Self Guided Walking Holidays & Cycling Holidays

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Discover the maritime past and cedar-shingled homes of Massachusetts' Colonial Islands


  • Discover windswept beaches, postcard lighthouses and the seafaring history of Massachusetts' Colonial Islands
  • Visit the Whaling Museum and boutique shops lining the cobblestone streets of Nantucket
  • Bike the Islands' network of 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.

Day 1: Arrive Hyannis

Hyannis can be easily reached via the Peter Pan Bus Line located directly outside Boston Logan International Airport. Southbound buses depart everyday and will drop you off at the Hyannis Transit Station (approx. 2-3 hours).

Walk along the waterfront, or call a local taxi, to your overnight hotel. Check-in and head to the nearby Veterans Park or Kalmus Beach, the perfect spot for sunset viewing, relaxing and watching sailboats in the distance. Tonight, peruse the harbor for a delicious seafood dinner of clams, chowder, lobster and fresh fish caught directly from the Atlantic Ocean.

Overnight: Hyannis

Day 2: Ferry to Martha’s Vineyard & Bike to Edgartown

This morning, head to the Hyannis Harbor Terminal to catch the Hy-Line ferry to Martha’s Vineyard. Enjoy this hour-long scenic cruise through Lewis Bay and Vineyard Sound from the ferry’s open-air upper deck. Upon arrival to Oak Bluffs, walk a few blocks to your overnight inn, to drop off your luggage and pick up your rental bike for the start of your island tour. Enjoy a gentle cruise along bike paths and coastline, passing inlets and golden beaches. Roam Edgartown’s neighborhoods and narrow streets full of Greek Revival and Victorian architecture. Bike back to Oak Bluffs, following the shoreline and taking breaks at your choice of countless beaches. Tonight, dine in town and visit the Flying Horse Carousel, America’s oldest platform carousel.

Bike: 12 mi. (+89/-79ft.)

Overnight: Martha’s Vineyard

Day 3: Bike Aquinnah to Oak Bluffs

Enjoy a morning stroll through the “Gingerbread Cottages” of Oak Bluffs, a cluster of brightly colored, fairy-tale like wooden houses and a main attraction in Martha’s Vineyard.

Take a private transfer from Oak Bluffs to Aquinnah, the westernmost point of Martha’s Vineyard. Enjoy Aquinnah’s red-clay cliffs, 200-year-old lighthouse and panoramic views of the Elizabeth Islands. Take the bike ferry across the channel to Menemsha, a timeless fishing village, where lobstermen roam the docks and fish markets. Visit the Galley Restaurant for a swordfish and pesto sandwich before bicycling along a network of country roads back to Oak Bluffs. Return your bike and explore Union Chapel and East Chop Lighthouse, before another dinner in town.

Bike: 24 mi. (+453/-528ft.) 

Overnight: Martha’s Vineyard

Day 4: Ferry to Nantucket & Bike to Madaket & Cisco

Embark on the ferry from Martha’s Vineyard over to the island of Nantucket. Enjoy strolling the cobblestone streets lined with grey-and-white trimmed, cedar-shingled buildings on your way to your B&B near the historic old town. Drop your luggage, load your daypack, and pick up your bike for a ride around town and a bike tour of the western half of Nantucket. Cycle to Brant Point for scenic photo’s of the lighthouse and wharf before stopping over in Madaket. Visit Millie’s Restaurant for incredible fish tacos before soaking in some rays at Madaket Beach. Pedal back towards town and Cisco Brewers, a rustic brewery and local hot spot for live music, brewery tours and tastings of local craft beer and wine. Return to your overnight B&B for a peaceful slumber.

Bike: 17 mi. (+125/-75ft.)

Overnight: Nantucket

Day 5: Bike to Siasconset

This day’s ride will take you along bike trails to the eastern side of Nantucket and Siasconset Beach. Enjoy a gentle ride through town and along the Polpis Bike Path  toward the Nantucket Life Saving Museum. Lock-up your bike for a tour of this museum’s relic gallery tracing the history of local shipwrecks and rescues. Continue south past bogs, ponds and the Sankaty Head Lighthouse to Siasconset Beach and Main Street. Bike or bus back to downtown Nantucket for an afternoon of exploring, shopping and touring the Whaling Museum; a historic highlight and home to a 46–foot sperm whale skeleton, an 1847 oil and candle factory and countless artifacts and treasures.

