Italy 5-Day Tours and Trips
Discover the best 5-Day tours in Italy with Bookmundi. We offer a total of 30+ Italy 5-Day tours and itineraries with 130+ customer reviews.
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Select from 30+ tours
10 Best Italy Black Week Deals
Black Week exclusive deals on 5-Day tours in Italy — massive savings for a limited time only!
Curated by Alessandra Galassi
Italy travel expert at Bookmundi37% Off Today
Our 5-Day Tour offers a perfect blend of history, culture, and natural beauty. Start by exploring the vibrant streets of Naples before embarking on a scenic day trip to the stunning towns of Sorrento, Positano, and Amalfi. The next day, hop on a ferry to the beautiful island of Capri, where you can wander through charming streets, enjoy panoramic views from Augustus Gardens, and see the iconic Faraglioni rocks. Finally, step back in time with a guided tour of Pompeii’s ancient ruins, uncovering the fascinating history of this Roman city. With expert guides, unforgettable sights, and plenty of free time to explore, this tour is the perfect Italian getaway.
5 days
32% Off Today
Discover the best Unesco World Heritage Sites of Italy in this five-day guided tour. This tour starts in Rome, the capital of Italy, but begins in earnest in a beautiful hill town of Assisi, the birthplace of St Francis, one of the patron saints of Italy.
After touring the several attractions of the town we head to the city of Florence, the cradle of Renaissance, and check out the city's top landmarks, arts and architectures created by past masters.
Next, we will head to Bologna, Padua and Venice in northern Italy, soaking in their art, history and culture. We then travel to Tuscany, the region in central Italy known worldwide for its wine, before returning to Rome, where we end our tour.
5 days
22% Off Today
Discover the Sorrento peninsula and the isle of Capri on this four-day tour beginning and ending in Rome. Along the way, stop to absorb the history of Naples and jump back in time by visiting the ghostly excavations of Pompeii. The Sorrento peninsula is easily one of the country's most lavish and beautiful regions, ideal for relaxing and sightseeing alike. From there, Capri and its famed Blue Grotto are only a ferry ride away.
5 days
8% Off Today
Rome, Venice, and Florence headline the 'Classical Italy' trip—a 5-day sightseeing tour ideally suited for seniors seeking a taste of Italy’s best cities. With all logistics, hotels, and meals included, this group trip allows you to relax and enjoy the highlights stress-free. The real draw is the concise itinerary—offering maximum cultural impact in a short, easy-paced journey designed to delight mature travelers.
5 days
22% Off Today
Discover the best of Malta during this short self-drive tour! Walk through the streets of La Valletta, often referred to as “the city built by gentlemen for gentlemen”, the capital of Malta offers both culture and relaxation. Visit the famous Mosta Basilica, which is the third-largest in Europe and one of the main highlights of Malta.
5 days
22% Off Today
Discover some of the most essential parts of Italy on this five-day cultural trip, beginning with an exploration of the ruins of ancient Pompeii and continuing to the magnificent views of Positano and its surrounding fishing villages.
5 days
32% Off Today
COACH TOUR: Explore the best of central Italy on this five-day journey from Rome to Venice, with scenic stops in Florence, Bologna and the Tuscan countryside. Visit Assisi and Siena en route to Florence, where Renaissance treasures and Tuscan cuisine await. Wander Bologna’s historic streets and enjoy a street food tasting before heading to Venice for gondolas, cicchetti and grand architecture. Wrap up with wine and views in hilltop Montepulciano before returning to Rome. With guided sightseeing, regional flavours and iconic landmarks throughout, this compact adventure is perfect for travellers keen to experience Italy’s cultural heart in style.
5 days
22% Off Today
Drive through some of Italy's most iconic locations on this five-day tour that takes you through Naples, Pompeii, Sorrento and Capri. Spend the second half of the tour explore the wonderful coastal town of Positano at leisure. Relax at the hotel, discover the breath-taking surroundings, or even plunge into the warm waters of the Mediterranean.
5 days
8% Off Today
If you’re longing for an authentic Italian escape, the 5-day Beautiful Puglia city sightseeing tour is a top pick for seniors. Beginning and ending in Rome, this guided trip uncovers the charm of Bari and Brindisi, blending historical exploration with regional cuisine. Group camaraderie and inclusive arrangements ensure a relaxed, social atmosphere. Its unique advantage lies in the focused exploration of Puglia—a region renowned for its distinctive culture and landscapes.
5 days
13% Off Today
See the best of Italy in just five days. This fast-paced tour starts and finishes in Rome, ensuring you experience the top sites: the historic centers of Siena and Florence, the vibrant cities of Bologna and Venice, and the stunning landscapes of Tuscany—complete with a wine region drive and a lunch stop in Montepulciano. It's the perfect itinerary for maximizing a limited vacation schedule.
5 days
See all Black Week Italy Deals
10 Best Italy 5-Day Tours
These 5-Day organized Italy tours are among our most booked—carefully curated for immersive, multiday travel.
