Martha's Vineyard & Nantucket Bike Tour

Itinerary Details

1. Day 1Day 1

   On the first day of the trip, meet your Trip Leaders at 1 p.m. on the porch of the White Elephant Hotel, located at 50 Easton Street on Nantucket Island, Massachusetts, a short taxi ride from Nantucket Memorial Airport and the ferry landing. Please arrive dressed in your biking clothes and bring your luggage and a daypack with your rain gear and anything else you may want for today's ride. (Note that while your room may not be ready, you can check in at the hotel before we meet and leave your luggage with the front desk.)

   Welcome to Nantucket! Upon arrival, your Trip Leaders fit your bike and give a brief talk on biking techniques and safety. We fuel up on snacks and sandwiches before setting off on a warm-up ride that takes you through scenic Nantucket Town and out to Cisco Beach, a beautiful white-sand surfers' haven. En route, stop by Cisco Brewers. A favorite local watering spot, Cisco creates Nantucket's most beloved microbrews, spirits and wines.

   At the end of the day, settle into your room at the waterfront landmark hotel, White Elephant Hotel. Then this evening, savor an elegant dinner at nearby Le Languedoc, an island institution that has been serving locals and visitors for more than 30 years.

   Cisco Beach Route: 10 Miles/16km  (200ft/60m elevation gain)
   

   • 9.9 miles
   • White Elephant Hotel
   • Lunch and Dinner

   • 

     White Elephant

     Spend two nights in classic Nantucket style accommodations in a lovely location by the harbor

   • 

     White Elephant

     Spend two nights in classic Nantucket style accommodations in a lovely location by the harbor

   • 

     White Elephant

     Spend two nights in classic Nantucket style accommodations in a lovely location by the harbor

2. Day 2Day 2

   After breakfast, follow a leisurely loop along Nantucket's wide network of bike paths. Consider parking your bike and going for a walk along the water at Siasconset and Surfside beaches, bordered by white sand and tall grasses. For a fascinating look into the island's maritime history, take a tour of the Nantucket Shipwreck & Lifesaving Museum. Exhibits include photographs of dangerous sea rescues, and you can check out original boats, rescue equipment and relics of some of the island's legendary shipwrecks. Enjoy your lunch on the museum grounds.

   Spend the afternoon discovering the wonderful museums, shops and galleries of downtown Nantucket or take a spin to Madaket Beach, the landing site of the first European settlers. The route takes you along rolling bike paths and quiet roads, past old barns, osprey nests, fields of wildflowers and verdant island grasses. Or return to the White Elephant and pamper yourself with a massage or body treatment at the spa. (Spa treatments are not included in the trip price. Advance reservations are recommended.)

   Later, gather for dinner at a favorite local restaurant, whose adventurous menu boasts some of the most divine flavor pairings on the island.

   BIKING OPTIONS:
   Nantucket Shipwreck & Lifesaving Museum Route: 21 Miles/34km* (500ft/152m elevation gain)
   Nantucket Loop: 26 Miles/42km (700ft/213m)
   Madaket Beach Loop: 40 Miles/64km (1,100ft/335m)
   *with shuttle
   

   
   

   • 21.1 - 39.8 miles
   • White Elephant Hotel
   • Breakfast, Lunch, and Dinner

   • 

     White Elephant

     Spend two nights in classic Nantucket style accommodations in a lovely location by the harbor

   • 

     White Elephant

     Spend two nights in classic Nantucket style accommodations in a lovely location by the harbor

   • 

     White Elephant

     Spend two nights in classic Nantucket style accommodations in a lovely location by the harbor

3. Day 3Day 3

   This morning, join a local guide to explore the rich history of Nantucket Town on foot. The locals are passionate about their community, and for good reason: the entire island is listed on the National Register of Historic Places. After the tour you'll have plenty to discuss over lunch on your own at the eatery of your choice. Then board the ferry for a scenic sail to Martha's Vineyard.

   We land at Oak Bluffs, a unique town and busy summer resort destination. In the mid-1800s, Oak Bluffs hosted Methodist camp meetings that grew in popularity, eventually drawing thousands of devotees each summer. Communal tents sprung up, replaced by individual wooden tents and finally by brightly painted cottages, earning Oak Bluffs its former name, Cottage City. Each August, Japanese lanterns illuminate these colorful gingerbread homes as well as the tabernacle where services once took place.
   
