How we wrote 49 pages in 5 days — tips and tricks from our workation in Tuscany

A workation is a paid work trip combined with aspects of taking a vacation. Like how that sounds? Well, what are you waiting for?

With most jobs becoming increasingly mobile, chances are that your team can work remotely — and why not from another country?

We at Truesix.co already knew we didn’t have to stay in the office to be productive. What we didn’t know is that we could write 49 pages of good content while on a trip — but more on that later.

We also knew we wanted to go someplace warm and beautiful with excellent food and wine.

It’s no shocker we chose the Italian nature and wine lovers’ paradise Tuscany. Specifically — the picturesque Oliviero Toscani farm and winery.

Sure, organizing a workation is easier with a smaller company like our dream team of four. We simply found cheap tickets a few months ahead and booked 5 days on our busy agendas.

But even if you have a bigger team, organizing a workation shouldn’t be a problem — that is, if most of your colleagues are active and love to travel. Check out these tips for traveling in a large group.

As none of us had done a workation before, we were also taking a leap of faith. And we managed to nail it!

Just like we managed to hold the Pisa tower in this picture.

Just joking.

In fact, we really did manage to do a lot and have fun meanwhile. Here’s how we made it work and how you can do it too:

1. Pick a suitable location

Once you’ve decided where to go, choose your accommodation carefully. Most probably, it will double as your office for the duration of the trip.

From our experience in Tuscany, the perfect “office out of office” should:

  • Have an internet connection
  • Be peaceful, but close to other sights and activities your team could do
  • Have enough desks and possibly alternative seating (couches, standing desks, etc.)

A Pro Tip: Get a place with a shady terrace for working outside. And furry friends around like our CCO (Chief Cuteness Officer) Gino here.

You can also work from the surrounding cafes and parks (why not have a brainstorm session on the beach?). For example, we used the first morning to work from a lovely cafe in the nearby town.

As I was sitting in the middle of a cobble-stoned street, sipping Italian coffee and listening to the church bells celebrating every hour, I thought — life is beautiful.

However, during the following days, we found that working from home in the mornings was more productive.

First of all, the marvelous Tuscan spring wasn't as distracting while we were indoors. And second, we could start our day in a quiet environment and at our own pace. And we were much more excited to leave the house for that well-deserved afternoon chill.

2. Set out to complete a certain goal or project

In case you had doubts, wine and pizza weren’t our main goals for the workation. We had a very solid plan in mind — to prepare a form of evergreen content that would help us share our writing expertise with more people.

Before going to Italy, we discussed the format of this project and agreed it should be a digital course. Then we had to decide how to organize our work to achieve the best result.

One thing was clear — the course project would be our primary focus for the duration of the trip. All the other work-related tasks would have to wait for a few days.

Looking back, this was a good decision. If we had lost focus for a moment, we wouldn’t have done as much work as we did. So make sure your workation has a very clear purpose that’s achievable during the time you’re away.

3. Use Agile Scrum framework

Scrum is a simple framework for effective team collaboration on complex products. It’s is a subset of Agile methodologies that’s mostly used for software development, but can also work for non-technical teams.

Adjusting the Scrum framework to our needs, we developed Scrum: Workation edition. Our sprints were shorter than the usual software devs’ sprints; however, we kept the main idea of the Scrum:

  • First, we created a backlog of all the tasks needed to be done for our project — from content writing to technical implementation.
  • Every morning we had a short sprint planning meeting to agree on tasks each of us would do during the sprint.
  • We had a 4-hours long morning sprint and a 1-hour long evening sprint.
  • After each sprint, we reviewed what was done and summarized the next tasks to be done.
Being able to change our working environment was a powerful creativity booster.

4. Work mostly in the morning

The Scrum model is designed to optimize flexibility and productivity, so we also adjusted our workflow on the go.

Our initial plan was to work three hours in the morning and three in the evening. However, after the first day we changed it to 4-hour and 1-hour sprints. We simply found that a longer uninterrupted morning session would be more efficient.

And, ok, let’s admit — we wanted to have more sightseeing and wine-time in the evening.

And, yes — we had horses right at our doorstep! How amazing is that??

So how much did we actually manage to do?

Incredibly much for such a short time that also seemed so relaxing and enriching.

Here’s what we accomplished:

As we are all using DeskTime to track our working hours and productivity, it’s interesting to look at our productivity stats during the workation.

Productivity stats: Left — office day; right — workation day.

These charts compare a regular office day for our team and a workation day. You can see that even though we worked fewer hours, the productivity for those hours was very similar to the productivity we have in the office.

5. Have lots of fun together

Team retreats are not only about working in a different environment — they’re also about team building.

You’re sharing unprecedented situations with your colleagues, like:

  • Cooking together
  • Driving up the winding roads of Tuscan mountains
  • Saving each other from getting lost in a horse farm at night
  • Running through the airport trying not to miss a flight

Make the most of this time and get to know each other.

We found that games work great for this purpose. As we hadn’t prepared any games in advance, we had to come up with those on the spot. Here’s a list of fun games to play with your colleagues, in different settings.

Each team is unique, and so is the list of activities you consider “fun.” But make sure you’ve designated enough time for relaxing. Otherwise, you might end up going back to office work and feeling more tired than before.

Find the right balance

The perfect recipe for your workation consists of balancing the right ingredients in reasonable amounts — working, having fun, relaxing, and team bonding.

As for us, we can proudly say that our first workation was like a rich, savory meal. A solid, wholesome base in the morning, spiced up with some Italian scenery and a fresh flavor of creativity. And that afternoon desert when your gelato melting seems like the only deadline in the world.

If you’re curious to see the product of our workation, sign up to the waiting list here. You’ll be the first to know when our digital course on Business Blogging is live!