Planning Something Special?

Make the trip memorable.
Skip the planning stress.

Mexico + Caribbean all-inclusive travel planning for men planning a getaway for someone special.

Mexico + CaribbeanAll-Inclusive SpecialistSurprise Trips
✦

"Tell me your budget, dates, and what she likes. I'll help you find the all-inclusive that actually fits the two of you."

That Is Getaway Wingman
How It Works

Stupid-simple. On purpose.

1

Tell me about the trip

Dates, budget, occasion, and what she likes.

2

I narrow the field

Instead of 100 resorts, you get the few that actually fit.

3

We build the trip

Resort, flights, transfers, activities, and special touches.

4

You take the credit

You enjoy the trip instead of stressing over the planning.

The Trade

You bring five minutes.
I bring forty hours.

What You Tell Me

  • Budget"Around $5,000, some flexibility."
  • Dates"Mid-February, our anniversary."
  • What she likes"Swim-up rooms, good cocktails, hates crowds."

What You Get Back

  • The short list — 2–3 resorts that actually fit her style and your budget, with the honest trade-offs of each.
  • The full trip — flights, transfers, room category, dinner reservations, and excursions, handled.
  • The special touches — the anniversary setup, the upgrade worth paying for, the one she'll post about.
  • A wingman on call — before, during, and after the trip.
Where We Specialize

Mexico + Caribbean.
Known room-by-room.

These are our starting specialties. If the right trip is somewhere else, we'll find it.

Signature Service · The Surprise Trip

Want to surprise her? Good.
Keep the secret. We'll handle the rest.

Every confirmation goes to you only. The packing list gives nothing away. The reveal — sealed envelope, boarding gate, or resort lobby — is planned like everything else.

Level I

Details Surprise

She knows the destination and dates — not the resort or special plans.

Level II

Destination Surprise

She knows the dates but not where you're going.

Level III

Full Surprise

She knows very little or nothing about the trip.

Level IV

The Home Run

We plan nearly everything — and make the reveal part of the experience.

Who's Planning Your Trip

Hi, I'm Brandon.

Some people relax by watching TV. I relax by comparing resorts — room categories, flight routes, which swim-up section gets afternoon sun. Getaway Wingman exists because a lot of guys want to plan something memorable but don't enjoy forty hours of research. I genuinely do.

More About Brandon →

The trip matters to you. The research doesn't have to. You take the credit for the part she'll remember — I'll never tell.

Brandon Tidwell · Founder
Good Questions

Before you ask.

Does using Getaway Wingman cost more than booking it myself?+
In most cases, no — my planning is paid through standard commissions from resorts and suppliers, the same way travel advisors have worked for decades. You'll know exactly how it works for your trip before you commit to anything, and the questionnaire is always free and no-obligation.
What if I have no idea where to go?+
Perfect — that's the most common starting point. "No idea yet, help me figure it out" is literally the first option on the trip brief. You bring the budget and what she likes; the destination is my job.
Can you really keep a surprise trip secret?+
Yes — it's a system, not luck. Every confirmation routes only where you say it's safe, destination names stay out of subject lines on request, and the packing list is written to prepare her perfectly without giving anything away. We can even coordinate a cover story.
What happens after I submit the trip brief?+
Brandon reviews it personally, usually within one business day. Straightforward trips move directly to a short list of resorts that fit. More customized or surprise trips may start with a quick Wingman Call. Either way, the goal is the few options that actually fit — never a list of forty.
Am I obligated to book if I fill out the form?+
No. Submitting the questionnaire doesn't create a booking, charge anything, or obligate you to purchase a trip. It just tells me what you're trying to pull off so I can tell you what's possible.
The Wingman Report

Weekly travel news & trip intel.

All Posts →
Ready When You Are

Planning something special?

Five minutes of questions. Then the research is my problem, not yours.

Start Your Trip → Free · No Obligation · About 5 Minutes
Start Your Trip →