The Hamptons Weekend: Beaches, Vineyards & Montauk

This trip starts in Islip. On the first day, we’ll meet at 16:00.

The group will officially meet at 4:00 PM at our base hotel in the Holtsville/Islip area for our first briefing and Welcome Drink. If you are flying into ISP, it is a short 15-minute Uber or taxi ride. On our final day, we will conclude the trip around 2:00 PM to allow everyone enough time for afternoon flights home.

This trip ends in Islip. The trip officially ends at 14:00 on the last day, so we recommend planning your return transfers accordingly. For example:

• if you need to book a flight, consider the time needed to reach the airport and complete check-in procedures;

• if you need to book a train or continue your journey independently, consider the time required to reach the station or your next destination.

 If you have any doubts, you can contact the coordinator assigned to your departure for advice.

For this itinerary, you can choose the type of luggage you prefer – we always recommend a backpack, but you can also travel with a duffel bag, a holdall, or (it breaks our heart to say it) a cabin trolley case or a checked suitcase, as long as it’s moderate in size. Our Group Leader will suggest the ideal luggage before departure in the WhatsApp group!

Return international flights are not included on our trips because we want to give you full autonomy and flexibility. You can choose your preferred airline, fly from the airport that works best for you, and decide how many stopovers you want to make along the way.

As flights are not included, you also have more flexibility with your travel dates: you could arrive at your destination a few days early or return home a bit later – or even continue independently to a nearby destination!

It depends on when you cancel, the status of your departure, and how much you have already paid. Here are all the cases.

If you cancel more than 31 days before departure - Tour not confirmed
You can cancel via email at hello@weroad.com

If it was your first unconfirmed booking (if you have more than one), nothing has been charged: no refund is needed.

If you paid the €/£/$100 deposit, the deposit is not refunded if you choose to cancel: you can, however, change trip from your MyWeRoad Personal Area and use the amount towards another departure.

The deposit is fully refunded only if WeRoad does not confirm the tour.

Tour confirmed – you paid only the €/£/$100 deposit
In case of cancellation by the WeRoader, the deposit paid is not refunded. However, you can change your trip from your MyWeRoad Account and use the amount for another departure.

Tour confirmed – you paid the full amount
In case of cancellation by the WeRoader, the amount paid is not refunded. However, you can change your trip from your MyWeRoad Area and use the amount for another departure.

If you cancel less than 31 days of departure
You can cancel your booking at any time. However, in case of cancellation of less than 31 days before departure, no refund of the amount paid is provided, nor is it possible to change your trip, unless you have purchased Flexible Cancellation.
The private room fee, included in the price of your trip, is not refunded under any circumstances within this time frame, unless you have purchased Flexible Cancellation.

If you have Flexible Cancellation
With Flexible Cancellation, for all departures from May 14 to September 30, 2026, you may cancel your trip up to 24 hours before departure and receive a refund, whatever the reason. The only amount not refunded is the cost of the Flexible Cancellation option itself.

PLEASE NOTE: before cancelling, keep in mind that you can move your booking to another trip or a different date. Find out how!

For any doubts about your specific situation, write to our team at hello@weroad.com - we’ll help you!

Yes, you can change your trip directly from your MyWeRoad personal area, up to 31 days before departure. If you purchased Flexible Cancellation, to give you maximum flexibility, for all departures from May 14 to September 30, 2026, you may cancel your trip up to 24 hours before departure and receive a refund, whatever the reason.

How to change your trip from MyWeRoad

• Enter your booking
• Scroll to the “Change your trip” section at the bottom right
• Select a different date for the same trip or a completely different trip

Things to know

You can change your trip up to 3 times from your MyWeRoad personal area. Further changes must be requested by contacting our team at hello@weroad.com.
The new trip must depart within 12 months from the original departure date.
If your original booking included a private room, Flexible Cancellation, discount codes, gift cards, or vouchers, we will notify you before confirmation if they cannot be applied to the new trip.

You cannot switch to sold-out trips. For “On request” departures, we will check availability. For “Last spots” departures, availability in rooms of your same gender may not be guaranteed.
If there is a price adjustment: if the new trip costs less, we will refund the difference; if it costs more, you will need to pay the difference.

