Frequently Asked
Questions

You absolutely could book it yourself. The internet has made that easier than ever. But easier isn't the same as better.

A travel advisor doesn't just save you time — we save you from the wrong hotel in the wrong location, the itinerary that looks beautiful on paper and falls apart in practice, and the hours of research that still leave you unsure. We bring taste, supplier relationships, and lived experience to every trip we plan.

"The result isn't just a booking. It's a trip that actually delivers the feeling you were after."

Yes. A planning fee reflects the expertise, time, and curatorial work that goes into every itinerary — and it ensures that every client we work with is genuinely invested in the process.

Fees vary depending on the complexity and scope of your trip. This will be discussed transparently during your consultation call before any commitment is made.

A traditional travel agent books what you ask for. Hensberry Travels curates what you actually need. The difference is taste, lived experience, and a genuine point of view.

We're not a booking engine with a pretty website. We're a trusted advisor who has spent years living inside other cultures — not visiting them — and who knows the difference between a beautiful hotel and a truly transformative experience.

Hensberry Travels is a proud member of the Fora Travel advisor network, which means we have access to exclusive rates, room upgrades, and amenities at hundreds of properties worldwide — benefits you simply cannot access by booking directly.

Our recommendations are always driven by what's right for you, never by commission incentives. If a hotel isn't the right fit, we won't suggest it regardless of the economics.

For European summer travel — especially Italy, Greece, and the South of France — we recommend starting at least six to nine months in advance. The best boutique hotels in the most sought-after destinations fill up fast.

The difference between starting in January versus April can literally be the difference between the perfect property and settling for second best. For more flexible or off-peak travel, three to four months is generally workable.

After your consultation call, a full itinerary proposal typically takes one to two weeks depending on the complexity of the trip.

We'd rather take the time to get it right than rush something to you that doesn't feel like Hensberry. Great curation can't be hurried.

We build in two rounds of revisions to make sure the itinerary is exactly right before anything is booked.

"Our goal is that by the time we present your itinerary, it already feels like yours — because we listened carefully during the consultation."

Yes, we can book flights as part of your full trip package. For clients who prefer to manage their own flights — especially those with points or miles strategies — we're happy to work around your existing bookings and handle everything else seamlessly.

Your bookable budget is your land-only budget — the amount allocated to the elements we actively plan and book on your behalf, such as accommodations, transfers, and pre-booked experiences and tours.

Flights are not included in this budget. If you would like us to book air travel for you, we are happy to do so for a separate flight-booking fee of $150.

Your land-only budget does not automatically include meals, personal shopping, gratuities, travel insurance, or spontaneous extras — the beautiful ceramic you find in a Positano shop, the extra boat trip you decide to take, or the long dinner that turns into a late evening.

Yes — and this is one of the most commonly overlooked parts of trip budgeting. Food spend varies enormously depending on how you travel. A couple eating at local trattorias in Puglia spends very differently than the same couple doing dinner at a Michelin-starred restaurant every night.

For our dream client — someone who sees great food as part of the experience — we typically recommend budgeting $150–$300 per person per day for meals, depending on the destination and your dining style. Japan and Southeast Asia tend to be lower; France and certain Italian cities can be higher.

"Food is part of the trip. It deserves a real number in your budget — not an afterthought."

Hensberry Travels specializes in elevated, boutique travel experiences. Our sweet spot is trips starting at $5,000 per person for the bookable elements. This allows us to access the caliber of properties, experiences, and service that defines what we do.

If your budget is more flexible, we'll work with what you have — but we'll always be honest with you about what's genuinely achievable at your price point. We'd rather have that conversation upfront than disappoint you later.

Always. Non-negotiably.

Travel insurance is the one thing every traveler wishes they had bought and never wishes they bought unnecessarily. Medical emergencies abroad, trip cancellations, lost luggage, flight disruptions — these things happen, and when they do the cost without coverage can be catastrophic.

We can recommend trusted providers and help you understand what coverage makes sense for your specific trip, destination, and budget.

Deposits and payment schedules vary by supplier and destination — most hotels and tour operators require a deposit at booking with the balance due 60–90 days before travel.

We'll walk you through the specific payment timeline for your trip during the planning process so you always know exactly what's due and when. No surprises.

Boutique properties with a strong sense of place, genuine character, and service that feels warm rather than stiff. Our sweet spot is the $250–$600 per night range — hotels that feel like a discovery, not a chain.

We love restored historic properties, coastal retreats, design-forward boutique hotels, and anything that makes you feel like a local rather than a tourist. The kind of place you tell friends about and feel quietly proud that you found it — even though we found it for you.

"The best hotel isn't necessarily the most expensive one. It's the one that was exactly right for you, in exactly the right location, at exactly the right moment."

Our deepest expertise is in European summer travel — Italy, France, Greece, and the broader Mediterranean — as well as Japan and soft adventure destinations like Morocco and Southeast Asia.

That said, we bring the same curatorial approach to every destination we take on. And if we don't know a destination well enough to do it justice, we'll tell you — and either deepen our research or point you toward someone who knows it better. Honesty is more important to us than appearing to do everything.

We don't disappear after you board your flight. Hensberry Travels clients have access to support throughout their trip for anything that needs attention — a hotel issue, a booking change, an unexpected situation.

We can't control everything — travel has a life of its own, and sometimes the unexpected detour becomes the best part of the story. But you will never feel alone navigating a difficult moment.

Beyond food, here are the things that most commonly catch travelers off guard:

Gratuities — especially on guided tours and private drivers. Visa fees and entry requirements for certain destinations. Personal shopping — and trust us, you will shop. Airport lounge access if that's part of your travel style. Travel insurance — always recommended and never included unless you specifically ask us to add it. And resort fees at certain properties, which are charged locally and not always reflected in the room rate.

Honestly — the fact that you're asking this question tells us you care about the experience, not just the logistics. So do we.

Hensberry Travels works with a small number of clients intentionally. That means every trip gets our full attention, every question gets a real answer, and every client is treated like the only one — because in that moment, you are.

"You're never a number here. You're the whole reason we do this."

That's actually one of our favorite conversations to have.

Sometimes the most transformative trips come from a feeling rather than a destination. I want to feel restored. I want something that surprises me. I want to disconnect completely. I want to feel alive again.

Tell us how you want to feel, and we'll tell you where to go. The destination is the answer to the feeling — and finding that match is exactly what we're here for.

Every client who works with Hensberry Travels can expect to feel completely themselves — in our planning process and in every destination we recommend.

Psychological safety isn't an add-on here. It's built into everything we do. We know what it means to need more than a beautiful hotel — to need the quiet confidence that you can hold your partner's hand at dinner, walk through a neighborhood without calculation, and simply be. Every itinerary we build carries that awareness, whether you ask for it or not.

Fair point — it is overused. Here's what it means when Hensberry Travels says it.

It means we have a genuine point of view. We've been inside the cultures we recommend. We know the difference between the hotel that photographs beautifully and the one that actually delivers. We know which neighborhoods feel right for your specific kind of travel, which restaurants are for locals and which are for tourists, and which experiences will still feel meaningful a year later.

Curation without taste is just a long list. We don't do long lists.

"Two or three perfect options, chosen for you specifically — that's curation. Everything else is just search results with better formatting."

Hensberry is a merger — Hensley and Carberry, two last names that became one shared name for a shared life. St. Louis meeting Brooklyn. Two different worlds, two different backgrounds, one home and one aesthetic built together.

It's not a coincidence that this is also exactly what travel does. You arrive from one world. You meet another. And something new gets made in the space between them.

"The name carries the whole story. And the story is the whole brand."