Organizing Our First Company Retreat as a Bootstrapped Remote Startup

For us the benefits of being a remote company are obvious. You can work when and where you’re most comfortable, you’re able to travel or spend time with family, and you can skip the office politics.

But despite software making it easier than ever to feel connected while being thousands of miles away from one another, it’s always nice to get some face-to-face time. Striking up random conversations about different topics just doesn’t happen as spontaneously over Slack, and getting to know one another a little better is always helpful.

That’s why we made it a priority to set up our first company retreat when we hired our first (and awesome) engineer Phil.

Here’s how I put it all together.

Getting the team together

It seemed like good timing to get together at the start of the year to organize our product roadmap. We’ve got a ton planned and it’s good to get everyone together face-to-face.

So, deciding on a location wasn’t too difficult. It had to be in Europe since low-cost airlines make it super affordable to travel around. And as you might’ve heard, British people hate the cold weather, so Northern Europe just wasn’t an option. We had to escape the winter chills.

That left the southern parts of Europe. The South of France, Portugal, Italy, and Croatia. Not too shabby.

What kind of accommodation and where?

Now that I’d narrowed down the options of countries, it was time to whittle it down further.

First up was deciding what kind of accommodation to choose. There were three choices in the end: villas, hotels, or apartments. Each had their pros and cons.


Turned out villas were a good fit for a company retreat. You sure get a lot of bang for your buck with a villa. There’s a ton of space to work, the furnishing are usually good, and many of them are serviced.

The big problem with villas is they usually require a car which affects the price somewhat. Driving for groceries is a must, and that’s just not very ideal, fun, or cost-effective. After looking for a couple hours, I found a couple good options, but they were an hour drive away from the airport.

When I positioned it against living in a city with a major airport, it just didn’t make sense for us.


I briefly looked into getting some rooms in a hotel, but not for long. Hotels in Europe are actually super expensive and coupled with having no way to cook (which means eating out all the time) it would totally blow our budget.

Not only that, but there’s less room to work. So that was a big no go.


Apartments are kinda in between the two. You can more space than a hotel room, and you can also get serviced apartments so if anything goes wrong, you’ll get help.

In cities, they’re close to airports which means less travel time and more things to do, places to go, and cafés to work from.

Because of all of these benefits, it was a no brainer to go for an apartment in a city with a major airport. Now it was time for me to choose where that would be.

Searching the internet for accommodation

Finding quality accommodation for a good price is tough, so by sharing my experience I hope you’ll find it quicker to find what you’re looking for. Here’s what I tried.

Searching for villas

To start with I tried, a site I regularly check out for booking places. Unfortunately, their selection of villas was pretty dire. The quality was terrible and the prices were pretty outrageous. It’s better for finding hotels and apartments, for sure.

After that, I went onto Airbnb and spain-holiday. Again, the quality for the price just wasn’t very good. It seemed like there was a split: cheap villas that weren’t appealing or luxury villas that would blow anyone’s budget.

After sifting through hundreds of listings, I finally just Googled ‘villas in PLACE’. I found a couple independent local villas companies who has way better prices for quality villas.

Trouble was, they were still too far from the airport which meant renting a car. Another issue was that some of them were simply too large for three people.

Searching for hotels

The easiest way to search for hotels I found was to use Kayak. If you add your filters and copy and paste the query parameters at the end of the URL, it’ll save you a ton of time.

Ideally, I was looking for hotels under Hilton, Marriott, Starwood, and Club Carlson as Jake has a card that gives us membership to their loyalty programs. You can earn a ton of points and get things like free Wifi and breakfast, bringing down the cost significantly.

The problem I faced with hotels was the fact we wanted to go in less than 3 weeks time. The prices seemed to get inflated closer to the time to a ridiculous degree. With all the disadvantages of hotels, I ditched this idea pretty quickly.

Searching for apartments

Depending on where you search, apartments can be hit or miss. I’ve been to really good ones and some terrible ones. Sites like Airbnb have a lot of selection, but can be overpriced for what you get.

I tried Googling ‘serviced apartments for CITY’. This worked pretty well. I managed to find several independent companies offering accommodation for a reasonable price.

In the end, I carried on searching on Airbnb and managed to find a gem. But it turned out the host was actually a company. So I hopped onto their website and found the exact same apartment for less. Booking direct certainly helped me get the price down.

Narrowing down the location

Now we’d settled on getting an apartment in a city, it was time to narrow down exactly where it would be. There were a few options here.

South of France

The south of France is a sought-after area and is only around two hours away by plane from London. There’s some lovely cities including Nice known for its lovely boardwalk and climate, Cannes for the film festival, and Montpellier for its wine.


  • We can kinda speak French. Jake and I know a little bit of French which is useful when visiting, well, France. Although admittedly, Jake is far better than me at speaking with locals.
  • Not far from the UK. As I mentioned, the South of France isn’t very far from the UK so it won’t take long to travel there. This means our customer support won’t suffer.
  • Cheap airfares. A flight from London to Nice can be had for less than £40 return. Not a bad price at all.


  • Lack of accommodation choice. When I looked for apartments there just wasn’t that much choice. It might’ve been because I left it so late (2 weeks before going 🙈).
  • Not very warm. The average temperature in Nice is around 6 ℃ which is still pretty warm compared to the UK, but not warm enough to escape the winter.

South of Spain

The south of Spain certainly has a tarnished reputation in the UK from tourism, but it’s still a beautiful destination with a great climate. Airports in Alicante and Málaga make it accessible and attractive for European travelers.


  • Warm climate. The average temperature in February is 13℃, much better than France and Northern Europe.
  • Plenty of accommodation in low season. Most flock to the south of Spain in the summer when it’s baking. In low season, there’s plenty of choice with apartments as most are empty.
  • Cheap airfares. Again, the airfares from London to Málaga are dirt cheap for how far away it is. You can get a return for £54—that’s less than a train ticket from Cambridge to London!


  • Quality of accommodation wasn’t great. Compared with the other cities I looked at, the accommodation in the South of Spain wasn’t great, even at the high end of our budget.
  • Much of the choice required a long drive to/from the airport. There wasn’t much choice is Málaga or Alicante, so driving further down the coast to other cities made sense. There’s Marbella, Calp, and Benidorm. In the end, this was the problem I was trying to avoid with villas.


Having spent some time in the Algarve (a lovely destination) I knew Portugal was definitely on the list. Lisbon and Porto are both becoming popular for digital nomads for their low cost of living and charming streets.


  • Quality Accommodation. Compared to the South of Spain, I found the accommodation to be pretty high quality.
  • Cheap airfares. The airfares from London to Lisbon are also cheap. A little more pricey than the others, but at the right time you can get a ticket for £80 or less.


  • Accommodation. While the accommodation was higher quality, the cost of the apartments were higher.

The destination of choice

In the end I decided on Madrid which is in central Spain. The airfare was a little more than in the cities but the city is an up-and-coming tourist destination which means the accommodation is high quality at lower prices.

The weather is good and it’s just over 2 hours from the UK. A good rounded choice for our first company retreat.

The future of our retreats

When we organize another company retreat, I’d do things differently. First of all, I’d hire a freelancer to help me narrow down the choices. As HelpDocs scales I have less time to spend on browsing accommodation.

I’d also consider places outside Europe as we’ll likely have employees outside of the area. The cost of flights has dropped dramatically and apartments in places like Bangkok and Vietnam is reasonable, offsetting the cost of the flights anyway.

Organized your own company retreat? Think there was a way I could’ve got a better deal or done a better job of organizing it? I’d love to know if you have any tips in the comments below. :)