Discover Martha's Vineyard's picturesque landscapes and charming towns at your own pace with guided or self-guided cycling adventures.
Martha's Vineyard, a beloved island escape off the coast of Massachusetts, offers a uniquely charming and accessible experience for cycling enthusiasts. Far more than just beaches, the island boasts a network of scenic paths that wind through rolling hills, past historic lighthouses, and into quaint villages. Island cycling adventures provide a fantastic way to immerse yourself in the natural beauty and distinctive character of this iconic destination, allowing you to cover more ground than walking while still enjoying an intimate connection with your surroundings. These tours are designed to showcase the island's diverse appeal. Imagine pedaling along coastal roads with breathtaking ocean views, exploring the serene beauty of cranberry bogs, or discovering the vibrant streets of towns like Oak Bluffs and Edgartown. Whether you're seeking a leisurely exploration of picturesque neighborhoods or a more vigorous ride through natural reserves, Martha's Vineyard cycling tours cater to various interests and fitness levels. They are an ideal way for individuals, couples, and families to experience the island's magic, offering a freedom to stop, explore, and soak in the atmosphere at your own rhythm. By choosing a cycling tour, visitors gain local insights and curated routes that might otherwise be missed. Many tours include stops at key landmarks, offering historical context and photographic opportunities. The island's commitment to preserving its natural landscapes means many paths are well-maintained and traffic-calmed, ensuring a safe and enjoyable ride. From the lively atmosphere of Oak Bluffs with its gingerbread cottages to the tranquil shores of Aquinnah, a bicycle is your key to unlocking the full spectrum of Martha's Vineyard's allure.
Discover our top picks for island cycling adventures in Martha's Vineyard

Make the most of your day in Napier - hop on one of our E-bikes and start exploring! Discover the beauty of Hawke’s Bay on a comfortable step-through E-bike—easy to ride all day long. The region’s cycle trails are renowned for their relaxed, scenic routes that link award-winning wineries and top local eateries. Along the way, take in stunning coastal views, peaceful wetlands, Māori heritage sites, lush vineyards and orchards, the historic Ahuriri village, and iconic Art Deco architecture. Our friendly team will set you up with your e-bike and all the info you need for a memorable adventure. Start your Hawke’s Bay journey with Napier City Bike Hire & Tours! Cruise ship passengers info: All passengers are transported on free shuttle buses from Napier Port to the Napier iSite Visitor Information Centre. Our store is located directly across the street from the Visitors Centre. We open outside our normal hours to match your ship's docking time - so you can make most of your visit!

We are, the only ones have four stops to get off the bus. We also offer a lot of amenities that no other tour offers. The tours keep you fully engaged and all we require is for you to be curious! We will not disappoint, what makes us entirely different is that we have a screen at the front of the bus that shows what certain sites looked like in the days of yore. To get a great depth and understanding of what Martha's Vineyard was, and how we are now. The All Island Bus Tour takes you on an adventure you will never forget. Capture the beautiful vistas, the quaint little cottages, the amazing clay cliffs and everything in between. We offer a lot of amenities and have some great stories that intertwine with the awesome history that has been waiting for us to share. With time to shop, dine and sightsee. Your tour will be the highlight of your vacation. We can't wait to meet you!

⭐Possibly the most outstanding wine tour by ebike in the country. ⭐ Embark on an adventure outside Queenstown to the Valley of the Vines to try many delicious award-winning wines ⭐ We only do Giant™ Talon E-bikes Trek Powerflys and Trek Marlin 6 (2024) pedal bikes as our standard. Probably the best bikes in NZ. ⭐Door-to-door options for direct booking only ⭐Ride arguably the best bike trail in New Zealand ⭐Perfect for the easy rider - Minimal hills, wide gravel trails, Easy Navigation. 1 hour ride ⭐Knowledgable, friendly guides ⭐Finish at any winery - Text us at 3pm or when you've decided your final stop.

Our very unique, immersive adventures are the only ones of their kind. We, unlike other companies, provide your very own remote, interactive, live host to assist and encourage you along through your phone. We are an Austin, TX-based global custom event design company offering scavenger hunts and other events in 300+ cities in North America and beyond. Our specially hand-crafted adventures are equal parts tour, creative challenge, detective hunt, and social experiment! Guests get to discover in an alternate reality our favorite hidden gems off the beaten trail and creatively interpret fun art, history, and culture clues - for points! They get to enjoy fame and glory while appearing on our website’s international leaderboard, no matter what their score. They get to essentially race other teams in other cities, even if they don’t have competitors who have signed up in their city that day. Get ready to discover unusual oddities, laugh out loud, and make the experience your own!

