Planning your dream trip to Italy can be overwhelming. Between choosing destinations, booking accommodations, and figuring out transportation, it’s easy to get lost in all the itty bitty details. That’s why traveling with a small group tour is one of the best ways to explore Italy stress-free while still enjoying an authentic, immersive experience! Plus the added camaraderie of like-minded individuals.
Whether you’re looking for custom Italy tours tailored to your interests or need an Italy trip planner (who’s actually a local) to handle the logistics from the inside, the right small group tour in Italy can transform your trip into something unforgettable.
But with so many options out there, how do you choose the best style of tour for you?
In this guide, we’ll walk you through what makes small group travel in Italy unique, key factors to consider when selecting a tour, and common mistakes to avoid—so you can truly experience Italy like a local, not just a tourist!
What Makes Small Group Travel In Italy So Unique?
When we talk about small-group travel in Italy, we’re talking about trading in the hot, sweaty 50-person bus tours that only hit all the bucket-list “must see” landmarks for an authentic travel experience that gives you access to hidden gems and real connection with your guides, local family-run businesses, and fellow travelers! We’re also not talking about tours that consider the average group size of 25 to be small group travel – psst… that is a big bus tour in our books. Big groups like this don’t offer the chance to connect with the local culture or gain insights which is why we consider small groups to be a maximum of 12 guests and a maximum of 6 guests to one tour host.
The reality is that most travelers will never get to see the real Italy. 70% of visitors see 1% of Italy—imagine all the authentic food and wine they’re missing out on! But when you choose the right small group tour, you don’t have to be a part of that majority.
You can eat authentic food from recipes passed down for generations, taste wine straight from the source overlooking sprawling vineyards, and connect with real Italian culture..
Stress Free Planning
Sure, you could try to Google Maps and TripAdvisor your way to an authentic Italian vacation. But, even beyond the time all that planning will take away from you actually exploring the real Italy, the stress & headache of figuring out the logistics alone will leave you feeling vacation burnout before you’ve even boarded your flight! And not to mention those tripadvisor reviews are not necessarily from the experts or even people who have visited those locations which is why Italy has been trying to crackdown on fake reviews and has proposed people, at the very least, having to prove they ate at those restaurants, wineries, etc….
Once you understand that scouring and scrolling the Internet for the hidden gems isn’t actually your ticket to experiencing the real Italy, planning gets a lot easier! Small-group tours, like ours, are curated and customized to remove the travel stress, local lingo, and logistical nightmares you might experience otherwise. Especially with two local hosts on your side who knows the ropes, the most stressful part of your trip is packing your bags and boarding the plane. We can help with that, too—don’t forget to grab your free packing list & tips!
Intimacy & Connection
There’s one key difference between travel and tourism: Travel is about immersing yourself in a culture that is different from your own and making real connections, while tourism is about the destination, even if it’s at the expense of the local community. Tourists try to see it all and spend too little time in one place, but travelers take the time to connect and soak in the nuances of everyday life. Travelers want a more fulfilling vacation which is why they come for the experience and focus less on bucket-list places and more on bucket-lists experiences.
This is one of the biggest mistakes first-time travelers make on their first trip to Italy—read the other 8 mistakes here!
With small group tours, you’ll naturally have closer interactions with your guides, your local tour hosts, small local business owners, and fellow travelers, enhancing your cultural immersion and conviviality which is essential to getting a feel for everyday Italian life. Not only will you feel like you’re making a positive impact on the communities you visit, you could even create lasting friendships with like-minded people. Which is why numerous of our past guests return on our trips with friends they’ve made on our tours. Even our solo travellers have made friends with couples and have returned together, because when you travel with like-minded food and wine lovers like yourself it’s easy to have a good time and make genuine connections on our tours.
Your Italian vacation will be made exponentially better by prioritizing culture & connection over destinations, and our guests are the proof. You don’t want to feel like you’re a student on a high school field trip, you want to feel like you’re traveling among friends.
Take it from Kimberly, who said she made “lifelong friends” while on tour with us! It’s the reason our guests come back again and again.
Worried about traveling solo? A small-group tour is the perfect solution for you!
Access to Hidden Gems
Finding the hidden gems of Italy on your own is almost impossible. Because if they’ve blown up on Instagram they’re not so hidden after all. That’s exactly the reason most tourists default to the easiest option—Rome, Florence, Tuscany, and all the destinations you’ve probably heard of before.
