How I Choose Hotels for My Clients When Planning Their Trip (It’s Probably Not What You Think)

When people ask me how I choose the right hotel for my clients when planning their trip, I think they expect the answer to involve star ratings, beautiful rooms, or a list of my favorite properties around the world.

Those things can matter, but they’re rarely where I start.

I’m not usually looking for the best hotel in a destination. I’m looking for the hotel that makes the most sense for this traveler, on this particular trip.

Because “nice hotel” means something completely different depending on who you ask.

For one client, it means a beautiful room, incredible service, a pool they’ll actually spend time beside, and a restaurant worth staying in for dinner. For another, it means walking out the front door and immediately being in the middle of everything they came to see.

For a family, it might have very little to do with the lobby or the thread count and everything to do with whether the kids have somewhere comfortable to sleep, whether there are two bathrooms, whether breakfast is easy, or whether Mom can do a load of laundry halfway through the trip.

So before I ever start comparing hotels, I need to understand the traveler.

I Start With How You’re Actually Going to Use the Hotel

One of the first things I want to know is whether the hotel itself is supposed to be part of the experience.

Are you imagining slow mornings, time by the pool, drinks on the terrace, and dinners at the property?

Or are you leaving after breakfast and returning at the end of a full day of sightseeing?

Those are two very different hotel searches.

For a honeymoon, I may prioritize the atmosphere, views, a beautiful pool, great dining, or somewhere that feels special when you return at the end of the day.

For a family, I’m immediately thinking about bedding configurations, connecting rooms, true bedrooms versus open-plan suites, bathrooms, laundry, breakfast, and whether everyone can actually sleep comfortably.

For an active traveler who plans to be out exploring all day, location and practicality may matter much more than having a long list of amenities they’ll never use.

And for a milestone birthday or anniversary, the hotel itself may become one of the experiences we’re building the trip around.

That’s why I don’t really have a blanket list of “best hotels” for most destinations. Best for whom?

The Hotel I Choose Has to Work With the Rest of the Trip

I almost never choose a hotel in isolation.

I’m looking at what you’re doing each day, where you’re arriving from, where you’re going next, whether you’re traveling by train or car, and what part of the city makes the most sense for the itinerary as a whole.

Sometimes moving a hotel ten minutes in one direction can make several days of a trip noticeably easier.

Especially in Europe, I care a lot about things like:

Can you walk to dinner?

How easy is it to get to the train station?

Are the places you’ll be visiting actually near the hotel?

Are you going to spend half the trip taking taxis back and forth because a property looked amazing online but isn’t particularly convenient once you’re there?

A beautiful hotel in the wrong location can create friction every single day. That’s why I would much rather put a client in a really good four-star hotel in the perfect location than a more impressive five-star hotel that makes the itinerary harder.

The same goes for short stays.

If you’re arriving somewhere at 6:00 p.m. and leaving at 8:00 the next morning, that probably isn’t where I want you spending the largest part of your hotel budget.

Give me clean, comfortable, well located, and easy. “Better hotel” and “better hotel for this trip” are not always the same thing.

Five Stars Doesn’t Automatically Mean “Best”

Star ratings are useful, but I think travelers sometimes give them more weight than they should.

A five-star hotel may offer more services, amenities, and staff, but that doesn’t necessarily mean it’s the hotel you’re going to enjoy the most.

I’ve recommended plenty of four-star and boutique hotels over five-star properties because they had more character, a better location, or simply suited the client better.

And “five-star” doesn’t feel the same everywhere.

A grand historic hotel in Europe can be a completely different experience from a five-star beach resort or a sleek luxury property in Asia.

What matters much more to me is whether the hotel delivers the things you actually value.

I Verify the Details You Probably Aren’t Thinking About Yet When Planning Your Trip

This is where hotel research gets much more detailed than scrolling through pretty photos.

Room configuration is a big one. Terms like family room, suite, and even two-bedroom can mean wildly different things depending on the hotel and destination.

I want to know:

What is everyone actually sleeping on?

Do the bedrooms have doors?

Is that “extra bed” really a sofa bed in the living room?

How many bathrooms are there?

Are connecting rooms guaranteed or simply requested?

I also look at the hotel's location on an actual map rather than taking “minutes from the city center” at face value. I want to know what those minutes really look like.

Depending on the client, I may also be checking elevators, air conditioning, parking, pool access, beach access, whether a balcony could be a concern with young children, or whether the particular room category we’re booking has actually been renovated.

None of those details sound particularly glamorous when you’re planning a vacation. However, they can matter a lot once you’re there.

Pretty Photos Aren’t Enough

There are also certain things that make me look a little closer, even when a hotel has beautiful photos and excellent reviews. Location is probably my biggest red flag.

If the hotel is in the wrong place for your itinerary, I’m going to keep looking.

I’m also cautious when room descriptions are vague. If I have to dig through five pages of information to figure out what someone is actually sleeping on, I want to investigate further.