Explore Timanfaya National Park and La Geria vineyards on a top-quality E-bike. Enjoy a smooth ride, breathtaking landscapes, and receive a photo & video keepsake. Ride through Timanfaya’s volcanic landscapes on premium E-bikes ✔ Cycle across the unique vineyards of La Geria ✔ Receive a photo & video package as a souvenir ✔ Enjoy an eco-friendly, thrilling adventure blending nature and culture

DURATION: 3-5 hours SKILL LEVEL: Easy – intermediate WHAT TO WEAR? Equipment suitable for cycling, trainers, a hat or cap Take a peek at the islands beauty and find a unique place of serenity somewhere within the allure of the numerous coves, little inland villages, remarkable vineyards and olive groves. Explore the most beautiful features of Hvar accompanied by local guides who share their undeniable passion for this Mediterranean heaven with you. Our starting cycling point is in small inland village in the central part of the island. Return car transfer from Hvar town to starting cycling point (and back) is not included. If you don’t have organized your own transportation, we can pick you up as an extra paid service.

Escape the city and discover the timeless charm of Martha’s Vineyard on this easy, full-day trip from Boston. Travel by (Optional) scenic ferry across the harbor before exploring the island on a (Optional) guided sightseeing bus tour that highlights its historic towns, coastal landscapes, and iconic landmarks. After the tour, enjoy generous free time to relax, shop, stroll the harbor, or enjoy lunch at a local restaurant. With round-trip ferry transportation and optional guided touring, this experience offers the perfect balance of structure and freedom for a memorable island getaway.

This is leisurely cycling at its best. Easy-paced with your loved ones to enjoy. Our friendly guides will take you through some of the most exquisite wine farms in South Africa. We have special access to famous farms such as Mont Rochelle, Grand Provence, La Bri, La Bougonne, Holden Manz and may others. Half day tours include two wine tastings on different wineries with time for an optional lunch (own account) on a third signature wine farm. We've also included a wine pairing where you can try spectacular wines with homemade chocolate or traditional South African biltong. A relaxed and rewarding day you will never forget! Our carefully constructed routes among the vines and backroads allow for plenty of flexibility. It’s your day – we can shorten or lengthen the distance no problem. Let’s get to the first farm for wine tasting and build your memorable day.

This is more than just a bike ride, it’s a crafted journey through Central Otago’s vineyard country. Cruise lakeside trails, roll through the gold-rush charm of Cromwell, and wind your way into the Bannockburn Inlet — a region world-famous for Pinot Noir and dramatic landscapes. What sets this experience apart is the seamless service from the Central Cycle Trail Co. tea, from personalised bike fittings and scenic shuttles to on-trail support and insider tips. Ride a premium e-bike, enjoy a gentle itinerary, and finish with a glass in hand at the beautiful Carrick Winery, with the option to upgrade to a private cabana and shared platter. Whether it’s a romantic escape, a group outing, or a solo wine-lovers’ ride, we make it easy to relax, explore, and taste the best of the region; effortlessly, safely, and in style.

This sailing trip is perfect for people who love being active and outdoors. Your daily activities will include sailing, hiking, cycling, paddle boarding, swimming and snorkeling. Daily activities are fun and not too demanding. You will explore the Peljesac and Elaphiti shorelines and Mljet Island; full of unique cliffs, caves, coves, rocks, beaches and pine forests. The trip is based in the Dubrovnik area, leaving time to visit and explore this famous walled town.

This adventure takes you from Arthurs Point to the Gibbston Valley, connecting two beautifully restored churches via one of NZ's most scenic and culturally rich cycle routes. Unlike typical bike hires, this is a fully curated experience—ride the Wharehuanui Trail beneath the ranges, pass through farmland and luxury golf resorts, explore Arrowtown’s gold rush history and the Chinese Miners’ Village, and glide across dramatic swing bridges into wine country. What makes it truly unique is the combination of local heritage, premium wine tasting, and seamless e-bike support. Perfect for couples, solo travellers, and active families looking for a half-day escape with historic charm and vineyard indulgence, this tour gives you the freedom to ride at your own pace—with expert support when you need it. Finish your journey at The Church Cellar Door, a stunning final destination for more hospitality, before we transfer you back. This is not just a ride, it’s an unforgettable story on two wheels.

