Erin Ewing

Because let’s be honest: you’re already tired before you even start packing for your trip. This guide is about keeping the magic alive while cutting down on meltdowns—yours and theirs. I’ve done Disney with my family four times, twice with grandparents in tow. If you’re considering a trip, do it. Yes, it’s hard. You’ll get into arguments. Your kids will complain about their feet hurting. You’ll probably end up carrying at least one child. Someone will cry (it might be you). And somehow, your kids will convince you to buy a $32 bubble wand that will never be touched again. I know I’m not exactly selling it, but here’s the truth: the pure joy on your kids’ faces and the memories you’ll walk away with are worth every penny (and meltdown). So buckle up—let’s break this down.

Belize sparked my curiosity as soon as Alaska Airlines opened a direct route. I’m always looking for tropical getaways that aren’t too hard to reach. I came prepared with my mediocre Spanish, only to discover that Belize is a former British colony—so English is spoken almost everywhere. Along those lines, I want to set expectations. I didn’t find Belize to feel quite as rich in culture and traditions as some other Caribbean destinations. But there are still plenty of unique experiences, incredible weather, and a laid-back island vibe that make it well worth a visit. The relative ease of travel also makes Belize a great option for families with young children dipping their toes into international travel with kids, honeymooners looking for both adventure and relaxation, or anyone who appreciates turquoise water, cool drinks, and a comfortable beach chair.

Costa Rica is one of my favorite places on the planet. I’ve been five times—four of those with my children—and every trip, I find new reasons to fall in love with this country. It’s the only place I’ve been where stunning beaches are virtually empty, waterfalls that feel like they only exist in movies are usually a short drive and short hike away, and wildlife is everywhere you look. But Costa Rica is also a large and incredibly diverse country, and even deciding where to spend your time can feel a little overwhelming. My goal with this guide is to give you a feel for a few of the most popular destinations—their vibe, what makes each area special, and some of the activities and sights you’ll find nearby—so you can start narrowing down where you’d like to stay and begin shaping a potential itinerary. And I’ll be honest: You’ll probably want to come back. So don’t worry about trying to fit everything into one trip. Set aside plenty of time to slow down and relax. If that doesn’t come naturally to you, I’m always happy to help. Pura vida!

I hadn’t been to New York City since I was in my 20s, when I visited my best friend in her tiny apartment that she shared with two other women. Her room was actually the living room, split in two with a pre-fabricated divider. It wasn’t quite what I had imagined after years of watching Sex and the City—the complete opposite of luxury (though still amazing). But I never forgot the energy of the city and always hoped to visit again with a little more experience and, honestly, more money, so I could enjoy more of what the city had to offer beyond French onion soup at TGI Fridays. So when Alaska Airlines had a flash sale and my daughter discovered a newfound love of Wicked (the movie, not the play), I thought—what better time to take my not-so-little girl to a city she’d only seen in movies and give both of us an experience of a lifetime? Flights were booked, Wicked tickets were purchased, hotel reservations were made, school was skipped, and we were off.

When my husband suggested seeing a show at the Sphere, I’ll admit I felt a little intimidated—like I’d be the “old” person in sensible shoes trying to blend in at the club, instead of a twenty-something in stilettos angling for VIP access. And yes, Vegas does feel different in your forties—but in a good way. I no longer need to share a room with four friends at the Excalibur just to afford the trip, and I have zero interest in drinking my weight in Red Bull vodkas to close down the clubs. Now it’s all about luxury at a relaxed pace—and actually having time to enjoy it without wasting half the day recovering from a hangover. Here’s my two-night itinerary (because two nights is plenty) for the more mature traveler who still wants a little glamour and VIP treatment.

The good news: I was fortunate enough to accompany my husband on a recent work trip to Porto, Portugal. The bad news: after travel days, I only had about 72 hours to experience the city, so we had to make the most of it. Our days were packed with sightseeing, guided tours, port tastings, and delicious food. It was short, but long enough for me to fall in love with Porto—and I’ve been dreaming about returning ever since. Since I only had three nights, I splurged on a stay at The Yeatman, a five‑star wine hotel perched on the Gaia hillside. With sweeping views of the Douro and Porto’s tiled rooftops, it’s an ideal home base for exploring—and unwinding. The pool deck view is ridiculous and the terrace is the perfect spot to share a bottle of wine at the end of the day.

I first discovered Punta Mita with my husband in 2010, when we were searching for true relaxation. After experiencing luxury travel in Thailand, we wanted to find something equally indulgent—but closer to home. Punta Mita delivered. Over the years, we’ve returned four more times. Every time we arrive, it feels like we can finally exhale and fully immerse ourselves in the luxury and calm. It has truly become our sanctuary.

The Caribbean is basically paradise on earth — crystal-clear waters that are surreal, palm trees, tropical heat, white sand beaches and enough sunshine to make you forget what winter even is. It’s full of diverse cultures, flavors and music, and every island has its own unique vibe, from laid-back beach shacks to lively festivals. Then there’s St. Croix, the biggest of the US Virgin Islands and kind of like the cool, quiet, underrated cousin of the Caribbean. It’s got history (some of it a little dark) and stunning beaches, and it provides the perfect balance of exploring and relaxation. Ok, maybe a little heavier on the relaxation. I spent a week in Frederiksted, on the west end of St. Croix, with my family and it was one of the best vacations we’ve ever had. And my 11-year-old and 13-year-old spent more time in the water than on their devices. I’d call that a success. Just make sure to leave your fancy clothes at home — you will feel overdressed in this highly shoes-optional location.