8% Off Today
Rome, Venice, and Florence headline the 'Classical Italy' trip—a 5-day sightseeing tour ideally suited for seniors seeking a taste of Italy’s best cities. With all logistics, hotels, and meals included, this group trip allows you to relax and enjoy the highlights stress-free. The real draw is the concise itinerary—offering maximum cultural impact in a short, easy-paced journey designed to delight mature travelers.
Duration
5 Days
Price per day
USD 129
Tour Type
Group Tour
5 days
32% Off Today
Craving a taste of Italy’s most iconic UNESCO sites in just five days? The "Italy City Break" is your passport to a whirlwind of art, history, and vibrant culture. Starting from Rome, you’ll journey to the medieval town of Assisi—birthplace of St Francis—before heading to Florence, the city where the Renaissance began.
Wander through Florence’s architectural marvels, then continue north to explore the artistic treasures of Bologna, Padua, and the canals of Venice. The adventure doesn’t stop there; Tuscany’s world-renowned vineyards invite you for a final taste of la dolce vita before a return to Rome.
Tailored for young adults and seasoned travelers who appreciate efficient yet immersive sightseeing, this trip ensures you soak up Italy’s best in record time. The guided tour package includes essential highlights, expert insights, and a seamless travel experience.
USP: A curated route through Italy’s cultural heartlands, blending world heritage sites, culinary delights, and breathtaking scenery—making it a perfect short escape for those who want to experience Italy’s essence without compromise.
Duration
5 Days
Price per day
USD 242
Tour Type
Group Tour
5 days
13% Off Today
Craving a whirlwind tour through Italy’s cultural icons? Veloce Italia is your answer—a five-day sightseeing trip ideal for families, seniors, and young travelers with limited time. Starting and ending in Rome, this guided group tour takes you to Florence, Venice, Siena, and even through Tuscany’s famed wine country.
Enjoy guided city tours, a Tuscan lunch in Montepulciano, and the best of Italy’s UNESCO heritage. The USP is its efficient itinerary—covering Italy’s highlights in record time without sacrificing depth or enjoyment. Accommodation, transport, and meals are included, ensuring a smooth, memorable Italian holiday.
Duration
5 Days
Price per day
USD 249
Tour Type
Group Tour
5 days
37% Off Today
Our 5-Day Tour offers a perfect blend of history, culture, and natural beauty. Start by exploring the vibrant streets of Naples before embarking on a scenic day trip to the stunning towns of Sorrento, Positano, and Amalfi. The next day, hop on a ferry to the beautiful island of Capri, where you can wander through charming streets, enjoy panoramic views from Augustus Gardens, and see the iconic Faraglioni rocks. Finally, step back in time with a guided tour of Pompeii’s ancient ruins, uncovering the fascinating history of this Roman city. With expert guides, unforgettable sights, and plenty of free time to explore, this tour is the perfect Italian getaway.
Duration
5 Days
Price per day
USD 260
Tour Type
Group Tour
5 days
22% Off Today
Unwind amid the splendor of Italy’s southern coast on the Naples Escape & Sorrento tour, a five-day journey designed for seniors seeking both relaxation and cultural immersion. Starting in Naples, you’ll travel through the historic streets of Sorrento and the eternal city of Rome, enjoying the ease of a self-guided art and architecture tour with all accommodations, transport, and meals thoughtfully arranged.
Highlights include exploring the Sorrento peninsula’s lavish scenery, ferrying to the enchanting isle of Capri, and marveling at the legendary Blue Grotto. Step back in time with a visit to the haunting ruins of Pompeii, and take in the vibrant history of Naples. The tour’s unique selling point is its balance of leisure and discovery—offering a stress-free, easy-paced trip that lets you savor Italy’s most beautiful coastlines and ancient wonders.
Duration
5 Days
Price per day
USD 288
Tour Type
Group Tour
5 days
22% Off Today
Discover some of the most essential parts of Italy on this five-day cultural trip, beginning with an exploration of the ruins of ancient Pompeii and continuing to the magnificent views of Positano and its surrounding fishing villages.
Duration
5 Days
Price per day
USD 354
Tour Type
Group Tour
5 days
8% Off Today
If you’re longing for an authentic Italian escape, the 5-day Beautiful Puglia city sightseeing tour is a top pick for seniors. Beginning and ending in Rome, this guided trip uncovers the charm of Bari and Brindisi, blending historical exploration with regional cuisine. Group camaraderie and inclusive arrangements ensure a relaxed, social atmosphere. Its unique advantage lies in the focused exploration of Puglia—a region renowned for its distinctive culture and landscapes.
Duration
5 Days
Price per day
USD 173
Tour Type
Group Tour
5 days
3% Off Today
Imagine waking up in a boutique cave hotel in Matera, then sampling local wines amid the sun-drenched hills of Apulia. The Highlights of Matera and Apulia Private Tour is a five-day, easy-paced escape designed for young adults and experienced travelers eager to savor the best of Southern Italy.
