March 9, 2022 / 

 PART I: Real-Life Struggles and Tips – Planning A Trip To Walla Walla

Time to put my own planning skills to the test and plan our trip to Walla Walla. This is what I do for a living, but planning-is-planning. Listen to my struggles and tips to make your next trip one to remember. 


Hi there! This is the first of two episodes that are all about the real-life struggle of planning a trip to Walla Walla. Which is one of Washington’s premiere wine tasting regions. It was important to me to drink my own Koolaid on this one, and plan just like so many of my customers do. It’s still so shocking to me, how much work goes into planning a quality trip. I wanted to document it, and share my advice from the perspective of a wine country curator. So let’s get started. 


Let me tell you how this whole trip came about. My husband had been planning a special surprise for my 4oth birthday. I had no clue what he had in store. We live in the middle of Oregon’s wine country. If it was for our kids it would be farm animals or bouncy houses, but what would a bunch of 40 somethings be impressed by?


On the day of my party, my husband comes down with the big unveil. It was a carefully crafted, hometown version of the show Survivor. You know the one hosted by Jeff Probst where they drop teams off on an island to survive for 40 something days. They do challenges, win immunity and participate in tribal councils.  Ringing a bell?

So that’s just what we did. Assembled teams, did challenges. And after each challenge the losers circled up by the fire and did a real-life tribal council.  Yes, people were voted off. 


When it comes down to the final tribal council, just like the show, the jury gets the final vote.  My husband (giving his best Jeff impersonation) announces the prize, which is a trip, with us…to Walla Walla Washington for some kid-free wine tasting.


So here we are six months later and two months from the big trip.  


I usually start all trip planning with accommodations. I’m not going to spend too much time explaining this one, as I’m really focused on the wine tasting portion of the trip. Since I had visited Walla Walla before and stayed in a cute little airBnB just outside of downtown, my request was to book a place in the heart of downtown.  


I wanted to be close to downtown restaurants and tasting rooms, which so often get overlooked.


This was a fairly easy task. We viewed listings on our preferred rental booking sites. Found one with our preferred amenities (HOT TUB of course) and booked it.


The next step is designing an itinerary. Even though I’ve been there before, this is no easy task. I always give major kudos to the planners of our wine tours. It’s a lot of work and pressure.


Where do I begin? Being a wine tour company, I naturally want to support other local tour companies.  


How do you find wine tour companies. You hit up google.


I first searched “wine tour walla walla.” I  like to scroll past the ads to see what companies have the best SEO. I’m a marketer, what can I say?  They had to earn this rank somehow. But really it’s just a way to break the mental block and get started.


The first URL was from the Walla Walla Wine Alliance. So I clicked on it. I figured it would be a list of tour companies and it sure was. I know this game all too well, it’s pay-to-play.  Don’t get me wrong. I have saved the link so I can reference it at a later time. Then, I went back to my original search and kept scrolling. 


The next URL to show up was The Touring Co.


The first thing I noticed was the mixed group tours. This is my style, and a huge motivator for the Wine Shuttle. Wait, $195 per person!!!! Includes lunch but no tasting fees.  This is clearly not meant for groups of 6 people as the total cost would be $1170, the 5hr private tour would only be $725 (excluding gratuity). 


What else can I find?


D’vine Wine Tour seems interesting. Their branding is a bit more old school, but their website is cleaner than the last. 


The best option on this site is a private tour for 6-11 guests. The cost is $99 per person making our total tour cost for six people around $600. Same 5hr tour experiences as The Touring Co.


Then I looked at IMBIBE Wine Tours and Winery Tours Walla Walla. They were either confusing or cost prohibitive. 


Ok, this was about the time I decided to check out the top 10 lists from Trip Advisor and Yelp.  I usually don’t rely on these sites, but so far I have not found the company I believe will host us.


They repeated the ones I had found, but did list a few others that I checked out. One that stood out, Freddy G’s, not because it’s website was flashy but the opposite. It was so easy to navigate and the wine tour price was a great $500.  So I decided to check out some reviews. To my surprise all 55 reviews on Yelp were five stars.  


After checking out a few other places, ruling them out due to price or poor websites. I decided to give Freddy G’s a call. 


In the next episode you’ll learn how the wine tour planning is going and how we planned to fill the rest of our time while we are there. 


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