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Biking Martha's Vineyard and Nantucket

6 Days & 5 Nights 3 Read 1 reviews
  • Discover windswept beaches, lighthouses and the seafaring history of Massachusetts'
  • Visit the Whaling Museum and boutiques lining the cobblestone streets
  • Pedal on bike trails through countryside, lobster ports and cranberry bogs
  • Explore Edgartown's Victorian architecture and Aquinnah's panoramic red-clay cliffs
  • Enjoy the fresh ocean breeze as you relax on the porches of 19th century sea captains' homes
Spend a week discovering the grandeur of Martha’s Vineyard and charm of Nantucket by ferry and bicycle, for an elegant, slow-paced island vacation. Ferry from Hyannis to Oak Bluffs on Martha’s Vineyard, the perfect introduction to bustling seaports and maritime livelihood. Pick up your bicycle to ride along the local bike paths exploring golden beaches, Edgartown’s Victorian architecture, Aquinnnah’s dramatic coastline and Oak Bluffs’ festive nightlife. Ferry over to the wharves and cobblestone streets of Nantucket, staying in B&Bs walking distance from high-end boutiques and cedar-shingled homes. Tour the Whaling Museum and ride to Brant Point Lighthouse, Madaket Beach and the Cisco Brewery for local libations and fresh seafood. Finish the week with a day off at Jetties Beach or a final ride to the town of Siasconset before returning for aperitifs and dinner at oceanfront bistros. Savor a smoked salmon brunch, search for seashells or shop for souvenirs before ferrying back to Hyannis on Cape Cod.
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What To Expect

This tour is perfect for those who want to explore the islands of Martha’s Vineyard and Nantucket. Take a ferry to each island, enjoying easygoing bike rides each day with plenty of time to shop, dine and relax at the beach. This trip is graded easy with average daily rides around 20 miles (2-4 hours) along paved bike paths, country roads and coastal streets. Each night, stay in charming B&Bs, the perfect base for morning rides and afternoons roaming sandy beaches and cobblestone streets.

Trip Style:

Self Guided | Go at your own pace on an independent holiday.


Inn to Inn Cycling | A classic point to point cycling holiday, staying in a different location each night

This trip is suitable for:

Solo Travellers, Multi-Generational

Ideal if you have an interest in:

  • Wine, Whisky & More...
  • Luxury & Unique Stays
  • Historical Journeys
  • Coastal & Island


  • Classic

Grade & Terrain

This tour is graded easy, with four days of biking and a maximum distance of 24 miles. Daily rides average around 14-20 miles (2-4 hours) along bike trail and country roads, with a mixture of exposed and forested conditions. The distances and ascents/descents are approximations of the recommended routes.


Navigating is easy using the Macs Adventure Navigation App. Your daily rides will be mapped in the app with GPX tracks, route notes and turn-by-turn directions. All of these resources are available to download for offline use.

You will be provided with local bike shop information in addition to 24/7 telephone support from Macs Adventure should you require assistance.

Experience & Fitness

When entering, connecting and leaving towns, bicyclists should expect to ride some sections on two-lane, paved roads with traffic and moderate speeds. Local buses, with bike racks, are available at specific locations around Martha’s Vineyard and Nantucket should you need them at any point along the route (not included). Bus lines, costs and general information will be detailed in the pre-departure information pack and daily route notes.

Accommodation Information

We specifically hand-pick your accommodations in family-owned, New England style hotels, inns and B&Bs to ensure that you enjoy every minute of your stay on Martha’s Vineyard and Nantucket.   

All accommodations are located along the bike route and offer a warm welcome to tourists and cyclists. Additionally, each offers individual character and welcoming hospitality.

Single Rooms & Solo Travelers

This trip is based on two people sharing a room. If you’d like separate rooms, a single supplement is required.

If you would like to request a twin room (same room with two separate beds), please notify us during booking so we can request this option.

This trip is also available to solo cyclists (a solo supplement is required).


