How to Make a 2–3 Day Property Trip Count

A Practical Guide for Buyers Visiting Livingston, Paradise Valley & Gardiner

A number of people who end up buying property in the areas of Livingston, Paradise Valley, Gardiner, or the nearby small towns don’t start with a long, leisurely search.

They start with a simple plan:

“We’ve got a long weekend. Let’s fly in, look around, and see if this could really work.”

A 2–3 day trip can be a great way to go from “we love the idea of southwest Montana” to “we actually know which areas and properties make sense for us.”

The key is to treat that visit like a working trip, not just a scenic drive. Here’s how I recommend structuring the trip with out-of-area buyers.

Before You Book Flights: Get Clear on What This Trip Is For

First, it helps to decide what “success” looks like for this particular visit.

Common goals:

Get a feel for town vs. valley vs. more rural pockets
Narrow down which areas fit your lifestyle and what “feels” right (that’s a strong move in this overall process)
See a short list of properties that are already serious candidates
Decide whether you’re ready to write on something now, or build a plan for later

You don’t have to decide everything in one trip. You just want to make sure your time here actually moves the ball forward.

1–2 Weeks Before Your Trip: Do the Heavy Lifting on Paper

The more we do before you land, the easier the trip will feel.

Ahead of time, we’ll:

Talk through lifestyle first, not just house features
- How you see yourselves using the place
- Comfort level with winter driving and distance from town
- Full-time vs. part-time use, guests, and long-term plans
Build and refine a property list together
- I’ll send options that fit what you’re after
- You’ll flag your “A-list,” “B-list,” and “probably not”
- I’ll give you honest feedback on each one so we don’t waste time on clear mismatches
Make sure your financing or funds are ready to go
- Pre-approval from a lender who understands our area, or
- Proof of funds if you’re using cash or mostly cash

That way, when you get here, we’re not starting from scratch. We’re confirming, comparing, and getting you real clarity.

A Common 2–3 Day Structure (That We’ll Customize to You)

Every trip is a little different, but a typical schedule looks something like this:

Day 1: Big Picture and First Impressions

Morning

Quick coffee and map review: Livingston, Paradise Valley, Gardiner, and nearby areas
Drive key routes together so you can see:
- In-town neighborhoods
- Bench areas and close-in rural pockets
- The valley, river corridor, and more rural stretches

Afternoon

See 2–4 of your top properties
At each one, focus on:
- Setting and road access to the property
- Layout and flow
- How it “feels” in person, not just in photos

Evening is usually for you to decompress, take notes, and talk things through without me in the room.

Day 2: Deeper Dives and Comparisons

Morning

Revisit your notes from Day 1
Sort properties and areas into:
- “Still very interested”
- “Nice, but not quite right”
- “Definitely out”

Daytime

See the strongest candidates again or see the next set of contenders
Spend more time on:
- Wells, septic, access, and other “behind-the-scenes” systems
- Outbuildings, shops, and guest spaces if that’s important to you
- How the property fits your real day-to-day (work, hobbies, guests, etc.)

If you’re seriously considering a particular property, Day 2 is often when we:

Talk through realistic numbers and terms
Discuss what an offer would actually look like
Identify any specific questions we’d need answered before writing (if you need more time to know what questions, we’ll have contingencies built into your offer to protect you)

Day 3: Decisions, Details, and Next Steps

Day 3 is less about seeing “one more random property” and more about getting clear on where you’re at.

Depending on how the first two days go, this might include:

A third look at a top contender, if that helps you feel settled
A slower, more detailed drive around the immediate area of your favorites
Sitting down to talk through:
- Pros and cons of each option
- Numbers, timing, and contingencies
- Whether it makes sense to write now or wait

If you’re not ready to write an offer on this trip, that’s okay. The goal is to leave with a clear plan instead of a scattered set of impressions.

If You Do Decide to Write While You’re Here

If the right place shows up and you’re ready, we’ll:

Go over recent activity and how your property fits into the current landscape
Talk about price, timing, and contingencies that make sense for your situation
Walk through what due diligence will look like from a distance (inspections, appraisals, etc.)

You don’t have to rush into anything. The idea is to make a decision that feels considered, not reactive.

If You Don’t Decide to Write (Yet)

A 2–3 day trip can still be very successful even if you leave without a contender or a contract.

You’ll go home with:

A much better sense of which areas work for you and which do not
A clearer, on the ground picture of what your budget really gets you
A list of “if something like this comes up, call us immediately” criteria

From there, we can:

Keep you updated on new listings that actually fit what you now know you want
Do targeted video walk-throughs for you
Plan a follow-up trip when it makes sense

The next time you come back, it’s often less about “getting oriented” and more about choosing between a small number of very real options.

How to Get the Most Out of Your Trip (A Few Simple Tips)

A few small things that make a big difference:

Travel light on other commitments.
Try not to layer in too many non-real-estate plans. You’ll want time to think, talk and explore things related to your possible move.
Write things down right away.
Properties start to blur together. A few quick notes and/or photos help a lot.
Be honest about your reactions.
If a place doesn’t feel right, say so. Crossing things off is progress.
Ask the questions that are really on your mind.
Even if they feel basic—winter access, neighbors, future plans—we can’t answer what we don’t know you’re wrestling with.

The Bottom Line

A 2–3 day trip to Livingston, Paradise Valley, Gardiner, or the surrounding areas doesn’t have to be rushed or overwhelming.

With a little planning ahead of time, a clear structure for your days, and someone local helping you use your time wisely, you can leave with:

A solid feel for the area
A realistic sense of what’s possible
Either a property under serious consideration or a clear plan for what comes next

If you’re thinking about blocking off a long weekend to explore the idea of owning here, I’m happy to help you design a trip that fits your schedule, your budget, and the way you actually live—so those 2–3 days do real work for you instead of just adding more questions.