Tonight, return your bikes and dine in town for a delicious seafood dinner and  in celebration of your island retreat.

Bike: 18 mi. (+103/-103ft.)  

Overnight: Nantucket

Day 6: Onward Travel

Depending on your travel arrangements, enjoy sunrise at Jetties Beach, a morning stroll through town or last-minute souvenir shopping before boarding your ferry back to Hyannis (approx. 1 hour).




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. 

Extra Nights

You can easily request to add extra nights during this itinerary. For further details, please ask us at the time of booking.


Hyannis Harbor Hotel

Experience quintessential New England charm and hospitality with a night’s stay at the Hyannis Harbor Hotel. Located directly on the waterfront, enjoy nautically inspired rooms, maritime artwork, outdoor firepits, modern amenities and a sophisticated ambiance that celebrates the spirit of the coast and its storied maritime heritage.







Madison Inn

Enjoy a cozy stay at this local inn, conveniently located near Oak Bluffs Harbor, historic sites, the local bus, in-town restaurants and hidden island highlights, for an unbeatable Martha’s Vineyard experience.







Century House

Built in 1833, this refined B&B is walking distance from Jetties Beach and the historic district of Nantucket. Once the mansion of Captain Robert Calder, Century House offers a quiet reprieve and deluxe accommodations.


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.

When to Go?

The best time to visit Martha’s Vineyard and Nantucket are during the summer months of July and August.

July and August are the most popular months, due to desirable beach weather. While temperatures can be a little hotter, visitors flock to the area for the brilliant beaches, cool ocean waters and crystal clear blue skies.

June and September are also highly recommended months to go, as these shoulder months usher in pleasant temperatures and less crowds. September also boasts the warmest waters, a residual effect from the hotter summer months.


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 & Grade

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.

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.


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.


Getting to Hyannis

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 from Hyannis

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.

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.


  • 5 Nights at hand-selected charming B&Bs
  • 4 Breakfasts
  • Ferry to/from Martha's Vineyard
  • Ferry to/from Nantucket
  • Bike rental, fitting and orientation
  • Macs Adventure Navigation App
  • Route notes with turn-by-turn directions
  • Detailed pre-departure information pack
  • 24/7 US telephone support


  • Flights
  • Transfer to/from Hyannis
  • Local buses, taxis and transfers
  • Lunches, dinners, drinks and snacks
  • Additional nights before, during or after the trip
  • Personal equipment
  • Travel Insurance
  • Gratuities and tips


  • Extra Nights in Hyannis, Chatham, Orleans and Provincetown
  • Single Room Supplement
  • Solo Supplement
  • Room Upgrades (only where applicable)

How do I get my rental bike?

Your rental bike will be arranged through a local bike shop located in Martha's Vineyard and Nantucket. The rental bike shops are conveniently located near the ferry terminals and only a short walking distance away from your overnight stay for a quick and easy pick-up. We will set this up ahead of time and provide all necessary details in your pre-departure information packet.

How does the luggage transfers work?

Due to your overnight accommodation's close proximity to the ferry terminal, and for staying two nights on each island, you can enjoy keeping luggage with you in the room and when transferring from island-to-island. We recommend bringing rolling luggage or luggage that is easy to carry when transporting luggage to-and-from the ferry to your overnight accommodation, and back.

What if I become ill or can't bike a stage?

If you are not up for biking the entire route, you can stop at any town along the way, or completely avoid the entire route, by transferring to the next town or overnight accommodation. The Martha's Vineyard Transit Authority is a bus system that connects each town visited while in Martha's Vineyard. These local buses have designated bus stops in each town and provides one-way rides (with bike racks) for a few dollars. Our bike rental partners are also available to call and are more than happy to help should you require any assistance at any time. Local partners contact information can be found in your pre-departure information pack, or you can ask the host at your overnight accommodation.

If you need medical services, you'll find information in your pre-departure information packet or you can ask for assistance at your B&B. As always, 24/7 support from Macs Adventure is only a phone call away.

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