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New York to Rhode Island: The Hamptons, Shelter Island & Newport

Ebikes Available on this TourNothing compares to a leisurely ride to the shore. And VBT invites you on a reel through two destinations where leisure has taken on new extravagances.

  • Activity Level: Easy
  • Daily Mileage: 9-36 mi
  • Daily Biking: 2 – 4 1/2 hr
  • Small Groups: 20
  • Biking Activity
  • Perfect for those trying a bike vacation for the first time.

New for 2019!

Ebikes Available on this Tour

E-Bikes Available

Limited quantities —
first come, first served.

Why You'll Love This Tour

Overview

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.

Cultural Highlights

  • 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

Climate Information

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

 

What’s Included:

Ebikes Available on this Tour

E-Bikes Available on this tour.

Limited quantities — first come, first served. Learn more.

Bicycle Vacation Only – without Air

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Land Only Single Supplement: $745

Please note: Web Special savings cannot be combined with any other offer. Standard Terms & Conditions apply when purchasing this trip. Every effort has been made to produce this information accurately. We reserve the right to correct errors. Prices are based on preferences selected above, including meals and sightseeing as specified in What’s Included. All prices are subject to change. Departure dates and prices shown may be updated several times daily, and apply to new bookings only.

Itinerary & Map
2019
Or, Expand All Days
Day 1: Arrive in Sag Harbor / Warm Up Ride

VBT Bicycle Vacation only guests: Please make a reservation on a Hampton Jitney shuttle, departing at 12:15 p.m. from the Hampton Jitney stop located on 40th Street between 3rd and Lexington, the jitney stop is located on 40th Street at the south west corner of 3rd Avenue,  approximately 1 mile from The Millennium Broadway New York Times Square. Wait for the shuttle outside the Shake Shack Restaurant as the shuttle driver may not leave the vehicle. You will arrive in Sag Harbor at 2:50 p.m. For help, call the Hampton Jitney call center at 631-283-4600 for additional information. Please allow for traffic delays. If you miss this shuttle, the next one to Sag Harbor will depart at 2:15 p.m., arriving in Sag Harbor at 4:50 p.m. (note that you will miss the warm-up ride). The cost is $33 per person one way. Hampton Jitney shuttle times and rates are subject to change. For current schedule and fares for the Montauk Line & Ambassador Eastbound South Fork shuttle visit: https://reservations.hamptonjitney.com/mobile/PDFS/MN_EB_20171012.pdf.

Take the Montauk line to Sag Harbor www.hamptonjitney.com, enjoy the quick stroll or arrange with the hotel, Baron’s Cove, for pick up. Walk South to Spring Street, turn right towards the water, make a left onto Garden Street, then a left onto Water Street. The resort is on the left.

2nd Option: Long Island Railroad (LIRR): A train departs Penn Station at 11:45 a.m. You will transfer in Jamaica at 12:10 p.m. and continue on to Bridgehampton, arriving at 2:25 p.m. Fare is approximately $30 per person for peak time if purchased at the station. Fare is approximately $5 more if purchased on the train. For current schedule and fares visit: http://lirr42.mta.info/schedules.php

Take the Long Island Rail Road (718-217-LIRR) to Bridgehampton, then a 4-mile taxi ride to the inn.

3rd Option: Driving from Manhattan: Take I-295 S, I-495 E and NY-27 E to Scuttle Hole Rd in Water Mill. Continue on Scuttle Hole Rd. Take Bridgehampton-Sag Harbor Turnpike to West Water Street in Sag Harbor. You may park your car at Baron’s Cove for the duration of your tour. When the tour concludes, you will need to transfer from Newport to Sag Harbor with the VBT Trip Leaders in the VBT vehicle. Allow for up to 4 hours transfer time back to Sag Harbor including the ferry to Orient Point, NY (approximate arrival time in Sag Harbor is 5:00 p.m.).

VBT Pre-Trip Extension guests: You have another few hours this morning to enjoy New York City. Please make a reservation on a Hampton Jitney shuttle, departing at 12:15 p.m. from the Hampton Jitney stop located at 40th Street between 3rd and Lexington, the jitney stop is located on 40th Street at the south west corner of 3rd Avenue, approximately 1 mile from The Millennium Broadway New York Times Square. Wait for the shuttle outside the Shake Shack Restaurant as the shuttle driver may not leave the vehicle. For help, call the Hampton Jitney call center at 631-283-4600 for additional information. Please allow for traffic delays. If you miss this shuttle, the next one to Sag Harbor will depart at 2:15 p.m., arriving in Sag Harbor at 4:50 p.m. (note that you will miss the warm-up ride). The cost is $33 per person one way. Hampton Jitney shuttle times and rates are subject to change. For current schedule and fares for the Montauk Line & Ambassador Eastbound South Fork shuttle visit: https://reservations.hamptonjitney.com/mobile/PDFS/MN_EB_20171012.pdf.

