The order we book
every trip in.
Flights first, because they decide everything else. Then where to stay, then the two or three things worth pre-booking, then the boring stuff that saves the trip when it goes wrong. This page is that process, with the tools we actually use — and the option to hand the whole thing to us.
We'll plan the whole trip.
We're not a travel agency. We don't book anything for you and we take no commission from hotels or airlines, which means there's nothing steering what we recommend. You get the plan we'd build for our own family, and you book it yourself.
- A 30-minute call to start, so we understand your family before we plan anything
- Flight routing from Boston — which airline, which days, when to buy
- A shortlist of places to stay, with why each one made the list
- A day-by-day plan built around one real thing a day, not a forced march
- Three rounds of revisions
- Email support for one month, answered within 48 hours
- Everything in the $499 tier
- Two additional one-hour calls — for working through the decisions rather than reading them
- Best when you're weighing several destinations, coordinating with another family, or planning a longer multi-stop trip
- Three rounds of revisions
- Email support for one month, answered within 48 hours
Changing destination entirely counts as a new trip and is quoted separately.
Where the links below go. Some of them earn us a small commission if you book through them, at no extra cost to you. It never changes what we recommend — you can ignore every link on this page and book direct. We only link to things we've used on our own trips, with our own kids.
Flights, before anything else.
Flights control every other decision — the dates, the arrival time, how wrecked everyone is on day one. We search to find the fare, then almost always book direct with the airline so we can pick seats together and get the fare class that actually includes a bag.
We search here first because it shows the whole month at once, which is how you spot that flying a day either side of vacation week saves hundreds. Then we book direct — the cheapest result isn't always the right fare.
SkyscannerOur maintained list of what actually flies nonstop from Boston, with the seasonal routes marked and a verified date on it. The single most useful thing on this site if you're starting from scratch.
Where to stay,
with four people.
The constraint nobody warns you about: most European hotel rooms cap at two or three people. A family of four is either two rooms or an apartment, and an apartment with a washer changes a two-week trip completely. We filter for two bedrooms and somewhere walkable before we look at anything else.
Our search is always the same three filters. Two bedrooms so the girls share and the adults sleep. Walkable to food, so nobody's driving after a long day. A washer, so we pack five outfits instead of fourteen.
Recommendation comingWe're pulling together the rentals and hotels we've booked ourselves and would book again — Iberlagos above Praia Dona Ana in Lagos, the Piraeus hotel we use the night before an early Athens flight, and the rest.
Then the two or three things
worth pre-booking.
We pre-book very little — one thing a day is the rule, and the rest is left loose. But a handful of things genuinely need buying in advance, and a handful more are the boring purchases that save a trip when something goes wrong.
Private kid-focused tours in Rome and Athens were worth every cent — a guide who talks to an eight-year-old beats any museum audio guide. Book the two or three big ones, leave the rest open.
GetYourGuideSet it up at home so it switches on the moment you land. Airports have WiFi; the taxi rank doesn't. This has replaced physical SIMs for us entirely and it's the cheapest peace of mind on the list.
AiraloFriends of ours got badly ill abroad and had to be airlifted — not covered by what they had. We carry travel medical separately from the trip-cancellation cover that comes with our card. Two different products, and most families only have one.
SafetyWingAirport WiFi, hotel networks, rental apartment routers you know nothing about. It also means the kids' shows still work, which matters more than it should on a rainy afternoon in a foreign apartment.
NordVPNAge by age, because what a family needs at two is nothing like what they need at eight. Includes the things we've never once regretted carrying and the ones we stopped bringing years ago.
Our picture book. The easiest way to get a five-year-old genuinely excited about a trip is to read her a story set where she's about to go — we wrote this one for ours.
Before you book us.
What does the $499 trip planning cover?
$499 covers a complete custom itinerary for one trip: a 30-minute kickoff call, flight routing from Boston, a shortlist of places to stay, and a day-by-day plan. It includes three rounds of revisions and one month of email support answered within 48 hours. You book everything yourself.
What's the difference between the $499 and $899 tiers?
They deliver the same itinerary. The $899 tier adds two further one-hour planning calls on top of the 30-minute kickoff, which suits families weighing several destinations, coordinating with another family, or planning a longer multi-stop trip where the decisions are harder.
Do you book the trip for me?
No. We're not a travel agency and we hold no supplier relationships, so we don't book on your behalf or take a commission on your bookings. You keep control of every reservation, every cancellation policy, and every loyalty point. We tell you exactly what to book and when.
How many rounds of revisions do I get?
Three. Most families use one or two — usually after showing the plan to grandparents or discovering a date has moved. Revisions cover adjusting the plan we built. Changing destination entirely is a new trip and is quoted separately.
Do you earn money from the links you recommend?
On some of them, yes. If you book through certain links we may earn a small commission at no extra cost to you. It never changes what we recommend, and you're free to ignore every link and book direct. We only link to things we've used ourselves.
Not ready to book anything?
Start with the Boston-to-Europe family flight guide — which routes run year-round, the order we book things in, and how far ahead to buy for a school vacation week.
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