Italy 14-Day Tours and Trips
Discover the best 14-Day tours in Italy with Bookmundi. We offer a total of 10 Italy 14-Day tours and itineraries with 550 customer reviews.
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Most popular Italy 14-Day Tours
These 14-Day organized Italy tours are among our most booked—carefully curated for immersive, multiday travel.
Curated by Alessandra Galassi
Italy travel expert at Bookmundi
Italy’s timeless beauty unfolds on the "Journeys: Iconic Italy" tour, a sweeping 14-day trip that weaves together the country’s most celebrated cultural, religious, and historic sites. From the canals of Venice to the ancient streets of Rome, you’ll traverse legendary destinations including Florence, Cinque Terre, and the sun-drenched Amalfi Coast.
This small group tour is designed for travelers seeking a deep connection with Italy’s illustrious past and vibrant present. Stand in awe of Renaissance masterpieces in Florence and Venice, explore the haunting ruins of Pompeii side by side with an archaeologist, and pause to enjoy the aromatic lemon groves while winding through coastal villages.
The tour includes comfortable accommodations, seamless transport, and select meals, allowing you to savor every moment without logistical worries. Along the way, discover the art of la dolce vita—from leisurely café breaks to immersive local experiences. The highlight of this package is the unique blend of expert-guided explorations and authentic encounters, ensuring you not only see Italy’s icons but truly experience them. For those dreaming of an Italian journey rich in history, culture, and culinary delights, this tour offers an unforgettable escape through the heart of Italy.
Duration
14 Days
Price per day
USD 450
Tour Type
Group Tour
14 days
Explore the crossroads of civilizations on "Southern Italy & Sicily featuring Taormina, Matera and the Amalfi Coast," a 13-day city sightseeing adventure rich in culture and history. Beginning in Palermo and ending in Rome, this moderately active tour immerses you in Sicily’s ancient wonders and southern Italy’s coastal beauty.
Uncover Palermo’s Moorish and Norman heritage, wander through Cefalù’s seaside splendor, and marvel at the Valley of the Temples in Agrigento. In Taormina, visit a local winery for a tasting and agriturismo dinner—an authentic taste of Sicilian life. Journey to the ancient cave dwellings of Matera before exploring Sorrento and Positano, the pearls of the Amalfi Coast. Walk in the footsteps of Romans at Pompeii’s evocative ruins.
With all accommodations, transport, and meals included, this group tour’s unique selling point is its artful blend of ancient monuments, spectacular coastlines, and local culinary experiences—making it the perfect package for those eager to soak up the essence of southern Italy and Sicily.
Duration
14 Days
Price per day
USD 314
Tour Type
Group Tour
14 days
Indulge in the romance and history of Italy on the Ultimate Italy trip, a two-week cultural odyssey from Rome to Venice. Wander the ancient ruins of Rome, admire the Renaissance glory of Florence, and traverse the colorful villages of Cinque Terre. Glide along Venetian canals, experience the elegance of Lake Como, and savor local wines and culinary delights in Tuscany. With expert guides and small group camaraderie, this tour package stands out for its comprehensive immersion in Italy’s art, history, and la dolce vita. The unique selling point: a seamless journey blending iconic sights with authentic local experiences.
Duration
14 Days
Price per day
USD 213
Tour Type
Group Tour
14 days
Southern Italy’s hidden charms come alive on the 'Italy: Amalfi Coast to Puglia' trip, a 14-day group getaway for travelers keen to explore beyond the usual tourist trail. Starting in Naples and finishing in Alberobello, this tour guides you through Minori, Lecce, Monopoli, and more, weaving together dramatic coastlines, historic caves, and artisan towns.
Marvel at the legendary Veiled Christ in Naples, sample volcanic wines near Pompeii, and bask in the chic vibes of Positano. Spend two nights in a unique cave dwelling in Matera and end your journey housed in a traditional Puglian abode. The itinerary’s moderate activity keeps things accessible while offering plenty of local flavor and cultural discovery.