Meet the rest of your group at Baron’s Cove in Sag Harbor, New York. This charming villages is listed on the National Register of Historic Places, nestled in the former whaling port of South Fork. Its tranquility attracted author John Steinbeck; he spent the last years of his life as a resident. Today, Sag Harbor is the jewel of the Hamptons, the world-renowned seaside resort.

Ask the reception desk for your welcome package at check-in. Please note that check-in time is 4:00 p.m. and your rooms may not be ready when you arrive. You may leave your luggage at the desk if necessary. Meet your Trip Leaders at 3:30 p.m. for a safety talk and bike-fitting, followed by a short warm-up ride. Tonight, gather for a welcome reception and dinner at the inn’s classic restaurant as the sun sets over Sag Harbor Cove.

Hotel: Baron’s Cove
Meals: D
Daily Options: 9 miles

Day 2: Elizabeth A. Morton National Wildlife Refuge / Wölffer Estate Vineyard

After breakfast, cycle along quiet back roads to the Elizabeth A. Morton National Wildlife Refuge, a peninsular stretch of protected land flanked by scenic bays. Leave your bikes behind and enjoy a self-guided walk along the Wild Birds Nature Trail, a 1.2-mile stroll through woodland to a beach where, if you wish, you may venture another two miles or so along Jessup’s Neck Peninsula. A huge variety of threatened and endangered species inhabit these shores, including piping plovers and roseate, common, and least terns. Kemp’s Ridley turtles and loggerhead sea turtles also rely on these coastal waters. The natural diversity here is important to wildlife throughout Long Island.

Later, follow the tranquil and shaded roads that skirt the 20 or so villages of the Hamptons. This is the playground of well-heeled New Yorkers, popular for its beaches, polo clubs, art galleries, and vineyards. Pause for ice cream and perhaps enjoy it in front of the Bridgehampton Community House with its handsome colonnaded façade. Continue to Sagaponack and the European-flavored Wölffer Estate Vineyard, the only international winery on the East End. (Their other vineyards are in Mallorca and Mendoza.) Here, grapes are sustainably farmed in former potato fields. Enjoy a wine tasting accompanied by cheese, charcuterie, and bread before returning to Sag Harbor.

This afternoon, you have free time to browse Sag Harbor’s shops and galleries, view the yachts in the marina, or relax by the pool at Baron’s Cove. Dinner is on your own at one of Sag Harbor’s restaurants.

Hotel: Baron’s Cove
Meals: B, L
Daily Options: 18 miles

Day 3: South Fork / Montauk Lighthouse / East Hampton

After a hearty breakfast, ride the picturesque coastal road from Sag Harbor to Montauk, perched on rugged shores at the far eastern reaches of Long Island. Your ultimate destination is the Montauk Point Lighthouse, the first public works project of the newly founded United States, built in 1796. It’s a short climb up Turtle Hill to arrive at this historic site. Should you choose to ascend to the beacon, you will enjoy unforgettable 360° views of Block Island Sound, the Atlantic Ocean and Long Island. As you cycle back to the village, you may see small fishing trawlers navigating the narrow harbor entrance. Montauk’s long fishing tradition is alive and well in the 21st century: It hosts the largest recreational fishing fleet in the country and lays claim to the most saltwater fishing records in the world. You’re sure to savor the bounty of the day’s catch during lunch on your own. After, return to the inn by shuttle or cycle back to Sag Harbor.

Later, relax by the inn’s pool. This evening, stroll into town for an included dinner at a favorite local restaurant.

Hotel: Baron’s Cove
Meals: B, D
Daily Options: 36 or 56 miles

Day 4: Shelter Island / Greenport / Orient Beach State Park / Ferry / Newport

Following your final breakfast at Baron’s Cove, cycle to bucolic Shelter Island, “the island protected by islands.” This 8,000-acre patch of land, 1/3 of which is owned by The Nature Conservancy, lies between South Fork and North Fork and is reachable only by eight-minute ferries—from North Haven on the South Fork and from Greenport on the North Fork.

Enjoy a largely self-paced ride today, taking in the island’s beauty as you go. You might pause at Mashomack Preserve to walk some of its nature trails, perhaps the 1.5-mile self-guided loop through interlacing tidal creeks, mature oak woodlands, fields, and freshwater marshes. Your leisurely reel continues to Ram Island County Park, then to the lovely Hay Beach on Menhaden Lane. This pristine beach is not for swimming, but for admiring. Perhaps you will see piping plovers skittering across the sands to their conservancy-protected nesting sites. You will have mesmerizing views of Gardiner’s Bay, the lighthouse known as Bug Light, and the meandering coastline leading to Orient Point on the North Fork. Next, ride to Shelter Island Heights to board the ferry to Greenport, where you may stop for lunch on your own and savor delicious seafood featuring world-class chowder at a local restaurant.

