People often assume my job is simple: someone tells me a destination, I send back a price, they book. It rarely works that way. Before I recommend any all-inclusive resort — whether it's a Caribbean villa for a family reunion or a Mexico suite for a couple's anniversary — I ask myself five questions first. Not because I'm trying to slow anyone down, but because the wrong resort at the right price is still the wrong resort. Here's what I actually check before I ever send you an option.
Who Is Actually Coming, and What Does the Room Need to Do for Them?
A "beautiful resort" and "the right resort" aren't always the same recommendation. A couple celebrating an anniversary needs something completely different from a reunion of eighteen people spanning three generations. Before I look at a single rate, I want the real headcount, the ages involved, and how the group actually wants to spend their days together — all under one roof, spread across a few connected rooms, or somewhere in between.
This is where room configuration matters more than the photo. A large family often does better in a villa with separate bedrooms and shared living space than in three disconnected hotel rooms down the hall from each other — even if the hotel rooms are individually nicer. I'd rather ask an extra round of questions up front than hand someone a rate for a room that technically fits but doesn't actually work for how they travel.
Is "All-Inclusive" Really Included — or Is It Billed Separately?
This is the question I see the most wrong assumptions about, so I ask it every time. "All-inclusive" isn't one universal thing across every property I work with, and I'd rather explain that up front than let someone find out at check-in.
At most Caribbean properties I work with, all-inclusive dining and drinks can be added for a full stay, select days, or not at all — it's quoted separately, not automatic. There are five villa lines at Puerto Plata, though, where it works the opposite way: those are weekly-rental-only, and the resort requires the all-inclusive program and bills it directly at check-in — it isn't something I collect or fold into the room rate. Cabarete, meanwhile, doesn't offer an all-inclusive option at all. And on the Mexico side, Vidanta stays are room-only with a usage fee; food and beverages are purchased separately from the room.
None of these are better or worse than each other. They're just different, and the only bad outcome is not knowing which one applies to the stay you're booking. I'd rather spend two extra minutes explaining this than have anyone surprised by a bill they didn't expect. If you want to see how this plays out property by property, the current Puerto Plata and Cabarete listings are on the Caribbean page, and the Vidanta room options are on the Mexico page.
What Does the Complete Travel Day Actually Look Like?
I don't book or ticket airfare — travelers handle that directly — but I still want to know the honest shape of the travel day before I recommend a resort. A grandparent with limited mobility, a toddler who doesn't nap on schedule, or a group of twelve moving through an airport together all change what "an easy trip" means. A short connection that works fine for two adults can be genuinely rough for a family of six.
So I ask about the home airport, the realistic travel window, and how much connection time the group is comfortable with — before I compare a single resort. Sometimes that changes the recommendation entirely; a slightly longer flight into the right destination can beat a shorter one into the wrong room configuration.
Weekly Rental or Nightly Stay — Which One Actually Fits How This Group Travels?
Some of the accommodations I work with only rent by the week; others are booked nightly. That's not a small detail — it changes the math on everything from total cost to how flexible the dates can be. A group planning a true week-long reunion is usually a great fit for a weekly villa rental. A couple wanting a flexible four-night getaway is not.
I'd rather ask which pattern actually matches your trip before I send a rate that technically exists but doesn't fit how you're planning to travel. Get this wrong, and even a fair price feels like the wrong fit once you're comparing it to what you actually needed.
What's the Plan if Something Changes?
Trips shift. Someone gets sick, a flight gets rescheduled, a group grows or shrinks by a few people. Before I recommend anything, I want to know how much flexibility this particular group needs, because that affects which accommodation and booking structure makes sense — not just which one is cheapest today.
I'd rather build in the right amount of flexibility from the start than have someone locked into a plan that stopped fitting their trip. This is also why I stay involved after the reservation is made, not just up to the point of booking it. If you want to see how I think through the rest of the planning process, I've answered the questions I get asked most often on the FAQ section.
None of this is a sales process — I don't do timeshare presentations, and I'm not trying to move you toward a specific property. I use my own Vidanta and LHVC memberships to help travelers find accommodations that are actually available and actually fit, and asking these five questions is how I make sure "fits" isn't a guess.
If you're weighing an all-inclusive resort right now, don't start with the price. Start with these questions instead — mine, or your own version of them.
Frequently Asked Questions
How many questions do you actually ask before recommending a resort?
Five — covering who's traveling and room fit, whether all-inclusive is really included or billed separately, the complete travel day, whether a weekly or nightly stay fits better, and what happens if plans change.
Is all-inclusive always included in the room rate?
No. At most properties I work with, all-inclusive dining and drinks are an optional add-on quoted separately. Five Puerto Plata villa lines require it and bill it directly at check-in, and Vidanta stays in Mexico are room-only with food and beverage purchased separately.
Do you book flights as part of this process?
No. I don't book or ticket airfare — travelers purchase flights directly. I do ask about the home airport and travel window so I can evaluate whether the complete trip, not just the resort, fits the group.