Curated small group tours have exclusive access to experiences that your average tourist doesn’t because if you choose the right company that designs all their experiences and itineraries from scratch, you’ll soon discover they have deep connections in their local community. And, by skipping the overcrowded sites, you’ll help to ease the effects of over-tourism on Italy’s most popular cities and historic landmarks. Making it a win-win for both you and the local communities you’re visiting.
If you want to visit Italy’s Largest Medieval fortress, sip your morning espresso at Ernest Hemingway’s favorite cafe, forage for truffles with Jamie Oliver’s truffle hunter, or sip wine made at multi-generational wineries, a small-group tour is the only way to go!
Immersive & Authentic Experiences
You don’t have time for deep cultural connections when you’re stressing about learning the local lingo or logistics of another country all on your own!
Here’s an open secret you need to know: Local Italians aren’t at the Colosseum or the Trevi Fountain ready to connect with travelers like you. You would never stand at the Empire State Building waiting around to make small chat and make new friends, it’s no different when you’re visiting Italy’s most tourist-trodden landmarks. By prioritizing the destination over the experience, you miss the opportunity for an Italian vacation that opens your eyes to perspectives different from your own.
When you travel with a small group tour like ours, you’ll come face-to-face with people that love and live in our territory! We have personal relationships with every local chef, farmer, and winemaker you’ll come into contact with. Not only are you getting an immersive and authentic experience, you’re helping locals, like our Co-founder Giovanni who hosts every single tour you travel with us on, return home to revive Italy’s hidden regions and celebrate Italian cuisine that connects you to the local culture.
What to Consider When Choosing a Small Group Custom Italy Tour
Now that you know the value of choosing a small group tour of Italy over the big-box bus tours of the bucket list destinations, the next step is to choose the right small group tour for you and your travel needs.
Not all small group tours are created equal—that’s why it’s important to put in the time to research and vet the people you’ll be entrusting your Italian vacation to!
Expert or Generalist?
One key consideration that most travelers miss is whether they are booking with a true expert or a generalist. Many large touring companies operate in multiple countries, making them generalists rather than true experts in any one destination. While these companies may offer convenient itineraries with all of the “bucket list” destinations, they often lack the deep-rooted knowledge that transforms a trip from a run-of-the-mill tourist experience to extraordinarily immersive.
By choosing a touring company that exclusively focuses on Italy, especially locals like us, you’re ensuring that your guides are true experts, and not just in Italy as a whole, but in the specific regions you’ll be visiting. Specialists have spent years building relationships with local artisans, chefs, and winemakers, meaning your experience will be far more authentic and immersive than any big box touring company can offer. Instead of a surface-level overview fraught with tourist attractions, you’ll gain insider access to hidden gems, small businesses, family homes and cultural experiences that most tourists would never find on their own.
Research Reviews & Testimonials
When choosing a small group custom Italy tour, reading reviews and testimonials is one of the best ways to gauge the quality of a tour provider. A well-reviewed company should have consistent feedback highlighting excellent experiences, welcoming hosts, knowledgeable guides, and seamless logistics.
First, it’s important to look for reviews, not just ratings. Take the time to read detailed reviews that describe specific aspects of the trip—how engaging the guides were, whether the itinerary felt well-paced, and how the company handled unexpected situations. For example, you’ll find dozens of detailed reviews from verified guests of The Italian on Tour® here.
And, since small group travel is all about intimate, immersive experiences, look for reviews that highlight cultural connections, off-the-beaten-path destinations, and personal touches that made the trip special. Comments about local guides and/or tour hosts, boutique accommodations, the people they connected with and small business visits are great indicators of an authentic tour. Another green flag is reviewers who mention taking multiple trips with the same company, like many of our guests.
With that, you should also look for consistency—don’t just rely on a single source for reviews. Check multiple platforms like Google Reviews, TripAdvisor, and even social media. If a company has glowing reviews on their website but mixed feedback elsewhere, that may be a red flag. Look for photo and video reviews to help you visualize what the trip may be like and ensure the tour aligns with your travel expectations and style.
By thoroughly researching reviews and testimonials, you’ll gain confidence in choosing a custom Italy tour that fits your travel style and ensures an unforgettable experience.
Compatibility with Your Travel Style
Choosing a tour that matches your travel preferences can make or break your trip. If you prefer a slower-paced itinerary with plenty of free time, but a company’s website and reviews frequently mention a packed schedule, that tour may not be the right fit for you.