The USP is the rare opportunity to experience local life—whether sleeping in centuries-old caves or sampling regional cuisine—making this beach trip an immersive, off-the-beaten-path Italian adventure.
Duration
14 Days
Price per day
USD 350
Tour Type
Group Tour
14 days
Delight in Italy’s treasures on the 14-day Golden Italy and Beautiful Campania tour, crafted for seniors who appreciate culture and comfort. Journey from Rome through Milan, Verona, and six other enchanting locales, experiencing a tapestry of art, architecture, and cuisine. With accommodations, transport, and meals taken care of, you’ll enjoy a worry-free exploration of Italy’s northern and southern gems. The standout feature of this tour is its blend of iconic cities and picturesque regions, providing a complete Italian sightseeing experience without the stress.
Duration
14 Days
Price per day
USD 171
Tour Type
Group Tour
14 days
Southern Italy and Sicily entice with a tapestry of flavors and historic marvels on the 'Country Roads of Southern Italy and Sicily' trip—a 14-day guided adventure that welcomes families and mature travelers alike. Setting out from Rome, you’ll be swept along a route that reveals the heart and soul of Italy, from the ancient streets of Catania and the sparkling shores of Taormina to Palermo’s vibrant culture and Sorrento’s dramatic views over the Bay of Naples.
Stroll Rome’s iconic sites with a local expert, tossing a coin into the Trevi Fountain as tradition dictates. In Sorrento, unwind at a luxurious resort with panoramic vistas of Mount Vesuvius, whose eruption famously preserved Pompeii. Meander through the sun-kissed hills of Apulia and savor a memorable dinner inside a historic trulli house—these unique, conical-roofed dwellings are a highlight of the region. Relish traditional orecchiette pasta and sample seasonal fare that honors Puglia’s rich agricultural heritage.
Palermo offers a deep dive into Sicily’s layered past. Guided by a historian, you’ll wander the old city, marvel at the ornate cathedral, and be dazzled by the Byzantine mosaics of the Palatine Chapel. Between immersive sightseeing and moments of leisure, the tour is perfectly paced for those who appreciate comfort and culture in equal measure.
With accommodation, transport, and meals included, this tour package affords travelers a seamless, enriching experience. The unique selling point? A rare chance to dine inside a genuine trulli house and savor authentic regional cuisine—a memory that lingers long after the final gelato. Experience Italy’s diverse landscapes and traditions on a journey crafted for lasting family memories and sophisticated exploration.
Duration
14 Days
Price per day
USD 328
Tour Type
Group Tour
14 days
Iconic sights and in-depth adventures with a local Trip Leader.Italy. Just thinking about this country makes your mouth water, your stomach rumble and your jeans feel tighter. Gastronomic delights aside, this place has got history by the bucket load, landscapes that look like they’ve been photoshopped, cities so romantic even the biggest cynics will turn into Julia Roberts from Eat, Pray, Love, and more duomos, churches and piazzas than you can remember. So pack your fat pants, this trip is Italy done right.
Duration
14 Days
Price per day
USD 168
Tour Type
Group Tour
14 days
Sicily’s sun-drenched coasts and timeless villages await on the 14-day "Highlights of Sicily" tour, a journey that begins and ends in Palermo. Wander through the charming streets of Cefalù, marvel at the volcanic drama of the Aeolian Islands, and soak up the history of Agrigento’s ancient ruins. This small group sightseeing trip is packed with immersive experiences: join a Sicilian cooking class, wander medieval hilltop towns, and discover a rich tapestry of Italian culture and tradition. Accommodations, transport, and meals are thoughtfully arranged, allowing you to relax and savor every moment. Perfect for anyone dreaming of an authentic Italian adventure, this tour’s standout feature is its seamless blend of breathtaking landscapes and deep cultural immersion across Sicily’s north and south.
