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

Nothing compares to a leisurely ride to the shore.

  • Duration: 6 Days|
  • Daily Mileage: 9 - 36|
  • Biking: 2 - 4.5 hr|
  • Group Size: 20
Activity Easy
Easy
E-Bikes Available
E-Bikes Available
People
Guided Group Tour

Starting From

Bike Vacation Only

$2,795

(per person, double occupancy)

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

Nothing 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. 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.

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.

  • Duration: 6 Days|
  • Daily Mileage: 9 - 36|
  • Biking: 2 - 4.5 hr|
  • Group Size: 20
Activity Easy Easy
Cycling
Bar Graph Beginner - Experienced
Cyclists
Bus Vehicle
Support

Tour 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
  • Pedal the coastal road to 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
  • Imagine the glamor of the Gilded Age as you visit The Breakers, the grandest of Newport’s summer “cottages”
  • Admire ocean views and grand estates as you ride along the spectacular Ocean Drive
  • Cycle to Beavertail Lighthouse from Jamestown
  • View Newport’s mansions and rocky shores along The Cliff Walk

Climate Information

Temperatures

Average High /
Low Temperature (°F):

Apr56º/40º

May66º/48º

Jun75º/58º

Sep74º/56º

Oct63º/45º

Nov54º/38º

Average
Precipitation:

Apr4.5 in

May3.8 in

Jun4.1 in

Sep4.6 in

Oct4.1 in

Nov4.3 in

What's Included

Bike Vacation Only

5 nights in harborfront inns Check
10 meals: 5 breakfasts, 2 lunches, 3 dinners Check

Tour Bikes

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Road Bicycle (Carbon frame)

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Step-Through Hybrid/Comfort Bicycle

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Biking Packages Include:

Custom VBT Bike and Helmet

Two Local, Bilingual Trip Leaders

Vehicle Support

Luggage Transfers

Ride with GPS and Daily Route Notes

Welcome Reception

Facilitated Cultural Experiences

Your Choice of VBT Branded Gear for Your Adventure

Itinerary

Sun, Jun 2 to Fri, Jun 7 - 2019

Show Itinerary:

VBT-Bicycle-Vacation-only guests: Your tour begins at 3:30 p.m. at Baron’s Cove in Sag Harbor, New York. Make your own arrangements for travel to Sag Harbor on Long Island, New York.

Option 1: Hampton Jitney Shuttle
If you made your own arrangements to stay at The Millennium Broadway New York Times Square, 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, approximately one mile from The Millennium Broadway New York Times Square. The cost is $34 per person one way. To find current schedule and fares for the recommended Montauk Line & Ambassador Eastbound South Fork shuttle visit: https://reservations.hamptonjitney.com. Reservations for the Jitney can be made as early as 21 days prior to your shuttle departure.

Taxi to Jitney Stop: If you would like to take a taxi to the Jitney stop, please arrange with the bellman of The Millennium Broadway New York Times Square, at your own expense. The taxi should be arranged to pick you up at the hotel at 11:45 a.m., allowing enough time to reach the Hampton Jitney stop located at 40th Street between 3rd and Lexington for your 12:15 p.m. departure. The taxi fare may range between $5-$12, depending on traffic.

Walking to Jitney Stop: If you prefer to walk from The Millennium Broadway New York Times Square to the Hampton Jitney stop, head southeast on W 44th Street toward 6th Ave. In 0.3 miles, turn right onto 5th Ave. In 0.2 miles, turn left onto E 41st Street. In 0.4 miles, turn right toward E 40th Street. In 259 ft, turn left on E 40th Street. Shake Shack Restaurant will be on your right.

Wait for the shuttle outside the Shake Shack Restaurant at least seven minutes prior to the scheduled departure time. Please note that the shuttle driver may not leave the vehicle. You will arrive in Sag Harbor at 2:50 p.m. If you know in advance you will miss the shuttle, please call Hampton Jitney at 631-283-4600, option 1, to reschedule to the 2:15 p.m. departure. Otherwise, Hampton Jitney will charge you to make a new reservation or will charge you as a “walk-on” to the shuttle, if space is available.

Once you arrive in Sag Harbor, stroll down South to Spring Street, turn right towards the water, make a left onto Garden Street, then a left onto Water Street where you will find your hotel, Baron’s Cove, on the left. Alternatively, arrange with Baron’s Cove for complimentary pickup at the Hampton Jitney drop-off location at the Sag Harbor Municipal Building next to the American Hotel.

Option 2: 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. For assistance, call 718-217-5477. When you arrive at Bridgehampton station, take a taxi four miles to the Baron’s Cove resort, your hotel for the night.

Option 3: 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 your hotel, Baron’s Cove, for the duration of your tour. When the tour concludes, you will need to transfer from Newport to Sag Harbor with your VBT Trip Leaders in the VBT vehicle. Allow up to four hours to transfer 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: VBT has made a reservation for you on a Hampton Jitney shuttle, departing at 12:15 p.m. from the Hampton Jitney stop located at 40th Street between 3rd and Lexington approximately one mile from your hotel, The Millennium Broadway New York Times Square. You will receive an email confirmation for your Hampton Jitney reservation 7 to 21 days before your vacation begins. Please keep the confirmation email handy on your phone at the time of boarding should the Jitney driver have any questions about the reservation or need to verify your reservation number.

