How it works

From an interview to a keepsake of your trip. Here's the whole path.

  1. 1 · Before you go

    An interview

    You tell us where you're going, how many days, who's coming, and what you actually love: slow mornings, museums, gardens, food markets, long walks. Just as useful: what you'd rather skip. It takes about 10 minutes, and you can stop and come back to it.

  2. 2 · Before you go

    Your day-by-day plan

    We build a full plan: where you'll sleep, what's fixed (a booked dinner, a train), and what's left open on purpose, because unstructured time is part of a good trip, not a gap to fill. Every day is laid out with a couple of good backup ideas, in case of weather or a change of heart. When your first plan arrives, you (and anyone planning with you) rate the stops you'd keep or change, and June sends you a revised plan. You can read it over and ask for changes before you leave: move a day, swap a stop, slow the pace down.

  3. 3 · During the trip

    Chat with your travel companion, June

    June comes along, in the voice you pick: warm and chatty, calm and organized, or quiet and curious, same good judgment underneath. Once you've left, you chat with her the way you'd text a friend: "is this worth the wait," "we're exhausted, what's close by," "can we move dinner." She answers in plain language, one thing at a time, and if a change is worth making to the plan, she'll show it to you before anything is changed — nothing updates itself behind your back.

  4. 4 · During the trip

    A scrapbook as you go

    With Companion, your travel companion asks each day for a photo and a line or two about how it went. It takes a minute and it's entirely optional, but it's what becomes your journal, which you can print or save as a PDF.

  5. 5 · After you're home

    A keepsake of your trip

    With Companion Premium, your plan, your photos and your own words come back as a keepsake, emailed after you get home.

TUSCANY & UMBRIA · 6 DAYS DAY 1 · 9:30 AM Pienza Town Wall UNRUSHED STOP · 1:15 PM Trattoria di San Giorgio RECOMMENDED BY JUNE Bagno Vignoni Waters June · Travel Companion A heads-up for your group “Rain is due in Montepulciano this afternoon. Want me to move the cellar tasting to the morning?” SWAP SUGGESTED · YOU DECIDE FINGERPOST NO COMMISSIONS
Planning, not booking

This isn't where you book anything.

We don't sell flights, hotels or tickets, and we don't take a commission for sending you somewhere.

In the spirit of the classic guidebook: real judgment about where to go and what to skip, not a page of links to click and pay. The plan is built around good judgment: what's worth the detour, what's overrated, and what to do with the loose hour before dinner. You book the things you want to book, the way you already do.

Arlington Row, a line of golden stone weavers' cottages in Bibury, in the Cotswolds.

How it works behind the scenes

Your travel companion's answers are written by an AI model, not typed by a person on the other end. It's given your plan, your trip's details, and clear rules about how to talk to you: short messages, one thing at a time, plain language, no jargon, and never a wall of bullet points. If it needs to check something before answering, it says so, the way a person would: "let me check and get back to you."

It's good at the kind of research a great local friend would do (routes, opening hours, what's actually worth the detour), but it isn't a booking system, and it can make mistakes like any assistant can. Where it matters, the plan notes its sources; treat anything it tells you about tickets, hours or availability as a good starting point to confirm, not a guarantee.

Ready to plan a trip?

Answer a short interview and get your day-by-day plan.

Plan a trip