If you’re down the rabbit hole of trying to find accommodations for your dream vacation to Italy, you may feel ready to call in the help of an Italy travel planner!
When it comes to where to stay in Italy, there are so many factors to consider: proximity, amenities, size of the rooms, quality of service, and authenticity. With that, it can feel like there’s always a compromise. Choosing an authentic option often means you sacrifice comfort and amenities, but choosing a more commercial option keeps you stuck as a tourist supporting big corporations instead of the small family-run businesses.
Ever wished you could have somebody on the inside scope out the room before you get on the plane? That’s where we come in! On our small group tours of Italy, we hand-pick our accommodations so that our guests have the most authentic, immersive experience while still having access to all of the luxury amenities.
In this blog post, we’re dishing on all the secrets of the trade you won’t find anywhere else.
Why Where You Stay Matters on Your Italian Adventure
There is no worse feeling than walking into your hotel room or AirBnb after a long flight, dropping your bags, and quickly realizing you’ve made a huge mistake in the accommodations you chose—that’s especially true during an international trip when you’ve flown across an ocean and may not know all the cultural lingo or what to do when things go wrong!
Where you stay can make or break your trip. If you’re not able to unwind and sleep well at night, hitting all the spots on your itinerary and actually enjoying your time is going to feel like an impossible task. As Italy travel planners, our number-one goal is to make sure that doesn’t happen, which is why we dedicate so much of our attention to the accommodations.
Stress-Free Travel Made Easy
When you’re a DIY-planner, you may rationalize that you’re taking on the stress of planning, researching, and booking hotels so that when you get to your destination, you can relax. But, the stress of planning doesn’t always end when you step off the plane, especially if you hit a snag in your carefully planned itinerary or your accommodations weren’t what you expected.
And here’s the thing: You might choose a four-star hotel, but there’s actually no guarantee of the quality, contrary to popular belief.
Choosing a small-group tour like ours with a curated stay eliminates not only the hassle of researching and booking, but also eliminates the chance of any stress when you arrive. We’ve personally vetted the accommodations, and we’re pretty picky! No surprises, no booking errors, no sub-par service, and you’ll step right into the swing of Italian life.
Every accommodation we book for our tours is chosen with authenticity in mind so that you can experience Italy as a true local rather than a tourist. With proximity to local spots, restaurants, and town squares, you’ll be able to truly embrace the la dolce vita lifestyle.
Authenticity Meets Comfort
If you’re looking into accommodations on AirBnb or other non-traditional options, you may find that when you choose authenticity, you sacrifice on the luxury comforts.
For example, the idea of a villa in the countryside sounds nice, but it can start to feel like a prison if you don’t have access to a car, have to cook and clean every day, or don’t feel comfortable driving in Italy. Your only other option if you don’t want to drive is to rack up a huge bill on private transportation—which takes away from the food and wine budget! And cooking and cleaning on vacation, really defeats the purpose of getting away from it all – aka your household duties.
And, keep in mind that taxis are difficult to come by in the Italian countryside, so unless you want to end up stuck in a villa and bored, your only other option is driving in a foreign country that doesn’t always have reliable Google Maps service.
But when you book a small group tour with us, we choose the option where authenticity can meet comfort. Your stay will still have all the historic charm of the region, while also offering the modern comforts you need to enjoy your vacation, like spas, pools, proximity to good restaurants, and of course, scenic views.
Our Tours Are Designed for Relaxation & Authenticity
In a day and age where it seems like travel is more about the bucket list than the actual experience, finding the happy medium between doing everything you wanted to do and actually using your vacation days to relax may feel like a daunting task, especially when the logistics and planning fall to you.
That’s why all of our tours are designed around an authentic Italian experience that feels relaxing, but never boring.
No 5AM Wake-Up Calls, Ever
If you’ve ever been on a high school field trip, you may remember the rigid structure and the planned-to-the-minute itinerary designed for a large group of teenagers. But, is that really the experience you want on your vacation?
