img
img
Top Holidays
img

The Art Of Travelling Better: 10 secrets from our concierge

Our Travel Services | 12 October 2026

The difference between a great holiday and an unforgettable one often lies in the details. From securing a reservation at a trending restaurant to knowing when to leave a little room for spontaneity, our award-winning Head of Customer Experience, Claire Baker, shares 10 of her top tips to enhance your holiday.
 

Claire Baker, Winged Boots' Head of Customer Experience

1. Start with the experience, not the destination

From Formula 1 race weekend to a Celine Dion concert in Paris, book your tickets and then build your itinerary around the event. And remember, your holiday doesn’t have to end once the chequered flag falls.
 

2. Get ahead of the impossible reservation

It’s always easier to cancel a reservation than try to make one at the last minute. So, if I know of a hard-to-get-into restaurant that a client will love, I’ll sometimes secure a table in advance and diarise the cancellation deadline. More often than not, they’re grateful we thought ahead and enjoy a brilliant meal without any of the last-minute stress.
 

Lake Braies in The Dolomites

3. Why stop at a twin-centre?

Why simply travel from A to B when the journey between them could become one of the highlights? Break up two safari camps with a night at Victoria Falls, sleep beneath the stars on Botswana’s salt pans, or turn a Seychelles stay into an island-hopping adventure. Sometimes the best way to elevate a twin-centre is to add a third chapter

4. You don’t have to fly private to make travel feel private

When you’re travelling, it is difficult to escape the chaos of an airport. However, airport meet and greet in destinations like Maldives does just that. You’ll be met at the plane door and whisked away to your own personal terminal, seated in a private lounge and can enjoy the private aviation experience, regardless of your cabin class.
 

Lady enjoying breakfast in Cappadocia, Turkey

5. A great itinerary leaves room to change your mind

I love to have the moments that matter booked before you travel, but not every hour needs a plan. Alongside confirmed restaurants and experiences, I’ll often suggest a café worth stopping at, a neighbourhood to wander through or somewhere for an impromptu drink. You have the reassurance of a plan, without feeling tied to one.

6. Upgrade the moments nobody thinks about

If you’ve got a late flight, why not arrange for your luggage to be collected and sent directly to the airport so you can enjoy your day at leisure? Another top tip for any holiday, regardless of destination, is to skip the buffet and enjoy breakfast somewhere new. Whether that’s a local coffee shop or after a sunrise hike at the top of a mountain, it’s a great way to start your day.

Overwater villa at Ritz-Carlton, Fari Islands Maldives

7. Don’t be afraid to ask ‘what would you do?’

With AI and social media, travel has become more accessible, but nothing beats personal experience. Some of my best recommendations come from places our team has experienced firsthand, feedback from our clients and trusted partners we’ve worked with for years.

8. You don’t have to upgrade everything

Flying Business Class can completely change the start or end of a holiday, but that doesn’t mean you need to book it both ways. Consider upgrading just one leg of your journey instead. The same applies when you arrive. You might not want a supercar parked outside your hotel all week, but hiring a Ferrari for a day in Mallorca can turn an ordinary drive into part of the experience.

Private yacht charter in Europe

9. A private charter is great for all ages

If the opportunity is there, I always recommend a private yacht charter. It’s a great addition to any holiday and is perfect for couples, groups as well as families. I also love to incorporate it with a beach club, allowing you to spend time exploring the coast, snorkelling hidden coves, and then dock for lunch before watching the sun set surrounded by the ocean.

10. Even the best planned trip can still contain a surprise

Whether it’s for a special celebration or simply to see their face, there’s something wonderful about keeping part of a trip a secret. From organising for a mermaid to swim past a family’s overwater villa to delight the little ones to booking a private dining experience to mark a milestone; Sometimes, the moments clients remember most are the ones they never knew we'd planned.

Let us take care of the details

The most memorable holidays aren’t simply booked; they’re thoughtfully considered, expertly curated and filled with moments you might never have discovered on your own. From the smallest finishing touches to once-in-a-lifetime experiences, our team is here to make every journey extraordinary.

Ready to travel better? Get in touch with our team and let us create something unforgettable.

img
Be inspired

Winged Boots:
The Lifestyle Brochure

img

Blending the latest luxury travel trends, inspiring editorial and exclusive customer interviews with our curated list of the top hotels in the world, allow our brochure to spark your wanderlust.

order your copy today
img
Inspired?
Start planning your
next trip today

Our expert team of personal travel managers are ready to craft your perfect journey. From business trips to luxury leisure holidays, simply put your pin in the map, and we’ll make it happen.