Four Breakfasts are included in this trip. Most breakfasts are continental and typically include a buffet spread of muffins, oatmeal, coffee, tea, yogurt, granola, fruit and baked goods.

Lunches and dinners are not included in this trip, so you can choose from nearby options. For breakfasts and lunches, you can find bakeries, cafés or restaurants located in town and along the biking route. For dinner, you can dine at local restaurants all within a short walking distance of your night’s stay. We recommend trying out the amazing seafood restaurants on Martha’s Vineyard and Nantucket offering local delicacies such as clams, lobster, oysters, seabass, and seafood chowders. 

  • 5 Nights at hand-selected charming B&B's
  • 4 Breakfasts
  • Ferry to/from Martha's Vineyard
  • Ferry to/from Nantucket
  • Bike rental (inc. fitting and orientation)
  • Information pack
  • Route notes, detailed maps and GPS tracks on the Macs Adventure smartphone navigation app
  • 24/7 Emergency telephone support from our US office
  • Travel to the start and end of the trip
  • Local buses, taxis and transfers
  • Lunches, dinners, drinks and snacks
  • Additional nights before, during or after the trip
  • Personal equipment
  • Travel insurance (required)
  • Gratuities and tips
  • Extra nights in Hyannis
  • Room upgrades

When To Go

This trip is available to start on a Thursday or Friday for the months of June and September, and on a Friday, Saturday or Sunday for the months of July and August. The variation of availability is in direct relation to the bus and ferry schedules during the shoulder and peak seasons.

If you are planning on renting or bringing a car for arrival or departure, please notify us during booking for additional dates available.

We suggest you book as soon as your plans are finalized to ensure availability for specific dates

Weather and Climate

The best time to visit the Cape Cod Islands (Martha’s Vineyard and Nantucket) is from May until September.

May-June: From May to June, the weather warms up into the high 60s and 70s (°F). Tourists enjoy sneaking in a visit during this short but sweet shoulder season due to its temperate climate and fewer crowds.

July-August: This peak season is the most popular time to visit, with warm waters, cool ocean breezes and temperatures ranging from the 70s and the 80s. Visiting between July and August is best if hitting the beach is a top priority.

September-October: The fall shoulder season is one of the region’s best-kept secrets. The weather stays pleasant well into November, with temperatures hovering between the 70s and the high 60s. While it is starting to get chilly in the morning and evenings, the water is usually warm enough to still go swimming into September.

For average climate information, please refer to the below chart. Another useful resource is https://www.capecodchamber.org/weather 


Getting to the Start

By Air

Boston Logan International Airport, has flights from international and national destinations.

By Bus

From Boston, Hyannis can be easily reached via the Peter Pan Bus Line located directly outside Boston Logan International Airport arrivals (lower level) in terminals A, B, C & E. Southbound buses depart everyday and will drop you off directly at the Hyannis Transit Station (approx. $24, 2-2.5 hours). Bus schedules, reservations and details are outlined in the pre-departure information pack.

By Rental Car

Budget and Enterprise both have rental car pick-ups at Boston Logan International Airport and drop-offs at Hyannis Barnstable Municipal Airport (approx. 2-3 hours). We recommend using a GPS service to help you get from the city to Hyannis. Taxis will be lined-up outside the Hyannis Barnstable Municipal Airport to get to your overnight accommodation (approx. 20 minutes).

By Taxi

Taxis are available on-call and are located outside the Boston Logan International Airport’s arrivals exit (approx. $180, 2-3 hours).

Getting Around

Getting to/from Martha’s Vineyard & Nantucket

Included in this trip is a Hy-Line Cruises island ferry from Hyannis Harbor to Martha’s Vineyard, a ferry from Martha’s Vineyard to Nantucket and a ferry from Nantucket back to Hyannis (all ferry transfers take approximately one-hour in duration each way). Enjoy this high-speed passenger ferry, with indoor and outdoor seating, luggage carriers, bike parking, snack and cocktail bar, as you transfer between each island. Tickets are arranged and purchased in advance, available for pick-up at the terminal window of each loading dock using your last name and confirmation number. Ferry schedules, reservation information and ticket transfers (missed ferries or change fee’s) can be found in your pre-departure information packet.