Many of the big-box bus tours you see today market based on what you’ll get to see, but they don’t mention the early wake-up calls, the rigidity of the schedule, and the lack of downtime. Curated trips often prioritize a more relaxed pace, where you actually have the opportunity to slow down and enjoy the pace of local life, starting your morning with a leisurely espresso or creamy cappuccino and cornetto (that’s an Italian style croissant).
No Crowded Buses or Herding Groups Around
Another thing your high school field trips and most big-box bus tours have in common is having to plan the entire trip around herding a large group of people from location to location. When you have to stick to only the locations that can accommodate a large group of people, you end up at the tourist traps and leave feeling as though you haven’t truly experienced Italy. Because the entire time you remained an outsider just looking in, but never being welcomed to small independent winemakers or inside family homes. The type of experiences that can only happen in a small group (as in 12 guests or less) format. Not to be confused with the numerous big tour corporations that call 24, or even up to 30 people, small group.
Smaller group tours with private transportation provide a stress-free and more intimate experience where you get to deeply connect with not only the destinations, but the people around you—other tour guests, your hosts, and the locals you’ll meet. Offering a more rewarding travel experience filled with the human connection that is slowly becoming a thing of the past with the world of customer service being more and more digitized by AI.
Not to mention, when you’re not spending half your vacation on a bus, train, or car, you have more time to actually enjoy your accommodations and the amenities that come with it.
As Travel Planners, This Is What We Look At When Picking Where to Stay
After many years of trial and error staying in hotels across Italy, we’ve learned a thing or two about what to look for to find the best accommodations for a fair price.
If you’re planning a trip on your own, we’ll pass on some of our knowledge to you. But, if you don’t have the time, the knowledge, or the desire to do all the planning for your Italian vacation, that’s where we come in to make things easy. We’ve already spent the hours personally vetting each and every hotel we choose for our tours—and here’s how we do it.
Location is Key
There is perhaps no larger factor in your overall experience than the location of your accommodations. Where you walk out the door each morning establishes a sense of place—you’ll hear the church bells tolling, see the morning bustle in the piazza, smell the fresh espresso in the morning, see umbrella pines, endless olive groves, and know you’re in Italy.
When choosing accommodations, proximity to the things you actually want to do is paramount to the day-to-day experience. Centrally located accommodations offer you proximity to cultural landmarks, local attractions, and breathtaking scenery, which means you’ll have more time to experience and spend less time commuting.
When we first built our curated tours of Italy, there was one thing we knew we needed: a centralized location where guests would only have to unpack once. Too many first-time Italy travelers make the mistake of attempting to do it all: two days in Rome, two days in Florence, two days in Venice, and so on until you’re so exhausted from packing and unpacking you’re ready to just get home by the end of it.
On our tours, the accommodations are chosen based on the strategic proximity to the UNESCO sites, natural history, culinary activities, and hidden villages you’ll visit with us, making for easy exploration and generally no more than a couple of hours total in the car for the entire day—and keep in mind we include the private transportation.
Boutique Hospitality
While booking an AirBnb may feel like your best bet for an experience authentic to the region, the accommodations don’t typically come with the service or hospitality that a hotel would. In addition to frequently contributing to the negative effects of overtourism. Airbnbs all too often have driven the prices of rent up so high that many locals in cities like Rome, Florence, Venice and Milan have been driven outside of the historic center.
But, there is a happy medium we’ve found: boutique hotels that remain authentic to the region, locally owned and operated, reflecting all of the unique personality and charm, while still offering excellent service. When you choose a small boutique hotel, you get the best of both worlds!
Personalized Experiences
On the same note, booking boutique hotels that are locally-owned provide the opportunity for unique, authentic interactions you won’t get anywhere else.
Simply by choosing local-owned and operated accommodations in lesser-known locations, you are helping to ease the effects of over-tourism and help passionate locals to revive the regions they call home. You can vacation feeling good about where your dollar is going: back into the community, rather than to a giant corporation.