Riding an e-bike along the beautiful trails of the town Vodnjan along stone walls through olive groves and vineyards. On start of the tour we visit old churches. Then we come to the area where are 7 fortresses and visit the largest one. After that we take a break from bikeing with a swim in the sea on a hidden beach. Upon our return we visit old field houses and we ride with beautiful view of Brijuni islands.

Explore beautiful Sipan island in a unique way: by kayaking and biking in small groups up to 8 people. Guided by professional local guides. Suitable for beginners. Experience and enjoy: beautiful nature away from the crowds, scenic paddling on crystal Adriatic sea, biking through olive groves and vineyards, exploring medieval towns and historical sites... Tour length: 11am – 6 pm (10 am - 5 pm Sunday & Holidays) Activity : Kayaking 10 km, Biking 10 km Included : top-end kayaking and biking equipment, watertight bags for personal belongings, professional instructions and an English-speaking local guide.

Explore popular summer destinations favored by US Presidents! Tour Martha's Vineyard on a vintage school bus, visit Aquinnah Cliffs, and enjoy scenic views of Essex aboard the Steam Train. Discover the historic Breakers Mansion in Rhode Island. Fun and Insightful Enlish&Chinese-Bilingual Tour Guides – Enjoy lively stories and spontaneous sharing along the way. Unlimited Bottled Water & Complimentary Snacks – Stay refreshed and energized throughout the journey. Themed Attractions with Seasonal, Adventurous & Playful Highlights – Carefully selected for excitement and discovery. Happy Family Time – Kids enjoy 50% off for a joyful and budget-friendly trip in July and August.(Prices shown are the final specials) Exclusive Travel Keepsakes – Includes a custom travel passport and share-worthy moments for your social media.

