Plan a group trip: dates first, then the money.

Before anyone opens a calendar, agree a rough budget per person, how many nights, the area, and who’s invited, plus-ones and kids included. Send one message with a proposal, not an open question: a suggestion is easier to answer than “what does everyone think?” A long weekend two hours away fits more calendars than a week abroad.

• Offer whole weekends or ranges, not single days. “Friday the 12th to Sunday the 14th” is one option, not three.
• Keep the list short. Doodle’s help center says its research found five options are enough to find a date.
• Set a deadline. Put the day in the message and close the poll then. On Doodle, deadlines are a Pro feature.
• Decide whether you need everyone or most people. If the trip is built around two friends, their answers decide it. For a bigger group, the date most people can make wins, and a Maybe counts for less than a Yes.

An iMessage poll is quickest if everyone has iOS 26 or later; anyone else gets a note that a poll was sent, and anyone in the chat can add options. Rallly is free with no accounts, but there, as in Doodle, an option is one day or a time, not a range. Our guide to Doodle alternatives compares the rest.

Book the place to stay and any shared travel first, while the date still works for everyone. Decide who fronts the deposits before anyone pays one: usually whoever books, if they’re happy to be paid back when you settle up after the trip. If not, everyone sends their share straight away.

• Log the deposit as the first shared cost, so it’s in everyone’s balance from day one.
• Agree what happens if someone drops out once a booking can’t be refunded: usually they still owe their share, unless someone takes their place.

Record every shared cost in one place as it happens: what it was, who paid, and who shares it.

• Equal shares for most things: the house, the car, the groceries.
• Couples who pay together can go in as one person with two shares, so they get one balance. Splitwise and Spliit split by shares; Tricount sets each person’s share.
• Someone who skips a dinner is left off that cost.

A busy day can pass the free Splitwise limit of 4 expenses. Our guide to the limit covers the ways around it.

Paying back after every dinner means dozens of transfers. Wait until the end. Some apps cut who owes whom down to fewer payments: Splitwise’s Simplify Debts, a group setting, does it, and Spliit says it optimizes transfers. Tricount suggests repayments when you settle.

Abroad, agree which currency you’ll settle in. On Splitwise, Simplify Debts works within each currency separately. Our guide to Splitwise alternatives compares the apps.

Date Poll and Trip Split are ours, and they aren’t free: they come with implements, $4.99 a month or $49.99 a year for every tool. The people you ask need no account. In Date Poll you offer up to 30 dates or ranges, and they answer Yes, Maybe or No. Unlike Rallly and Doodle, one option can be a whole weekend. Each date gets a score, with a Maybe worth half a Yes, so the date most people can make rises to the top. There’s no automatic deadline: you close the poll yourself.

Once you pick the date, Date Poll offers to start the trip in Trip Split, with the poll’s title and dates and everyone who said Yes or Maybe ticked; you can untick anyone. Friends see every cost and their balance from one link, but only you add costs. It splits by shares for couples, settles in fewer payments, and uses one currency a trip. For a trip across several currencies, Tricount or Splitwise Pro does more. For the date alone, Rallly is free.