Continue by bike or shuttle along the North Fork to Orient Beach State Park, a long sliver of sand, forest, and marsh paralleling North Fork to its south. There’ll be time to stroll its pristine shores before you ferry to New London, Connecticut (1 hour, 20 minutes) and shuttle to coastal Newport (1.5 hours), straddling the southern tip of Rhode Island’s Aquidneck Island. Upon arrival, enjoy free time to settle in and explore. Like Long Island, Newport has long been a retreat for the New York elite. The 19th– and 20th-century titans of industry built some of the nation’s most palatial mansions. Its rich social history is second only to its breathtaking shorelines and distant sails glimmering on Narragansett Bay. Meander next door to your hotel to the 18th-century Bowen’s Wharf to stroll its brick walkways and granite quays. Dinner is on your own, with many choices in the neighborhood.

Hotel: The Newport Harbor Hotel and Marina
Meals: B
Daily Options: 32 miles

Day 5: Ocean Drive / Jamestown / Farewell Dinner

After breakfast, ride through the historic district of Newport, following the stunning Ocean Drive past sweeping ocean vistas and opulent houses. As you cycle the most southern reaches of Aquidneck Island, once a fertile farmland kissed by sea breezes, watch as roiling waves crash on the rocks at the feet of extravagant homes perched on cliffs. Pause at Fort Adams State Park, where a coastal fortification protected the harbor from 1841 through the mid-1900s. Spend time here exploring the grounds, which today host the world-famous Newport Jazz Festival, and visiting President Eisenhower’s Summer White House, a grand Victorian with a gracious wrap-around porch.

Later, embark the Jamestown-Newport Ferry to the island of Jamestown, where lovelier coastal rides lead to picturesque parks, harbor views, and beaches. If you choose not to cycle this afternoon, take advantage of free time to swim at your inn’s pool or explore the shops along Thames Street, visit the International Tennis Hall of Fame in the Newport Casino, or stop by the White Horse Tavern, one of the oldest in the U.S.

Tonight, enjoy a festive farewell dinner at the inn and recount the high points of your ride with your fellow travelers.

Hotel: The Newport Harbor Hotel and Marina
Meals: B, D
Daily Options: 12 miles and 12 miles

Day 6: Cliff Walk / Depart for home

Today, you will take in the dramatic vistas and splendid houses of Newport when you follow the city’s National Recreation Trail in the National Historic District. After breakfast, board the RIPTA Trolley to the western end of Easton’s or First Beach at Memorial Blvd. There, you will set off on The Cliff Walk, a spectacular 3.5-mile cliffside path tracing the rocky coast of Aquidneck Island and skirting the backyards of Newport’s sprawling gilded mansions, including Rough Point, Ochre Court, and the Vanderbilts’ Breakers. Pause to enjoy a boxed lunch in a scenic spot along the way. Return to your inn for your shuttle to Boston Logan International Airport, departing at 12:30 p.m. and arriving at 2:30 p.m. We recommend a flight out of Boston no earlier than 4:00 p.m. A second drop-off will be offered at Boston’s South Station Train Terminal for those who need to return to New York City.

Meals: B, L
Daily Options: 2-mile walk

Map of Long Island

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Accommodations

New York to Rhode Island: The Hamptons, Shelter Island & Newport

The Millennium Broadway New York Times Square

The four-star Millennium Broadway New York Times Square puts you at the center of all the action. The renowned theaters of Broadway are steps away and all of New York is at your feet via subway. This comfortable retreat offers spacious guestrooms with skyline views, each providing generous amenities and decorated with a modern touch, including a smart TV and work station. The Times Square-42nd Street Subway Station is a three-minute walk from the hotel. Complimentary Wi-Fi is available throughout. A/C is available.
Free WiFi Included

Baron’s Cove

Baron’s Cove is located in Sag Harbor and it is the perfect getaway to this casually sophisticated village in the Hamptons. Amenities include a harbor side heated saltwater pool, tennis court, fitness studio, spa services, and complimentary beach service with transportation. Watch the sunset over the cove from the second floor dining room and outdoor terrace. A/C is available.
Free WiFi Included

The Newport Harbor Hotel and Marina

The Newport Harbor Hotel and Marina is a premiere green hotel in Newport sitting next to Bowen’s Wharf. Its extraordinary staff will offer you the best possible hospitality experience. Enjoy panoramic views of the harbor of Narragansett Bay from your room. A/C is available.
Free WiFi Included
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