From the pace of the itinerary to the types of activities included, choosing a tour that fits your preferences will make your trip to Italy much more enjoyable. Here’s what you need to consider:
Pace of the Tour
Do you prefer a packed schedule with multiple destinations, or would you rather settle into one region and explore at a more relaxed pace? Some custom Italy tours move from city to city every day, while others allow you to immerse yourself in a single area. Be sure to check the itinerary and consider whether it feels rushed or offers enough downtime for you to get a feel for the local culture. If you want to unpack once without the stress of train travel, our small group tours are the perfect pick for you.
Activity Level
Think about how active you want your trip to be. Some tours focus on leisurely walks through historic towns and scenic countryside, while others include hiking, biking, or more physically demanding activities. Look for descriptions that match your preferred level of activity so you’re not caught off guard. While keeping in mind if you want to truly experience Italy without the crowds the best way is often by exploring the local villages and cities on foot.
Free Time vs. Structured Itinerary
Some travelers love a well-planned itinerary where every detail is handled, while others prefer flexibility and time for independent exploration. If having free afternoons to wander charming Italian streets at your own pace sounds ideal, look for tours that balance structure with personal time. Our tours, for example, offer the perfect balance of both. See for yourself here!
By carefully considering these factors, you can select a custom Italy tour that complements your travel style and ensures a memorable and enjoyable experience!
We often see retirees make the mistake of choosing the wrong type of tour—click here to read the 7 biggest mistakes retirees make when planning a trip to Italy, and what to do instead!
Know What’s Included
Understanding exactly what’s included in a small group tour will help you to avoid being caught off guard when you arrive in Italy. Transparency about costs and inclusions ensures there are no surprises along the way! When deciding on a small group tour, it’s important to consider the style of accommodations, meals, transportation, and additional activities and fees that may be optional add-ons or extras. Other considerations include:
Meals
One of the biggest mistakes travelers make when selecting a tour is assuming that “all meals included” means high-quality, authentic dining experiences. In reality, many tours opt for convenience over quality, offering generic meals at tourist-heavy restaurants rather than showcasing the true flavors of Italy. If food and wine are a priority for your trip, it’s essential to consider not just how many meals are included, but where and what style of dining you’ll be experiencing.
Our tours, for example, are expertly crafted by discerning foodies, Chantelle and Giovanni, who have designed every itinerary around our own personal deep love for Italian cuisine and wine. This means no uninspired buffet lines or mass-produced menus with cookie-cutter choices for picky eaters. Instead, you’ll experience curated tasting menus that highlight regional specialities of each area we visit, dine at some of Italy’s Top Restaurants, and sip on award-winning wines from multi-generational vineyards. Wine and food are deeply intertwined in Italy and were here to show you the best each region has to offer!
Unlike big bus tours that prioritize serving the entire popular and logistics over experiences, we are dedicated to food and wine lovers and believe a meal should be the highlight of your day, not just a necessary stop on the well-trodden tourist trail. That’s why our guests return year after year, not just for incredible destinations, but for those unforgettable best-meal-of-your-life moments. In fact, many of our guests say the culinary experiences alone are worth the trip!
So, when choosing a trip, ask yourself the question: Do you want to be served the same generic pasta dish as every other tourist, or do you want to savor the taste of Italy as the local food and wine experts do?
Experiences
A destination is more than just its landscapes and landmarks—it’s the people who bring it to life! That’s why we believe that truly experiencing Italy means forming genuine connections with the locals who call it home. Whether it’s a winemaker sharing their family’s centuries old traditions or your local expert hosts like Chantelle and Giovanni sharing their personal stories, these interactions are what transforms your trip into something unforgettable.
Let’s face it, these moments are nearly impossible in large tour groups. You’re one of 25 (or more), trying to catch a few words as the guide speaks to the crowd, with little opportunity to ask questions, engage in meaningful conversations, or form a real connection. That’s exactly why we cap our small group tours at just 12 guests—so that you have the time and space to truly immerse yourself in the place you’re visiting.
With our intimate group size, you won’t just be listening from the back of a crowd like a high school field trip, you’ll be engaged in conversations, asking winemakers about their craft, and getting hands-on with unique experiences that are impossible for large groups to access. If you want more than just sightseeing, a small group tour customized around authentic experiences is the only way to go!
Group Size
The size of your group plays a significant role in the pricing of your tour and first and foremost your overall experience. Ideally, a small group travel experience should feel intimate and personal. Which is why we don’t believe an average group of 25 people should be considered small.
