How to Not F-Up Your Vacation — Like I Did Last Summer
Luxury Travel Advisors Share Their Insider Tips
Traveling is the true love of my life. And probably explains why I dragged the family from Australia to live in NYC — it’s a beautiful island at the bottom of the world, too far from anywhere. I love discovering new places, new cultures, and sitting on a beach in the Mediterranean. Give me a Greek island, Ibiza, the south of France, or Italy any day.
I’m also a beta mum. So while I’m always jetting off to Europe every summer (in my mind, anyway), I’m never organized or cashed up enough to book the actual trip in advance. Like a normal person.
Last year, I managed to throw together a last-minute trip to take my boys to Greece and Sicily. Tiago was already on an eight-week jaunt around Europe with friends, so Javi and I flew to Athens to meet him. It was Javier’s first trip to Europe, so it was doubly special. We spent the first ten days in Greece — Athens, Paros, Antiparos, and Milos. Heaven. We’re beach people: fresh fish, plenty of swimming, lots of chillaxing. Tiago crashed our rental car, but that’s another story.
Then we flew to Sicily. Tiago wanted to rent a car and drive around, but after Crashgate and because I couldn’t handle the idea of navigating the crazy Italian roads, we settled on Taormina. A little history, quintessential charm, Italian food, and the beaches. Perfection. Taormina is where they shot The White Lotus 2 — where a paranoid Tanya becomes convinced the gays are out to kill her. What could go wrong?
Everything. We booked a sucky Airbnb, left, and had to battle for a refund. We upgraded to a hotel (more money I hadn’t budgeted for). We went from eating fresh fish for €10 by the ocean to €30 Sicilian dishes (mid) in the kind of restaurants that display their menus out front. And we’d arrived during Ferragosto — Italy’s busiest week of the year, we discovered after the fact. There were throngs of tourists everywhere (not our vibe), shoulder to shoulder through the winding cobblestone streets. Not exactly cute.
We hated Taormina. We wanted to escape to the islands — Salina, Panarea — but we were locked into the hotel, so we were forced to suck it up.
Maybe it’s the White Lotus effect, but Taormina has become a tourist trap. My friend Lauren, who’s Sicilian, had raved about it. When I texted to say we weren’t loving it and asked when she’d gone, she replied: 25 years ago. ” On her honeymoon. My other friend Amanda went recently, and when I quizzed her on the best place she’d ever been, she said, “Honestly? Taormina.”
Determined to make the most of it, we booked a day boat tour: it rained, we got lost, missed the boat to the next stop, and had to shell out for an expensive water taxi to meet the group at the volcano everyone was dying to see. What a buzzkill — it smelled like sh*t and rotten eggs, and all we could think was what a nightmare trip from hell.
And no, of course, I haven’t booked my trip for this summer.
I’d like to see more of Sicily — but next time I’ll do it properly. I see exactly why people use travel advisors. I spoke to some of the best in the biz when I was editor of Travel Curator, and they shared their insider secrets to ensure your trip goes off without a hitch.
David Prior, Prior World
“Rather than ask what they like, we ask them how they want to feel.”
“The Prior World audience is seasoned travelers with a creative spirit who are curious, seeking connection, and resonate with a certain aesthetic. The goal is to empower them with honest reviews of hotels and destinations, industry insights, and knowledge of global cultures and traditions. I care so much more about a hotel reflecting the character of the place than the consistency of the thread count.
Our clients come through referrals — people who’ve traveled with us or who’ve seen or read something on our site or social media — so they trust us and our point of view. Rather than ask what they liked in the past, we ask them to tell us how they want to feel. Everyone wants to feel alive again, so if they tell me they want to feel sweaty on the dance floor in Berlin, taste that restaurant in Stockholm, or dive into the ocean and taste the salt on their lips in Sydney — we write the prescription.”
Jack Ezon, Embark Beyond on Substack
We Let Them Ask the Questions
“At Embark Beyond, we take a very different approach. Rather than have our clients ask us questions, we ask them questions — to get to know them, so we can match the right experience and the right place to stay with the right client. We don’t like to ask about bucket lists that focus on destinations; we focus on aspirations and the ingredients our clients seek to build a plan that creates meaningful travel experiences — ones that enhance and enrich their lives, furthering their goals and passions.
