Let’s face it. Planning a group trip usually falls to one person and in my friendship group, that’s me. I’m the one who suggests dates, books the venue and plans activities.
For 2022, I was dreaming of getting a crowd of friends together for a big group holiday, something I’ve been craving since moving from London to Sicily as an expat. I love friends from home coming to visit but hosting means I become the chef, driver, cleaner and tour guide. Renting a villa would make it a holiday for all of us.
I booked our property through Villatravellers, a Sicilian company that rents out villas all over the largest island in the Med. We stayed in Villa Respiro, a 5-bedroom property in the hills above Taormina, a historic town on Sicily’s east coast.
The villa overlooked the sea and the panoramic view must be what inspired its name, meaning ‘breathe’ in Italian. We all let out a long and satisfied sigh seeing that view after our early start.
It marked the perfect beginning of a relaxing long weekend reconnecting with old friends. But it took some careful planning and preparation to make sure everything worked out. I’ve broken down the steps I took in planning, which started four months before checking into Villa Respiro.
1. What’s the perfect guest list for a villa holiday?
The first step in planning is deciding who to invite. If you’re going with family or a close friendship group, it may be obvious who’ll be coming. But if you plan to merge different social groups, such as friends and colleagues, it pays to think carefully about how the personalities will gel together.
One way to work out if the group will bond is to ask everyone what sort of holiday they want. If half are bookworms and the other half can’t sit still, it could create some division. You don’t have to spend every minute at the villa together, but some agreement on how you’ll spend time together as a group will make for a more enjoyable holiday.
Think about whether you want to invite children or to keep it child-free. We opted for child-free so we didn’t need to think about car seats, naptime, early bedtimes and everything else that comes with little ones.
2. How much does a villa holiday cost?
It’s easy to get caught up in awkward situations over money and friends, and with cost of living so high right now, everyone is being careful with money.
To avoid any misunderstandings or surprises, my advice is to discuss money early and often. As soon as you start inviting people, give them an idea of what the villa will cost per person. You can easily find approximate prices on booking websites. Also be upfront about added costs that will be split amongst the group, such as food, alcohol and group activities.
Feedback from the group on proposed costs will give you a budget to work with when you’re searching for your perfect villa.
Splitwise is a free and quick-to-use app for keeping track of who has spent what and settling up at the end of the trip.
3. Where is best to book a villa holiday?
Multi-generational travel is booming right now as families reunite after the pandemic. But if you’ll be bringing everyone from the newborn to granny, make sure you find a villa that suits everyone’s needs.
There’s more than just the number of bedrooms to think about. Do you need somewhere step-free? Is reliable WiFi a must? Maybe you need toys for different aged kids? Writing a must-have and a nice-to-have list will make it much easier to narrow down using search criteria.
The good news is that the options in Europe are endless, and more properties become available every year. This is especially true right now as some travellers favour private accommodation over hotels to stay safe from COVID. Expect villa holidays to become more and more popular in the years to come.
When you know what sort of holiday your group wants, it will be easier to narrow down locations. If you want beach time and swimming, opt for beachfront. Whereas if time in nature is the priority, a property in the mountains or a forest would be a better fit.
Don’t be afraid to lean on the company you’re booking with for recommendations and local know-how. When booking with Villatravellers, I asked for a 10-bed villa, close to an airport and with a pool.
I hadn't considered Villa Respiro at first because I wanted to be within walking distance of a town. But in the end, it was an excellent recommendation from the company - we only left the villa gates once in the three days we were there.
4. What’s the best transport on a villa holiday?
Villas tend to be outside of big cities so you’ll need to plan ahead for your onward journey from the airport or train station.
If you’re planning to do like us and just hang out at the villa, public transport or private transfers are the best option. Hiring a car for it to sit in the driveway is just a waste of money. Private transfers are the most hassle free option, but taking public transport will be much cheaper and means far less carbon emissions.
If you want transport for while you’re at the villa, hire cars are the way to go. Remember, if you’re a big group you’ll need more than one, unless you can hire a van or people carrier.
There’s lots of online car hire comparison websites where you can easily get quotes. Don’t forget to account for luggage space when calculating size and number of cars.
Decide who in the group will be driving the cars. They’ll need to make sure their drivers licences are valid where you’re travelling to, especially for Brits in a post-Brexit world. When booking, the drivers will also need to choose between automatic or manual cars.
5. What is there to do on a villa holiday?
The beauty of a villa is that it’s going to be your home from home. That said, having a rough idea of what you’ll do at the villa will make for a more relaxing experience once you get there.
The advantage of using a company like Villatravellers is that they know their properties really well, as well as what’s around them. The website listing for Villa Respiro was really comprehensive, so I knew in advance that it had a pool, heated jacuzzi, fully-equipped kitchen, laundry room, TV with Netflix, and barbecue area.
On top of all that, Villatravellers can arrange experiences in and around your villa. These include a jeep tour up local volcano Mt. Etna, boat trips or a chef coming to cook for you.
Once our booking was made, a Villa and Experience Specialist got in touch to design the rest of the trip. One thing our group all had in common was a love of food and drink - perfect given that Sicily is known for both.
We reluctantly forewent the visit to a local vineyard in case of October rains, and instead opted for a cooking lesson at the villa. Two wonderful local women brought all the ingredients and their extensive know-how of Sicilian food and we spent an afternoon cooking with them.
We made a three-course meal, including macaroni from scratch. Getting the knack for rolling out the pasta was harder than it looked, creating some healthy competition amongst the group. But we all made up when it came time to sit down and feast on what we’d created. Best of all, we didn’t have to do any of the washing up.
I’d recommend checking in advance how long any pre-booked activities will take. Our cooking class was very Sicilian in that nothing was rushed and everything was done with care and attention. But it did last longer than expected so check timings in advance if you want to make evening plans.
6. What to bring on a villa holiday
Now it’s time to pack your bags - but don’t use up precious packing space by taking stuff that the villa provides.
We were pleasantly surprised by just how much was included at Villa Respiro. There was a welcome basket which was more like a week’s shopping - it had cooking essentials like salt and oil plus everything for a lovely breakfast and some snacks too.
On top of this, we decided to get some food shopping delivered to the villa. I expected to have to arrange this but I just gave Villatravellers the shopping list and they organised for it to all be delivered just after we’d arrived. It was so nice to know we didn’t need to venture out to find a local shop.
The welcome basket was very generous but we were surprised that there was no shampoo or shower gel in the bathrooms. So it’s worth checking what comes with the villa and what you need to bring from home. Be aware of liquid limits if you’re travelling with hand luggage by plane. One of the benefits of train travel is that you can pack any size of liquids.
Your rough plan for what you’ll do while there will be key when deciding on clothes and shoes to pack. Check ahead, or ask the villa company, for the weather forecast so you’re not caught out.
My favourite evening at our villa was spent playing games that one of the couples had brought with them. Cards and silly word games were the perfect post-dinner fun and much better for group bonding than slobbing in front of a movie.
7. How to make sure your villa holiday is the perfect break
Once you’ve done all the planning and preparation, my final piece of advice is to let it unfold and just enjoy whatever happens.
You might have an itinerary for each day in advance but the reality is that some things will not go to plan. That’s the beauty of travel - the unexpected twists and turns are often the best bits.
Approach your holiday with an open mindset. Leave behind preconceptions about your friends and family, or which bits you’ll enjoy the most. Remember you’re on holiday to relax, especially after all the organising.
Villa Respiro is available through Villatravellers from €3,400 per week.
Ruth Wright and friends were guests of Villatravellers.