It’ll be early on. You’ll round a corner on one of the beach roads, maybe in 'Sconset or Aquinnah. And it will hit you. The quiet. The open Atlantic pulsing on the shore. Sea birds above and a beach breeze rustling the dunes. It gives you that "I’m never going back" feeling where you imagine selling all your possessions and buying a lobster boat. It’s okay, the feeling passes eventually. But you’ll have five days to enjoy it.
Days 1-2 Downshift into easygoing island life
on Nantucket 
A gentle ride to Cisco Beach leads past beautiful 18th- and 19th-century sea captains’ homes and lighthouses Circle the island on two wheels - gardens, cranberry bogs, harbors and dunes enliven your route The Nantucket Shipwreck and Lifesaving Museum chronicles the area’s maritime heritage Up for a stroll along the Atlantic? Siasconset and Surfside beaches beckon with pristine stretches of sand.
Day 3 Edgartown's Colonial roots and art galleries
Soak up the rich history of Nantucket Town on a walking tour A private boat transports us to Martha’s Vineyard, simply called "The Vineyard" by locals Stroll through historic Oak Bluffs, a chic stop for shoppers Pedal a bike path to Edgartown, known for spectacular Greek Revival, Federal and Victorian architecture.
Day 4 The red-clay cliffs of Aquinnah, with a 200-year-old lighthouse
Spin inland through forests and open meadows, past houses sporting every shade of gray Fond of art? Galleries tempt you off your bike with watercolors, photography and sculptures by local and world-renowned artists Explore the Cape Poge lighthouse - its first keeper in 1801 was appointed by Thomas Jefferson.
Day 5 Exhilarating ocean views and breezes
Ride to Vineyard Haven for lunch at the ever-popular Black Dog Tavern Ferry across Nantucket Sound to Woods Hole.
Trip Highlights
- Gentle, tranquil rides past scenic beaches and cranberry bogs
- Fresh seafood and gracious island hospitality
- Tackle hills to the red-clay cliffs of Aquinnah, with a 200-year-old lighthouse
- Edgartown's Colonial roots and art galleries
- Learn maritime history at the Nantucket Shipwreck & Lifesaving Museum
Premiere Inns
White Elephant (2 nights): A "stylishly refurbished in-town hotel on a quiet waterfront, a brief walk from the historic district," noted Andrew Harper of this Travel + Leisure favorite. (spa)
Hob Knob (2 nights): This 19th-century Gothic Revival home - a Condé Nast Traveler editor's pick - is now a country-style boutique hotel with lovely gardens. (spa)
Daily Mileage Options & Cumulative Elevation Gain
Day 1
- Level 1 1 Route Option Available
- 10 miles
- 0 - 500 feet elevation gain
Day 2
- Levels 2 to 3 4 Route Options Available
- 19, 24, 30, 37 miles
- 0 - 500 feet elevation gain
Day 3
- Level 1 2 Route Options Available
- 6, 15 miles
- 0 - 500 feet elevation gain
Day 4
- Levels 1 to 4 4 Route Options Available
- 10, 24, 36, 51 miles
- 0 - 500 feet elevation gain
Day 5
- Level 1 2 Route Options Available
- 10, 15 miles
- 0 - 500 feet elevation gain
Routes For All Abilities
Every Backroads trip is designed to appeal to a wide variety of interests
and fitness levels. We know your pace may vary from one day to the
next-and your traveling companion's may differ somewhat from yours.
So we present a range of mileage options, and each day you decide exactly
what and how much you want to do.| Activity Level | Average Time | Biking Average | Walking Average |
|---|---|---|---|
| Level 1 | 2-3 hours | 10-20 mile | 2-5 miles |
| Level 2 | 2-4 hours | 21-30 miles | 5-7 miles |
| Level 3 | 3-5 hours | 31-40 miles | 7-9 miles |
| Level 4 | 4-6 hours | 41-55 miles | 9-11 miles |
| Level 5 | 5-7+ hours | 56-75+ miles | 11-13+ miles |
2012 Dates & Pricing*
CLASSIC TRIPS
- 6/10-14Price: $2698 pp dbl. occ., (+ $1080 for sgl. occ.)
- 9/2-6Price: $2698 pp dbl. occ., (+ $1080 for sgl. occ.)
- 9/9-13Price: $2698 pp dbl. occ., (+ $1080 for sgl. occ.)
- 9/16-20Price: $2698 pp dbl. occ., (+ $1080 for sgl. occ.)
- 9/23-27Price: $2698 pp dbl. occ., (+ $1080 for sgl. occ.)
- 9/30-10/4Price: $2698 pp dbl. occ., (+ $1080 for sgl. occ.)
*Prices may change. Once you book your trip, your price is guaranteed.
Guest Trip Reviews
This was one of the most memorable vacations I've ever had! The inns where we stayed were awesome. The museums really helped me to get a better historical perspective, especially in Nantucket. It was very clear to me that our leaders really wanted us to have the trip we desired. And that van was always there!- Napa, CA
Wonderful trip! Really beyond my expectations.- Pittsburgh, PA