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The Fitz Roy range above the road into El Chaltén, Argentina

Some people do crosswords. I plan trips.

Deep research for a few trips at a time, with every option and every price in front of you.

Contact Kevin

Hi, I'm Kevin, a travel advisor in the San Francisco Bay Area. I grew up in a Montana outfitting family: my grandfather guided, my father carried it on, and my brothers run it today. I spent 35 years building software and traveled to more than 40 countries along the way. For me the planning was always half the fun: the research, the logistics, getting the details right so the trip itself goes smoothly. Retiring gave me time to plan trips for other people too.

Kevin in a green jacket and knit cap on a dirt trail through pines, holding the leash of his black Labrador, Kukui
Kevin and Kukui near South Lake Tahoe

I plan those trips the way I plan for myself. The cheapest and the most expensive versions of any trip are easy to find. Most of my work goes into the middle: finding the options where spending a little more changes the trip, and skipping the ones where it just costs more.

Updated October 2026

Trips I'm planning now

Shown with the travelers' permission. Photos are stock until the trip happens.

  • Green and violet northern lights over a snowy hillside

    Northern Lights cruise

    March 2027 · Three travelers, two cabins, 14 nights from Southampton up to Tromsø and Alta.

    Cruise booked, excursions next

  • The green ridges of Padar Island above the sea, Komodo National Park

    Japan and Bali

    May 2027 · Four people, two weeks. Village to village walking in Japan, then a boat through the Komodo islands.

    Flights decided, choosing the boat

  • A road winding up through alpine meadows toward Cottonwood Pass, Colorado

    Colorado

    September 2027 · Four nights around Salida with a drive up to a 12,000-foot pass, then two in Boulder. A soft test of the altitude before Atacama.

    Itinerary drafted, picking the week

  • Sand dunes and eroded red rock in the Valle de la Luna, Atacama Desert

    Atacama Desert

    April 2028 · A group of four: two nights in San Pedro de Atacama, four at Explora, then one traveler crosses to the Salar de Uyuni.

    Picking the week, nothing booked

Stock photos: Lightscape, Simon Spring, Bret Lowrey, Bailey Hall / Unsplash

Smaller jobs

  • A weekend in the Bay Area. One traveler, in town for a convention. Flights and getting around locally.
  • Utah. Flights and a rental car for a photography tour that was already booked, and maybe a day or two after it.
  • Egypt. Helping with flights for a guided tour. The one-stop connections from SFO arrive at bad hours, so stopovers are part of the research.
  • Vietnam, maybe Cambodia. Helping with flights for three open-ended weeks, and making sure an undecided flight home doesn't cause a visa problem.

Trip reports

Two riders on horseback from behind, following a trail through open pine forest

Western Montana

Every summer · An insider's perspective

People tell me Montana sounds great but they wouldn't know what to book. Here's a week, and what it costs. No research fee on Montana trips.

Read about the trip
A small group of hikers on the blue ice of the Perito Moreno glacier

Patagonia

February 2026 · A trip I took

Two weeks from Buenos Aires to Valparaíso, with hiking in El Chaltén and Torres del Paine and a day on the Perito Moreno glacier. I booked it through another agency, and what I missed is why I work the way I do now.

Read about the trip

Where I've been

A rough picture of where I've traveled. A shaded country doesn't mean I know every corner of it, but it gives context and direction to the research.

Kevin in a knit cap and sunglasses in front of the Perito Moreno glacier
At the Perito Moreno glacier, February 2026
FijiTanzaniaCanadaUnited StatesArgentinaChileMexicoCosta RicaBelizeFranceCambodiaVietnamSouth KoreaSwedenAustriaHungaryEstoniaGermanyGreeceTurkeyCroatiaSwitzerlandNetherlandsPortugalSpainIrelandNew ZealandAustraliaChinaItalyDenmarkUnited KingdomIcelandPhilippinesSloveniaFinlandCzech RepublicJapanBosnia and Herzegovina

45 countries · 24 US states

How I work

Most travel services give you two options. Book everything yourself and hope you don't miss something, or hand the whole trip to an advisor and lose sight of what's happening. I think most people want something between those two.