Some top things you should be prepared to answer:
What are your five favorite hotels?
Do you like or dislike beach, adventure, culture, or shopping vacations?
Do you want action or serenity?
Do you like to stay in one place or move around?
Do you like exotic, familiar, or close-to-home?
Is the purpose of your trip to see things so you can say you’ve seen them, or to explore somewhere in more depth?
Do you travel heavy or light? (It determines how much you can move around.)
Lia Batkin, CEO of Vacation Style, Co-Founder of In The Know Experiences
Consider Your Travel Advisor Like a Financial Planner
“They should be someone you know and trust, who will help you plan out a running bucket list of trips for the future. Getting to know each other and giving them as much information as possible ensures they know exactly what kind of trip you want, what you want to get out of it, and when something doesn’t fit the bill.
If you’re going on a girls’ trip, you might want to wake up to a beautiful, relaxing view and have a great spa. If it’s a couple’s trip, you might want a super-romantic room to spend time in, some activities, and a place with great food that your partner likes. My best advice is to narrow your must-have list to five things, because you won’t always get everything in one destination.
Working with a luxury travel advisor means more perks, personalized service, and intel — they take care of the little touches that make your experience special. If you’re celebrating your honeymoon, they can arrange a lovely bottle of champagne when you arrive and have your wedding song playing. Expedia can’t do that. Nor can they tell you the pool is closed, the service is lacking, or the road to the hotel is terrible.”
Meg Nolan van Reesema, FOF Consulting
Know Why You’re Really Going
“Making sure a trip is a dream one comes down to personal travel preferences, so I’ve created a very customized, bespoke service model. It’s an iterative process — like interior design, travel isn’t one-size-fits-all. In the initial phase, I work closely with the client to build rapport and determine their likes, dislikes, and motivation through preference forms and phone conversations.
If they say they want to go somewhere because they saw it on Instagram, or because a blogger went, I dial it back and ask what they’re trying to accomplish. Do they want to unplug? Check a box? Take a multi-generational vacation to create lasting family memories? Once I know their purpose, I customize the trip to reaffirm that theme and their goals. Because while every trip is different, you’re not the same traveler for every trip — so knowing why you want to go is everything.”
Misty Belles, Virtuoso · VIRTUOSO’s Substack
Interview Your Advisor — and Ask About Upgrades
“Don’t be afraid to interview your travel advisor — you’ll find the ‘where’ becomes about the ‘how’ and the ‘why.’ Ask them how they travel, why a destination is a favorite, and their firsthand experiences. Share everything about your own travel style, too — from your passion points and dislikes to what you want in the minibar.
And always ask about any additional benefits they can secure. A Virtuoso advisor can get you complimentary room upgrades, daily breakfast, welcome amenities, and resort credits. Our Advisor Catalog does the investigative legwork for you, showing advisor bios, areas of specialization, personal experiences, reviews, and recommendations.”
Kim Hopkins, Kim Hopkins Travel
Go Where Your Travel Advisor Has Been
“The most important thing to ask your travel advisor is whether they’ve actually been there. I always try to send clients to destinations and hotels I know and love. My local contacts are my biggest asset — if I’m sending someone to Morocco or Italy, I book my own driver and guide, so I can text them and make sure everything’s going to plan.
A local perspective is critical: it saves you time and money, and means you’ll have the best possible experience. Anyone can book a flight and a hotel. But when you engage a travel advisor, you’re paying for their experience, expertise, and personal connections — and that’s the most valuable part of any trip.”
Silvia Castellano, Iamitalianissima
Always Read the Fine Print
“The first thing to ask about is the insurance and cancellation policy. It’s crucial that every service on your itinerary is covered, and that you have a robust ‘cancel for any reason’ policy so you can cancel 30 to 45 days before departure. It’s just as crucial to talk to an advisor who actually knows your destination.
When I went to Asia, my trips were planned by an advisor who’s a real connoisseur of that part of the world — I still remember the tiny, remote places she sent me to. She described them vividly, and experiencing them for real was wonderful. Being honest about your expectations and goals is key to a successful itinerary. And always follow your own interests and passions: traveling on a friend’s advice, or a social trend, is a recipe for disaster.”
Been on your own trip from hell? Tell me in the comments — misery loves company.