   Jump on your bike and head out of town on an invigorating ride along a flat paved bike path offering fantastic views of water on both sides. For additional miles, pedal first through the adorably historic Cottage City of Oak Bluffs and then cruise past the stately homes of the West Chop peninsula, before continuing on to Edgartown and the Hob Knob, a 19th-century residence turned eco-boutique
   hotel. Settle into your spacious, individually decorated room before exploring Edgartown.

   Founded in 1641 as the island's first European settlement, Edgartown is known for its spectacular Greek Revival, Federal and Victorian architecture. Walk through the nearby neighborhoods and you'll see examples of some of the extravagant homes built during the 1800s by sea captains who made their fortunes in the whaling industry. There are also myriad galleries, boutiques and cafés to visit. Or you can head to the Hob Knob's spa for a little "you time." Dinner is on your own; Edgartown offers plenty of outstanding culinary options.

   NANTUCKET TOWN GUIDED WALK 1¼ Hours
   FERRY TO MARTHA'S VINEYARD 1½ Hours
   
   BIKING OPTIONS:
   Edgartown Route: 6 Miles/10km (100ft/30m elevation gain)
   Cottages to Hob Knob Route: 11 Miles/18km (300ft/91m)
   West Chop to Hob Knob Route: 22 Miles/35km (800ft/244)
   

   • 6.2 - 21.7 miles
   • Hob Knob
   • Breakfast and Lunch

   • 

     Hob Knob Luxury Boutique Hotel & Spa

     Modern amenities, charming decor, and gracious hospitality await you at this luxurious property

   • 

     Hob Knob Luxury Boutique Hotel & Spa

     Modern amenities, charming decor, and gracious hospitality await you at this luxurious property

4. Day 4Day 4

   Today you'll cover plenty of ground and get a real taste of the island's diverse landscape. Gently graded bike paths lead to more challenging climbs en route to Aquinnah, one of only two Native American townships in Massachusetts and the spot where Jacqueline Onassis once bought an estate. Since 1799, its lighthouse has warned ships away from the dramatic cliffs and dangerous reefs, though a number of vessels have met a rocky and watery fate here. Enjoy your lunch and explore the roadside galleries, such as Granary Gallery at the Red Barn Emporium, filled with local artists' watercolors, photography, sculptures,
   furniture and hand-woven rugs. You can also spend time photographing the rustic farmland scenery or exploring the Aquinnah Cultural Center, which celebrates the rich history of the Wampanoag tribe. From Aquinnah, continue on the loop ride or shuttle back to Edgartown for shopping or a spa treatment.

   Tonight we savor a farewell dinner featuring organic local produce and fresh-off-the-boat seafood.

   BIKING OPTIONS:
   Gallery Route: 10 Miles/16km (300ft/91m elevation gain)
   Aquinnah Route: 23 Miles/37km* (800ft/244m)
   Chilmark Loop: 36 Miles/58km* (1,200ft/366m)
   The Vineyard Loop: 51 Miles/82 (1,900ft/579m)
   *with shuttle
   

   • 9.9 - 51 miles
   • Hob Knob
   • Breakfast, Lunch, and Dinner

   • 

     Hob Knob Luxury Boutique Hotel & Spa

     Modern amenities, charming decor, and gracious hospitality await you at this luxurious property

   • 

     Hob Knob Luxury Boutique Hotel & Spa

     Modern amenities, charming decor, and gracious hospitality await you at this luxurious property

5. Day 5Day 5

   On our last morning, take in the exhilarating sea air on your way to Katama Beach on the southern coast of the Vineyard and enjoy more spectacular ocean views. Along the way, pass through the Great Plains of Martha's Vineyard, a protected ecosystem known as a sand plain grassland. After the ride, we'll have time to freshen up at the Hob Knob before taking a short shuttle to Tisbury. In
   colonial times, Tisbury's residents demanded freedom of worship and openly supported the American Independence movement much earlier than most other colonists. In response, a British naval force occupied and pillaged Tisbury in 1778. A century later, the Great Fire of 1883 destroyed most of its buildings. Today this bustling little town is home to the island's only year-round port
   and is known for its shops, restaurants and beautiful harbor.
   
   After one more lunch together, we shuttle to the Martha's Vineyard Airport and ferry terminal, where our trip comes to an end.

   KATAMA BEACH LOOP 10 Miles/16km (100ft/30m elevation gain)
   

   • 9.9 miles
   • Breakfast and Lunch