How to organize group travel!

How to organize group travel blog
Group Travel

I have been organizing group travel for the past five years and I can safely start this article by saying, organizing group travel, well it is not for sissies. Oh, yes, it is a whole lot of fun, lots of laughter, lots of incredible moments and adventure too. My tagline is It’s always an adventure! for a reason. However, it is also a whole lot of planning and logistics.

Visiting Valkenburg

If you have ever planned a family get-together, meal or trip, you know bringing all the elements together to create a symbiotic experience can be a bit challenging. Luckily, I like challenges.  

Whether you are planning a family trip to Disney World, a girl’s spa weekend or a couples trip to Cancun you need to nail down your logistics before you go.

ELEMENTS of an Itinerary

Getting organized is your first step. Here are the elements of an itinerary that will help you, “get it together!” Here are the when, how, and where’s of a great trip that will have incredible memories, less stress, and even enough time for you to enjoy yourself.

I don’t worry about the what or the why in itinerary planning, because we know what we are doing right, we are traveling. Why?  So that we can go, explore, discover and embrace and enjoy! 

When to go?


This question seems to stump people and I am not sure why it would stump them. They could easily travel to Scotland or Ireland in September or January and have the most amazing weather and freeze your tootsies off in July. I have had this happen to me by the way. First-hand experience. 

View of Edinburgh, Scotland from the hill
View of Edinburgh, Scotland from the hill in Spring

Traveling in the summer to Italy is hot! I mean, hot, hot! My Italian friends head north for the summer and my German friends head south. It really depends on what you are looking for, some people prefer the heat others, not so much.

I don’t let the weather or time of year determine my decision on where to travel. We are in fact having climate change. We are, just own it. 

Advantages of off-season travel

I have countless stories of visiting destinations in their off-season and enjoying it all the more. Fewer tourist crowds, more local festivals happening and discounts galore.

One hile visiting Ireland in January on the Dingle peninsula we were basically the only tourists for miles around. The beauty of this was that we were welcomed with open arms by the locals. We were invited to a “fiddle off” (no kidding) and had authentic fish n’ chips on brown paper served out a window in front of the harbor. These are sold mostly to the working fisherman on the dock. 

On one particularly rainy day, we stayed in our cottage that overlooked the Atlantic Ocean and started a fire in the peat fireplace, snuggled, read books and played board games. I am sure it was a bit different than the spring break my daughter was thinking about, however, we talk about that vacation along the coast of Ireland quite often with such fond memories. 

Booking in advance (Tips and tricks)

  • It used to be that there were last-minute deals. Not so much anymore. Ask any experienced travel advisor or traveler, when you think you might want to travel, look into booking it as soon as possible. Rates will only go up the closer to your date of departure.
  • Booking in advance will not just save your money but a ton of stress. Some travel advisors even make it possible for you to make a deposit, pay installments or just pay in full. Before booking ask for what best fits you.
  • Check out my podcast with great travel advisor Vicky Turbak who can walk you through building an itinerary one-on-one too.

How to get there?


  • Air, Train, Car or a combination
    • Traveling today has never been easier. I can safely say that! It will all depend on what you want to pay or how you want to travel. 
    • Group travel by Air – if you are traveling with a group of 18 or more, call the airline – Most airlines like Delta  or using FlymyGroup will accommodate and if you pre-book will give you a bit of a discount
Over the island of Malta
Travel TIP

You will need the passport numbers for all your travelers if you book group travel through the airline. Do not share this information on Facebook or social media. Sounds obvious, but I’m here to say it is not. 

Group travel by Car – this was the most common way we traveled in my groups in Europe. Renting a 9 passenger van and splitting the cost between 6-8 passengers was a much more affordable way to see Europe. Also, we were able to stop frequently for sights to see along with potty breaks and to stretch legs along the way. 

Carpooling can also be a bit stressful, and we had lots of stories to share in the van as well. 

Group travel by Train – one of the easiest and most affordable ways to organize group travel in Europe is to travel by train. While in Germany, help was everywhere including the daily, weekly and quarterly specials the Deutschbahn will run. If you’d like to know more details, check out my E-BOOK!

Taking the train - Stuttgart

Where should we go?

  • Location 
    • Choosing a location might be one of the hardest elements to agree on. Here is how I tackle this one.
    • Ask, ask and then do a little bit of research. 
    • Travelers in your group may have their heart set on Florida or Barbados but you will want to all be in agreement before booking anything
Travel TIP

  • Beach, Adventure, Relaxation, Exploration (Historical) 
  • Combination (most people choose a destination because of what they have seen or read) 
  • I use Pinterest to help with inspiration – follow my boards there for more ideas.
Beach in Cannes, French Riviera
Beach in Cannes
  • Accommodations
    • This element can trip up a group. Some people prefer to stay in an all-inclusive brand name hotel while traveling and others prefer the homey feel of a B&B. Also, others may prefer AirBnb or hostels. 
    • Definitely, a newer TRAVEL TIP is to book these and ASK about deposits. More and more accommodations, especially in Europe, are requesting a deposit. Sometimes a full payment and NON-REFUNDABLE. If you are booking for the whole group be sure you know this tip prior to arrival. 
©TWW Stop sign girl does have some great cancellation policies, however, read the fine print. Sometimes it will indicate after a certain time, this much is refundable or not and if deposit is not received by ? date, the reservation is not confirmed.

Managing Expectations

One of the most challenging aspects of group travel is managing expectations. Pretty much every person I have ever traveled with has expectations of the upcoming journey. Your job as the organizer is communicating the itinerary as well as you can ahead of time. 

Green girl!

I create a separate private Facebook Group page for my travelers and post and post about upcoming elements of the trip. Sometimes the details will be about a wine tasting, a cooking class or tour. Most of the time,  I lead with the wonderful accommodations we have chosen because I have personal connections with the owners. I will talk about the breakfasts that you can expect, walking trails around the space, free time to explore (with maps), etc. 

Now, I will let you in on another secret. EVERY single tour I have planned a few clients have said,”I never really read the itinerary, I’m just happy to be here.” However, I also have learned that it is much better to “overshare” information than catch people off guard.

Ooops! How to go with the flow ~

Adventure happens! It just does, with over 50 small group tours in Europe in the past five years I can safely say, there was an adventure on every single tour. Most of the time they are super fun stories that we would continue to share over time and make us laugh.

One time we saw a truck in Assisi hang over a cliff in front of us and a few men gathered together and lifted it to “right” it. Don’t worry, no one was hurt in this story. We laughed about it afterward, the delay created a story. 

Another story, this past May while in Assisi we happened to be there during the incredible celebration of Holy week festival. While we were touring the town, they closed down portions of the old town. Yes, they closed it down! Totally displaced and hanging out in the city square at night, we entertained ourselves while our driver drove clear across town at another entrance, parked the car illegally and finally found us. Again, another great story.

Go with the flow!

Another trade secret is to not take yourself too seriously! Things happen! When they do, ask questions, check things out and go with the flow. Chill. I haven’t always used this approach but as I traveled more and learn to anticipate the uh-ohs! I learned to laugh and de-stress more.

These are just a few secrets to successful group travel. Getting your trip organized way ahead of time is key. I like to visualize myself in the location, accommodations, activities way ahead of time before going. I hope they help you plan your next group adventure!

It’s always an adventure when you ©Travel with Wendy!

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