Built for the widest, messiest poll you'll ever run

“Sometime in the next few months”, with fifteen people across three generations replying whenever they get round to it. These features are built for exactly that.

Finding the week is the hardest part

Everyone gets excited about the destination and the accommodation. The part that actually kills a group holiday before it starts is a date that half the group can't make. Get the week right and the rest falls into place.

How it works

1. 1

   Create your holiday event

   Name it, pick the months you're considering, and turn on multi-day so it looks for the best consecutive stretch. Ten seconds.

2. 2

   Share the link with the group

   Drop it into the family WhatsApp, the friends group chat, or an email. Nobody needs an account to open it.

3. 3

   Everyone taps the weeks they're free

   Twenty seconds per person, checked against school holidays and annual leave they've already got in mind.

4. 4

   Lock in the winning week

   Pick the week with the strongest coverage, book flights and accommodation that afternoon, before the good ones go.

The 5-minute group holiday plan

The whole plan boils down to seven steps, in this order. Follow them and you'll get a holiday that actually happens instead of one that talks itself out of existence.

1. 1
   Get the date window agreed first. Poll a wide range, then use the month view to narrow it down to the strongest week or two.
2. 2
   Confirm who's actually in. Headcount drives everything else, cottage size, villa cost per head, how many cars or airport transfers you need.
3. 3
   Agree a rough budget early. Say the range out loud before anyone starts sending Airbnb links. It avoids an awkward conversation later.
4. 4
   Book accommodation around the confirmed dates. Not before. Booking the villa first and hoping the dates work out is how half these trips fall apart.
5. 5
   Sort travel logistics once dates are locked. Flights, trains, or who's driving, all easier to plan once the actual week is fixed.
6. 6
   Put one person in charge of money. Deposits, shared costs, who's owed what. One point of contact avoids chasing eight people individually.
7. 7
   Send a shared itinerary a few weeks out. Travel times, addresses, and a rough day-by-day plan so nobody's guessing when they land.

Which time of year should you pick?

Not every window is equal, and the right one depends on who is coming. Here's the honest ranking:

If the group spans multiple families, poll the school holiday weeks first, they'll usually decide the date before anyone else's preference gets a look-in.

Common mistakes that sink a group holiday

• ✗

  Booking accommodation before confirming who's free

  The single most common way a group holiday falls apart. Agree the date first, then book around it.

• ✗

  Assuming everyone has the same school holidays

  Different regions, schools, and countries have different term dates. Never assume, always check.

• ✗

  Running the whole decision through one group chat

  A chat is great for banter and terrible for collecting structured availability from fifteen people. Use a poll for the date, keep the chat for everything else.

• ✗

  Not agreeing a budget before proposing dates

  Money conversations get much harder once people are emotionally invested in a specific week or villa.

• ✗

  Forgetting people in different countries or time zones

  Give them enough runway in the date range to book flights, and don't assume everyone's constraints match the local majority.

• ✗

  No single point of contact for deposits and shared costs

  Splitting costs eight different ways with no one in charge guarantees at least one awkward chasing message.

Group holiday planning guides

• Holiday Date Auto-Fill: Type 'Christmas Party' and Let WhosFreeWhen Do the Rest

  WhosFreeWhen detects holiday keywords as you type your event name and offers to pre-fill the relevant date range automatically, saving time at the start of scheduling.

• How to Plan a Stag Do Without Losing Your Mind

  Planning a stag do is stressful enough without the scheduling turning into a month-long nightmare. Here's the fastest way to find a date that works for the whole group.

• How to Schedule a Hen Party or Stag Do Without the Chaos

  Planning a hen party or stag do means coordinating people across multiple locations with wildly different availability. Here's how to find a date everyone can actually make.

• How to Schedule a Family Reunion Without the Family Drama

  Family reunions are brilliant but notoriously hard to schedule. Here's how to coordinate everyone's availability across locations, time zones, and strong opinions about dates.

Frequently asked questions