trip
Plan your active adventure.View relaxed booking conditions.
4
Introductory to Moderate
Activities
  • Self guided Cycling
Accommodation
  • 3 nights B&B
Meals
  • 3 Breakfasts

4 Days$1499USD

Hit the trails with confidence

Flexible Cancellations
Stress free booking, learn more about our flexible terms

COVID-19 safety measures
Read our Covid-19 travel policy and what we're doing to keep you safe

Remote adventures
means social distancing comes naturally

Small groups only
Guided group sizes are strictly limited to maximum 16 people, average of 8-10


 
 
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.


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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

Expand all | Collapse all

This tour starts in the historic and quaint Stony Brook Village. Upon arrival there will be welcome refreshments, introductions, orientation and bike fittings. You will relax, refresh and take in and explore the historic Stony Brook village by foot or bike. Possibly tour the Reboli Gallery or the Stony Brook Grist Mill, which is in the backyard of the Inn. Dinner is your choice 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

Your ride today takes you down secluded roads while you pass by the houses and taverns that housed the Washington Spy Network of the American Revolution. Not a history buff? Choose a route that includes a beach, a harbour, or horse farms. The routes take you up and down rolling hills but they are short and are rewarded by spectacular views. As you return at the end of another beautiful day, you may want to visit the winery about a half a mile from the Inn or have dinner at one of the several taverns within walking distance.

Meals:  B

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

Meals:  B


Inclusions

  • 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)

Departure dates

Sundays and Mondays from May to October

* Guaranteed status denotes minimum trip numbers have been met, however the trips operation will be subject to there being no COVID-19 restrictions or other government travel advisories. Please contact us for further information.


Dates or itinerary don't fit?

Create a custom made itinerary for the perfect adventure. Choose when you travel, what you see and where you go.

Total Priceper person from

$1499USD

Options & Supplements*
  • 4 Day Single SupplementUSD$330
  • Additional DayUSD$360
  • 5 Day Single SupplementUSD$440
*Prices listed are per person

Essential Information

Ready to book? Make sure you download and read the detailed Cycle the Hamptons trip notes which contains all the essential information you need to know before booking. Once you’ve booked, we will supply you with a Pre-Departure document which contains a detailed gear list and other important information to help you prepare for your adventure ahead.


Trip reviews


Why travel with us

Award Winning Adventures

Enhancing your journey with authentic experiences, genuine cultural exchange and real exploration are the focal points on all of our adventures. In 2019, we were crowned by our peers as the best in adventure travel at The Travel Awards in Sydney.

Thoughtful Travel

Responsible travel is at the heart of every program we offer as a fundamental and long held philosophy. When you book one of our 100% carbon offset adventures you’re supporting true sustainability in the protection of local communities, natural environments and wildlife.

Ultimate Value

 When you book one of our adventures, you will receive quality services at the best prices with plenty of inclusions. There are no hidden costs, single travellers don’t pay more and you’ll enjoy many ‘extra touches’ that ensure your holiday is excellent value for money.

Positive Impact Travel

By joining this trip you are directly supporting positive impact projects in line with the UN Sustainable Development Goals (SDGs).

We’ve offset the carbon emitted by this trip by purchasing credits that support important projects that address the UN’s seventeen SDGs, like reducing poverty, affordable and clean energy, reducing hunger, clean water and climate action.

Proceeds from this adventure purchase carbon credits through the world’s largest and most awarded carbon project developer, South Pole, which are invested into projects accelerating the transition to renewable energy sources in developing countries.

Supported projects are based on internationally recognised standards and are third-party audited. They entail a series of positive impacts on the ground, which benefit local communities and ecosystems, that are aligned with the UN Sustainable Development Goals.

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