Taxi to Jitney Stop: If you would like to take a taxi to the Jitney stop, please arrange with the bellman of The Millennium Broadway New York Times Square, at your own expense. The taxi should be arranged to pick you up at the hotel at 11:45 a.m., allowing enough time to reach the Hampton Jitney stop located at 40th Street between 3rd and Lexington for your 12:15 p.m. departure. The taxi fare may range between $5-$12, depending on traffic.

Walking to Jitney Stop: If you prefer to walk from The Millennium Broadway New York Times Square to the Hampton Jitney stop, head southeast on W 44th Street toward 6th Ave. In 0.3 miles, turn right onto 5th Ave. In 0.2 miles, turn left onto E 41st Street. In 0.4 miles, turn right toward E 40th Street. In 259 ft, turn left on E 40th Street. Shake Shack Restaurant will be on your right.

Wait for the shuttle outside the Shake Shack Restaurant at least seven minutes prior to the scheduled departure time. Please note that the shuttle driver may not leave the vehicle. You will arrive in Sag Harbor at 2:50 p.m. If you know in advance you will miss the shuttle, please call Hampton Jitney at 631-283-4600, option 1, to reschedule to the 2:15 p.m. departure. Otherwise, Hampton Jitney will charge you to make a new reservation or will charge you as a “walk-on” to the shuttle, if space is available.

Once you arrive in Sag Harbor, your VBT Trip Leader will meet you at the Hampton Jitney drop-off location at the Sag Harbor Municipal Building next to the American Hotel and will transfer you in the VBT van to your hotel, Baron’s Cove.

For assistance, call the Hampton Jitney at 631-283-4600. 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 $34 per person one way for “pay on board” reservations (subject to availability). To find current schedule and fares for the recommended Montauk Line & Ambassador Eastbound South Fork shuttle visit: https://reservations.hamptonjitney.com. Hampton Jitney shuttle times and rates are subject to change.

Follow these directions if you did not take the 12:15 p.m. Jitney shuttle. Once you arrive in Sag Harbor, stroll down South to Spring Street, turn right towards the water, make a left onto Garden Street, then a left onto Water Street where you will find your hotel, Baron’s Cove, on the left. Alternatively, arrange with Baron’s Cove for complimentary pickup at the Hampton Jitney drop-off location at the Sag Harbor Municipal Building next to the American Hotel.

For all guests: Meet the rest of your group at Baron’s Cove in Sag Harbor, New York. This charming village 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: Dinner
Daily Options: 7.6 miles

After breakfast, cycle along quiet backroads 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: Breakfast, Lunch
Daily Options: 24.6 miles

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: Breakfast, Dinner
Daily Options: 23 or 35 or 61 miles

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 local restaurants.

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 town.

Hotel: The Newport Harbor Hotel and Marina
Meals: Breakfast
Daily Options: 19 or 34 miles

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.

This afternoon, 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. Board the RIPTA Trolley to The Breakers for an included innavative audio tour. After your visit, you will set off on The Cliff Walk, a spectacular 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.

If you choose not to walk 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: Breakfast, Dinner
Daily Options: 13 or 22 miles and 2.1 or 2.6-mile walk

After breakfast, transfer to the island of Jamestown, where lovely coastal rides lead to picturesque parks, harbor views, and beaches. Pause at Beavertail Lighthouse, marking the entrance to Narragansett Bay.

Return to your inn (showers available at the pool) 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. A boxed lunch will be provided.

Meals: Breakfast, Lunch
Daily Options: 11 miles

New York to Rhode Island: The Hamptons, Shelter Island & Newport 1

Download PDF Itinerary:

Bike Vacation Only View Activity Chart

Enjoy Your Vacation Longer With Low-Cost Trip Extensions

Pre-Trip Extension - New York City

2 Nights From $495 per person, double occupancy

  • 2 nights at The Millennium Broadway New York Times Square
  • Daily breakfast
  • City Information
  • Transfer to the main tour (on Hampton Jitney)

Make your own arrangements for travel to New York. Take a bus or taxi to your pre-trip hotel, The Millennium Broadway New York Times Square. There are helpful links in your Traveler’s Handbook under Tour Arrival and Departure Information.

Hotel: The Millennium Broadway New York Times Square

Pursue your own interests in this spectacular city. Your hotel is conveniently located in midtown, so you’ll enjoy easy access to the highlights by foot or by subway. Perhaps you will stroll one of the city’s latest additions, The High Line, a narrow 1.45-mile-long public park built on a historic elevated rail line above Manhattan’s West Side. It runs from Gansevoort Street in the Meatpacking District to West 34th Street, between 10th and 12th Avenues. Take the ferry out to Ellis Island, entry point for countless immigrants. Or ascend the new One World Trade Center, the tallest building in the Western Hemisphere, for breathtaking views. This evening, perhaps you will take in a Broadway show.

Hotel: The Millennium Broadway New York Times Square
Meals: Breakfast

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Dates & Prices

Bike Vacation Only

6 Days. Includes bike vacation only.

Single Supplement: $745

Limited Availability

Sun, Jun 2 - Fri, Jun 7

From
$2,995

Reserve Online

Sun, Sep 22 - Fri, Sep 27

From
$2,995

Reserve Online

Sun, Oct 20 - Fri, Oct 25

From
$2,795

Reserve Online

For more information, call: 800-245-3868

Please note: Web Special savings cannot be combined with any other offer. Standard Terms & Conditions apply when purchasing this trip. Prices include all airline surcharges and Government taxes and fees. Ask our Tour Consultants for details. 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.

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