Kate Van Dell

Anguilla and St. Barth are close enough to combine easily in one Caribbean honeymoon, but different enough that the trip genuinely feels like two vacations. I like starting in Anguilla, where the beaches are extraordinary and there is very little pressure to do anything at all, then finishing in St. Barth with its restaurants, shopping, beach clubs and distinctly French sense of fun. Four nights on each island gives you enough time to settle in, and the logistics between them are surprisingly easy.

Anguilla in July is not the Caribbean trip most people think to book, which is part of the appeal. I spent a week on the island in summer with my family, when Meads Bay was calm and startlingly clear. The island felt wonderfully unhurried, and getting a great table did not require treating dinner reservations like an Olympic event. Summer comes with real tradeoffs—including heat, hurricane-season risk, and some seasonal closures—but for the right traveler, it can be one of the loveliest ways to experience Anguilla.

Every time I go to Zermatt, I tell myself I will try somewhere new next year, and yet I always come back. There is just something about arriving in this little car-free village with the Matterhorn looming over everything that feels instantly magical. The standard is so high that there is no bad choice when it comes to hotels. The real question is whether you want to be right in town, on a resort with ski-in ski-out convenience, or tucked away in the mountains where it feels like your own private world. For me, Zermatt is where the holidays feel exactly the way they should: snowy, cozy, and a little bit magical.

Papagayo is the rare place where a family vacation actually feels like a vacation. The water is calm, the days unfold naturally, and nothing requires heroic levels of planning or stamina. Mornings are for the beach, afternoons are for the pool, and the wildlife steps in to entertain your children every time you need a moment. There is enough adventure to have fun and enough calm to feel restorative. It is Costa Rica at its most effortless.

Guanacaste is the part of Costa Rica that feels almost designed for families and people who love beauty without too much effort. The beaches are calm, the wildlife is constant, and the airport is close. Mornings unfold gently, afternoons melt into pool time, and every sunset looks like someone dimmed the sky just for effect. It’s simple, cinematic, and deeply restorative in a way that sneaks up on you. There are more than enough activities to keep you active, along with plenty of beaches and pools to keep changing scenery while still doing nothing if that's what you prefer.

Greece is one of those rare destinations that manages to balance history and horizon in perfect proportion. I designed this itinerary to highlight both sides of the experience: the cultural pulse of Athens and the quiet, architectural calm of the Peloponnese. Staying at The Dolli and Amanzoe creates a seamless week of design, wellness, and awe. It’s for travelers who want to see the world’s oldest city, then retreat to a place that feels completely timeless.

The South of France is my favorite kind of honeymoon. Long, slow mornings, markets that smell like lavender, and at least one night where you drink too much wine and call it romance. This itinerary mixes Riviera polish with Provençal calm, art, sea air, and a little sport for balance. It’s designed for couples who want luxury without the rush and who understand that the best memories happen somewhere between lunch and nap time.

I first went to Bali with my now husband, Jasper, when we decided the best way to find out if we worked as a couple was to take a very long trip. We spent our first month here, and it has lived in my mind ever since. There’s something about Bali that’s both deeply romantic and disarmingly human. It smells like incense and ocean air, people actually smile at you, and the light makes everything look like a movie scene. It’s hard to go once and not spend the next decade planning your return.

Here’s the thing about St. Barth: it’s glamorous, yes, but it’s also surprisingly easy. Once you’re here, the only real decisions are whether to have rosé with lunch (the answer is yes) and how late you’ll stay out at Le Ti (that one’s optional). I love this island for the way it makes you feel like a regular by day three, even if you’ve never been before. This five-day itinerary is the exact flow I’d follow to balance beaches, long lunches, and just enough sparkle at night.

The Netherlands is special to me because it’s where my husband is from, so we’ve been visiting regularly for the past decade (minus the Covid gap). Every trip has been memorable, especially with our son, who always has the best time here. He loves the quirky museums you find all over the country, pancake houses with giant playgrounds, and the Efteling theme park—which never gets old and somehow grows with him each year. There’s never a shortage of things to do. The people are genuinely friendly, and it’s no surprise that Dutch kids are consistently ranked among the happiest in the world.

I’ve been to Paris in nearly every season of my life: as a wide-eyed kid, a moody high school student, a study-abroad student eating crêpes on a budget, a single 20-something walking everywhere in boots I couldn’t afford, a newlywed, and now—most recently—with my son. And the surprising thing is: Paris is just as magical with a kid as it was in all those other phases. Maybe even more so. The key, of course, is not trying to see everything. You’re not racing through a checklist—you’re building memories. Paris rewards slowing down. Stopping for ice cream three times in one day. Taking the metro just for fun. Watching boats on the Seine as the sun sets and the city starts to glow. This guide is built around moments that feel joyful and doable with kids, without sacrificing the beauty and rhythm that makes Paris feel like Paris.

This is the little black dress of beach vacations: timeless, flattering, and always a good idea. It works for a long weekend or a full week—easy to slip into, never fussy, and somehow exactly right every time. Grand Cayman is where you go when you want a truly nice vacation but do not have the bandwidth to overthink it. The beaches are pristine, the service is top notch, and the food is consistently good. It is English-speaking, safe, and incredibly easy to get to. You will be on the beach 10 minutes after clearing customs. We loved the Ritz-Carlton Grand Cayman so much that we went back two years in a row, and every single person I have sent here has had a wonderful time. It is one of those rare destinations where everything works. Your kids are happy, you are happy, and the hardest decision you will make all day is whether to order another cappuccino at breakfast.