Many custom tours, like ours, cap their groups at 8-12 travelers to ensure more meaningful interactions with fellow travelers and guides, access to smaller, off-the-beaten-path locations that larger groups can’t visit, and a more relaxed and flexible atmosphere, avoiding the rushed feel of big tours.
When selecting a small group tour, check the maximum group size to ensure it is actually a small group tour or a tour company that defines “small group” as much larger which leaves you just being another number in a crowd of nameless tourists. Italian culture is about conviviality and having a small group size is truly conducive to embracing the local way of life which is why we limit our small group tours to just 12 guests. Learn more here about why we think small-group travel is the best way to experience Italy!
Timeline & Location
Would you rather immerse yourself in one region to two regions or move between cities every day? Some travelers think they need to cover multiple destinations in just one trip and end up coming home exhausted from checking off a bucket list. Only to realize upon their return home that slow travel is the best way to go because they never had the opportunity to truly connect with the people and the places they visited. This is why we’re big proponents of slow travel especially if you want a trip filled with lifelong memories. When selecting a tour, consider carefully the pace, regions covered, and the length of your stay.
Will you be changing locations daily, or does the itinerary allow time to explore? Is there too much travel time on a daily basis? Are you focusing on one or two regions, or is it a jammed packed unpacking and repacking trip across Italy? Will you be there long enough for a true cultural immersion?
Our tours, for example, range from 8-10 days and focus on one to two regions, the perfect sweet spot for travelers looking for a slower-paced experience that allows for deep cultural connections. Just the right amount of free time, interesting places, great food and wine plus time to fit in a massage and treat yourself, because it is your vacation after all.
Tour Focus
The best small group tours in Italy cater to specific interests, whether it’s food and wine, art, history, or outdoor adventures while keeping in mind that Italy is a country filled with millennial history that seeps its way into all aspects of Italian life. Opting for a specialized, locally crafted tour enhances your experience by connecting you with like-minded travelers and offering curated experiences that align with your passions.
If food and wine are a priority, look for tours that include visits to boutique wineries and local markets, offer hands-on experiences like cooking classes or olive oil tastings, and provide access to authentic, regional dining experiences including numerous curated tasting menu that showcase the cuisine alongside the local wine.
For history lovers, a tour with expert-led explorations of UNESCO sites and historic landmarks will be more rewarding. Or, if you’re both—travel with us for the perfect, curated balance between the two! Good food, wine, and a splash of history and unique sites to round out your Italy trip!
Expert Guidance
The quality of your guide or host can make or break your experience. Ideally, your guide or host should be someone who’s knowledgeable, passionate, and most importantly, has deep connections to the country. In fact, it’s important to know the difference between “guides” and “hosts” when choosing a tour of Italy.
In Italy, tour guides are highly trained professionals who go through a certification process and earn a degree in their field. This is why guides are considered history experts in their specific region. Their primary focus is on history and factual storytelling, offering in-depth knowledge about historic landmarks to help you understand the cultural significance.
Hosts or leaders, on the other hand, is the person who accompanies you throughout your journey, ensuring that everything runs smoothly on the day-to-day, while also providing deep local insights into daily life, culture, food, and traditions. They are your point of contact for everything, from logistics to local recommendations, and they create experiences that go beyond just sightseeing.
The best tours include people that are both local hosts and guides. Unlike some touring companies that bring in hosts from abroad, we actually live here and bring firsthand knowledge of Italian life to every aspect of the journey.
Before booking your trip, ensure you understand who’s leading the tour—are they true local experts or generalist tour leaders? Do you want a guide that will just take you to the destinations and rattle off facts, or one that will make you feel like their closest friends from the moment they greet you at the airport to your final goodbye?
If you chose the latter, we’re ready to plan your next trip! Learn more about Chantelle & Giovanni here.
Itinerary & Flexibility
Balancing structure with flexibility is key to a great tour experience. Some travelers prefer a packed schedule, while others want time to wander on their own. When choosing a tour, consider how structured the days are, any customization options that may be available, and the balance of guided vs. solo exploration time.
A great itinerary will give you the best of both worlds in allowing for spontaneity, but also having structure—which is exactly what you’ll get when you travel with us.
Social Interaction
Are you an extravert, fueled and energized by social interaction, or are you an introvert who needs time to recharge following a gathering? When choosing a small group tour, it’s essential for you to know this about yourself and choose accordingly!
