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Personal Travel Advisory

Adventures crafted around who you are

I don't just book trips—I learn what makes you tick, then build an experience around it. From hidden gems to perfectly-timed surprises, every detail is designed for you.

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He knew the dad loved Winston Churchill. So he found Churchill's snooker table in a Vegas casino—and a piece of the Berlin Wall in the men's restroom.

That's the kind of detail Damon finds. The kind that turns a trip into a story you tell forever. It's what happens when your travel advisor actually listens.

Damon Sipe - Travel Advisor

Why I do this

Technology has been my passion since the 4th grade. When my family got our first computer—a 386—I told my dad after about a month: "I don't know what I want to do when I grow up, but I want it to have something to do with THIS." That led to a career I love as a Chief Technology Officer.

But somewhere along the way, I discovered I had another obsession: planning travel. The same research-driven, detail-oriented mindset I bring to technology? I bring it to trips. I'm the guy who spends hours finding the perfect hidden restaurant, the uncrowded viewpoint, the experience that makes you say "how did you even find this?"

For years, I planned trips for family and friends. In 2024, I decided to stop waiting for retirement and started The Road Not Taken—a travel advisory built on one simple idea: your trip should feel like you.

"Two roads diverged in a wood, and I—
I took the one less traveled by,
And that has made all the difference."

— Robert Frost

That poem has stayed with me since my days at The Citadel. It's why I named this business what I did—and it's the spirit I bring to every trip I plan.

What I Do

I can handle as much—or as little—as you need. From a quick price check to a fully planned adventure, I'm here to make travel easier.

Custom Itinerary Planning

Day-by-day plans tailored to your interests, pace, and budget—whether you want adventure, relaxation, or the perfect mix of both.

Full Travel Booking

Cruises, resorts, hotels, flights, transfers, activities—I handle all reservations so you have one point of contact from start to finish.

Group Coordination

Family vacations, bachelor trips, reunions—I manage logistics, communication, payments, and room arrangements for your whole crew.

Price Monitoring

I watch for promotions and price drops—even after you've booked—to make sure you're always getting the best value.

Cruise & Resort Matching

With so many options, choosing the right one can be overwhelming. I match you with the best fit for your style and budget.

Concierge Support

Travel hiccups happen. From flight delays to last-minute changes, I provide responsive support before and during your trip.

Recent Adventures

A glimpse at some trips I've recently planned—from ski slopes to river cruises to tropical getaways.

Ski trip

Snowshoe, WV

Group ski & snowboarding adventure

Viking River Cruise on the Rhine

Rhine River Cruise

Viking cruise + Prague & Alps extensions

Bahamas Cruise

Celebrity Bahamas

Group cruise to the islands

South Korea

South Korea

Family adventure — in progress

How It Works

Simple, personal, and built around your timeline—not mine.

1

We Talk

Quick intro call or message. I learn about you—your travel style, interests, must-haves, and dealbreakers.

2

I Research

I dig into options, hunt for deals, and find the experiences that match who you are. This is the part I love.

3

You Choose

I send curated options with my recommendations. You pick your favorite—no pressure, no rush.

4

I Handle It

I book everything, manage the details, and support you through travel. You just enjoy the journey.

What Travelers Say

Real feedback from real adventures.

"Damon planned our Vegas trip and somehow knew my dad would love seeing Churchill's snooker table. The personal touches made it unforgettable."

J
The Johnson Family
Las Vegas Group Trip

"I told him we wanted a European river cruise that wasn't too 'touristy.' He delivered exactly that—plus restaurant recommendations in every port."

M
Margaret & Bill
Rhine River Cruise

"Coordinating a cruise for 12 college buddies sounded like a nightmare. Damon handled everything—rooms, payments, excursions. We just showed up."

C
Chris & The Citadel Crew
Group Cruise

Ready to Start Planning?

Whether you're dreaming up a new adventure or already knee-deep in planning one, I'm here to help. Let's bring your trip to life.