We spend most of 2025 traveling through Italy checking out the best tours for next summer. Families thinking of a 2026 trip to Italy for summer vacation may want to consider the following all-inclusive summer Italy tours.
Summer is a popular time for people from all over to tour Italy. The cities such as Rome, Florence, and Venice are crowded with foreigners on holiday in Italy. The Italian beaches are crowded with local Italians and northern Europeans looking for surf, sun, and fun. The small towns such as the very popular ones in Tuscany and Umbria have a full schedule of summer festivals.
Throngs of visitors crowd the tiny towns for the weekend festivals. Therefore, it is often easiest when planning a summer family vacation to Italy to consider joining an all-inclusive Italy tour. The itinerary is already thought through. Travel and accommodations are set. And you’ll avoid potential pitfalls that may derail the best planned Italy summer family vacation.
Check out these all-inclusive summer tour packages for your family to visit Italy during summer 2026.
The Great Cities: Rome, Florence, Venice Summer Tour Packages
This tour includes Italy’s great cities Rome, Florence, Venice. Enjoy three nights in each city.
For those wanting a slow paced tour and an authentic taste of Italian life this is the tour. The pace allows for enjoying each city and its rythm from morning, through the afternoon and into the evening.
Excursions include visitng Assisi, Pisa and Bologna. There is optional tour to Pompeii.
Price includes escorted tours of the primary sightseeing highlights. For more information click classic Rome, Florence, Venice tour.
For more Rome, Florence and Venice tours click here.
Northern Italy Summer Tour Packages
With the 2026 Winter Olympics in northern Italy this area is going to be vey popular. Many travelers aren’t familiar with the area’s beauty will be drawn to explore northern Italy tour packages.
Our two favorite Northern Italy tours for summer 2026 are the following:
This escorted tour travels round trip from Milan. It includes the Dolomites area including Bolzano and Cortina, both areas where Olympic skiing will take place. It then travels down to Venice before returning to Venice. This is a first class tour of Northern Italy’s Olympic areas.
This Italy summer tour package may be renamed the “jetsetters Italy summer vacation package” with the northern Italy highlights Tuscany and the Italian Riviera on the itinerary.
Tuscany and the Italian Riviera are loved by all who visit. Their natural beauty coupled with culinary traditions make these two areas the perfect destination for a family summer vacation to Italy.
For more information about the Tuscany and Italian Riviera summer tour departures click here.
Southern Italy is the quintessential vacation destination. And this tour brings you to the best beaches in Southern Italy.
This summer vacation package explores the regions of Campania and Puglia.
Campania was the summer playground of the ancient Romans. And when you arrive you will fully understand. The area is built around the main attractions; the Bay of Naples, Pompeii and the Amalfi Coast.
Puglia’s charming towns and beautiful coast are perfect for a low key, causal summer vacation. Enjoy the beaches by day and the towns by night. You will fall in love with Puglia’s towns.
With summer weekends come festivals that highlight the cultural heritage of Tuscany’s and Umbria’s charming towns. This small group tour is a fabulous way to jet off on a family summer Italy tour of these two very popular regions.
The tour ends with a night in Rome. For more information about summer tour departures to Tuscany and Umbria click here.
Luxury Travel Advisor & Co-Founder of ItalianTourism.us
Lorena Basualdo is a travel specialist and Italy tour expert with firsthand experience designing and leading immersive travel experiences across Italy. Their work focuses on helping travelers go beyond tourist highlights and navigate Italy with confidence, cultural insight, and practical expertise.
👉 View full author profile, media features & articles by Lorena Basualdo.
To avoid Venice crowds, plan your trip to Venice off season as the ItalianTourism.us team did this past winter. The spot where this photo was taken would typically be inaccessible during spring, summer and fall. Here we are with the Venice to ourselves.
Expert Advice from the Italy Specialists at ItalianTourism.us
By Lorena Basualdo, last updated January 1, 2026
Planning a vacation to Italy in 2026 can feel overwhelming, with so many destinations, attractions, and travel options to consider. Backed by our 15+ years of experience designing Italy vacations, and our most recent experience in 2024, 2025, and into 2026, these 10 expert tips reflect how we are advising our travelers to plan smarter for 2026 and into 2027 — helping you avoid common pitfalls and create a memorable, stress-free Italian journey.
While most travelers are planning Italy trips for 2026, these expert tips also apply to early planners looking ahead to 2027, especially as demand remains high.
Whether you plan to travel independently, join an escorted tour, or combine both approaches, these insights from ItalianTourism.us cover everything from timing and accommodations to sightseeing, food, and cultural experiences — ensuring your 2026 Italy trip is seamless and enjoyable.
