How do you pick dates for a group trip when nobody is free at the same time?

Flip the question. Instead of asking when everyone is free, ask each person privately which dates they cannot do. Then pick the window with the fewest clashes, give the group a short deadline and treat silence as a yes.

Practical steps

1. Ask for the dates people cannot do. Most people have a handful of fixed clashes and are flexible about everything else. A list of blocked dates is shorter, more honest and easier to compare than a list of free ones.
2. Ask privately, not in the chat. In a group chat the first person to answer sets the tone and the quiet friend just agrees. Private answers show what really works for each person.
3. Offer a window, not a single weekend. Give the group a range of two or three months to answer against. That gives you enough options to find an overlap without the choice becoming endless.
4. Rank the options by how many people can come. Count how many people are free for each possible weekend or week. The best option is the one that loses the fewest people, not the one the loudest person prefers.
5. Set a deadline of two days. Tell the group when answers close. Anyone who has not answered by then is counted as free for everything. That keeps one slow reply from holding up the whole trip.
6. Announce the dates, do not reopen them. Once the dates are picked, say so clearly and move on to budget and destination. Reopening dates is the most common way a trip stalls.
7. Check leave early. People with jobs may need to book annual leave weeks ahead. Ask them to request it as soon as the dates are fixed.

Where annamo helps

annamo does this step for you. The organiser shares one link, and each friend marks the dates they can and cannot do on a calendar in about thirty seconds, with no sign up. annamo ranks the dates that suit the most people and shows the organiser who would miss out on each option, so the decision takes minutes rather than a week of messages. Each person also gives a budget and a home airport at the same time, so the next decisions are ready when the dates are.

FAQ

What if one person can never make it?

Pick the dates that work for everyone else and tell them early. A trip that never happens is worse for everyone, including them.

Should we include bank holidays?

Yes. They save annual leave, but flights and stays cost more, so check prices before you commit.

How many people need to be free?

Aim for everyone. If that is impossible, choose the option where the people who miss out are the fewest.

How long should we give people to answer?

Two days is enough. Longer deadlines are forgotten rather than used.