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If you've ever tried to book a hotel for a family of five, you've probably run into this exact wording: "connecting rooms available upon request, subject to availability at check-in." That single phrase is doing a lot of quiet damage to family trip planning, and almost nobody stops to unpack what it actually means. The connecting hotel rooms type you want usually isn't a real booking category Most hotel booking systems are built around a handful of standard categories — king,

The Amalfi Coast photographs like the easiest yes in Italy — cliffside terraces, lemon groves, a boat pulling up to a private dock. What those photos don't show is that the coast's biggest charm is also its biggest logistical problem for a family of five: almost nothing here was built with a family that size in mind. Why go now, instead of waiting There's a quiet assumption a lot of parents make without saying it out loud: that a trip like Amalfi is a "someday, once the kids

"How early do we need to book?" is one of the most common questions families ask when planning a European trip — and it's also one of the hardest to answer honestly, because the real answer isn't a number. It's "earlier than you think, for reasons that have nothing to do with the hotel filling up." Why "the hotel isn't full yet" doesn't mean you're fine Most families think about booking windows the way they'd think about a flight — prices go up, but you can usually still get

For years, Puglia has been one of Italy's best-kept secrets. There's just one problem: finding a luxury hotel room—especially if you're a family of five. With both Four Seasons and Rocco Forte set to open new luxury resorts in Puglia in 2028, many travelers are asking me the same question: Will it become easier to book Puglia? The answer is... yes and no.

Milan is one of my favorite Italian cities to build a family trip around — and not just because it's stylish and easy. It's one of the best gateway cities from the U.S., with nonstop flights that make arrival day smoother and less chaotic with kids in tow. Instead of rushing straight to Lake Como or Tuscany, I love building in 2–3 nights here first, to adjust, reset, and ease into Italy before the rest of the trip picks up pace. Milan is walkable, compact, and surprisingly ma

When I talk about Cruises, I usually talk about Celebrity and above — Explora Journeys, Ritz-Carlton Yacht Collection, Four Seasons Yacht Club. So it might surprise you that I want to talk about Princess. I just spent a week on one, going Rome, Amalfi Coast, Messina, Montenegro, Corfu, Naples, and back to Rome. It's not super luxurious, and I'm not going to pretend it is. But for the right trip, that's exactly the point. Why a Princess Cruise with kids works for the right fam

where to stay and what to do in Puglia with kids

Planning a trip to Florence with kids often means rethinking the typical European hotel setup. When you have five people—especially little ones—you want more space to spread out, room configurations that make sense, and properties where you can balance sightseeing with downtime. Many families find the ideal rhythm is one major sightseeing outing per day, followed by something relaxing: swimming in the pool, exploring the gardens, or letting kids roam beautiful grounds at thei

Discovering Portofino: A Family-Friendly Adventure There’s something timeless about Portofino — pastel houses, gentle waves, and the kind of slow pace that’s perfect for family travel. This was one of our favorite cruise stops in Italy, and here’s how to spend a day in Portofino with kids that makes both the grown ups and kids happy. Portofino marina Start at the Marina Begin your day at the marina, watching boats glide in and out. Little ones will love the sea life and brigh