Massachusetts Island Hopper: Nantucket and Martha's Vineyard

Massachusetts Island Hopper: Nantucket and Martha's Vineyard

5 Day Inn Bike Tour

Tour Information

Date: 09/04/25 - 09/08/25
Meet: Nantucket, MA
Time: 2:00pm
Tour Price: $2790
Single Upgrade: $800

By combining the lovely paved paths of Martha’s Vineyard with those of the smaller island of Nantucket, we’ve put together a bicycle tour that shows off the best these isolated islands off the coast of Massachusetts have to offer. Enjoy the ocean breezes, moors, beaches, and forests of these two islands, all while bicycling on paved bike paths. The islands are as different as they are unique, but they each offer some wonderful car-free cycling.

5% Discount

The first 6 women to sign up receive 5% discounts.

Leisurely

Leisurely

Mostly flat terrain on traffic-free, paved bike paths. Leisurely cycling level.

4 nights lodging, 4 breakfasts, 2 picnic lunches, 3 dinners, snacks, ferry between Nantucket and Martha’s Vineyard, ferry to Chappaquiddick Island, van support, digital maps and GPS cues, and trained guides.

$195 for a Cannondale W Quick hybrid or Cannondale Topstone 2 adventure road bike; $350 for a Gazelle T10 Ultimate low-step e-bike or Specialized Vado step-thru e-bike.

Quick

Topstone

Gazelle

Vado

Accommodations are subject to minor changes. 

Nantucket Inn

Summercamp Hotel

Fly into Nantucket for the start of our tour and out of Martha’s Vineyard at the end of the tour. Cape Air and JetBlue offer connections through Boston, NYC, and Providence. Or drive to Hyannis, MA, leave your car there, and take the ferry. Once in Nantucket, take the hotel’s free shuttle or a taxi to the start of our tour. At the end of the tour, you can walk to the ferry to get back to Hyannis, or take a taxi to the airport if you've flown.

FAQ

How do I sign up?

You can Register / Sign-up for a Tour online. Or call our office at 585-424-2124 to do it over the phone, Monday - Friday, 9:00-5:00 Eastern Time. We’ll need a Visa, MasterCard or Discover number or a check for the deposit. If you sign up within 30 days of the start of the tour, we require payment in full. Then we’ll send you a tour confirmation packet with many more details about your trip, including travel arrangements, a packing list and an optional training schedule. Most of our tours fill completely and have waiting lists, so don’t wait too long before deciding to join us!

What about electric-assist bikes (e-bikes)?

Electric-assist bikes - or e-bikes - have quiet, battery-powered motors that add power to your pedalng. They increase your speed and assist you in cycling up hills. Most e-bikes have a range of assistance, so you can choose how much of a boost you'd like. E-bikes make it easier to do all the miles in all types of terrain. We allow electric-assist bicycles on our tours if you'd like to bring your own. We also have e-bikes available for rent on most of our trips -- look for the e-bike symbol. We do not make e-bike recommendations if you're considering purchasing your own. We suggest you rent one on a tour first so you can try it!

I am coming alone on this tour. Will I be the only one traveling alone?

Absolutely not. Many of our participants come by themselves. That is part of the reason for the existence of WomanTours--to provide women with riding partners as well as scenic vistas and interesting tours.

What about the rental bikes?

We have a fleet of women-specific bicycles available for rent for $195 for most tours in the U.S. We will need your height and inseam measurement to fit you properly. You can choose a hybrid bike with straight handlebars or an adventure road bike with racing-style drop handlebars. We also have electric-assist bikes, Gazelle T10 or the Specialized Vado, available for $350 for most tours. Our rental bicycles have a phone holder, back rack, water bottle holders, and back bag.

What if I have to cancel a tour within the USA?

We understand that personal circumstances sometimes force women to cancel their travel plans. Therefore, we have tried to be as generous as possible with the following domestic tour cancellation policy for our regular tours:

  • 75+ days before tour departure: forfeit $150 of your deposit.
  • 50 - 74 days before tour departure: forfeit 25% of the complete tour price.
  • 30 - 49 days before tour departure: forfeit 65% of the complete tour price
  • 15 - 29 days before tour departure: forfeit 85% of the complete tour price.
  • 0 - 14 days before tour departure: forfeit 100% of the complete tour price.
  • No refunds are possible after the tour begins.

