How to Create the Perfect Tailored Luxury Itinerary for Your Next Holiday

Planning a getaway should be just as relaxing as the trip itself. When it comes to luxury travel itineraries, the real magic begins with personalisation. Every journey should reflect you — your style, your pace, your passions. That's what transforms a holiday into an experience you'll never forget.

Gone are the days of rigid group tours and one-size-fits-all packages. Today, it's all about freedom, flexibility, and unforgettable moments. Whether you're dreaming of a private island escape, a gourmet tour of Italy, or a cultural immersion in Japan, a bespoke itinerary can make it happen — seamlessly.

At Awake & Wander Luxury Travel, our motto is simple: "Where every journey begins with you." Let’s explore how to create the perfect itinerary that blends style, comfort, and your unique travel personality.

Why a Tailored Itinerary Makes All the Difference

A well-crafted itinerary isn’t just a plan — it’s your story in motion. Tailored luxury travel itineraries reflect who you are. They skip the guesswork, eliminate stress, and maximise every moment.

Here’s why it matters:

• You choose the pace — no rushing, no waiting.
• You focus on what you love — not what a guidebook tells you.
• You stay in handpicked accommodations — not generic hotels.
• You get exclusive access — not tourist traps.

It’s a level of control and comfort that makes your travel feel effortless.

Understanding Your Travel Personality

Before we build your itinerary, we need to understand you. Are you a wellness enthusiast, a foodie, an adventurer, or all three?

Asking these questions helps tailor your trip:

• What excites you most when you travel?
• Are you after relaxation or discovery?
• Do you love spontaneity or a perfectly timed plan?

Every detail — from your ideal wake-up time to your dream dining experience — matters. A luxury travel itinerary is only perfect when it feels like it was written just for you.

Balancing Structure with Freedom

Luxury travel itineraries are often misunderstood as rigid or overly planned. In reality, the best ones strike a balance between thoughtful structure and the freedom to follow your instincts.

You want enough detail to know what’s coming — but not so much that you feel confined by it.

That’s why we help you build a “skeleton” plan: key experiences, anchor points like hotel check-ins and transfers, and a sense of daily flow. Around this, we leave space to adapt. Some clients even choose a “light itinerary” — just flights, transfers, and accommodations, with everything else booked spontaneously on arrival.

This approach works well for creative travellers who thrive on being in the moment.

It’s also perfect for repeat travellers who already know a destination but want to experience it with fresh eyes. We can plan daily options for you to pick from each morning, with no pressure.

A structured plan that supports freedom is where true luxury lies.

Customisation Starts with Conversation

Creating exceptional luxury travel itineraries begins with listening. Every traveller has a story, and that story is the key to crafting a holiday that fits like a glove. At Awake & Wander, our planning starts with real, human conversation — not forms or algorithms.

We ask the right questions. How do you define luxury? What’s your most memorable travel moment? What comforts do you never want to compromise on? And what little surprises would make you smile?

Even preferences you didn’t think mattered — like window seat vs aisle, or evening flights vs early mornings — help shape an itinerary that flows naturally with your energy and rhythm.

By listening carefully, we translate your travel goals into a step-by-step plan that respects your time and delights your senses.

Choosing the Right Destinations

When it comes to curating luxury travel itineraries, destination choice is everything. A city might dazzle one traveller and overwhelm another. We help you choose places that match your preferences.

Some ideas to get you thinking:

Amalfi Coast, Italy

Craving sun-drenched villages, cliffside views, and plates of fresh seafood? The Amalfi Coast is elegance with a Mediterranean twist. Stay at Le Sirenuse, a 5-star property in Positano with jaw-dropping views and personalised service.

Thinking of exploring this iconic coast? Ask us about current offers for Amalfi holidays — we often have exclusive deals that elevate your stay.

Kyoto, Japan

For culture lovers, Kyoto offers a peaceful, refined pace. Think temple gardens, artisan workshops, and kaiseki cuisine. Stay at The Ritz-Carlton Kyoto, blending traditional ryokan features with modern luxury.

If Japan is on your wishlist, we’ve got tailored packages waiting. Let us know what experience you’re after and we’ll craft it perfectly.

Bora Bora, French Polynesia

For pure escape, it’s hard to top Bora Bora. Stay in a luxury overwater bungalow at The St. Regis Bora Bora Resort, where turquoise water laps at your doorstep and every detail is taken care of.

Ready for island life? Ask about our exclusive Bora Bora itineraries for honeymooners or once-in-a-lifetime retreats.

Building in Local Experiences

Luxury isn’t just about where you stay — it’s about how you feel while you're there. The most memorable moments are often found off the beaten path.

Consider these ideas:

• Private pasta-making class with a nonna in Tuscany
• Sunrise yoga in Bali overlooking rice terraces
• Wine tasting at a boutique vineyard in South Africa
• Exclusive art gallery tour in Paris, before opening hours

Adding these moments transforms your itinerary into something personal and truly unforgettable.

Leveraging Insider Knowledge and Hidden Gems

There’s something special about discovering a place through the eyes of someone who knows it intimately. That’s where local insight comes in — and it’s one of the most valuable aspects of working with a travel expert.

At Awake & Wander, we don’t rely solely on online reviews or glossy brochures. We build relationships with destination specialists, in-destination concierges, and hotel staff who offer insight you won’t find in a guidebook.