Duration
14 Days
Price per day
USD 205
Tour Type
Group Tour
14 days
Italy by rail offers a journey of timeless allure. On this 14-day adventure from Venice to Sorrento, with stops in Rome, Florence, and the Amalfi Coast, travelers experience the country’s iconic sights through a blend of city sightseeing and coastal exploration. The tour is tailored for those who appreciate a moderate pace, combining the freedom of train travel with guided discovery.
Wander Venice’s romantic canals, browse Bologna’s bustling food markets, and marvel at Florence’s architectural masterpieces. Two full days in Rome allow deep dives into the Colosseum and Roman Forum. The sun-drenched Sorrento Peninsula awaits, with optional excursions to Capri and walks along the scenic Path of the Lemons. Pompeii’s legendary ruins and the dramatic silhouette of Mount Vesuvius complete the experience.
This trip’s unique selling point is its seamless integration of Italy’s urban grandeur and coastal serenity—all connected by the comfort and efficiency of rail travel. It’s a tour package designed for those who want to see it all, at just the right pace.
Duration
14 Days
Price per day
USD 396
Tour Type
Group Tour
14 days
From Amsterdam’s charming canals to the majestic Swiss Alps, the Europe Jewel trip is a two-week art and architecture tour that spans the best of both Western and Eastern Europe. This immersive group journey takes you through 10 countries, including the Czech Republic, Austria, Hungary, and more. Explore vibrant capitals like Vienna and Budapest, sample authentic Italian cuisine, and lose yourself in the historic ambiance of Prague and Bratislava. Travelers who relish a balance of sightseeing, cultural experiences, and natural wonders will love the diversity on offer. The tour’s unique highlight? A seamless blend of Western allure and Eastern intrigue, ensuring an unforgettable, all-encompassing European adventure.
Duration
14 Days
Price per day
USD 186
Tour Type
Group Tour
14 days
See all Italy 14-Day Tours
10 Best Italy Summer Deals for 14-Day Tours
Summer exclusive deals on 14-Day tours in Italy — massive savings for a limited time only!
Indulge in the romance and history of Italy on the Ultimate Italy trip, a two-week cultural odyssey from Rome to Venice. Wander the ancient ruins of Rome, admire the Renaissance glory of Florence, and traverse the colorful villages of Cinque Terre. Glide along Venetian canals, experience the elegance of Lake Como, and savor local wines and culinary delights in Tuscany. With expert guides and small group camaraderie, this tour package stands out for its comprehensive immersion in Italy’s art, history, and la dolce vita. The unique selling point: a seamless journey blending iconic sights with authentic local experiences.
14 days
Sicily’s sun-drenched coasts and timeless villages await on the 14-day "Highlights of Sicily" tour, a journey that begins and ends in Palermo. Wander through the charming streets of Cefalù, marvel at the volcanic drama of the Aeolian Islands, and soak up the history of Agrigento’s ancient ruins. This small group sightseeing trip is packed with immersive experiences: join a Sicilian cooking class, wander medieval hilltop towns, and discover a rich tapestry of Italian culture and tradition. Accommodations, transport, and meals are thoughtfully arranged, allowing you to relax and savor every moment. Perfect for anyone dreaming of an authentic Italian adventure, this tour’s standout feature is its seamless blend of breathtaking landscapes and deep cultural immersion across Sicily’s north and south.
14 days
La dolce vita comes alive on the Best of Italy tour, a 14-day city sightseeing journey from Rome to Venice. Savor Italian culture as you stroll Rome’s piazzas, breeze through the Tuscan countryside on a leisurely cycle along the Serchio River, and admire Pisa’s iconic Leaning Tower. The adventure continues with hiking trails along Cinque Terre’s stunning coastline and a walk through the glamorous Portofino Peninsula. Wine tastings in rural villages, ferry rides on Lake Como, and time to relax in Milan and Venice round out this immersive Italian experience.
The tour’s unique selling point is its diverse activities—offering a perfect blend of city exploration, cycling, coastal walks, and culinary delights—making it a true celebration of Italy’s endless charm.
