New York to Rhode Island: The Hamptons, Shelter Island & Newport
Explore the eastern reaches of Long Island, where the Hamptons open doors to charming harborside villages and stunning rides along unspoiled and protected coastlines and marshes. And pedal among the fruits of the Gilded Age in Newport, home to palatial mansions and dramatic rocky shores. Pause along the way to sample seafood at its freshest, wines at their fruitiest, and seaside vistas at their most breathtaking.
- Cycle the scenic byways of Long Island’s South Fork
- Taste distinctive wines and learn about sustainable farming practices at Sag Harbor’s Wölffer Estate Vineyard
- Smell the salt air and feel the ocean breezes at quaint harbor inns
- Walk the tranquil trails at Elizabeth A. Morton National Wildlife Refuge and Mashomack Preserve
- Savor scrumptious chowder in Greenport
- Pedal the coastal road to Montauk Point Lighthouse, the easternmost end of South Fork
- Pause for lunch in charming Montauk, where fishermen and surfers alike set out into the waters
- Spot the majestic osprey nesting on high platforms in the wetlands
- Stroll the brick and stone promenades of Bowen’s Wharf, home to inviting shops and restaurants
- Cruise on the Jamestown-Newport ferry around lower Narragansett Bay and admire views of coastal fortifications, a working lighthouse and the renowned mansions and yacht club
- View Newport’s mansions and rocky shores along The Cliff Walk
What to Expect
This tour offers mostly easy terrain with the occasional rolling hill and the opportunity for longer rides. The VBT van support shuttle is always available.
Average Daily Mileage: 9 – 36 miles and one day with a 2-mile walk
Average Cycling Time: 2 – 4 1/2 hours
Average High/Low Temperature (°F) – Sag Harbor
Apr 56º/40º May 66º/48º Jun 75º/58º Sep 74º/56º Oct 63º/45º Nov 54º/38º
Average Precipitation (in.) – Sag Harbor
Apr 4.5 May 3.8 Jun 4.1 Sep 4.6 Oct 4.1 Nov 4.3
E-Bikes Available on this tour.
Limited quantities — first come, first served. Learn more.
Bicycle Vacation Only – without Air
- 5 nights in harborfront inns
- 10 meals – 5 breakfasts, 2 lunches, 3 dinners
- FREE use of our custom VBT bicycle and helmet – E-Bikes available
- Service of two VBT Trip Leaders
- FULL VAN SUPPORT
- Daily route directions and maps
- Welcome reception
- Sightseeing and cultural activities
- One included wine tasting at local vineyard
- Entrance to the Elizabeth A. Morton National Wildlife Refuge
- Earn 5% Frequent Traveler Credit on this tour to use on a future VBT vacation. See details.
- The option to add our Low-Cost Trip Extension:
Pre-trip Extension: New York City – 2 nights from only $495