Ask The Swank Guide

Answers to frequently asked questions about how we roll

We promise to get back to you within 24 hours (on weekends it might take a few hours more).

One of the reasons we exist is to try and remove the friction involved in planning a vacation. To do that, we have to rub a lot of info together. We research using websites and magazines we kinda trust, blogs, the NY Times "36-hours in...", and often some local insider knowledge. We also have years of travel experience and go back to hotels we know are great. Check out How We Curate Our Picks.

On paper, the perks may look similar—free breakfast, hotel credits, potential upgrades. But in reality, Swank travelers get a very different experience. Because we work through Fora Travel and top-tier programs like Virtuoso and Four Seasons Preferred, you’re flagged as a VIP from the start—not buried in some Expedia-powered backend. That means a much better chance for that coveted upgrade, VIP treatment from hotel staff (let us surprise you), and when something goes sideways, you deal with us—not a foreign call center who doesn't understand boutique travel, or you.

Our advice? Use your Amex to earn points—especially on flights, where redemptions are strongest—but when it comes to booking hotels, you’ll get better perks and far more personal service through us. There’s no annual fee to access what we offer, no prepaid confusion, and no wondering whether your loyalty number got lost in a system glitch. And here's the kicker: every time you book through us, you're supporting our independence. We personally test and pay for the hotels we recommend—no comps, no pay-to-play. That means we tell you the truth, even when it’s uncomfortable. You’re not just booking a room—you’re helping keep honest travel curation alive.

Yup. Stay there, eat there, do as much as we can to get the full experience. Sometimes we stay a few days, sometimes only a day. It depends on how much time we have, and how many places we need to cover in a region.

We do occasionally, but very rarely. It's infuriating to pay a lot for a mediocre - or even bad - hotel. Sure, it's tempting to want to expose bad hotels. But we want to keep things positive and doubt people want to watch someone complain for 10 minutes.

Besides our razor-sharp insights, we can often secure perks that aren’t available through the Expedia and Booking.com’s of the world. Often we can get you late checkout, breakfast included, and other VIP treatments. Plus, we typically match or beat direct booking rates.

No, not a penny extra. We make our living through hotel commissions, not by picking your pocket. You'll pay the same (or often less) than booking direct, but with added perks that make your accountant wonder if there's been a mistake.

Absolutely. While we can't personally vouch for every property in existence, we have access to an extensive network of 6,000 vetted hotels through our partnership with Fora.

We show you what Instagramers won’t – the real size of that "spacious" room, the actual walk to the beach, and yes, even that slightly awkward lobby layout. It's like having a brutally honest friend scout it out first.

For peak travel seasons (summer in Europe, winter in the Caribbean), we recommend booking weeks ahead. Though if you're planning a last-minute escape, we'll do our best to squeeze you in – we're good at making the impossible merely improbable.

It scales from "just the hotel, please" to "plan my whole trip". We can book your accommodations, arrange transportation, and arm you with insider knowledge. We charge a trip planning fee that scales with the complexity and duration of your trip.

Yes, though currently we're focusing on select destinations where we can guarantee our recommendations won't send you to that tourist trap masquerading as an "authentic local experience." We’re rolling out more and more itineraries every month.

Think of it as a first date, just less awkward. We'll discuss your travel style, desires, and deal-breakers over video chat, then craft suggestions that match your vision. Book your consultation.

We handle it; assuming your reservation is cancellable. We have strategies to help minimize the risk, but there’s always tension between lowest price and the ability to cancel. If you’ve paid a trip planning fee, there’s no charge to cancel. If not, we charge a $199 cancellation fee. We’re not looking to penalize anyone—but trip planning takes real time, and by the time we’ve made your bookings, someone’s already done the work.

We can make some. In our focus destinations we make restaurant recs… but we’ll let you book them yourself for now.

In select locations, yes. We can arrange everything from airport transfers to that private sunset sail you didn't know you needed until now.

We believe in treading lightly but living fully. We offset our carbon footprint and prioritize properties that do more than just ask you to reuse your towels. More about our commitment to Sustainability.

Whether it's a family reunion or a yoga retreat, we can handle group bookings.

We're constantly expanding our reach, but we won't pretend to be experts everywhere. Check our destinations guide for our current coverage – we'd rather be masters of some than jacks of all.

“Luxury”... well, we always say a hotel "doesn't have to be expensive to be great”. So, unlike many travel advisors, we’ll try to steer you to something that won't bankrupt you. Of course, we like it fancy sometimes too. Regardless of budget, we combine the access of a luxury travel agency with the honesty of your most direct friend. Plus, we actually show you what you're getting into, not just tell you about it.

We'll make sure you get every point and perk you're entitled to, plus a few you probably didn't know existed. Consider us your loyalty program optimization specialists.

Hotel prices change constantly based on season, demand, and room type—so we don’t post rates that might mislead, but we give you expected rates for high, low and shoulder seasons for every hotel. When you reach out, we’ll confirm up-to-date pricing and perks for your dates and even compare options to help you decide.

Often, yes. We typically match or beat the “best available rate”—plus, we unlock added perks (think: breakfast, upgrades, late check-out) you can’t get through DIY sites. It’s like getting a free VIP upgrade without lifting a finger.

Not at the moment. We're laser-focused on the parts of travel we know best: hotels, experiences, and logistics on the ground. But we’re happy to help coordinate around your flights if needed.

We aim to personally test and film every hotel we recommend, but sometimes that's not possible due to timing or availability. In rare cases, we’ll still recommend a place based on Don’s past stays or trusted intel from Fora advisors we know and vet. When that happens, we’ll always make it clear.

100%. We've helped clients plan everything from secret engagement weekends to milestone birthdays and post-elopement getaways. Tell us what you're thinking of - we’ll help make it happen.