And when nearly all the photography focuses on the lobby, restaurant, or pool?

I want to see the rooms.

Reviews can also be useful when you read them for patterns rather than individual opinions.

One person complaining about noise doesn’t worry me. Twenty people mentioning noise gets my attention.

Knowing Where to Splurge Matters Too

I don’t think every hotel on a trip needs to be the splurge. I’d rather spend where you’re actually going to feel the difference.

If you’re spending four nights in Tuscany and part of the reason you’re there is to slow down, enjoy the countryside, have dinner at the hotel, and sit by the pool, that may be exactly where I tell you to spend more.

If you’re staying somewhere for one night because you have an early flight the next morning, probably not. And sometimes the best place to spend that money isn’t the hotel at all.

Maybe it’s a private guide.

Maybe it’s an incredible food experience.

Maybe it’s upgrading the room somewhere else on the itinerary where you’ll actually have time to enjoy it.

A bigger hotel budget doesn’t automatically create a better trip. Spending intentionally does.

Sometimes the Hotel Is Part of the Destination

There are also destinations where your hotel fundamentally changes the experience.

A masseria in Puglia.

A wine resort in Tuscany or Umbria.

A safari lodge.

A ryokan in Japan.

A mountain hotel in the Alps.

Those properties aren’t simply somewhere to sleep between activities. They are part of why you’re going. And if I’m recommending a hotel like that, I also want to make sure your itinerary gives you time to enjoy it. There’s no point in paying for an incredible property and then scheduling activities away from the resort from breakfast until dinner every single day.

Sometimes one of the most important things I can put into an itinerary is simply space.

I Don’t Rely on One Source to Choose a Hotel

Online reviews absolutely have a place in my research, but I don’t treat a Google or TripAdvisor rating as the final answer. People rate hotels based on completely different expectations. A hotel can have glowing reviews from travelers who aren’t anything like the client I’m planning for.

My own firsthand experience matters.

So does feedback from clients I’ve sent there.

And I rely heavily on trusted partners in the travel industry who can often tell me things that aren’t obvious online—what the rooms really feel like, which categories are worth upgrading to, whether the location works well, or whether something about the property has recently changed.

I use all of those pieces together. That’s very different from simply sorting a hotel search from highest rated to lowest.

And Yes, Sometimes I’ll Suggest Something Different

Every once in a while, a client comes to me with a specific hotel already in mind.

Maybe they saw it on Instagram.

Maybe it appears on every “best hotels” list.

Maybe a friend stayed there.

My job isn’t to talk them out of it simply because it isn’t the property I personally would have chosen. But if I see something that doesn’t align with what they’ve told me they want, I’m going to say something.

I recently worked with a family with young children traveling to Costa Rica. They came into the planning process with specific properties they thought they wanted to stay at.

Once we talked through the actual experience—the vibe of the hotels, amenities for younger children, the number of steps involved, and the lack of space for their kids to explore—they realized those properties weren’t quite the fit they had imagined.

I suggested alternatives that aligned much better with the way their family actually travels, and they came home glowing about their trip of a lifetime.

That’s the difference between finding a highly rated hotel and finding the right hotel.

When I Know I Got It Right

The best hotel recommendations aren’t necessarily the ones where a client comes home talking about how fancy the property was.

They’re the ones where the hotel becomes part of the story of the trip because it simply worked.

They loved being able to walk out the door and explore.

The room setup made traveling with the kids easier.

They sat on the terrace every evening with a glass of wine.

The staff remembered them.

The view really was worth the upgrade.

Or they come home and tell me:

“That location was perfect.”

“We never would have found that hotel ourselves.”

That’s when I know I got it right.

Because the hotel didn’t just look good on the itinerary.

It made the trip better.

And ultimately, that’s what I’m trying to accomplish with every hotel I recommend: not simply finding you somewhere nice to stay, but choosing a property that supports the way you want to experience the entire trip.

Frequently Asked Questions About Choosing Hotels

Is a five-star hotel always better than a four-star hotel? No. A five-star hotel may offer more services or amenities, but that doesn’t automatically make it the best fit for your trip. Location, room configuration, atmosphere, and how you’ll actually use the property can matter much more.

How important is hotel location when traveling in Europe? Very. I look at hotel location in relation to the full itinerary—not simply whether a property is “centrally located.” Being able to walk to restaurants, reach the train station easily, and avoid unnecessary taxis or backtracking can make a noticeable difference in how a trip feels.

When is it worth spending more on a hotel? I usually recommend splurging when the hotel itself will be part of the experience—such as a countryside resort, safari lodge, wine property, beach stay, or milestone trip where you’ll actually spend meaningful time at the property.

What should families look for when choosing a hotel? Beyond price and star rating, families should pay close attention to actual bedding arrangements, whether bedrooms have doors, connecting-room guarantees, bathrooms, breakfast, laundry, pools, elevators, and how practical the location is for traveling with children.