PLEASE NOTE: before cancelling, keep in mind that you can move your booking to another trip or a different date. Find out how!

In some cases – for example when a departure is not yet confirmed and it is your first unconfirmed booking – you can book without paying the €/£/$100 deposit upfront.

This means that you can secure your spot at zero cost: nothing will be charged until the departure is confirmed. Once the departure is confirmed, the €/£/$100 deposit will be automatically charged within 48 hours according to the terms agreed at the time of booking.

Yes, but fees are non-refundable. If your plans change, you can modify your trip free of charge up to 31 days before departure.

How cancellation works Fees paid are not refundable in cash, regardless of whether your trip is confirmed or not. You can move your booking to another trip free of charge, up to 31 days before departure. After this deadline, changes are no longer possible.
Please note: if it's your first unconfirmed booking, you will only be asked to provide a credit card, PayPal, or Revolut as a guarantee, but nothing will be charged. From the second unconfirmed booking onwards, a mandatory £/$100 deposit will be required.

Exception: trip not confirmed by WeRoad If you wish to cancel, the rules above always apply. However, if WeRoad is the one not confirming the trip, you are entitled to a full refund of any amount paid.

Flexible Cancellation If you purchased the Flexible Cancellation option (available in the first step of the booking process), for all departures from May 14 to September 30, 2026, you may cancel your trip up to 24 hours before departure and receive a refund, whatever the reason. The only non-refundable amount is the cost of the Flexible Cancellation option itself.

How to cancel your trip Write to hello@weroad.com indicating your booking code. We will reply as soon as possible applying the cancellation conditions for your booking.
PLEASE NOTE: before cancelling, keep in mind that you can move your booking to another trip or a different date. Find out how!

We offer several payment methods to fit every need:

1. Credit or debit card (Visa, Mastercard, American Express);
2. Instalment payment with Klarna (you’ll pay for the trip in three equal amounts);
3. PayPal (for selected destinations);
4. Revolut Pay to pay even faster straight from your Revolut account.

Yes! We might not know the flights for everyone else in the group, but there are ways to find out which flights your fellow WeRoaders will be taking. 

1. All travellers can share their flight details after booking on their My WeRoad account so that other travellers on the same trip can see these details anonymously. 

2. Alternatively you can join our Facebook group: Solo Travellers | WeRoad Community – (here is the extended link: https://www.facebook.com/groups/963298767843213 ) Look for a post about the trip you’re interested in or ask the group admin for help in getting in touch with your future travel companions!

3. If the Group Leader has already been assigned to the trip you’re keen for, you can easily find their Facebook post on the website. 

If a departure is “Open to book”, it means that the trip is not yet confirmed and we are waiting for a few more bookings… maybe yours!

The good news? If it’s your first booking on an unconfirmed departure, you can book without paying anything! Just. leave your credit card details as a guarantee: no immediate charge, €/£/$0 deposit.
In the meantime, wait for the departure to be confirmed before purchasing your round-trip flights!

Generally, our groups have an average of 11 people. Everyone on our trips speaks English, and travellers join us from across the UK, Europe and beyond. Our trips are open to travelers between 18 and 49 years old. The indicated age is meant to give you an idea of the type of group, but it's not a strict limit: it's possible to participate even with a few years more or less, as long as you can keep up with the pace and energy of the group you're traveling with.

Each group will be joined and led by one of our experienced Group Leaders, who’s there to ensure everything runs smoothly and the group feels well-supported. 

If you’d like to know more about our typical WeRoad groups do reach out to us on WhatsApp on +44 7716573700. 

Yes! If you're curious, you can take a sneak peek at the group before booking. 
You’ll find the info in the ‘Group’ section for each trip on the departures page, showing how many WeRoaders have already booked. 

Click the little arrow and you’ll even see their gender and ages – but hey, that’s exclusive info, so we’ll ask you to log in or sign up to see that!

For our trips we usually use locally owned accommodation instead of big hotel chains. It’s our favourite way to really experience the local culture and, whenever we can, support the local economy. Typically, you’ll stay in hotels, apartments, guesthouses and hostels with the same standard maintained across all trips in the same destination.