They know when a quiet museum is best visited. Which beach avoids the crowds after midday. Where to find a sunset view that locals keep to themselves.

This insider access ensures your itinerary isn’t just personalised — it’s full of unexpected joys.

We also tailor recommendations to your interests. If you're a fan of photography, we’ll find golden-hour walking routes. If you love food, we’ll point you to markets and family-run eateries that aren’t on Instagram yet.

It’s the knowledge behind the itinerary that makes all the difference.

The Benefits of Booking with Awake & Wander

Booking your luxury travel itineraries through us means more than just ticking boxes. We offer:

• ATOL protection for peace of mind
• Supplier Failure Insurance and Scheduled Airline Failure Insurance
• A dedicated travel advisor from planning to post-trip
• 200+ trusted suppliers and luxury tour operators
• Insider knowledge and exclusive upgrades

You’re not just a booking reference. You’re a valued client — and your travel experience reflects that.

Our Take:

"A great itinerary should feel effortless, but deliver everything you dreamed — that’s when luxury becomes personal."

How to Keep Your Itinerary Flexible

The best luxury travel itineraries include room for spontaneity. Rigid schedules can sometimes get in the way of real discovery.

We always recommend:

• A buffer day — great for jet lag or last-minute changes
• Flexible timing for activities
• Private guides who adjust based on your interests

That way, your trip flows naturally, with time to explore, rest, or change course if inspiration strikes.

Planning the Journey — Not Just the Destination

The luxury starts from the moment you begin your journey. We consider:

• Airport fast-track and VIP lounge access
• Chauffeured transfers with meet-and-greet
• First-class rail or private jet options
• Bespoke welcome gifts on arrival

Every detail should make you feel cared for and celebrated.

The Role of Concierge-Level Planning

Luxury is as much about anticipation as it is about delivery. That’s where concierge-level planning plays a pivotal role in elevating your itinerary from good to exceptional.

Imagine arriving at your suite to find your favourite wine already chilled. Or securing a last-minute table at a restaurant that books out months in advance. These aren’t lucky breaks — they’re the result of thoughtful planning and insider relationships.

At Awake & Wander, we act as your concierge before you even leave home. From reserving VIP tickets to cultural events, to organising a proposal in a remote vineyard, we turn ideas into reality.

And when you’re on the ground, we remain available — a quiet presence in the background ensuring your plans continue smoothly. Should anything shift unexpectedly, we’re ready to adjust your itinerary with minimal fuss.

This hands-on attention gives you the freedom to focus on enjoying the journey — and nothing else.

True concierge service is built on relationships and deep knowledge of internationally recognised standards of service, like those outlined by Forbes Travel Guide.

Designing a Multi-Destination Itinerary

Why visit one destination when you can blend two or three? We specialise in seamless, multi-stop luxury travel itineraries.

Popular pairings include:

• Singapore & Bali: city buzz followed by beach serenity
• South Africa & Mauritius: safari and sand
• Peru & Chile: ancient history and modern wine country

We coordinate flights, transfers, luggage handling, and more — so all you need to do is enjoy the adventure.

Making Room for Meaningful Moments

Luxury travel isn’t about cramming every hour with activity. It’s about intentionally carving out space for presence — the chance to connect deeply with your surroundings, your travel companion, or yourself.

When crafting tailored itineraries, we often find that the most memorable experiences aren’t the headline activities, but the quiet moments: sipping coffee in a side-street café, watching the sunrise without a phone in hand, or taking a spontaneous walk in a place you’ve never seen.

We build time for this into every itinerary. It’s the luxury of being unhurried.

We also encourage one 'slow day' in every itinerary. No set plans. Just a place, your senses, and the freedom to decide how to spend your hours.

Travel isn’t a checklist. It’s a state of being. And the perfect itinerary honours that.

Final Tips for Creating a Memorable Luxury Travel Itinerary

• Prioritise what truly matters to you
• Don’t over-pack the schedule — leave room to breathe
• Say yes to at least one once-in-a-lifetime moment
• Trust your travel consultant — that’s what we’re here for
• Choose quality over quantity in everything

It’s your holiday. Let’s make it extraordinary.

Sustainability and Conscious Choices in Luxury Travel

As the world becomes more interconnected, so too does the impact of our travel. That’s why many of today’s luxury travellers are seeking itineraries that reflect not just indulgence, but intention.

At Awake & Wander, we help you make mindful choices — without compromising on quality.

We work with partners who prioritise environmental stewardship, community engagement, and ethical tourism.

Whether that’s a resort with zero single-use plastic, or a lodge that supports indigenous employment, these decisions become part of your story.

We can also tailor experiences that allow you to give back — such as supporting marine conservation or learning about cultural heritage in respectful ways.

Creating a luxury travel itinerary isn’t just about what you get — it’s also about what you contribute. And for many travellers, that adds a richer dimension to the journey.

Ready to Plan?

There’s no such thing as a standard trip when you travel with Awake & Wander. Whether you want inspiration, planning help, or the full service, we’re here for you.

You can even start crafting your own luxury holiday directly on our website. But if you’d prefer to sit back and let us handle the details, we’re only a phone call or message away.

Give us a ring on 01495 400011 or use our holiday enquiry form to begin planning your perfect escape. With over 200 trusted suppliers, ATOL protection, and expert support, your next adventure is in the safest hands.

Frequently Asked Questions