Introductory to Moderate
  • Self guided Cycling
  • 3 nights B&B


4 daysfrom



Trip code: HAP

Trip highlights

  • Sweeping vistas along Long Island's beautiful coastline
  • Explore the vineyards of the North Fork
  • Discover the beaches and villages of the Hamptons in South Fork

The northeastern state of New York is recognized worldwide for many iconic landmarks such as Niagara Falls, the Statue of Liberty, the Brooklyn Bridge and most famous, New York City. Just a short way from the city brings you to the summer getaway region known as the Hamptons. This group of small towns and villages are located on the eastern end of Long Island and welcome tourists and posh celebrities alike to experience the island’s natural beauty and relaxing seaside vistas.

From the beautiful and historic village of Stony Brook you will explore the two long eastern points of the island called the North and South Forks. In the South Fork are the quaint villages of the Hamptons. There are many options here making it hard to choose a visit to museums and art galleries, beautiful beaches or the famous Montauk Lighthouse at the tip of the island. The North Fork offers quiet farms in the countryside, vineyards and wineries and a small town feel.

Choose between our 4 or 5 day itinerary.


This tour starts in the historic and quaint Stony Brook Village. Upon arrival, you will be welcomed with refreshments, orientation and bike fittings. Depending on your arrival time, we suggest that you explore the historic Stony Brook village by foot or bike. If time permits, we recommend a tour of the Reboli Gallery or the Stony Brook Grist Mill. Many dinner options are available in the village.

Meals:  Nil

Rise early this morning and head to the posh village of Southampton by shuttle. Begin exploring along the Shinnecock canal and the historic town of Southampton. Your ride takes you to Sagg Main Beach (rated as one of the top 10 beaches in the US). Then our route takes you across the fork on rolling secluded roads to the historic whaling town of Sag Harbor, with a stop in Bridgehampton on the way. After lunch, head back on the north side of the fork past the world famous Shinnecock golf course back to Southampton where prime shopping and dining spots abound. If you are up for a few additional miles, we can route you into the town of East Hampton where you can try to spot celebs. If you are up for the challenge you may continue to Montauk.

Meals:  B

Enjoy breakfast at the inn before being shuttled to your start out of Riverhead and along the scenic Peconic bay. You will then ride along the North Fork wine trail to enjoy one of the United State's premier wine producing districts. Plan to stop at about lunchtime to take advantage of a light lunch and wine tasting at one of the many vineyards. You can also stop for lunch as you wind your way along the water. Heading back along scenic Sound Road you will find beaches, farms and more wineries. Today may be a beautiful scenic ride, a physical challenge or a wine tasters delight depending on the option you choose. End your day at the beach in Wading River and your return shuttle will meet you there.

Meals:  B

After enjoying a delicious breakfast, we will transfer you back to the LIRR for your journey back to the airport.

Meals:  B


  • 3 nights accommodation on a twin share basis with private ensuite facilities
  • 3 Breakfasts
  • Information pack including route notes & maps and GPS tracks
  • Snacks for each cycling day
  • Emergency hotline
  • Hybrid bicycle
  • Shuttle transfer to the start of the daily tour and from the end of the daily tour

  • Travel to and from New York
  • Guide (this is a self-guided tour)
  • Meals where not specified
  • Unscheduled transfers requested during the trip
  • Entrance fees
  • Helmet (mandatory)


Introductory to Moderate


Departure dates

Sundays and Mondays from May to October

Want to organise a customised tour?

School groups, friends, family trips, corporate events or just tailoring a trip to suit your own needs - learn how you can tailor your own Customised Tour.

Priceper person from


* All prices subject to applicable taxes

Options & Supplements*
  • 4 Day Single SupplementUSD$330
  • Additional DayUSD$360
  • 5 Day Single SupplementUSD$440
* Prices listed are per person. All prices subject to applicable taxes.

Trip reviews

Why travel with us

Our Expertise

Everyone who works with us, from our office staff, ground staff and guides is the ‘’real deal’’. Our team is comprised of actual hikers and cyclists who have explored or live in the region in which you will be traveling. Our entire network is highly-specialised in active travel.

Great Value

Quality services at the best price make our active trips great value for money. Having essential items included like National Park fees, accommodations, most meals, bikes for cycling trips, maps and support for peace of mind. Our inclusions allow you to better budget for your big adventure.

Innovative Itineraries

We look beyond the horizon to find new and exciting adventures. We’re passionate about shaping the next generation of outdoor travel in North America, and constantly seek different ways, routes and alternatives to exceed our clients’ dreams.

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We are committed to responsible travel and true sustainability, formed when the company was established, and in the face of a multitude of threats to the environment, our commitment is stronger than ever. We aim to "leave no trace" in both an environmental and cultural sense.