When researching, consider carefully the accommodations, group dynamics, and meals/activities planned.
Will you be staying in a shared space or have your own room in a boutique hotel? Do you feel more comfortable blending into the crowd, or do you want to travel amongst friends in a smaller group that fosters close connections? Do you want to eat every meal together, or have the option to go out on your own?
The truth is, it’s going to be hard to find your people if you stick to big tours in popular, crowded destinations. Smaller groups with flexibility in terms of social interactions provide you with the opportunity to forge connections with people you actually like! We believe travelling with like-minded people is key to having a better Italian Vacation—read more here. Which is why our tours are specifically designed for the cultural food and wine lover who wants the perfect balance of planned activities and free time to explore.
Common Mistakes to Avoid When Choosing a Small Group Italy Tour
Planning your dream trip to Italy should be exciting, but with so many tour options out there, it’s easy to make mistakes that can impact your experience. Many travelers unknowingly book tours that don’t match their travel style, leading to a rushed, impersonal, or underwhelming trip.
To ensure you choose a small group tour that delivers the authentic and enriching experience you’re looking for, here are some of the most common mistakes to avoid:
Choosing Based on Price
It can be tempting to go for the most budget-friendly options, but when it comes to small-group tours, cheaper isn’t always better!
Low-cost tours often cut corners on things like transportation, which limits access to smaller towns and villages, accommodations, and packing in too many places. Consider not just the price, but the value of a well-curated tour with high-quality inclusions that make your trip unforgettable.
For example tours that have free time but leave you in the middle of nowhere at an agriturismo with no way to reach the closest town, will most likely be more affordable but you will end up feeling like a prisoner. On top of that you won’t get to take advantage of your allotted free time as you’ll be stuck in your room miles away from the closest services.
Booking with Large Groups that Lack Personalized Experiences:
One of the biggest benefits of small group travel is the personal touch. But, even tours that go up to 20-30 people can lead to limited interaction with your guide, less flexibility in the itinerary, and a rushed, touristy feel.
Book tours with groups of 8-12 people will ensure a relaxed, intimate trip where you can enjoy deeper conversations and interactions with locals! Plus most of Italy’s Top Restaurants can’t even service large groups, which means whenever you see groups for 20 plus people you automatically know that food is subpar.
Booking with companies that don’t have local roots and are running off affiliate pricing
Italy is best explored with people who truly know the culture, history, and hidden gems!
Many larger touring companies operate from abroad, relying on affiliate pricing and outsourcing guides, which can lead to generic, cookie-cutter itineraries, a lack of authentic experiences, and guides more focused on keeping schedules than sharing their insights.
Look for companies with deep local connections, whether they’re local or have strong ties to the communities they visit!
Overlooking itineraries that feel too rushed or rigid
Your Italy tour should strike the perfect balance between structure and flexibility.
Common pitfalls include an itinerary that changes cities everyday, meaning you’ll spend more time packing and traveling than actually experiencing Italy, or itineraries that leave too little time for spontaneous activities like relaxing at cafes or wandering through a charming piazza.
Well-designed tours should allow for a blend of planned activities and free time, ensuring you see the highlights while having space to enjoy the moment.
Avoiding these common mistakes will help you choose a tour that aligns with your expectations and travel style. When done right, a small group Italy tour isn’t just about sightseeing—it’s about immersing yourself in the culture, savoring every moment, and creating memories that last a lifetime.
Ready to Try Small Group Travel? Let Us Be Your Trip Planners!
Choosing the right small group tour can make all the difference between a standard, cookie-cutter trip of sightseeing and an unforgettable, culinary and culturally immersive journey.
With our carefully curated itineraries, you won’t have to worry about the logistics—we’ll handle everything for you, from boutique accommodations in the perfect locations and local guides to seamless transportation and exclusive experiences.
Our tours strike the perfect balance between structured activities and free time, allowing you to explore charming, off-the-beaten-path destinations while still making space for your own discoveries.
Whether you’re a food and wine enthusiast, a history buff, or someone who simply wants to experience Italy beyond the tourist hotspots, we customize each itinerary with care and connect you with the local communities reviving Italy’s hidden regions, ensuring a meaningful and immersive adventure for you.
Let us take the stress out of planning so you can focus on enjoying every moment. Your Italian dream trip starts here—are you ready to join us? Choose your itinerary to get started today!
