Part-time traveller, Full-Time Brummie

Guest Post: Organising an Amazing Group Holiday in Italy

When it comes to organising holidays, it’s no secret that I like to take charge, from organising the destination, to planning where to eat and what to see. It doesn’t always work out as planned, but Mr Fletche is patient and puts up with my slightly OPD (Obsessive Planning Disorder) tendencies. A larger group may not be so patient…
It’s also no secret how much I love Italy – the cities, the coast, the countryside, the language, the food, the wine, the Aperol Spritz… So when Emily Jones and I spoke about a guest blog it was a no-brainer what the subject matter would be – Travel Planning + Italy = “Organising an Amazing Group Holiday in Italy” 
Group Trip to Italy
Take it away Emily…
Group holidays can be a little stressful, but they can also be an amazing way to cut loose and get away from the everyday routine, in the company of your closest friends and/or family. There are lots of tips out there on how to organise the planning- like picking a leader, organising an itinerary, and definitely booking ahead. If you’re unsure of a destination, a great location for a group holiday is Italy as it has something to offer anyone and is sure to please the whole group- whether you want relaxation on a beach, adventure in the mountains, amazing food, fashion, lakes and active volcanoes- Italy has it all. Here are a few of the many locations to pick from!


If you and your group are looking for a location that involves unbelievable history- walking around ruins, visiting museums and spending your days gazing up at statues, Rome is your destination. The eternal city is Italy’s capital, and rightly so! Rome has activities that every group member will enjoy-whether that be boat rides on the Tiber river that runs through the city, Segway tours from one monument to the next, or gazing at the churches’ singular artworks, you are all in for a great treat. Rome is also famous for it’s typical dishes such as Roman style pizza and carbora, you can finish a long day of sightseeing with an incredible glass of wine and delicious freshly made food.

Organising an Amazing Group Holiday in Italy - Rome

Picture source: Pixabay


Not many know that the pictures you tend to see of Sicily are taken in Taormina, which is a gorgeous picturesque coastal town on Italy’s famous island. If you choose Italy’s tip of the boot expect to find delicious seafood menus, adventures in the Sicilian wilderness, and breathtaking beaches where you can soak up the sun. Not only will it be a trip to remember, but you and your group will definitely have the best holiday possible. Indeed, it’s ideal for group holidays as you can live like a local in a gorgeous villa using a company like Wishsicily who offer visitors incredible holiday rentals in Taormina, often walking distance from the beach.

Organising an Amazing Group Holiday in Italy - Siciliy

Picture Source: Pixabay


Do you and your group want to feel like you’ve been transported back to medieval times, and be surrounded by beautiful landscapes? If so, Umbria is the place for all of you. One of Italy’s smallest regions, Umbria is full of unique restaurants for you and your friends and/or family to spend delightful afternoons and evenings at. Keep in mind that you will be able to visit many towns that are all picture worthy- making it even better when you’re boasting about your incredible Umbria holiday once you’re back home. Of the many towns, be sure to visit Perugia- it is home to one of Italy’s best chocolate brands and holds an annual chocolate festival too for any visitors with a sweet tooth!

Organising an Amazing Group Holiday in Italy - Umbria

Picture Source: Pixabay


If you’re looking for a location where you can shop, don’t look any further than Milan! Known as Italy’s fashion capital, you and your friends or family will be able to shop till you drop. Of course Milan also has many other great activities for your holiday, and does not shy away in terms of monuments, so rest assured you will have lots to do. Whether you choose to visit the iconic Duomo, see Leonardo Da Vinci’s Last Supper painting, or try one of Milan’s many signature dishes, you’re in for a wonderful holiday.

Organising an Amazing Group Holiday in Italy - Milan

Picture Source: Pixabay

Once you’ve chosen your location, start counting down the days until your departure day arrives! However, you should double check that: everybody’s passports are in order; that your travelling information is correct; that everybody has insurance; and that you can organise a payment plan that will make all of your lives easier once you are there. Once you have arrived remember to be flexible and go with the flow as though it is easy to get wound up by people going against your ideas- it’s not worth falling out over, and you don’t want to be resented for being too bossy throughout the trip.

Guest post by Emily Jones

So what are your top tips for travelling in a group? And does the idea of a group trip to Italy float your boat? Let us know in the comments below!

Organising an Amazing Group Holiday in Italy - A guest post by Emily Jones on A Brummie Home and Abroad


6 responses to “Guest Post: Organising an Amazing Group Holiday in Italy”

  1. I’m so obsessed with Italy it’s not funny. Anyone would think I was the one with family there not my husband!! I just have such a passion and bond for the country….. just love it. Great post about travelling in groups guys. X

  2. Don’t forget your pocket travel book, “Conversational Italian for Travelers”. I’ve put all the phrases I have needed when I travel to Italy in one small, lightweight book.

  3. Haven’t heard too much about Umbria but the annual chocolate festival is tempting! Also hoping to visit Sicily next time too.

  4. My favorite off the beaten track place in Italy is Milan.

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