Massachusetts Island Hopper: Nantucket and Martha's Vineyard

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'.