Nothing roots me into my purpose faster than planning a trip. Oh, the frustration! Each experience, each property seemingly just like the last. They all look the same, they all sound the same.

Why? Whyyyyy?

“I have decision fatigue!” I cry to my husband, pretending to chuck the laptop out the window. Who knew the paradox of choice could be so disheartening? And I’m a fairly seasoned traveler, shouldn’t this get easier with time?

There’s no doubt a recommendation from a well-informed friend is the easiest route, which is why I always advocate to design word-of-mouth-worthy experiences.

As the daughter of a travel agent, you would think I’d just have someone plan it all for me, but I NEED to go through this process. I have to see what’s out there, but most importantly, I need to put myself in the traveler’s shoes so that I can design and market with empathy.

And friend, let me tell you. My empathy cup is full up right now. So today, I’m sharing a few musings and reflections from my recent booking journey:

Most experiences put travelers in boxes

In Florence, like most destinations, you have the choice of history sightseeing tours OR food tours, OR the elusive (but growing) creative cultural tours and wellness tours. But if you’re traveling halfway across the world to experience the birthplace of the RENAISSANCE of all places, why should you have to choose?

Why do we have this weird propensity to segregate aspects of culture and package them up like this? That’s not how culture is really experienced out in the world, and culture is most immersive and exciting when all the layers are beautifully woven together into one moment. I want my history with a side of something delicious, I want some entertainment with my outdoor adventure, and I want my wellness pursuits blended with creative crafts. Now we’re talking…

Your values are magnetizing

Remember last week’s email on value-driven guests? The moment I stumble upon a host that seems to care about what I care about, I am all ears. I stop skimming and pay closer attention to what they have to say. I instantly feel a greater sense of trust with them because, well, I know they’re my kind of people. And that’s just how cognitive biases work: we like people who like what we like.

When I found Manila of Emotional Sicily, I was already sold on whatever she had to offer. I mean, hello – her values are baked right into her business’s name. And if you’ve followed me for any amount of time, you know how big of a role emotions play in my work. And so, I am most excited for what she has in store for us, which of course you will hear all about when I return from Sicily later in September!

Personality is the easy differentiator

If your experience is similar to your competitors and you want to differentiate without actually modifying your experience, go with a bold personality. When I’ve scoured the internet and I’m finally deciding between two seemingly identical experiences offerings, it comes down to the vibe: imagery & words used, brand aesthetic, etc.

BUT (and this is a big but) this is really just a bandaid for a bigger issue. In fact, there is a real ‘romanticization’ of travel experiences happening, and if your online identity is more exciting than what you actually offer, you’re going to have some seriously unamused guests on your hands.

Hotels still aren’t on the experience train

This one boggles my mind because hotels and experience hosts can be such great partners! I’ll be staying in five small boutique hotels over my two-week Italy trip, and only one of them offers experiences and activities. As someone who typically leaves 3-4 hours in my day for unplanned play, I believe this is a massive missed opportunity.

Sure, some guests just want to plop down in their free time and read a book, but as we explored in the 3-day Experience Exploration, 75% of luxury guests aren’t traveling just to chill. So, give talented hosts in your destination a place to share their brilliance! Your guests will thank you.

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After spending hours and hours combing the internet, it seems the last few years haven't done much for people’s creativity, as the majority of experiences are still offering up the expected. Which means there’s MASSIVE opportunities to cater to the high-value guest that is looking for something thoughtful, meaningful, and enriching.

In addition, Skift found that on average 74% of millennial and gen-z travelers reported looking for travel experiences that their friends and family may not have thought of. So the quest for novelty is rising, and mass market is just not cutting it anymore.

The good news is: if you implement half of what I advocate for and teach, you’re way ahead of the game.

PS - Reverie can help you conceptualize something novel and values-driven, have you checked it out yet?