Our tours are meant to feel like a true immersion into the culture, not simply an itinerary—that’s exactly why we carefully select our accommodations and our activities to partner with local small businesses, providing you with a personalized experience you’ll never forget.
Comfort & Relaxation
Although often overlooked, the amenities should absolutely be a consideration in where you stay. Those small, luxury touches can take your trip from a vacation to a true escape, where you have the opportunity to unwind after a busy day exploring.
From gyms, spas and wellness facilities to scenic views, the overall experience matters when you’re making a place your home for more than a couple of days—which is why the accommodations on our tours have access to amenities like gyms, pools, spas, and of course, gorgeous scenery just outside your window. Whether it be a beautiful town square or stunning garden where you can relax by the pool, each hotel is a representation of the region’s history and unique landscape.
A Regional Breakdown of Our Handpicked Stays
Your accommodations should help you to experience the best of a region, offering cultural and culinary immersion. If you’ve ever wanted to be an Italian for a week, the handpicked stays on each of our tours will help you to accomplish that goal!
Veneto
As the largest wine-producing region in Italy, any stay in Veneto should be near the vineyards! Agriculture and wine production make Veneto a top location for agriturismo as well, and the diverse landscape means there’s something for every food and wine lover.
When you join us on Northern Italian Delights, you’ll stay in a four-star (actually!) boutique hotel in the city center of Castelfranco Veneto, a charming and historic city with a well-preserved medieval citadel.
You’ll have fabulous shops, quaint cafes, top restaurants, and artisan gelateries right outside your doorstep—all the amenities you need, including a gym inside your hotel. You’ll even have the chance to experience a favorite Italian pastime for yourself: the weekly outdoor market!
We chose the boutique hotel for the proximity to the historic town square steeped in Old World charm, but we chose the location of Castelfranco Veneto for its convenient location, close enough for day trips into the Prosecco Hills, where you’ll see the Palladian Villas, a UNESCO Heritage Site, and taste organic, artisanal cheese with a glass of DOCG Prosecco.
You’re also a one-hour train ride away from Venice and the Venetian Lagoon for an exploration off the tourist path on the secret islands.
Le Marche & Abruzzo
If you’re looking for Italy’s next Tuscany, look no further than the Le Marche region. Home to many of Italy’s Most Beautiful Medieval Villages, pristine coastlines, and award-winning wineries, you need a homebase that reflects all the charm of this best-kept-secret region.
And that’s exactly what you’ll find on Italy’s Epicurean Journey at your four-star boutique hotel in our hometown, the City of One Hundred Towers, Ascoli Piceno!
Your quaint accommodations with spa amenities are just steps away from one of Italy’s most beautiful town squares and one of Italy’s 150 historic cafes, where you’ll have plenty of time to shop and try out the local cuisine, of course with personalized recommendations from real locals.
Ascoli Piceno is also the perfect home base for our exploration of the neighboring Abruzzo region, where you’ll visit Italy’s largest medieval fortress and experience the top slow-food restaurant amongst the vines of Montepulciano d’Abruzzo grapes. You’ll feel just as at home in Ascoli Piceno as we do by the end of your time with us on Italy’s Epicurean Journey!
Puglia
You’ll find your fix of Vitamin Sea on the heel of Italy’s proverbial boot in the gorgeous coastal region of Puglia, which also produces around 40% of Italy’s olive oil.
Your Passport to Puglia awaits, where you’ll stay in luxury, five-star accommodations in the Valle d’Itria, famous for the Trulli Houses! It’s the perfect blend of luxury and cultural immersion.
Your hotel not only has two restaurants on site (including a Michelin star restaurant with a female chef at its helm), with other dining establishments within walking distance and is also just a quick taxi ride away from the local dining scene in town, which you’ll actually have enough down time to experience for yourself. You’ll also have access to all the amenities you need on a coastal vacation: a relaxing spa, a swimming pool, a gym, and even one of Italy’s Largest Organic Wine Cellars on site. While being just outside of the historic center allowing you to enjoy the peace and tranquility of the beauty of Puglia’s countryside.