You decide how much you want to do. Research destinations yourself, or ask me to. Compare hotels on your own, or get a shortlist from me. The goal is that you keep the parts of trip planning you enjoy and hand me the parts you don't. Either way, you see every option and path I'm researching, and what each part of the trip costs.

  • A few trips at a time, so nothing gets rushed. If I'm full, I'll tell you.
  • If you can do better booking somewhere else, I'll say so. Rental cars are the usual example: Costco Travel or Expedia is often cheaper.
  • No minimums, and no pressure to book anything through me.

What it costs

Research is a flat fee quoted up front: $100 for a second opinion, $300 for a simple trip, $600 for a bigger one. With full engagement, where I manage the bookings, the fee is waived.

1

Research

We start with research: the route, where to stay, how to get between places, what excursions to book. It comes back as a planning page made for your trip, with maps, the itinerary day by day, and the options I looked at side by side with what each one costs. Everyone traveling gets a link, marks the options they like, and asks questions on the page.

AI has made the first pass at research much faster. It also states things confidently that are wrong. Most of the time I spend goes into the gaps: finding what's missing and checking what's there, using the booking systems and supplier portals the public sites sit on top of.

Research is the core of what I do, and there are two ways to hire me for it. You don't have to choose until the research is done.

Research only is a flat fee, quoted before we start, covering up to a set number of hours. You keep the planning page and book the trip however you like.

Full engagement means I manage the bookings for you. You still see every option and what it costs. The research fee is waived, and you get access to the Rugg Travel app for trip support.

Second opinion You bring the itinerary, from an AI tool or your own planning. I check it for gaps and mistakes.
$100 up to 1 hour Research only
Simple trip A weekend in Las Vegas, or a road trip with a few hotels
$300 up to 3 hours
Bigger trip A week in Portugal, three stops and a rental car
$600 up to 6 hours
Anything bigger Many stops and border crossings, or a destination that's still undecided
Quoted 6+ hours

If your trip needs more time than the quote covers, I'll tell you and quote the extra time before going past it.

Founding clients

My early clients get 50% off research, on this trip and every trip after it. 7 of those spots are still open as of October 2026.

2

Booking

With full engagement, I handle the bookings. You still see what each one costs and how it gets booked.

Many hotels booked through me come with preferred-partner perks. I'm an independent advisor with Fora Travel, which gets my clients into programs like Virtuoso, Four Seasons Preferred and Rosewood Elite. That usually means breakfast, a resort credit, late checkout, and an upgrade when one is available, often at the same rate as booking direct.

Same hotel, better stay.

Sometimes the research turns up options you can book directly that beat anything I can book as an advisor, even after paying the research fee. If you're comfortable making and managing those bookings yourself, research only is often the better choice.

When I make the booking, the hotel or provider often pays me a commission, which allows me to waive the research fee. Commissions vary a lot from one booking to the next. They don't decide what I recommend, and you still make the call on where your money goes.

3

While you travel

Full engagement includes support through the Rugg Travel app. Your itinerary and travel documents go on a private page for your trip. Open it on the web, or add it to your phone's home screen. Travel companions can follow along with a shared link, no account needed.

Already a client? Sign in, or open your planning pages.

Questions

Do I need to know where I want to go?
No. You don't need dates or a destination yet. Choosing one can be part of the research.
Can I book some of it myself?
Yes. There are no minimums and no pressure to book anything through me. If you can do better booking somewhere else, I'll say so.
How do you get paid when the fee is waived?
When I make a booking, the hotel or provider often pays me a commission. Commissions vary a lot from one booking to the next. They don't decide what I recommend.
What happens after I email you?
I'll get back to you within a day with a few questions about the trip. Then I quote the research fee, before any work starts.
The Cuernos del Paine above Lago Pehoé, Torres del Paine, Chile

Get in touch

Tell me what you're thinking about, even if it's just "we want to go somewhere warm in February." You don't need dates or a destination yet. I'll get back to you within a day.

Contact Kevin