With demand remaining high and most travelers now planning 9–12 months in advance, careful planning is more important than ever.
Why trust our advice?
The team at ItalianTourism.us plans Italy vacations every day — from escorted tours to custom itineraries — working directly with licensed local guides, hotels, and regional partners throughout Italy. The insights below reflect real-world planning decisions, firsthand travel experience across multiple regions and seasons, and feedback from travelers planning Italy trips in 2025–2026 — not generic travel advice.
1. Start Planning Earlier Than You Think
Italy remains one of the world’s most sought-after travel destinations. Flights, centrally located hotels, licensed local guides, and timed-entry tickets to major attractions often sell out well in advance.
For 2026 travel, planning a vacation to Italy 9–12 months ahead is essential. Waiting too long can limit your options, increase costs, and add unnecessary stress.
When we were making bookings late into 2025 for the second half of the year we found preferred hotels sold out. And the same for the main attactions. We found tickets unavailable, of if available, at undesireable times.
At popular hotels in Rome and Florence, rooms for peak 2026 dates are already 70% booked, highlighting the need to plan early.
Pro Tip: For escorted tours and centrally located hotels, availability often tightens first in Rome, Florence, and Venice — even before airfare pricing peaks.
Why escorted tours help: Escorted programs secure hotels, transportation, and sightseeing early, taking the guesswork out of planning and ensuring a smoother, more relaxed experience.
Based on our 2024 and 2025 Italy vacation planning, we found that the planning process beaks down into the following timeline:
18 Months Out: Researching regions.
12 months Out: Booking escorted tour packages.
10 Months Out: Booking flights.
6 Months Out: Securing private guides when traveling independently.
2. Choose the Right Time of Year
The ItalianTourism.us team swimming in Polignano a Mare in late September. The weather was beautiful. We swam at many Puglia beaches in late September and early October. The Adriatic sea was still warm and salty.
Timing can dramatically affect your Italy experience.
Best overall months: April–June and September–October
More challenging periods: Peak summer heat and major holiday weeks
When we plan trips for our travelers we factor in weather, crowd levels, and seasonal events when designing itineraries — an increasingly valuable advantage as Italy continues to manage visitor access in busy destinations.
Traveling in shoulder seasons also helps avoid crowds at top attractions, making for a calmer, more immersive experience.
For example, we’ve intentionally planned visits to Venice during the Christmas season, when crowds are lighter and the city feels more intimate. Cooler weather and fewer visitors allow travelers to experience Venice without the usual congestion.
We also take into account traveler’s interests so we can suggest authentic seasonal experiences. For example, Italy’s regions celebrate festivals year-round. Planning your trip to coincide with a local festival can enhance the experience and provide a more authentic glimpse of Italian culture.
Pro Tip: Shoulder season travel not only reduces crowds, but often allows guides more flexibility with timing and pacing — a noticeable difference at major attractions. If you don’t mind shorter days and cool weather, winter is a viable season to visit Venice, Florence, and Rome. During winter crowds are significantly lighter and hotel rates are more competitive.
3. Decide: Independent Travel, Escorted Tour, or a Hybrid Approach
Italy can be traveled independently, but it can also be complex — especially for first-time visitors.
Independent travel: Offers flexibility but requires detailed planning
Escorted Italy tours: Provide structure, expert guidance, and seamless logistics
Hybrid trips: Combine escorted touring with leisure stays and free time
We our finding that for 2026 many of our travelers are choosing a hybrid approach — escorted touring in major cities like Rome and Florence, followed by leisure time in regions such as Tuscany, the Amalfi Coast, or the Italian Lakes.
For example, spend 3 days on an escorted tour in Florence with a licensed guide, then 2 days independently exploring the Tuscan countryside at your own pace.
Our travelers are also adding a cruise or extension. The benefits of all travel coordinated through one trusted advisor cannot be overstated.
Pro Tip: Many first-time travelers underestimate transfer complexity between regions. A hybrid approach reduces logistical stress while preserving flexibility.
Pro Tip: When you coordinate all your planning with one advisor be sure to have the advisor have your travel insurance cover the entire trip, start to finish, all pieces. This will save money. And more importantly there will be no conflict between providers regarding coverage if a claim has to be filed.
For those who prefer everything arranged from start to finish, with a tour director allways on call, exploring all-inclusive Italy vacation options can be an excellent solution.
4. Focus on Fewer Destinations — Travel Slower
One of the strongest trends shaping Italy travel is slow travel.
Rather than rushing through multiple cities:
Choose a few key regions
Stay longer in each destination
Allow time to experience daily Italian life
Well-designed escorted tours reflect this philosophy, minimizing hotel changes while still covering Italy’s most important highlights. Many of our small-group Italy tours are intentionally designed with a more relaxed pace.
