What Makes a Big Trip Great? 11 Expert Opinions

“The best way to live in the moment is to plan ahead.”

While I’m often a fan of the “leave things to serendipity” mindset, I don’t suggest it for a big trip. This is when you want to be enjoying yourself, not worrying about whether you can get into a certain restaurant or rent that specific boat. Planning ahead means you’ll spend your time in the moment.

– Yolanda Edwards, founder/editor, Yolo Journal

“A new place every few days keeps the adventure going.”

If it’s a full relaxation trip, I’m happy to stay put, but on a big trip, I’d rather keep moving. It’s actually one of the reasons Bhutan was so perfect. We trekked between two COMO hotels, so we were constantly discovering somewhere new. That sense of movement is a big part of what makes a trip feel like an adventure.

– Nell Diamond, founder/CEO, Hill House Home

“Four nights is the sweet spot.”

We like to stay somewhere an average of four nights. We tend to get more out of our time and go deeper into a place when we aren’t constantly on the move.

– Stuart Brioza and Nicole Krasinski, chef-owners, State Bird, The Progress, The Anchovy Bar

“There’s nothing better than losing track of time when you’re traveling.”

Lingering longer than expected at a restaurant; wandering for hours with no destination; stumbling into a church, a tiny museum or an antiques shop you didn’t even know existed: The truest form of travel is unplanned, intuitive and spontaneous. That’s where the magic happens.

– Pili Restrepo, cofounder and creative director, Grassfed Culture Hospitality

“Find someone who balances your travel style, not mirrors it.”

Everything is better with my husband, Alex. We have a great dynamic and respect each other’s travel philosophies. Learning how people travel is an intimate experience—some people are activity doers, and others are more chill. It takes time to learn the balance, and 10 years in, we both know that I’ll ensure we trek across whatever city we’re in twice, and he’ll ensure we take time to recharge.

– Amanda Shulman, executive chef of Her Place Supper Club and cofounder of Libbie Loup Hospitality

“Life’s too short to pack light.”

I’m on team checked luggage. We have the sweetest little girl who needs all her dresses, cute outfits and toys for our trips. I am also the type of person who gets very stressed trying to find bin space. Being a considerate flyer is something I strive for.

– Alex Kemp, executive chef of My Loup and cofounder of Libbie Loup Hospitality

“The more you respect a place, the more it reveals itself.”

People talk about Hawaii as if it’s been loved to death, but that ignores the place beneath the postcard surface. Each return has taught me more about stewardship, community and the responsibility of travel. When you engage respectfully, the islands reveal extraordinary nature, living culture and a strong sense of malama—care for land and people. Those layers, and the fact that my wife was born and raised there, are what keep pulling me back.

– Michael Crawford, CEO, Beckons

“Every other trip pales after a safari.”

A safari in Africa cannot be replicated elsewhere. The time spent in vast, unspoiled landscapes, observing wildlife in their natural habitat, creates distance from daily life and offers a truly immersive experience. I took my wife to Tanzania, and it was the trip of a lifetime.

– Dillip Rajakarier, group CEO of Minor International and CEO of Minor Hotels

“Great destinations work for every generation.”

Recently my family went on a very successful trip to Egypt. There were 10 of us, ranging from 22 to 84, with an equally broad range of attention spans. The secret to the trip’s success was that we each immersed ourselves in the history and culture in our own ways, then came together to share meals and entertainment. Any journey that accommodates different interests creates the best environment for a special time together.

– Catherine Powell, CEO, AmaWaterways

“The best part of a group trip can be spending time apart.”

If you’re with a group where one person wants to read their book and another wants to go ride a horse on the beach, it’s important for everyone to have time to do what’s fulfilling to them. People can get what they need and then come back together and share that. It’s really important to have blocks of unstructured time. I think of it as freedom time.

– Hadley Allen, CCO, Wilderness

“The bigger the milestone, the slower you should go.”

For a major celebration, my recommendation is an Italian island like Panarea. It’s the perfect place to switch off the phone and be present with friends and family. I’m also a big believer in matching the destination to the season to get the best out of it, so in France I love Brittany during the summer, or Megève for a proper Christmas. In the winter, I love heading to Saint Bart’s, specifically Gouverneur Beach. These are spots where you can truly reset.

– Arnaud Champenois, SVP brand, marketing and communications, Belmond