An ideal tour for the explorers of Mykonos’ cultural and natural heritage. A fun and informative cycling experience, featuring a fascinating blend between our religious tradition, easy off-roading, a pristine beach and the rural & wild landscapes of the island. - We meet at our organic vineyard “Mykonos Vioma Organic Farm”. - We are local guides, sharing our love for Mykonos with our guests. - A tutorial on the use of mountain bikes will be offered. - The route is 15km/9,32mi, ideal for average or frequent riders comfortable with urban cycling and with difficulty level 3/5. - We stop at different spots for an interpretative talk on our local traditions. - At Ano Mera village we rest, refresh with lemonade & a snack and allow you free time to visit its monastery. - At the beach of Fokos we have time for swimming & underwater photo shooting (weather permitting) OR hiking. - Our ride back takes only 30 minutes and then you can unwind at the soothing ambience of our vineyard.
Experience the island's stunning coastal vistas, rolling hills, and serene natural landscapes up close.
Cover more ground and discover hidden paths at your own pace, with options for guided and self-guided tours.
Enjoy a sustainable way to explore, minimizing your environmental impact while experiencing the island's charm.
Easily navigate and explore the unique character of villages like Oak Bluffs, Edgartown, and Chilmark.
Cycling tours offer an engaging activity suitable for families, couples, and solo travelers with various routes available.
Many guided tours offer historical context and local anecdotes, enriching your understanding of the island.
Join a small group led by a knowledgeable local guide, covering popular routes and highlighting key attractions. These tours often include historical commentary and stops for photos or refreshments.
Rent a bike and follow curated routes provided by the operator. This offers maximum flexibility, allowing you to set your own pace and explore specific areas of interest at your leisure.
Focus on specific aspects of Martha's Vineyard, such as lighthouse tours, culinary explorations, or nature-focused rides through protected areas. These are great for travelers with particular interests.
Utilize electric-assist bikes to tackle hills with ease and cover more distance comfortably. Ideal for those who want to explore further without strenuous effort.
Tours typically range from 2 to 4 hours, with self-guided rentals offering flexibility for all-day exploration.
Martha's Vineyard experiences varied weather. Tours usually operate rain or shine, but cancellations may occur in severe conditions. Check your tour provider's policy.
Guided tours often operate with small groups, typically between 6-12 participants, ensuring a more personalized experience. Rentals offer private exploration.
Most tours include bike rental, helmet, and a guide (for guided tours). Some may offer water, snacks, or admission to specific points of interest. Always verify inclusions.
Meeting points vary but are commonly located in central areas of Edgartown, Oak Bluffs, or near ferry terminals for convenient access.
Consider costs for ferry tickets to the island, personal snacks or meals, and optional souvenirs. Gratuities for guides are customary.
Book your ferry tickets to Martha's Vineyard well in advance, especially during peak season, to secure your desired departure times.
Many cycling tours require advance booking, particularly during the summer months, so plan ahead to ensure availability.
Wear comfortable, breathable clothing and closed-toe shoes. Sunglasses and sunscreen are essential, even on cloudy days.
Consider the island's topography; some areas are quite hilly. Electric bike rentals are an excellent option if you prefer less strenuous riding.
Bring a reusable water bottle. Many tours provide access to water refills, and staying hydrated is key for an enjoyable ride.
Familiarize yourself with the basic rules of the road on the island, including respecting pedestrians on shared paths.
If opting for a self-guided tour, download any provided maps or GPS tracks offline, as cell service can be spotty in some island areas.
Don't forget your camera! Martha's Vineyard offers countless picturesque spots perfect for capturing memories.
A: The shoulder seasons, late spring (May-June) and early fall (September-October), offer pleasant weather and fewer crowds. Summer is popular but can be busy and warmer.
A: Yes, many tours cater to various fitness levels and offer routes that are relatively flat and easy. Guided tours often set a moderate pace, and electric bikes make it accessible for everyone.
A: It's highly recommended to book both bike rentals and guided tours in advance, especially during peak season (June-August) and weekends, to guarantee availability.
A: Tour operators have different cancellation policies. Typically, tours will run in light rain, but may be canceled or rescheduled for severe weather. Check your booking details for specifics.
A: While some operators focus on rentals, you can bring your own bike to Martha's Vineyard via ferry. However, many organized tours and rental packages are designed for convenience.
A: Martha's Vineyard has a great mix of dedicated bike paths and quiet, scenic roads. Most tours and suggested routes utilize both to offer a diverse riding experience.
A: Comfortable, weather-appropriate clothing is key. Think moisture-wicking fabrics, closed-toe shoes, and layers as the ocean breeze can be cool. Don't forget sunscreen and sunglasses.
A: Yes, helmets are standard and typically included with all bike rentals and guided cycling tours for safety. You can usually request different sizes.
Escape to Martha's Vineyard for charming New England towns and stunning Atlantic coastline views.
Experience the unique island vibe and picturesque harbors of Oak Bluffs and Edgartown.
Enjoy car-free exploration with excellent public transit and bike paths throughout Martha's Vineyard.
Discover a rich history of Wampanoag culture and classic Victorian architecture.
Savor fresh seafood and explore local artisan shops for a true island getaway.
Find quintessential coastal charm and a relaxed pace of life on Martha's Vineyard.
Martha's Vineyard experiences a temperate maritime climate with distinct seasons. Summers are warm and humid, with ocean breezes moderating the heat, while winters are cool and damp, though generally milder than inland New England. Spring and fall offer pleasant, crisp air, ideal for outdoor activities.
The shoulder seasons, May, June, September, and October, are often considered the best months to visit Martha's Vineyard due to pleasant weather, fewer crowds, and lower accommodation prices.
Peak season runs from late June through August, offering the warmest weather perfect for beach days and lively island life, but expect higher prices and significant crowds.
The off-season, from November to April, brings cooler weather and a quieter atmosphere, with many seasonal businesses closed, but offers a more local and peaceful experience.
Explore comprehensive guides to plan your perfect trip, including food tours, cultural experiences, and more.
Discover the island's stunning shoreline, from sandy beaches to dramatic cliffs, with curated tours and activities.
Explore iconic lighthouses and stunning coastal vistas on Martha's Vineyard with expertly guided tours.
Explore Martha's Vineyard's rich food scene, from farm-to-table delights to fresh seafood on curated culinary trails.
Discover the unique character and vibrant history of Martha's Vineyard's distinct towns with expertly guided walking and bus tours.
Discover the rich heritage of the Wampanoag Nation through guided tours and immersive activities on Martha's Vineyard.
Getting around Martha's Vineyard is quite convenient. The Island has an extensive public bus system, VTA, which connects all the main towns and beaches, making it easy to explore without a car. Day passes are reasonably priced. Renting a bike is another popular and scenic option, with dedicated paths throughout much of the island. Taxis and ride-sharing services are available, especially in the larger towns. Ferries from the mainland are the primary way to arrive, and some offer car transport, but many visitors opt to leave their vehicles behind.
Rent a car for maximum flexibility and explore at your own pace on Expedia USA.
Find the perfect accommodation for your Martha's Vineyard adventure. From luxury resorts to cozy hotels, we've got you covered.
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