This trip or that one?
Eight family head-to-heads.
Every pair here is two places we've written full guides for, compared on the things that decide a trip with kids: the flight from Boston, how you get around, what a week costs and what ages it suits.
Which family trip should you pick?
Short version: the shorter the flight and the fewer the moving parts, the better for a first trip. Italy beats Greece on logistics, Iceland and Ireland are the easiest first trips abroad, and the Azores is the only off-the-beaten-path pick that fits a single vacation week. Bali and Thailand both need two weeks.
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| Pair | Our pick | Why | Flight from Boston | Best age |
|---|---|---|---|---|
| Greece or Italy | Italy for a first trip; Greece for the payoff | Italy is fly, then train. Greece adds a ferry or short flight to reach an island | Rome nonstop about 11x a week. Athens nonstop about 9 hours, sold as a summer route | Both 2 to 12 |
| Iceland or Ireland | Either. Pick the trip style, not the difficulty | Ireland is a west-coast road trip. Iceland is waterfalls, glaciers and geothermal scenery | Both nonstop, year-round, under 6 hours. Icelandair about 2x daily, Aer Lingus to Dublin 2 to 3x daily | Iceland 2 to 12 (glacier walks and lagoons have age limits). Ireland all ages |
| England or Ireland | England for a city week; Ireland for a road trip | London has the most flights from Logan. Dublin clears US customs before you board | London Heathrow about 8x daily on 5 airlines. Dublin 2 to 3x daily | England 2 to 12. Ireland all ages |
| Portugal or Spain | Nerja on price; the Algarve if Lisbon suits your routing | Both are home-base beach weeks. Nerja is the cheaper of the two | One connection each. Lisbon, then 55 minutes to Faro. Madrid, then 1h15m to Málaga or the AVE | Both 2 to 12 |
| Amsterdam or Paris | Amsterdam and Bruges for a short trip; Paris for a full week | Both fly nonstop year-round, so trip length decides it | Both nonstop, year-round. Delta, KLM and JetBlue to Amsterdam. Air France, Delta and JetBlue to Paris | Amsterdam 4 to 12. Paris 2 to 10 |
| Switzerland or Iceland | Iceland on price; Switzerland on getting around | Switzerland is car-free by train. Iceland usually means a rental car | Both nonstop. SWISS to Zurich about 2x daily. Icelandair to Reykjavik about 2x daily | Both 2 to 12. We did Switzerland with a 1-year-old |
| Azores or Bali | The Azores for one vacation week; Bali if you have two | A 5-hour nonstop against a real long haul with a connection | Azores 5h05m nonstop to Ponta Delgada. Bali one stop via Hong Kong, Doha, Dubai or Seoul | Both 2 to 12 |
| Bali or Thailand | Bali. We have done it with our kids; Thailand, not yet | Bali is the shorter flight and our real family trip | Neither is nonstop. Bali one stop. Thailand about 20 to 21 hours via Abu Dhabi or Istanbul | Bali 2 to 12. Thailand 6 and up |
Flight details from our Boston nonstop guide, verified August 2026. Ages come from each destination guide. Schedules change, so check before you book.
Greece vs Italy with kids: which is easier?
Italy's routing is simple: fly into Rome, take the train to Tuscany, and you're done. Greece asks for one more moving part, a ferry or short flight from Athens to reach an island. It's worth it, but it is one more thing to manage with kids and bags.
Cost won't settle it. Italy runs $5,500 to $9,000 for a week and Greece $6,000 to $9,000, close enough that budget shouldn't be the deciding factor. If this is your first trip to Europe with kids, we'd pick Italy for the easier logistics. Greece rewards a family with a European trip or two behind them who want real island time.
Our pick: Italy for a first trip; Greece for the payoff. The full guides: Greece with kids, Athens and the islands and Italy with kids, Rome and Tuscany.
Iceland or Ireland for a first trip abroad with kids?
These are our two picks for an easy first trip abroad: reliable year-round nonstops under 6 hours, English spoken, and very little culture shock. Neither is harder than the other for a family new to international travel.
Ireland is built for a rental-car road trip. Our guide runs the west coast through Galway, Dingle, Kenmare and Killarney. Iceland leans into scenery that reads as otherworldly to a kid: waterfalls, glaciers, black sand. We did Iceland in September 2018 with Selima at 8 to 9 months old. The glacier hike outside Vík was incredible, but the adults took turns, and we'd save it as a family hike for kids around 8 to 10 and up.
If your family wants to drive and explore at its own pace, go with Ireland. If you want scenery that feels unlike anywhere else, Iceland wins.
Our pick: Either. Pick the trip style, not the difficulty. The full guides: Iceland with kids, Reykjavik and Vik and Ireland with kids, the west coast.
England vs Ireland with kids: the easy-flight castles trip
Both are easy-flight, English-speaking trips with real castles and coastline. Our England guide spends a full week in London before heading out to the Cotswolds. Ireland is a rental-car road trip from day one.
The coming-home perk goes to Ireland. Dublin has US preclearance, so you clear customs there and walk straight to baggage claim when you land at home. With tired kids, that matters, and England doesn't offer it. England edges ahead on flight frequency: about 8 London flights a day across 5 airlines, the busiest route from Logan.
Our pick: England for a city week; Ireland for a road trip. The full guides: England with kids, London and the Cotswolds and Ireland with kids, the west coast.
Ireland tours are in the Iceland or Ireland section above.
Portugal vs Spain with kids: the Algarve or Nerja?