Slower travel also gives you time to interact with locals, discover hidden gems, and appreciate regional culinary traditions. You may also find yourself a regular at the evening passagiatta.
Pro Tip: When traveling independently consider longer stays in one place with day trips to nearby towns. Alternatively, travel one direction to avoid wasting time backtracking. Traveling independently by train means travel days are not sightseeing days.
5. Reserve Major Attractions Well in Advance
Italy’s most iconic sights now require advance reservations, including:
For instance, skip-the-line access at the Vatican Museums can save up to 2 hours — time better spent wandering piazzas or enjoying local cafes.
Escorted tours typically include pre-reserved skip-the-line entry and licensed local guides, ensuring access while providing historical context and storytelling you won’t get on your own.
The tickets on the official websites become available typically within 90 days. We have found it very hard to secure tickets for the Last Supper on its official website. Therefore, to guarantee you are not disappointed we suggest booking Last Supper tickets through a local tour operator.
During the Jubilee the Vatican Museum Tickets were tight. Into 2026 and 2027 we expect this demand to sustain.
Pro Tip: Schedule visits to crowded attractions with the first entry of the day. Timed entry tickets can sell out months in advance, especially for early morning slots, which tend to be the least crowded.
6. Make Food and Wine Central to Your Italy Experience
Lorena Basualdo in Rome cooking class. Plan your cooking class based on the regional food you are interested. For example in Rome the pasta class may be Cacio e Pepe or Amatriciana, while in Bologna it would be Bolognese.
Italian cuisine is officially recognized as cultural heritage, and food remains one of the most powerful ways to understand the country.
Consider incorporating:
Wine tastings in Tuscany or Piedmont
Cooking classes
Farm-to-table meals
Regional specialties unique to each destination
Many escorted tours thoughtfully include culinary experiences, helping travelers avoid tourist traps while enjoying authentic local flavors.
Choosing culinary experiences curated by locals ensures you taste authentic dishes rather than tourist-standard meals.
Cooking classes, for example, are social, hands-on experiences where you meet like-minded travelers while learning to prepare dishes such as pizza, ravioli, fettuccine, gelato, and tiramisu — followed by enjoying the meal you’ve created together.
Pro Tip: When you schedule a cooking class keep in mind the cuisine of the region and stick to learning that. For example, don’t go to Emilia Romagna to learn Cacio e Pepe. And don’t go to Rome to learn Bolognese…
7. Use Trains — But Know When a Coach or Driver Is Better
Italy’s high-speed rail system is excellent between major cities like Rome, Florence, Venice, and Milan.
However:
Hill towns
Wine regions
Rural countryside
…are often better explored by private coach, rental car, or with a driver. Escorted tours simplify these transitions — no luggage transfers, station navigation, or worries about missed connections.
For hill towns like Montepulciano or Montalcino, private transfers or a driver are far more efficient than relying on regional trains.
We recently spend two weeks in Puglia. We rented a car in order to visit all the towns at our leisure. There is no easy and efficient way to explore Puglia by train.
8. Understand Crowd Management in Italy for 2026
Take a sunrise walk to Rome’s monuments if you want a photo like this one of the ItalianTourism.us team without the crowds.
Italy continues to manage overtourism with timed entries, capacity limits, and regulated access in major destinations.
What this means for travelers: Poor planning can result in long waits or missed experiences.
Escorted tours adapt easily, using pre-reserved tickets, alternate sightseeing times, and expert guides who know how to navigate busy periods.
Experienced guides often schedule visits to major sites early morning or late afternoon to avoid peak crowds — something most travelers don’t know.
Even the Trevi Fountain now requires a timed entry to get close. And even with that you won’t be able to take a picture like the one here.
Pro Tip: To get a photo like this one without a crowd at a popular Rome monument like the Trevi Fountain, Spanish Steps, Pantheon, Four Rivers Fountain in Piazza Navona, etc. set your alarm and go out for a sunrise walk around.
9. Build in Free Time — Even on a Tour
Today’s escorted tours are not rushed or rigid.
Look for itineraries that include:
Free afternoons
Optional excursions
Leisure stays in scenic destinations
This balance allows you to enjoy expert guidance while still having time to wander piazzas, shop local markets, or enjoy a long Italian lunch.
Escorted tours aren’t about giving up freedom — they’re about traveling with confidence.
Pro Tip: Have ideas, or even reservations, for where you’ll eat before you go. Avoiding bad meals and rushed decisions will reduce stress and result in a more fulfilling vacation when you avoid bad meals.
