Between busy schedules at work, kids in school, relatives growing old and just the fast-pace of our day to day lives, finding the time to get all of your loved ones in one place can seem like an impossible dream. Yet, after talking about it and dreaming about it for ages, you’ve finally decided now is the time to orchestrate that big complicated trip while you can. But now what? Where to begin? How do we take this dream and make it a reality?

At Homebase Abroad we help take the stress out of planning your big trip so all you have to do is sit back, relax and enjoy the company of those around you. Using our expert experience and knowledge of luxury villa vacations in Italy, we help plan the perfect trip in the most stress-free way possible. Sharing new experiences with family and friends is a great way to enhance special relationships. What’s even better? Creating those incredible new memories in a luxurious setting and an unforgettable vacation.

Here are eight easy steps to help set yourself up for success in planning your dream Italian villa vacation with a large group.

Villa di TornoStep 1: Decide Your Experience

Food and wine, art and architecture, outdoor activities and sightseeing, dramatic landscapes or a bustling city? The options for vacation ideas in Italy are endless and there is so much to consider.  Initiate a conversation with your group to brainstorm the type of trip you are all looking for. Poll your group for their priorities and make a list of what sorts of activities and experiences they’d like to get out of your trip. Having a strong, shared, vision of the WHY of the trip will get everyone in your group excited and onboard for a great vacation.

Step 2: Determine a Realistic Budget

The most successful trips we have seen at Homebase Abroad are those in which the basic cost sharing and parameters are established up front. Of course, when traveling there will be more expenses than you anticipate. Make sure you figure a solid 20% contingency. Ask yourself questions such as: how much of the planning is going to be top down? How much of the participation will involve the group? How are decisions being made? Who is in charge?

Villa BiancaStep 3: Pick the Perfect Location!

Italy is rich with choices when it comes to breathtakingly beautiful locations to host your dream vacation. There are so many stunning regions to visit that it can be overwhelming to decide. We encourage you to determine your location based on how your group wants to spend its time and energy while on holiday. This is where an expert Villa Travel Specialist can bring lots of experience to the table. A Villa Travel Specialist who is an expert with insider knowledge of Italian regions can provide important logistical advice. There are picturesque hill towns all over central Italy but the logistics can have a huge impact: How much walking do you want to do? Do you mind having to climb many steps in order to get a great view? What are your priorities?

Step 4: Secure Your Dream Vacation Villa

Now that you’ve determined what type of vacation you’d like and your ideal Italian destination, it’s time to secure your dream vacation villa. You want the best of the best for your holiday of a lifetime so we encourage you to start your search for the perfect holiday home well in advance to keep all of your options open. Those precious mid-June to mid-July dates are in high demand with limited inventory— we recommend securing the home at least one year in advance.

Homebase Abroad Ca di PesaStep 5: Have Some Fun

If you’ve been spearheading the vacation planning on your own have some fun in sharing the excitement with the rest of your group! Now that you’ve got your location and house locked in, get the rest of your party counting down the days by hosting a reveal party. Treat your group to a themed dinner with wines and other foods that are local to where you will be staying. Have a film party and screen a movie shot in the Italian countryside or on the streets of Rome.

Step 6: Get Organized      

Don’t wait until the last minute! Picking a destination and finding your ideal vacation home are the fun parts, but you have to do your homework if you want your trip to go flawlessly. If anyone in your group don’t already have a passport be sure and start the application process as soon as you’ve decided you would like to travel abroad. Acquiring a U.S. passport typically takes 4-6 weeks but it’s better to give yourself as much time as possible. If you already have a passport make sure it’s still in date and will be valid for at least six months from the date of travel. After you have secured your dream villa and begun the passport process, we recommend you begin your search for flights. We suggest setting alerts on your preferred routes so that you’ll be sent an email when the fares drop. is a great sight for finding affordable airfare and tracking price drops or increases on specific routes. Also, don’t forget to encourage everyone in your party to sign up for travel insurance.

Homebase Abroad I CappucciniStep 7: Create a Vacation Wish-List

In most cases, a large home suitable for such a vacation must be booked at least a year in advance which gives you plenty of time to create a vacation wish-list. Visualize yourself holidaying in luxury and creating lifelong happy memories with your family and friends. Do some further research on specific activities you’d like to do. Spend time perusing travel guidebooks, the internet and travel magazines to find activity ideas to your wish-list. Make notes and call your Villa Travel Specialist for guidance on how structure the trip so that you and your group get the best possible experience out of your trip.

Step 8: Design the Itinerary Best for You

As your trip gets closer, begin to finalize a loose itinerary with your Villa Travel Specialist. Having a (somewhat) flexible itinerary will eliminate the need for large groups of people to negotiate what to do each day. Instead, you can tell people what you’ve planned for the day and invite them to join you with the expectation everyone will gather for dinner at the end of each day. You can also share itineraries on Google Docs or Google Calendars so that everyone can see and comment on the plans. Careful preplanning with a Villa Travel Specialist ensures time to enjoy your company and your surroundings rather than racing from activity to activity.

Attempting to singlehandedly plan a dream vacation for a big group of people in an unfamiliar place can be stressful. Having a trusted advisor reduces the stress and helps you plan a trip with everyone’s interests in mind. Putting time and effort into planning your dream vacation pays off tenfold. Proper planning is critical in making your trip run as smoothly and joyfully as you dreamed it would.


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