With your own private guide and driver, you’ll explore Matera’s UNESCO-listed cave dwellings, the whimsical trulli houses of Alberobello, and the dramatic Castellana Caves. Stroll the charming streets of Polignano a Mare, and immerse yourself in the region’s culinary delights. Unique accommodations—including an authentic Apulian farmhouse—add a special touch to your stay.
The USP of this tour package is its personalized approach: expert guidance, handpicked stays, and immersive tastings ensure a journey tailored to your tastes, blending culture, comfort, and local flavor at every stop.
Duration
5 Days
Price per day
USD 440
Tour Type
Group Tour
5 days
3% Off Today
Venice, with its shimmering canals and secret corners, sets the stage for the "Venetian Treasures" cruise tour—a five-day escape through Italy’s most romantic waterways. Starting and ending in Venice, this trip sails via Chioggia and back, offering a front-row seat to the serene beauty of the Venetian Lagoon.
If you’ve ever dreamed of gliding beneath ancient bridges in a gondola or savoring gourmet Italian cuisine at every turn, this tour package is your invitation. Stand in the grandeur of Saint Mark’s Square, lose yourself in the city’s labyrinthine alleys, and experience the quiet magic of Chioggia—a lesser-known gem that captures the spirit of authentic Italy.
Tailored for travelers who seek a blend of relaxation and cultural indulgence, this cruise promises enchanting panoramas and unforgettable moments. The unique selling point: an intimate discovery of Venice and its lagoon, far from the crowds, with opportunities for both iconic sightseeing and hidden local delights.
Duration
5 Days
Price per day
USD 115
Tour Type
Group Tour
5 days
3% Off Today
Let the sun-drenched Amalfi Coast sweep you away on the "Splendid Amalfi Coast - Small-Group Tour." Starting and ending in Rome, this five-day art and architecture journey is crafted for young adults, seniors, and families seeking Italy’s classic beauty with a touch of sophistication.
Wander the ancient streets of Pompeii, its ruins frozen in time by Mount Vesuvius’s eruption. Delight in Sorrento’s charms and retreat each evening to a welcoming hotel. The adventure continues with a day trip to Capri, renowned for its natural wonders and cultural allure, and a visit to the iconic cliffside town of Positano.
This guided tour package is designed for easy enjoyment, blending sightseeing with relaxation and culinary delights. Its unique selling point? A seamless, small-group exploration of Italy’s most storied coastline, offering maximum comfort, insight, and unforgettable memories at every turn.
Duration
5 Days
Price per day
USD 407
Tour Type
Group Tour
5 days
Top Tour Activities for 5-Day Italy Tours
Explore 5-Day Italy multiday tours that match your travel style—whether it's art and architecture trips, city sightseeing tours or other tour styles.
Italy 5-Day Tours for all Age Groups
Find 5-Day tours in Italy designed for different age groups—from young adventurers to experienced travelers, seniors and families. Travel with like-minded explorers and enjoy experiences tailored to your needs.
Frequently Asked Questions about traveling to Italy
Your top questions answered by Bookmundi's travel specialists.Are 5 days enough for a tour of Italy? How many destinations can you cover in 5 days?
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Italy 5-Day Tour Reviews
Honest insights from past guests on our 5-Day Italy tours
HIBA R. | Traveled in May
The tour guide Gaby and the local guides. The itinerary is brief but good. You get to do a lot of things but just as an overview which is fine because it is only 4 days. I loved it.
Brandy | Traveled in September
I never thought I could learn so much while on a vacation. This trip truly feeds your stomach and your brain! Above all our cooking class was incredibly fun and we even got to make stuffed olives which turned out to be quite good! In the end we felt the value of the tour was very high and would like to return in 2019 for a longer trip. Thank you so much for making us discovered this wonderful part of Italy, we will be back!
Patricia S | Traveled in April
This was our first trip to Italy. A fabulous trip with a fantastic mix of scenery, walking , culture and food experiences. Italy is a fantastic place to travel because there are so many historically significant locations and attractions to see. We felt the tour was excellent value for money – the hotels were very good and well located, and we were surprised and impressed by the services of our tour leader Maria. She was really amazing, funny and cultivated. Perfectly organized, amazingly knowledgeable tour guide. Overall the tour exceeded expectations.Highly recommending.
Tamara A. | Traveled in February
The tour was amazing, well organised, our guide Patricia very professional, energetic and helpful all over the tour. The tour had a well organised program, old they offered us optional tours and free time, which gave me more relaxing feeling, thank you, definitely will go with this company again.
Ben C. | Traveled in May
The trip to Capri was such a pleasant surprise. Anacapri was peaceful and scenic, and I got some of the best photos of my life from the Augustus Gardens. Transfers were smooth and well coordinated.
Rachel G. | Traveled in May
From walking ancient Pompeii streets to relaxing in Positano, this tour had it all. The balance of guided tours and free time made it feel relaxing yet enriching. Excellent experience overall!
Traveler Photos For Trips in Italy
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