suitable for intermediate to advanced riders who want a more active experience. It’s the only one among the three that involves a full-day exploration and covers a broader area, including Fort Hill Overlook, Camp Hero State Park, and the legendary Montauk Point Lighthouse.
Your Bosch-powered e-bike makes it possible to easily ascend the high-elevation overlooks for spectacular views, while the guide ensures you don’t miss key landmarks. The ride follows paved and off-road paths through diverse landscapes, including oceanfront cliffs and historic military sites. After the scenic ride, you’ll enjoy a stop in downtown Montauk for refreshments, making it a balanced mix of activity and relaxation. The small group format ensures personalized instruction and safety.
Bottom Line: This tour is best suited for those with good fitness and a desire to see Montauk’s most iconic sights at a comfortable pace. It’s a perfect blend of adventure, scenery, and cultural highlights.
How to Choose Your Perfect Long Island Bike Tour
Selecting the right bike tour depends on your interests, fitness level, and how much time you want to spend riding. If you love wine and want a relaxed, private experience, the Private Guided Wine Country Bike Tour in Mattituck is an excellent choice. For a quick, scenic sunset ride, the Sagaponack Sunset Electric Bike Tour offers a shorter, intimate experience. If you’re eager to explore Montauk’s coast and landmarks more extensively, the Electric Bike Tour at Montauk Point provides a full-day adventure with plenty of highlights.
Consider your budget, fitness level, and how much time you wish to dedicate. Book early during peak season, especially for tours with limited availability like the Sagaponack sunset ride or Montauk excursions. Weather can influence riding conditions, so plan accordingly—spring and fall are usually ideal, with summer offering longer daylight hours.
Final Thoughts
Long Island offers a variety of bike tours that showcase its scenic beauty, from wine country backroads to rugged coastlines. For a personal touch and wine tastings, the Private Guided Wine Country Bike Tour is hard to beat. If you’re after a quick but stunning sunset ride, the Sagaponack Sunset Electric Bike Tour is a wonderful option. For those craving a more vigorous exploration of Montauk’s iconic sights, the Electric Bike Tour at Montauk Point delivers.
No matter which you choose, these tours promise memorable experiences—so consider your interests, book early, and enjoy pedaling through Long Island’s beautiful landscapes.