The list of accommodation for your trip will be shared with you by your Group Leader 2-5 days before departure, along with other useful details for your adventure!

For some trips, in the itinerary section, you’ll find the number of nights and the location (not the hotel) where you’ll be spending the night(s). The location shown is the one we usually go for on most trips, but in some cases, you might stay in a nearby town. This will depend on logistics or availability of accommodation. 

The list of accommodation for your trip (and therefore also the exact locations) will be shared by your Travel Group Leader 2-5 days before departure, along with other useful information for your adventure!

The WeRoad Travel Group Leader is an experienced and skilled traveler who will be the perfect companion for your trip. They will manage all the logistical aspects of the itinerary like transport, timings, accommodation, restaurant bookings and meeting points, so that you can enjoy the trip without this hassle. They’re there to support the group, ensure everything runs smoothly and will no doubt make the trip a lot of fun along the way too! 

The Group Leader will set up a WhatsApp group approximately 2 weeks before departure. This will be the moment to ask any pre-departure questions and get to know the rest of the group! If the trip you are interested in already has a Travel Group Leader assigned, you can contact them before booking. Their details will be on the trip page, or you can search for their name here. After booking, you will find their contact details in your My WeRoad account, under ‘Bookings and Trips’ > ‘Your Upcoming Trips’ > ‘Trip Details’.

When you set off on a WeRoad trip, you’re officially a WeRoader – and as we often say, 'once a WeRoader, always a WeRoader'. This means that once you’re part of the community, a little piece of WeRoad will always stay with you.

But you’re not just a WeRoader during your trips, far from it! The community is alive and active all year round: you can stay in touch by following and interacting on our social media channels, like the Facebook group or the Instagram profile. You can also come along to one of our many events that we run in different cities worldwide. Check out and sign up to our events by downloading the WeMeet app here. 

Yes, on all our trips you will share a room with other WeRoaders in your group. The bathroom will either be private or shared only with other travelers on the trip. The rooms might be twins, triples, quadruples or multi-share (up to 8 people in exceptional cases), depending on the destination and availability.

You will never share with people from outside of the WeRoad group, except in certain cases for local experiences, which are specifically mentioned in the itinerary or communicated before booking. These typically involve specific nights in unique accommodation like tents, homestays, or camping, offering a more adventurous travel experience in exchange for some comfort.

During the booking process, you can also choose to stay in a mixed-gender room. If needed, only travelers who have opted in to this option may share a room with travel companions of a different gender.

On some of our trips we can offer a private room for an additional cost. Just tick the ‘Private Room’ option at checkout to get this added. For some of our trips if you book as two travelers together you can add this private room free of charge. Look out for this option at checkout. 

Please note that if you do book a private room with a friend/partner this could be either a double or a twin room so please email hello@weroad.com if you have a preference on this. 

Find out the entry requirements for United States of America, and, if needed, apply for your visa through our partner Sherpa.

Before traveling, always remember to check the government website of your country of origin for updates on the entry requirements for United States of America – you wouldn’t want to stay home due to a bureaucratic detail!

• UK residents: review the FCDO Travel Advice.
• US residents: consult the US Department of State Travel Advice.
• Other residents: refer to your government or local consulate's travel advice.

Important! If you have visited certain countries - for example Cuba - you cannot apply for ESTA. Check for other visa rules.

The United States of America spans multiple time zones, so the time can vary depending on where you are. Here are the main time zones:

• Eastern Standard Time (EST): 5 hours behind the UK. If it's 12pm in the UK, it's 7am on the US East Coast.
• Central Standard Time (CST): 6 hours behind the UK. If it's 12pm in the UK, it's 6am in the US Central region.
• Mountain Standard Time (MST): 7 hours behind the UK. If it's 12pm in the UK, it's 5am in the US Mountain zone.
• Pacific Standard Time (PST): 8 hours behind the UK. If it's 12pm in the UK, it's 4am on the US West Coast.

Remember that the US observes daylight saving time, typically from the second Sunday in March to the first Sunday in November, which may alter these differences by one hour.