Pro Tip: Free time isn’t unstructured time — it’s intentional space to absorb Italy at your own pace.
10. Work With Specialists Who Know Italy
Italy rewards experience. Small planning mistakes — such as poorly located hotels, inefficient routing, or unrealistic pacing — can impact the entire trip.
Working with Italy specialists provides:
Carefully vetted accommodations
Experienced tour directors and licensed local guides
Well-balanced itineraries
One point of contact throughout the planning process
For many travelers, this results in less stress, better value, and a richer overall experience.
Pro Tip: Italy-focused advisors recognize small planning issues before they become costly mistakes during travel.
Final Thought
Planning an Italy vacation is about more than checking off famous sights — it’s about understanding how Italy works.
At ItalianTourism.us, our escorted tours and custom itineraries are designed to remove the guesswork and help you travel confidently and comfortably.
If you’re beginning to plan your 2026 Italy vacation, start by exploring your options with Italy specialists who know how to make every detail work together.
Frequently Asked Questions: Planning a Vacation to Italy in 2026
** How far in advance should I book Italy tours for 2026?
For travel in 2026, we recommend planning your Italy vacation 9–12 months in advance to secure preferred hotels, licensed guides, and timed-entry access to popular attractions.
** Are escorted Italy tours a good option for first-time visitors to Italy?
Yes. Escorted tours provide expert planning, local insight, and seamless logistics — especially helpful for first-time travelers navigating busy cities and complex regions.
** Can I combine an escorted tour with free time when planning a vacation to Italy?
Absolutely. Many travelers choose escorted touring with added free days or leisure extensions, providing a balanced experience of guided exploration and personal discovery.
** What is the best way to plan a vacation to Italy for the first time?
First-time travelers should begin by identifying priority destinations and travel style, then plan 9–12 months ahead. Escorted tours or professionally designed itineraries help avoid common mistakes related to timing, routing, hotel locations, and attraction access.
** Do escorted tours include skip-the-line access to major attractions in Italy?
Most escorted tours include pre-reserved entry and licensed local guides at key attractions such as the Colosseum, Vatican Museums, Uffizi Gallery, and Pompeii, saving time and enhancing your experience.
** What is the best month to visit Italy in 2026?
For the best combination of pleasant weather and manageable crowds, we recommend visiting between April–June or September–October.
Luxury Travel Advisor & Co-Founder of ItalianTourism.us
Lorena Basualdo is a travel specialist and Italy tour expert with firsthand experience designing and leading immersive travel experiences across Italy. Their work focuses on helping travelers go beyond tourist highlights and navigate Italy with confidence, cultural insight, and practical expertise.
👉 View full author profile, media features & articles by Lorena Basualdo.
Book your 2021 Italy vacation with airfare now. Take advantage of the lowest Italy airfares we’ve seen for 2021. Combine this low airfare with a hotel in Italy and you have the lowest priced Italy vacations with airfare 2021.
Vacation to Italy airfare starts at $663 for Autumn, Winter and Spring 2021 trips to Venice from New York. The least expensive Italy vacation departure dates for round trip Venice airfare from New York by 2021 month are below:
New York to Venice Italy Airfares by Month
November 20-27 – $680 per person
December 28-January 2 – $676 per person
January 14, 2014 – $664 per person
February 3, 10, or 24 – $664 per person
March 1-26, 2014 – $676 to $694
April 1-30, 2014 – $681 to $694 per person
May 1-31, 2014 – $683 to $1,000 per person
June 1-30, 2014 – $923-$1,025 per person
July 1-31, 2014 – $972 – $1,172 per person
August 1-31, 2014 – $850-$1,008 per person
September 1-30, 2014 – $
2021 Italy airfare to Rome from other popular United States cities:
Atlanta – $805
Austin – $973
Baltimore – $947
Boston – $844+
Charlotte – $948+
Chicago – $677+
Dallas – $954+
No One Beats Our Italy Vacation Prices!
Get the best price on your Italy vacation. Simply fill out this form or call us now at 800-227-1577.
Prices are correct as of publishing this article September 24, 2020. Air availability is very limited because of these great prices. These are easily the best prices we have seen for 2021 Italy vacations. They may change at anytime.
Winter Italy vacations are often less expensive because of the lower winter airfares. This sale includes great deals for late Spring and Summer 2022 travel to Italy. Popular Italy tour months May 2022, June 2022, July 2022, and August 2022 are attractive with this Italy airfare sale.
When in Venice you may consider the following hotels. ItalianTourism.us guarantees the lowest rate on all Italy hotels. And be sure to check out our Venice day tours.
To book your 2022 Italy vacation submit form or call us at 800-227-1577 for rates, special requests, and other Italy vacation needs.
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