A Scenic Island-To-Island E-Bike Tour In Massachusetts Brims With Vibrant Historic New England Charm

Swept off the southern coast of Cape Cod lie two of America's most picturesque islands that are also rife with maritime history. Both Nantucket and Martha's Vineyard became wealthy in the 17th and 18th centuries from the profitable whaling industry. The larger of the islands is Martha's Vineyard, known for its historic harbor town of Edgartown, dramatic Aquinnah cliffs, and colorful gingerbread cottages in Oak Bluffs. Nantucket, which is further afield at 30 miles off the coast, reflects its past as the "whaling capital of the world" with grand Greek Revival mansions and shingled cottages that line some of the most charming cobblestone streets in America. Nantucket town boasts excellent seafood restaurants, chic boutiques, and luxury hotels, while the island is also ringed by sweeping sandy beaches and the rose-filled waterfront village of Siasconset. Across both islands are excellent biking trails that link the villages and beaches. Backroads, one of the leading group tour companies specializing in active travel, is now offering a Martha's Vineyard & Nantucket Easygoing E-bike Tour, a five-day, four-night e-biking adventure spanning both islands.

This Backroads' e-bike tour is offered in May, June, August, September, and October and is priced starting at $4,449 per person. The tour includes luxury accommodation at the White Elephant on Nantucket and Hob Knob Inn in Martha's Vineyard, most meals, bike guides, tours, transfers, and e-bike rental. Both leisurely riders and expert bikers will enjoy this five-day tour pedaling past scenic overlooks, rose-covered cottages, Atlantic Ocean beaches, harbor towns, and seafood shacks.

You will spend your first two nights on Nantucket, which was spotlight in September 2024 when Netflix murder-mystery show "The Perfect Couple" propelled it to the top of travel wish lists. The island's idyllic harbor town feels frozen in time, blissfully free from development or chains. You will check into the White Elephant, a luxurious shingled resort right on the water. Here you can revel in the island's beauty, both coastal and inland, with a landscape crisscrossed by flat, paved bike paths. One of the island's most popular paths leads out to Cisco Beach, a surfer favorite known for its powerful swells and sandy shoreline. On the way back, don't miss a stop at the convivial Cisco Brewers, where beers and cocktails are served in their alfresco courtyard to the tunes of live music. 

The next day, you can head out to the island's eastern coast to visit Sconset, a charming community of rose-covered cottages and the panoramic Bluff Walk where you can see gracious mansions on one side and the stunning Atlantic Ocean on the other. Otherwise, bike westward to Madaket for a relaxing beach day and stop by Millie's for lunch. Later, factor in time for a tour of Nantucket's iconic Whaling Museum, which traces the history of the isle's rich maritime heritage. On your last morning on Nantucket, take a guided tour of the town to see the most famous 19th-century mansions of whaling captains.

After departing Nantucket, you will take the ferry over to Martha's Vineyard, enjoying endless ocean views and fresh breezes along the way. Edgartown is your first stop, the oldest town on the island where you will find a posh but leisurely blend of shops, beaches, and nightlife. You will check into the charming Hob Knob Inn, a Gothic Revival 17-room retreat in the heart of elegant Edgartown. Spend the rest of the afternoon browsing around the lovely local art galleries, stylish shops, and buzzy restaurants. 

The next day, you can choose at which level you want to bike, whether a leisurely pace or intense incline ride. Martha's Vineyard's rolling green hills and sea cliffs make it a far different biking experience than Nantucket. Leisure riders should pedal north to quaint Oak Bluffs, a community of colorful gingerbread cottages built in the 19th century, or south to the island's famous Katama Beach, a three-mile long sandy stretch buffeted by the Atlantic Ocean on one side and the calmer salt pond on the other. For more active pursuits, bike to the island's remote western coast to see the dramatic Aquinnah Cliffs, which plunge a hundred feet down to the Atlantic Ocean, and the historic Gay Head Lighthouse that stands guard over them. Before your final lunch, you can cruise past the grassy plains that swath the heart of the island. "The inns and especially the food was outstanding," raved a Backroads reviewer. "It was a perfect trip ... will always repeat Backroads."