Long Island isn’t just about sprawling beaches and busy villages; it’s also a fantastic place to explore by bike. With its flat terrain, scenic vineyards, farmland, and charming coastal spots, riding here offers a uniquely intimate way to see the region. We love how some tours blend wine tastings and farm visits with leisurely rides, like the Mattituck New York Guided Farm and Wine Country Bike Tour, which combines stunning vineyards, beaches, and farm stands in a small-group setting. It’s perfect for those who want a relaxed, immersive experience that includes tastings and professional photos.
Long Island’s bike tours appeal to a range of travelers—whether you’re after a half-day escape, a private adventure, or an electric-assisted cruise with sunset views. Whether you prefer vineyards, beaches, or farmland, there’s an option that fits your style. Below, we highlight the best six bike tours, each with its own unique flavor and experience.
1. Mattituck New York Guided Farm and Wine Country Bike Tour
At number one, this guided farm and wine tour offers a delightful way to explore North Fork’s scenic beauty in about 5.5 hours. It’s perfect for those who want a laid-back ride with plenty of tastings and personal attention. The tour includes stops at two vineyards, a beach with herb-infused oil and vinegar tastings, and a farm stand with fruits, jams, and veggies—some of the oldest on the North Fork, dating back over 50 years. The small-group size (limit of 12) ensures a relaxed vibe and more personalized experience.
What makes this tour stand out is the combination of vineyard visits, beach stops, and farm stands, all with professional photos included. The bike ride is leisurely, with helmet use provided and the option of single or tandem bikes. Guests consistently praise the guides’ friendliness and the well-planned itinerary. One reviewer notes, “The guides were super-friendly and fun, making it a memorable day.” The price of $139.99 includes all tastings and photos, making this a good value for a full day of scenic exploration and local flavor.
Bottom Line: If you’re looking for a friendly, family-style day with wine tastings, farm stands, and beach views, this guided tour hits the mark.
2. Mattituck Bike Wine Country and Fruit Orchard Tour
This bike tour combines scenic riding with in-depth visits to vineyards, orchards, farms, and the Peconic Bay, all in about 5 hours. It’s ideal for those eager to explore more of the North Fork’s farmland and wine scene in one go. Covering around 13.5 miles on flat terrain, the ride is accessible for most riders.
Highlights include special vineyard access, herb-infused olive oil and vinegar tastings, and a stop at a fruit orchard where you can pick your own fruit. The tour supports you with a support vehicle for any purchases, and photos are provided afterward—an extra touch of convenience. Guests love the supportive atmosphere and relaxed pace, with one calling it “a superbly organised tour with tasty buffet lunch and friendly guides.” The price of $141.99 offers good value, especially since it includes many tasting opportunities and a scenic ride.
Bottom Line: Best suited for those who want a comprehensive, farm-to-vineyard experience with plenty of tastings and easy riding.
3. Guided Farm and Wine Country Bike Tour in Mattituck NY
At position three, this guided tour offers a 5.5-hour, leisurely ride through North Fork’s boutique vineyards, farms, and beaches. It’s tailored for those looking for a personable experience with a focus on boutique wineries and live music (depending on the date). It starts with a fitting for hybrid bikes, with options for e-bikes if you reserve ahead.
The itinerary includes visits to a vibrant boutique vineyard with butterfly gardens and outdoor patios, a charming beach on the Peconic Bay, and a farm offering herb-infused olive oils and vinegar tastings. The guides are known for their attention to detail and local knowledge, making the experience feel authentic and engaging. One reviewer highlights, “The bike ride was fun, the wineries wonderful, and the lunch excellent.” The price of $132.99 is reasonable considering the inclusive stops and the personal touch.
Bottom Line: Perfect for travelers who appreciate boutique wineries, outdoor settings, and optional live music, with a flexible, friendly guide.
4. Sagaponack Sunset Electric Bike Tour
For those craving a shorter, scenic outing, this Sunset Electric Bike Tour in Sagaponack offers a 2-hour ride perfect for an early evening escape. It’s an intimate experience, limited to five participants, making it ideal for couples or small groups seeking a relaxed yet picturesque adventure. The e-bike makes covering the 15 miles of bucolic Sagaponack scenery easy, allowing you to focus on the views and the atmosphere.
The tour begins from School Street, with the guide ensuring everyone is comfortably fitted. The ride takes you to Sagg Main Beach, a well-known spot for gazing at the sunset, with the historic, architecturally interesting surroundings adding to the charm. Reviews are limited, but the focus on a quiet, scenic ride at sunset makes it a lovely choice for a romantic evening or a peaceful way to unwind.
Bottom Line: Best for those wanting a short, stress-free ride with beautiful sunset views and a small, intimate group.
$165.00 per person
5. Electric Bike Tour at Montauk Point
This e-bike tour covers Montauk’s top sights in about 3.5 hours, making it a great option for active travelers. It’s suitable for intermediate to advanced riders, with a guided route that includes Fort Hill Overlook, Camp Hero State Park, and the iconic Montauk Point Lighthouse. The Bosch-powered e-bike helps you conquer hills and cover more ground with less effort.
The tour begins with a proper fitting, then the group heads east past Ditch Plains surfers and historic sites, with stops for photos and sightseeing along the way. The guide shares insights into Montauk’s natural beauty and history, making the tour both fun and educational. For $240, it’s a pricier option but offers a comprehensive experience of Montauk’s rugged landscape and lighthouse.
Bottom Line: Ideal for active, somewhat advanced riders who want to see Montauk’s highlights without breaking a sweat.
$240.00 per person
6. Half Day Private North Fork Bike Tour Thru Wine Country
Finally, this private tour is perfect for groups of up to six looking for a flexible, personalized experience. Over about 3 hours, the ride covers 14-19 miles on mostly flat terrain, with scenic stops at the Peconic Bay, a farm stand, and a boutique vineyard. It’s a leisurely, tailored experience that can include anything from herb-infused tastings to wine sharing.
The guide leads you on backroads through lush vineyards and farms, with opportunities to relax in beautiful settings. The tour’s private nature means it can be customized to your interests, making it ideal for families or small groups wanting an exclusive day. While pricier at $834 per group, the personalized approach and flexibility offer excellent value.
Bottom Line: Best for small groups seeking an exclusive, customizable ride with a focus on wine and farm visits.
$834.00 per group (up to 6)
How to Choose Your Perfect Long Island Bike Tour
When selecting a bike tour in Long Island, consider your budget, fitness level, and interests. For a comprehensive tasting experience, the Mattituck Guided Farm and Wine Country Bike Tour offers great value, especially if you enjoy wine and farm visits. If you prefer a private, tailored experience, the Half Day Private North Fork Bike Tour provides customization for small groups.
Active travelers who want to cover more ground quickly might opt for the Montauk Electric Bike Tour, while those seeking a romantic sunset ride should consider the Sagaponack Sunset Electric Bike Tour. Booking early is recommended, especially in peak season, to secure your preferred date and ensure availability.
Final Thoughts
Long Island’s diverse landscape makes it a superb destination for bike touring—whether you’re into wine, beaches, farms, or sunset views. The highlighted tours offer something for all, from full-day guided adventures to intimate private rides. Whether you’re a seasoned cyclist or just looking to enjoy a relaxing outing, the options above will help you find a perfect match. Planning ahead and booking early will make sure your experience is smooth and memorable, so don’t wait to lock in your spot. Happy cycling!