A travel advisor talking about how to use AI to plan your vacation might seem like the canary praising the proverbial cat poised to eat it.

But at Travel with Awestruck, we’re not worried.

Artificial intelligence has completely changed how our clients dream about, research, and plan travel. Tools like ChatGPT, Gemini, and AI-powered search engines make it easier than ever to brainstorm destinations, build packing lists, and explore sample itineraries.

We love watching our travelers explore more and drive discovery through AI-powered tools, but the more mature AI becomes, the more our initial hypothesis has begun to look like an undeniable truth: AI cannot substitute real expertise, lived experience, or the nuance that the world’s most discerning travelers expect (and that makes a journey truly unforgettable).

As a luxury travel advisor, I love watching AI push my clients to explore destinations and experiences that they might not have considered previously. Nothing makes me happier than when my clients come into a conversation with ideas of their own that they found through ChatGPT, Gemini, and other AI-backed tools. But I also see exactly where travelers go wrong when they try to DIY their entire itinerary using AI (and have the horror stories to back it up).

This guide breaks down how to use AI to plan your vacation (intelligently), where AI falls short, and when the guidance of a trusted, expert advisor becomes indispensable.

How to Use AI to Plan Your Vacation (The Right Way)

1. Get Inspired

We often see AI used most effectively in the early stages of trip planning, when the top question our travelers are asking is, “Where do I go next?”

Of course, we’re always happy to help with that, but AI can be a fast path to quickly compare weather, seasonality, budget, flight duration, interests, and travel style instantly.

Useful prompts might include:

• “Where should I travel in July if I want beaches, luxury hotels, and mild weather that is under 4 hours from Cleveland?”
• “Recommend family-friendly destinations for families with children under 10 who love animals and the outdoors with nonstop flights from NYC.”
• “The best trip I’ve ever taken was a vacation my travel advisor planned hiking the mountains of Peru. What are five other destinations that could provide a similar experience?”

These prompts will get you about 10% of the way to a vacation, but using AI to plan your vacation in this way can be helpful to generate inspiration or put new ideas on the table, so that your next design consultation with your advisor is targeted.

2. Generate Idea Starters for Your Itinerary

AI aggregates thousands of data sources at once, making it a great place to generate a long list of ideas for your itinerary. This might include:

• Day-by-day inspiration
• First-pass route planning
• Lists of top attractions, restaurants, and neighborhoods
• Cultural etiquette and history

AI tools can give you a broad sense of what’s possible before you refine it. While AI is great for generating long lists, be wary of taking it for truth or using it for full, end-to-end design (more on that later).

3. Create Packing Lists, Budget Templates & Checklists

When you use AI to plan your vacation, look to one area in which it excels: list building and logistics. Some examples include:

• Packing lists tailored to climate
• Rough travel budgets and estimated spend per day, based on local cost of living
• Transportation comparisons across flights, trains, ferries, and transfers, helping you see options quickly, even if the timing or feasibility still needs expert verification

These can reduce the legwork it takes to find out if a destination is really best suited for your style.

How Not to Use AI to Plan Your Vacation (And How Your Travel Advisor Fills in the Gaps)

While AI is powerful, it has real limitations that travelers need to understand, especially for discerning travelers who value privacy and experience exclusivity.

1. AI Can Be Outdated or Flat-Out Wrong

AI tools are not updated in real-time, and cannot track things like:

• Recent hotel renovations
• Restaurant closures
• New museum policies
• Seasonal ferry schedules
• Construction impacting routes
• Political or safety changes

A single outdated detail can throw off an entire itinerary, a reason to be cautious when using AI to plan your vacation.

2. AI Doesn’t Have the Relationships to Deliver Unique, Rare Experiences

AI aggregates what is already out there online. By its very nature, AI will never be able to find, source, and provide you with true, off-the-beaten-path, once-in-a-lifetime luxury experiences because it is (by definition) drawing from source material on what exists already and is most prevalent online.

AI might tell you that it would be wonderful to experience a private tour of the Vatican at dawn…but it cannot connect you to Ornella, a doctor of art history and Vatican museum guide who security guards greet by name as she whisks you past the line of people who planned their trip on ChatGPT and Booking.com wrapped around the Vatican.

ChatGPT might find you a great hotel…but it can’t access exclusive rates, and it certainly doesn’t have the GM on speed dial to make sure a bottle of champagne and a suite upgrade is there when you arrive.

AI can tell you that it’s important to have travel insurance, maybe even send you to the best website for a quote…but it can’t have a local Italian doctor in your hotel room within the hour if you start to feel sick (true story).

Expert travel advisors invest in building their networks, and working with one allows you to unlock exclusive experiences for you that everyone else can’t find online. We have spend decades building deep relationships with the world’s most coveted brands and underground local suppliers to bring your wildest imaginings to life through human connection, something that AI can never deliver.

If you are okay with a trip that looks like everyone else’s Instagram feed, then using AI to plan your vacation might be the choice for you. But for those who value their time even more than money and want to invest in differentiated experiences tailored to them, AI fails to deliver.