For additional transportation services outside the provided itinerary, such as a taxi to a specific restaurant or location, the host at your evening’s accommodation can help assist you in making the necessary arrangements.

Getting from the End

From Hyannis, Boston can be easily reached via the Peter Pan Bus Line located at the Hyannis Bus Terminal. A northbound bus departs everyday and will drop you off directly at Boston Logan International Airport, Airport at terminals A, B, C, & E at designated bus stops (approx. $24, 2-3 hours). Bus schedules, reservations and details are outlined within the pre-departure information pack.

If you need help in planning your travels back, our team here at Macs Adventure would be more than happy to share our tips and advice.

Baggage Transfer

All of our hand-selected accommodations are conveniently located near the ferry harbors for ease of navigation and short walking distances. As such, we do not provide a luggage transfer service on this trip. You will be responsible for transporting your bags on and off the ferries, and to and from Martha’s Vineyard and Nantucket. As there are many tourists during the summer peak season, please be sure to know the whereabouts of your luggage at all times when traveling by bus, taxi or ferry, and clearly mark your bag with the luggage tag provided.

If you would prefer to have a taxi take you and the bags from the ferry terminal to your accommodation, please let us know and we can arrange this ahead of time or you can grab a taxi lined outside the ferry terminal upon arrival (additional costs apply).

While exploring the island on bike, you will only need to carry your daily provisions with you in a day pack. If desired, you can request a handlebar bag, pannier or basket when you pick-up your rental bike to store loose items in. Take plenty of water as well as sunscreen, water resistant clothing, warm jacket/layers, camera, small first aid kit and snacks. For lunches, feel free to purchase a packed lunch to take with you, stop at a local restaurant along the way, or wait until arrival at your final destination to find a place to dine. For all other equipment or items to store in your day pack, our packing list in our Book of Adventure will give you plenty packing ideas.

General Information


Our pre-departure information pack has detailed advice and a packing list on what to bring. This includes warm and cold weather cycling gear, rain gear, swimwear and lots of other specifics.

Please be prepared by packing all the necessary items for a comfortable trip. If you have any questions about what to take, we'd be happy to share our own top tips and advice.

Bike Rental

A bike rental is included in the cost of this trip. Bike rental includes an easy-to-ride Comfort Hybrid bike for exploring Martha’s Vineyard and Nantucket. These bikes are top choices for riders who spend their time in the saddle riding on pavement, smooth trails, gravel and sand, with plush saddles, wide tires and lightweight frames. All rentals are outfitted with a helmet, lock and flat pedals. An All Terrain/Sports Bikes, road bikes or kids bikes can be available at an additional charge. Bicycle on-call service and pick-up is also provided by our local partners should you have any problems while on route. Rental bike details and contact information is further outlined in the pre-departure information pack.

If you are interested in renting an E-Bike while exploring Martha’s Vineyard, please let us know at the time of booking so we can make the necessary arrangements(additional costs apply). E-Bikes are not available on Nantucket.

To help expedite the bike rental process, please supply us with your height and frame size you currently ride during booking.


Travel Insurance

Travel insurance helps protect your travel investment, your belongings and most importantly you, from unforeseen circumstances that may arise before or during your trip. For more information, please visit our travel insurance page by clicking this link.

How do I get my rental bike?
How does the luggage transfers work?
What if I become ill or cant bike a stage?


Day 1 Arrive Hyannis Day 2 Ferry to Martha’s Vineyard & Bike to Edgartown 12 miles / 19.5 km Day 3 Bike Aquinnah to Oak Bluffs 24 miles / 39 km Day 4 Ferry to Nantucket & Bike to Madaket and Cisco 17 miles / 27.5 km Day 5 Bike to Siasconset 18 miles / 29 km Day 6 Onward Travel

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