Three friends sitting together on a blanket at the beach

The Group Trip

Nobody wants to be the trip parent.

The group chat has been threatening this trip for two years, and whoever finally plans it becomes the villain about money. Hand it to me instead.

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Where group trips actually die

The trip dies in the group chat, not at the destination.

A burst of enthusiasm. A poll that decides nothing. Someone volunteers, and for the next four months that person collects deposits, chases stragglers, referees the hotel debate, and absorbs the blame when the friend who booked separately ends up a ferry ride from everyone else.

I replace all of that. One link goes to the group: the property, the rooms, one rate, everyone together. People pay for their own rooms directly, so nobody fronts money and nobody chases it. Decisions come to the group as a short menu instead of an open question.

What is included

Every piece a group trip needs.

  • The property

    Villa, estate, or hotel room block, sourced and negotiated, with the group perks attached. I’ll do the villa-versus-hotel math with you honestly, against your headcount and budget.

  • The money, handled cleanly

    Individual booking links and per-room payment, so no one fronts thousands and no one plays collector.

  • In-house staff

    A private chef for the big dinner, a bartender for the first night, yoga on the terrace before anyone is ready to speak.

  • The days, à la carte

    Boats and sails, tastings and vineyard runs, golf tee times, cooking classes, spa blocks, nightlife tables, tickets. Built as options people join, all reserved in advance.

  • The moving parts

    Airport transfers timed to real arrivals, group shuttles, drivers for the day trip. Nobody navigates, nobody is stranded.

  • The insurance

    Because in any group of ten, someone’s plans will change. Protecting the group from one person’s emergency is just good design.

How it works

Three steps.

1

We talk

Twenty minutes. Who’s going, roughly when, what a great trip looks like to you, and the budget you’re comfortable with. I’ll tell you honestly what’s possible, including when the answer is “go somewhere else, and here’s why.”

2

I build

A real proposal: the property, the rooms, the day by day, the transfers, the reservations, and the reasoning behind each choice. We revise it together until it’s yours. Planning is complimentary.

3

You go

I book every piece, confirm it, and stay reachable for the length of the trip. When plans meet reality, you make one call and go back to your dinner.

Questions

The things people ask first.

What does this cost us?
My planning is complimentary. The properties and suppliers pay me from their side, and your group typically pays the same or better than booking piecemeal, with perks attached. Any exception gets named before we start.
How do payments work?
Each person or couple books and pays for their own room through their own link. Shared costs like the chef or the boat get split by arrangement up front. Nobody fronts the trip, nobody collects.
What happens when someone drops out?
Someone usually does, so I plan for it. Room blocks are held with clear release dates, villas get sized with a realistic count, and I’ll tell you honestly where the financial edges are before anyone commits.
How far out should we start?
For a villa in high season or a bachelorette in a hot destination, six to ten months buys the best options. Less runway than that, call me anyway. Shoulder season and good relationships rescue short timelines regularly.
We’re a big group. Or a tiny one. Does it matter?
The architecture works from six people to sixty. Past a certain size we shift from villa logic to room-block logic, and if your group trip is actually a wedding, I have a whole page for that.
Can you keep parts a surprise?
Happily. Surprise guests, a toast, the thing the birthday person swore they didn’t want and absolutely wanted. I plan it with one of you and keep the secret with professional discipline.

Contact

Four ways to reach me.

Twenty minutes, no obligation. Tell me roughly what you have in mind and I’ll tell you what’s possible. Planning is complimentary.

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Email steph.irwin@fora.travel
Text or call (408) 420-0126