Umbria
One of the few landlocked regions of Italy, Umbria otherwise known as the “Green Heart of Italy,” is a region untouched by tourism compared to its neighboring region of Tuscany. Umbria is a place where you can still experience the real Italy. If you’ve ever wanted to stroll through medieval towns frozen in time, complete with grand cathedrals and charming piazzas, on a backdrop of rolling vineyards, this is the region for you.
When you join us on Italy Uncorked, your accommodations are just an easy fifteen minutes walk from Gubbio’s historic center, one of the most romantic cities in the world where the original Romeo and Juliet was filmed! Complete with a swimming pool and spa/gym amenities, this four-star small boutique luxury hotel was once a 17th century monastery. With proximity to the city center, this hotel is perfect for ending off your free evenings on tour with some of Umbria’s best food and wine. It’s also where we’ll spend our first evening on tour together and get to gather around the Italian table for a beautiful meal filled with local Umbrian ingredients.
With Small Group Italy Tours, You Don’t Have to Worry About Where to Stay
Finding a place to stay is one of the most stressful parts of planning any vacation, there’s no doubt about that. Particularly when you don’t know the area and you don’t have somebody on the inside you trust to guide you or let you know what to avoid!
Arriving in Italy for the first time (or your tenth!) should be a magical experience, but booking your own accommodations and ultimately not knowing what you’re getting into can ruin the moment. When you book a small group tour, where every aspect of your trip has already been carefully selected and vetted by two locals, you’ll be able to leave your stress at the airport gate knowing that your accommodations have not only been selected for amenities but strategic locations so you don’t spend your entire vacation in transit from point A to B.
Intimate and Exclusive Access
Booking a large group tour will keep you stuck as a tourist in accommodations that can accommodate larger groups. Boutique hotels with only a couple dozen rooms simply aren’t able to take large booking requests, which prevents you from supporting the small, family-owned and operated businesses that keep Italy’s hidden regions alive.
When you choose a small group tour, you’ll have intimate and exclusive access to local culture you simply can’t get anywhere else when traveling with big-box touring companies.
No Need to Plan; We’ve Done It For You
When you DIY your trip, it doesn’t end at booking the accommodations. On your own, it can seem like every moment requires pre-planning, which doesn’t leave a lot of space for the serendipitous, spontaneous moments that make your trip memorable.
We’ve got your back when you tour with us: logistics are pre-arranged for a seamless, worry-free stay, down to the tips for drivers, restaurants, and guides, as well as entry fees to monuments. And, we’ll pick you up from the airport and drop you off for a seamless entry and exit—all private transportation with your small group, so no need to worry about navigating public transportation or taxis.
There’s no limitations on what you can do based on the transportation available to you. We’re taking you to the sides of Italy that the trains don’t reach, which the majority of travelers will never get to see. We personally inspected everything so you can soak up every ounce of relaxation and the perfect amount of sightseeing and activities resulting in the most rewarding Italian vacation that will leave you wanting to book after trip with us. Because it’s just that easy and stress-free that you want to come back again and again.
Ready to Explore the Real Italy, Travel Planner Style?
Typically, your travel planner doesn’t go on vacation with you—but we do! If you’re ready to explore the real Italy, with the experts in your back pocket the entire time for pro-tips and recommendations, booking a small-group tour is the way to go.
We personally vet each and every aspect of our tours, and if it doesn’t get our stamp of approval, it won’t be on your Italian vacation! Not only will you save time planning, but you’ll maximize your time in Italy and spend your vacation actually relaxing, enjoying, and soaking in the pace of local life, which is every traveler’s secret dream.
Your accommodations are chosen taking multiple factors into account, including location, distance from tour activities, amenities, hospitality, and giving back to the local community by supporting small businesses. Most importantly, you’ll feel like an honored guest instead of just another number.
We want to match you with your perfect tour! Take the quiz to find your Italian Traveler Personality and get matched in just sixty seconds with your dream Italian vacation.
