Prepping for a Month in Italy

Aug 16, 2023

In this Blog Post

  • Life updates and why we are spending a month in Italy.
  • How we planned our elopement.
  • Preparing my business for a month-long hiatus. 
  • What I'm packing for a 24-hour travel day.
  • How to plan and organize a month-long trip + a free planning template!

Major Life Update

I'm engaged and we are eloping to Italy this August! John and I have been dating for nearly 2 years and on July 1, 2023, he asked me to marry him. Without sounding like a total cheeseball, I am so thrilled to have met my person... John is a fellow entrepreneur -- we met during the soft opening of his brewery. He made me smile and laugh so much. We couldn't take our eyes off each other all night... and now, 2 years later, here we are getting married! 

Eloping in Italy

From early on in our relationship, John and I planned to elope. We love our friends and families dearly, but we wanted this day to be about us and our marriage. Admittedly, we are both perfectionists and John prides himself on throwing amazing parties, so the thought of all this pressure on one day just to make other people happy seemed stressful. Since we had told our families well before we got engaged that we were eloping, it was no surprise to them that was our plan.

Planning Our Elopement

We chose Italy for its beautiful scenery and because we planned to start traveling throughout the country for our honeymoon. I had some trouble picking the location for the actual ceremony. Our parameters for the trip were: flying into and out of Rome, having a home base at a family friend's house in Tuscany, and keeping our travels Rome and north. I made sure to prep all of my travel essentials for a long-haul flight to Italy. Here's everything I packed! 

We love the coast (John was a beach lifeguard growing up and I chose to live in Pensacola solely for the gorgeous beaches), so I thought at first that Lake Como would be a good option. Turns out, the logistics of planning a wedding in a place where a water taxi is the preferred method of transportation has its challenges! 

Then, I decided to find a wedding location in Tuscany that could give us everything we wanted all in one place. After lots of research and help from my wedding photographer, we settled on a medieval village turned 5-star hotel called Il Borro. It looks SO beautiful and we will be able to stay, eat, get married, and take photos all on their property. I cannot wait!! 

Prepping for a Month In Italy

After the wild year we've had, both personally and professionally, I wanted to take this opportunity to really unplug. John and I decided that not only would we elope (just us two!), but we also wanted to travel Italy for an entire month for our honeymoon. There is a lot to organize and plan. I wouldn't say I'm an absolute pro at this, but planning ahead and getting really organized certainly is helping me feel more prepared and actually excited for a month away.

Preparing My Business for a Month Away

  • Scheduling an email to my clients, students, and subscribers (on Flodesk, of course!) that I would be away for the month and my team would be taking a break as well. 
  • Putting an OOO away message on my business & our support email letting people know where to find things while we're gone and when to expect us to start returning emails. Superhuman is amazing for keeping all my incoming emails organized & reminders ready for when I'm back!
  • Tying up loose ends on projects and setting communication expectations with my team and 1:1 clients.

Planning Our Trip to Italy

Ok, here's where we get to the fun stuff - especially for all my fellow organizers. I am obsessed with Airtable, so I planned out our entire elopement and month-long honeymoon trip in their app. If you aren't familiar, Airtable is like Google Sheets and Excel had a baby that decided to get all color-coded and intuitive; it's fabulous.

I use Airtable for many things in the Smarter Not Harder: 3-Day Workweeks for Millennial Entrepreneurs© program and the Pro Organizer Success Kit, so why not use it to plan our trip?? 



For planning this trip, I made 4 tabs: 

  1. Calendar - for planning out each day including hotels and activities
  2. $$$ - for tracking our budget including what we've already paid for and what still needs to be paid for
  3. Links - for frequently used links like our Google Map and car rental info
  4. Recommendations - for every hotel, Airbnb, restaurant, or activity that was recommended to us along the way

I created the template (free for you to download above!) on my desktop and largely filled it in while sitting at my computer, but it was very easy to keep track of everything on the mobile app as well. You'll see some categories in the budget specifically that pertain to our courthouse wedding and elopement ceremony that may or may not apply to you, so feel free to delete those if you don't need them! John is more of a paper guy, so from time to time as I update the Airtable doc, I will print it out for him to have a hard copy :) 

Once you check it out, I would love to hear what you would add to the Airtable template for your next trip! Shoot me a DM on Instagram to let me know! 

I'm sure there are things I missed in this post, but this is the meat of what we did to prepare for our trip. Can't wait to share more about our adventures once we are back! 



Owner + Founder, Kate Waldo + Co. 

P.S. Curious how you can grow your 6-figure business while slashing your workweek in half? Click here to learn about the Smarter Not Harder© program!


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