The currency used in the United States of America is the US Dollar (USD). As of recent rates:

• 1 British Pound (GBP) is approximately 1.21 USD
• 1 Euro (EUR) is about 1.05 USD
• 1 US Dollar (USD) equals 1 USD

You can exchange currency at airports, banks, and currency exchange centers throughout the country.

In the USA, you can pay using credit cards, debit cards, and mobile payment apps like Apple Pay and Google Pay. Cash is also widely accepted. Most places take major credit cards like Visa, MasterCard, and American Express, but it's a good idea to carry some cash for smaller businesses or tips. Always check if your card provider charges foreign transaction fees to avoid surprises.

Yes, tipping is customary in the United States and is an important part of the service industry. For restaurants, it’s standard to tip 15-20% of the total bill before tax. In bars, leaving around $1-2 per drink is common. For taxi drivers, hairdressers, and similar services, a tip of 10-15% is usual. Hotel staff, like bellhops, usually receive $1-2 per bag, and housekeeping staff generally get $2-5 per day. Tipping is how many service workers earn a significant portion of their income, so it's appreciated and expected.

In the United States, internet connectivity is generally reliable and widely available. However, if you want to stay connected while on the road, buying a local SIM card or an e-SIM data plan is a good idea. Providers like AT&T, T-Mobile, and Verizon offer various prepaid plans. If you're primarily staying in urban areas, you'll find free Wi-Fi in many places, such as cafes, restaurants, hotels, and public spaces. However, in rural areas, Wi-Fi might be less available, so having mobile data is handy.

In the United States, the primary language spoken is English. However, you'll find a rich tapestry of languages due to its diverse population. Here are some useful colloquial expressions you might hear or use:

• How's it going? - How are you?
• Awesome! - Great!
• No worries - It's okay, no problem
• Catch you later - See you later
• What's up? - What's happening?

These can help you get by and sound like a local during your visit!

In the United States, the plugs are Type A and Type B. The voltage is 120V, and the frequency is 60Hz. If you're coming from a country that uses different plugs, you'll need a universal adapter to charge your devices. Always check your device's voltage compatibility to avoid any damage.

The main religion in the United States is Christianity, with a majority of the population identifying as Christians. However, the U.S. is a melting pot of cultures and beliefs, so you will find a variety of other religions practiced here, such as Judaism, Islam, Buddhism, and Hinduism. The U.S. is known for its religious freedom, allowing people to practice their faith openly. There are no specific dressing requirements tied to religion in the U.S., and religious holidays are diverse, with Christmas and Easter being widely celebrated.

When packing for the United States, consider the vast climate differences across regions and seasons. Here's a handy list to help you pack your backpack:

• Clothing:
  • T-shirts, sweaters, and a light jacket
  • Jeans and shorts
  • Swimwear if visiting coastal areas or warm regions
  • A warm coat and gloves if traveling in winter to northern areas
• Shoes:
  • Comfortable walking shoes
  • Sandals for warm weather
  • Boots if visiting snowy or rugged areas
• Accessories and Technology:
  • Sunglasses and a hat
  • Universal travel adapter
  • Power bank for your devices
  • Camera or smartphone for capturing memories
• Toiletries and Medication:
  • Travel-sized shampoo and conditioner
  • Toothbrush and toothpaste
  • Sunscreen and insect repellent
  • Basic medications like pain relievers and motion sickness tablets

Be sure to check the specific weather for the region you're visiting to pack accordingly.

The weather in the United States varies greatly depending on the region and the time of year:

• Northeast (e.g., New York, Boston): Cold winters with snow, warm and humid summers. Best time to visit is spring or fall.
• Southeast (e.g., Florida, Georgia): Mild winters, hot and humid summers with frequent rain. Best time to visit is winter or early spring.
• Midwest (e.g., Chicago, Detroit): Cold and snowy winters, hot summers. Spring and fall are pleasant for visiting.
• Southwest (e.g., Arizona, New Mexico): Mild winters, extremely hot and dry summers. Fall and spring are ideal for travel.
• West Coast (e.g., California, Oregon): Mild and wet winters, dry and warm summers. Best time to visit is late spring to early fall.

Always check local forecasts before your trip as weather can be unpredictable.