3. AI Can’t Vet Quality the Way a Travel Advisor Can

AI can give you a recommendation for a “beautiful hotel,” which it only knows to be “beautiful” or “luxury” based on thousands of aggregated online commentary. No two travelers I have met share one definition of beauty or luxury. What is beautiful and classic to one might be dated and slow for another, and AI cannot describe a feeling or sense of place beyond its digital footprint.

At Travel with Awestruck, we invest in travel, so that we can tell you firsthand which rooms have the best views, which skippers along the coast tell the best stories, which safari lodges are worth the splurge, and which bartenders you absolutely must meet in sleepy mountain towns. We can also tell you which property’s quietly fall short of expectations (despite the prestigious name brand), where service will surprise you (and not in a delightful way), and which “central” neighborhoods you want to steer clear of.

True vetting requires firsthand experiences that are necessarily sensory. AI can never close the gap with data aggregation and “reason.”

4. AI Doesn’t Understand You

AI can tailor to preferences, but not the way a human being who you have built a relationship with for decades can. One of my clients sent me a hotel that had come recommended by ChatGPT for its “rustic charm.” I had to laugh. Rustic charm to my client meant cliffside saunas and a true five-star spa in a (freshly renovated) classic property, all within reach of a bustling metropolis. Rustic charm to Chat meant a veritable cabin 90 minutes away without a massage therapist in sight.

Language is decidedly interpersonal. ChatGPT doesn’t know what you mean by luxury (and how it differs from the hundreds of millions of other internet users who use that word to describe properties, experiences, and destinations). It can’t see your face and pivot if it senses hesitation in your micro-expressions on a consultation call. AI doesn’t know if your trip to Patagonia was full of hostels and 15-mile days or luxury lodges and hot springs.

Your travel advisor does. We get to know you (and know how to read subtext well enough to understand what you really want) in order to build a trip that is truly designed for you, not our best analytical picture of you compiled through our cold data analysis of millions of others. Expert travel advisors are relationship builders and matchmakers first and foremost.

Distinctive luxury travel requires emotional intelligence, not data analysis.

5. AI Cannot Handle Complexity

AI struggles with sequence and human timing. It does not do well with:

• Coordinating flights, ferries, trains, and transfers
• Avoiding long layovers
• Ensuring the pacing feels natural
• Building hidden-gem experiences (and connecting you with the ground teams that actually make them happen)
• Navigating permit systems and permit timing
• Ensuring logistics work across borders

Humans are still the best filter for human needs.

6. AI Won’t Pick Up Its Phone at 3am

No matter how perfectly planned the itinerary, travel is unpredictable. Whether you miss a connection or spontaneously decide that you would like to book a spa appointment mid-trip, plans change. AI cannot support you in those moments where things don’t go according to plan.

ChatGPT won’t sit on the phone with Delta for three hours on a Friday evening, re-routing your flights to get you home on time even though weather was supposed to have you grounded for three additional days. Gemini won’t call executives to hold the Ritz-Carlton Yacht in port to ensure you make it back from your day trip in time for departure.

I live for those moments. At Travel with Awestruck, concierge service is our vocation, and we’ve built the networks needed to deliver on that promise. Working with one of our trusted travel advisors means that you have support in your corner when you need it most for the moments you didn’t anticipate.

How Smart Luxury Travelers Use AI to Plan Their Trips

1. Use AI for Inspiration

AI is a powerful tool for sparking ideas, exploring new destinations, and getting a sense of what’s possible. Let it help you dream big before you start narrowing things down.

2. Consult Your Trusted Advisor

Once you have a sense of what excites you, bring those ideas to someone who understands the nuances behind every destination. A travel advisor can translate general inspiration into meaningful direction and push your ideas further with on-the-ground knowledge and expertise.

3. Refine Your Itinerary with Your Travel Advisor

Your travel advisor will put together a custom itinerary to deliver on your vision. Then, we’ll work together to shape a well-paced, personalized itinerary that aligns with your interests, travel style, and non-negotiables. This is where rough AI suggestions become a trip designed specifically for you (and delivered by trusted, carefully-vetted partners).

4. Book with Your Travel Advisor

We handle every reservation with precision, ensuring accuracy, preferred rates, and exclusive perks you can’t unlock on your own and suppliers that are not available to the general public. It’s the difference between booking a trip and creating a unique journey filled with rare, meaningful experiences.

5. Use AI for Support in Logistics

Supplement your travel advisor’s guidance with AI-generated tips to help you prepare to travel. AI is excellent for simple checklists, packing guides, and preliminary budgeting, helping you feel organized as you prepare.

6. Turn to Your Travel Advisor for In-Destination Support and Firsthand Knowledge

When questions arise or plans shift, your advisor provides real-time, human support grounded in experience and relationships. This personalized insight ensures your journey stays seamless from start to finish.

Why Use Travel with Awestruck + AI

We aren’t AI haters. We won’t laugh if you come to us and tell us the ideas you came up with through ChatGPT.

At Travel with Awestruck, we love the way that AI is pushing our clients to dream bigger (and look further) than ever before.

And we recognize that it is our role to take those raw, newly-augmented visions, refine them alongside you, then bring them to life in a way that only we can through deep firsthand knowledge, exclusive partnerships, and close relationships.

AI can help you imagine trips. We look forward to delivering the rare, distinctly personal experiences that only a human touch can.

Reach out to our team to get started.