In addition, you may transfer $350 to another trip up to 75 days before departure. On domestic US trips (excluding Alaska,) you may also transfer 50% of the trip price, less $50 up to 30 days before departure. WomanTours will hold any “transfer funds” on account through December 31 of the following year. Any money left on account beyond this deadline will be forfeited.

Please note that our cross-country and epic tours have their own cancellation policies, depending on the tour's payment schedule. The $300 registration fee for these tours is nonrefundable and nontransferable.

"I was worried that everyone would be faster or more in shape. I found that there were all kinds and one could fit in wherever she felt most comfortable. Accommodations were always top-knotch. I especially loved the Nantucket Inn, very quiet and quaint. Fantastic leaders, detailed instructions. When a couple problems did arise they were taken care of quickly. Always felt very well taken care of and appreciated."

Deb J. St. Paul, MN

Bike Tour Itinerary

DAY 1: We begin our tour on the pristine island of Nantucket. This small island, only 14 miles long and 3 miles wide, has protected nearly half of its land from development. All of its 82 miles of beautiful beaches are public. Lucky for us, it also has an extensive network of paved bike trails.

We meet at 2:00pm at our inn just outside of the center of Nantucket Town for an orientation, followed by a rental bike fitting. We’ll have a short warm-up ride to Surfside Beach, before enjoying our first dinner together at 7:00pm. 7 miles, ±206'.

DAY 2: After a wonderful breakfast, we’ll begin our bike path tour of the island, first heading northeast toward the cliffs of Siasconset. We’ll pass what used to be the largest cranberry bog in the country before stopping at the Sankaty Head Lighthouse. After a picnic lunch at Cisco Beach, you can stop at the Cisco Brewery, Nantucket Vineyard and Triple Eight Distillery for a close-up view of island life. Then head back to our inn and dinner together. 33 mile, ±970'.

DAY 3: After another hearty breakfast, we’ll head out toward the westernmost beach on the island. Along our way to Madaket, we’ll pass the historic old mill. Built in 1746, it is the oldest functioning mill in the country. We’ll also pass a Quaker cemetery dating from 1760. After a stop at Dionis Beach, we’ll head toward Nantucket town for lunch.

We should have time to stroll the shops along the cobbled streets before boarding our ferry. The designer dress shops, art galleries and small cafés will look different from any you’ve seen in a mall, as chain stores are banned here. The high-speed ferry will take about an hour to get to Martha’s Vineyard.

Then it’s a short bike ride to our inn in the town of Oak Bluffs. Be sure to walk among the gingerbread cottages hidden behind our hotel. Their pretty pastel-painted porches are in stark contrast to the highly regulated, cedar-shingled structures of Nantucket. 19 miles, +588'/-626'.

DAY 4: Martha’s Vineyard is named for the daughter of the 17th-century explorer Bartholomew Gosnold who discovered the island full of grapes growing wild. Now full of forests, scrubland, beaches and old stone walls overgrown with vines, the island is rich in diversity and beauty. Unlike Nantucket, it has 6 separate towns and we’ll cycle through three of them today.

We'll have water on both sides of us as we cycle a pristine bike path and over the bridge made famous by the movie Jaws. We'll head out toward a beautiful beach and then by a lighthouse in Edgartown. After stopping for lunch on your own, you can catch a 5-minute ferry to the tiny island of Chappaquiddick. If you like gardens, be sure to stop in at the free Mytoi Japanese Gardens for a respite before returning to our inn. Enjoy dinner on your own tonight. 28 or 34 miles, ±730'.

DAY 5: Our last ride takes us through 5000 acres of state forest in the center of the island. Originally created as a reserve to save the Heath Hen, it is now one of the largest environmental restoration projects in the country, working to bring back the island’s native ecosystem. We’ll cycle past a huge sculpture of the Heath Hen, a tribute to this now extinct bird. After our peaceful ride, we’ll return to our inn for our last picnic lunch together. We'll say our farewells at 1:00pm, and then you're free to walk to the ferry or take a taxi to the airport for your trip home. 21 miles, ±511'.