How to (sanely) plan a group trip with free online tools

plan a trip with free online tools

It’s official! We have convinced some of our family to travel to Italy with us next year, and we are psyched! Paul’s parents, as well as his brother and girlfriend, are joining us for a couple weeks in Italy this spring.

While we are really excited, we are also realistic about how difficult it can be to wrangle six adults into making decisions sometimes. We all have different schedules, interests, and communication preferences. But since we started the planning, we have figured out a few tips to make it a bit easier. Are you planning a trip with a bunch of people? Read on, as this may just save your sanity...


Since we all don't live in the same location, Google Hangouts allowed us to chat face-to-face and share screens. This was especially helpful during our early planning. Sometimes it's useful to see people's facial expressions so that tone isn't misunderstood like it could be in an email or text.

Deciding When

Aligning schedules can be hard. How do you get input from everyone efficiently and gain consensus painlessly? Doodle works wonders in situations like these. It's a simple poll that helps a group of people decide on a schedule. And it's free. Prego!

Deciding Where

Once we decided on our destination, Google Maps really helped us with the basics of figuring out just how much distance we are willing to travel once we are there. But the magic of Google Maps doesn't stop there. We have created shared maps so that we can save restaurants that we come across in our research. In the days leading up to our trip, we will download the areas where we'll be traveling so we can access them offline. That way when we are hungry and don't know where to eat, we will have a pre-saved list in our pocket. Genio!

Figuring out the Details

Google Drive works wonders as a shared repository when doing research. For example, when researching Airbnbs, we created a shared sheet where we all could keep track of good looking locations, and their pros and cons. After a while the options tend to blur together, so this was immensely helpful to keep us organized.

Capturing the Plans

Finally, as we make plans, we are inputting our itineraries on a shared calendar. The nice part about Google Calendar is that you can select different timezones for the same event.This means if you depart DC, have a layover in Reykjavik, with a final destination in Rome, you can mark each timezone separately, which keeps things nice and organized! We are able to share these events on one calendar so that we are all aware of each others' arrival and departure times.

So to peek behind the curtain...what did we decide on?

So you many be wondering how we used these tools to begin planning our trip to Italy with six adults?

When we're going

The first thing we all had to agree upon was WHEN. Since Paul’s brother and girlfriend are both in grad school, this became an easy decision; we leave after the completion of their spring classes, and before the beginning of the summer term. This means a May 2018 trip to Italy!

While we have traveled to Italy in April in years past, we are looking forward to warmer weather in May. Last year we found April in Florence to be particularly bone-chilling at times. We are curious to see how much thicker the crowds might be in May, though. So we will be sure to report back on how traveling a month later works out!

Where we're going

Our next big decision was WHERE! Paul’s parents had the idea to take a family trip and we all got on board. But deciding on where to go took some time. We were all over the map (literally). We looked at everything from the Jersey Shore, to Hawaii, and finally settled upon Europe.

We are excited to return to Italy once again, and to be able to share some of our favorite spots with our loved ones! Within Italy, we have decided to keep Rome and Florence as our home bases, and will plan day trips from there. Using Google Maps to figure out distances was really important. It helped us realize that trying to fit both Cinque Terre and Tuscany in as day trips was going to be a lot of time on the road. So, wine won, naturally...a Tuscan wine tour is booked! 

The sleep sitch.

Figuring out our sleeping situation took some time. Last summer we rented an Airbnb with Paul’s parents in Vermont, so we are all familiar with the idea of Airbnbs. We will have common areas where we can hang out, yet still have our own rooms in which we can retreat at the end of the day.

It’s also a good way for us to be a little more economical — depending on the comparison, we are saving money compared to having three separate hotel rooms. And, we will have access to a kitchen, so we can eat some meals in, and have access to a fridge and washing machine. 

Deciding the exact Airbnb in each city was a team effort. We fired up Google Drive and kept track of the good-looking homes available in real-time.

Keeping track of the plans

As we are booking everything, we have been putting it all into a shared Google Calendar. It's beginning to feel more and more real! Can't wait for it to be here! As we complete more planning, we'll keep you posted! Ciao!