Two Iberian home-base beach trips, each one connection from a Boston nonstop. The Algarve routes through Lisbon, then a 55-minute flight or a drive to Faro. Nerja routes through Madrid, then a flight to Málaga or the AVE train.
Nerja runs $5,000 to $7,500 a week, one of the lowest ranges on our site, so it's the pick if budget decides it. It's also the one we know best with the girls: the tourist train out to the Cave of Nerja was a highlight, passing the old aqueduct on the way.
Our pick: Nerja on price; the Algarve if Lisbon suits your routing. The full guides: The Algarve with kids, Lagos and Nerja, Spain with kids.
Amsterdam or Paris for a family weekend?
Both fly nonstop from Boston all year, so this is less about the flight and more about the shape of the trip. Our Amsterdam guide is a shorter trip by design: fly in, take the train to Bruges for frites and chocolate, fly out.
Paris has the depth to fill a whole school vacation week from one home base, plus day trips if you stay two. If you have a long weekend, go with Amsterdam and Bruges. If you have the full week, Paris won't run out of things worth doing.
Our pick: Amsterdam and Bruges for a short trip; Paris for a full week. The full guides: Amsterdam and Bruges with kids and Paris with kids, the real way.
Switzerland or Iceland with kids: mountains or glaciers?
Both are scenery trips, and both fly nonstop from Boston. Iceland is meaningfully cheaper: we put a week at roughly $6,000 to $10,000 at today's prices, against $8,000 to $12,000 for Switzerland, our most expensive destination, where lodging and food both cost more.
Switzerland wins on getting around. Our Lauterbrunnen Valley guide uses a scenic train from Zurich and no rental car, and we did it with a 1-year-old. Iceland usually means driving yourselves, which is doable but a different kind of trip with young kids. Both hold up for February vacation week.
Our pick: Iceland on price; Switzerland on getting around. The full guides: Switzerland with kids, Lauterbrunnen Valley and Iceland with kids, Reykjavik and Vik.
Iceland tours are in the Iceland or Ireland section above.
Azores or Bali: two ways off the beaten path with kids
Both take a family somewhere most American travelers haven't considered, but the flights couldn't be more different. Azores Airlines flies Boston to Ponta Delgada nonstop in about 5 hours, the shortest hop to Europe from Logan. Bali is one stop via Hong Kong, Doha, Dubai or Seoul.
That short flight makes the Azores realistic for a single school vacation week. We wouldn't do Bali in under two weeks. We've done both with our own kids, including a Sanur base through Boundless Life in Bali.
Our pick: The Azores for one vacation week; Bali if you have two. The full guides: The Azores with kids, Sao Miguel and Bali with kids, Ubud and Nusa Penida.
Bali vs Thailand with kids: two long hauls compared
Neither is a short trip. Bali routes one stop via Hong Kong, Doha, Dubai or Seoul. Thailand has no nonstop, and the fastest routings, via Abu Dhabi or Istanbul, run about 20 to 21 hours gate to gate.
The bigger difference is experience. We have a real base in Sanur through a Boundless Life worldschool stay, so our Bali guide comes from a family trip. Our Thailand guide comes from our own time there before kids, and we say so rather than inventing a family itinerary. We wouldn't do our Thailand plan with kids under about 6, given the flight and a full day at Elephant Nature Park. Plan at least two weeks for either.
Our pick: Bali. We have done it with our kids; Thailand, not yet. The full guides: Bali with kids, Ubud and Nusa Penida and Thailand with kids, our 16-day plan.
Bali tours are in the Azores or Bali section above.
One thing we set up before every trip.
What families ask us.
Is Greece or Italy easier with kids?
Italy is simpler logistically: fly into Rome, train to Tuscany, done. Greece adds a real extra step, a ferry or short flight from Athens to reach an island. That step is worth it, but it is one more moving part with kids.
Is Iceland or Ireland easier for a first trip abroad with kids?
Both are easy: reliable year-round nonstops under 6 hours from Boston, English spoken, and little culture-shock risk. The choice comes down to trip style. Ireland is a road trip; Iceland is dramatic scenery.
Does Ireland have an advantage over England coming home?
Yes. Dublin has US customs preclearance, so you clear customs before boarding rather than after landing at home, a real convenience with tired kids. England wins on flight frequency, with about 8 London flights a day from Boston.
Which is cheaper with kids, the Algarve or Nerja?
Nerja, at $5,000 to $7,500 for a week from Boston, one of the lowest ranges on our site. Both are one connection from a Boston nonstop, through Lisbon or Madrid.
Is Amsterdam or Paris better for a shorter family trip?
Amsterdam, because our guide pairs it with a train to Bruges rather than a full week in one city. Paris is the better pick for a full week, with a one-week home-base plan and day trips for a longer stay.
Is Switzerland or Iceland cheaper for a family trip?
Iceland, meaningfully. We estimate a week for a family of four at roughly $6,000 to $10,000 at current prices, against $8,000 to $12,000 for Switzerland, our most expensive destination.
Is the Azores or Bali an easier trip with kids?
The Azores, by a wide margin. It is a 5-hour nonstop from Boston, short enough for a single school vacation week. Bali is a long-haul trip with a connection that really needs two weeks.
Have you taken your own kids to Bali or Thailand?
Bali, yes, with a real base in Sanur through a Boundless Life worldschool stay. Thailand, not yet. Our Thailand guide is built from our own pre-kids trip, and we would not do it with kids under about 6.
Where this fits.
Seven destinations, priced for four from Boston.
What the same money buys on each side.
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