14 days
Southern Italy and Sicily entice with a tapestry of flavors and historic marvels on the 'Country Roads of Southern Italy and Sicily' trip—a 14-day guided adventure that welcomes families and mature travelers alike. Setting out from Rome, you’ll be swept along a route that reveals the heart and soul of Italy, from the ancient streets of Catania and the sparkling shores of Taormina to Palermo’s vibrant culture and Sorrento’s dramatic views over the Bay of Naples.
Stroll Rome’s iconic sites with a local expert, tossing a coin into the Trevi Fountain as tradition dictates. In Sorrento, unwind at a luxurious resort with panoramic vistas of Mount Vesuvius, whose eruption famously preserved Pompeii. Meander through the sun-kissed hills of Apulia and savor a memorable dinner inside a historic trulli house—these unique, conical-roofed dwellings are a highlight of the region. Relish traditional orecchiette pasta and sample seasonal fare that honors Puglia’s rich agricultural heritage.
Palermo offers a deep dive into Sicily’s layered past. Guided by a historian, you’ll wander the old city, marvel at the ornate cathedral, and be dazzled by the Byzantine mosaics of the Palatine Chapel. Between immersive sightseeing and moments of leisure, the tour is perfectly paced for those who appreciate comfort and culture in equal measure.
With accommodation, transport, and meals included, this tour package affords travelers a seamless, enriching experience. The unique selling point? A rare chance to dine inside a genuine trulli house and savor authentic regional cuisine—a memory that lingers long after the final gelato. Experience Italy’s diverse landscapes and traditions on a journey crafted for lasting family memories and sophisticated exploration.
14 days
Iconic sights and in-depth adventures with a local Trip Leader.Italy. Just thinking about this country makes your mouth water, your stomach rumble and your jeans feel tighter. Gastronomic delights aside, this place has got history by the bucket load, landscapes that look like they’ve been photoshopped, cities so romantic even the biggest cynics will turn into Julia Roberts from Eat, Pray, Love, and more duomos, churches and piazzas than you can remember. So pack your fat pants, this trip is Italy done right.
14 days
From Amsterdam’s charming canals to the majestic Swiss Alps, the Europe Jewel trip is a two-week art and architecture tour that spans the best of both Western and Eastern Europe. This immersive group journey takes you through 10 countries, including the Czech Republic, Austria, Hungary, and more. Explore vibrant capitals like Vienna and Budapest, sample authentic Italian cuisine, and lose yourself in the historic ambiance of Prague and Bratislava. Travelers who relish a balance of sightseeing, cultural experiences, and natural wonders will love the diversity on offer. The tour’s unique highlight? A seamless blend of Western allure and Eastern intrigue, ensuring an unforgettable, all-encompassing European adventure.
14 days
Unleash your wanderlust on the Classic Europe tour—a 14-day, expertly guided journey that weaves through five diverse countries. From London’s regal Buckingham Palace to Rome’s ancient wonders, this active and outdoor trip covers everything: canal cruises in Amsterdam, Rhine River landscapes, and the awe-inspiring Swiss Alps. Savor Tuscan cuisine, sample German brews, and indulge in sweet Belgian waffles. With ample free time in cultural capitals like Paris, Rome, and Amsterdam, travelers in their prime or those seeking a sophisticated exploration will appreciate the balanced mix of structured sightseeing and personal discovery. The standout feature? A fast-paced, yet thoughtfully curated itinerary that ensures no major highlight goes unseen, all while enjoying the camaraderie of a group tour.
14 days
Are you keen for winter travel? Europe in winter is a wonderland! Starting in Amsterdam, admire the canal-side sights before travelling to the scenic German Rhine Valley and the historic city of Nuremberg. Enjoy a magical Christmas Day in the must-see city of Prague! Travel between Bratislava, Budapest, Vienna and Ljubljana. Get immersed in the Italian charms in Tuscany, toast the New Year in Switzerland and marvel at the festive atmosphere in Paris. What better way to spend Christmas than exploring enchanting Europe over two weeks?
14 days
Set off on an unforgettable 14-day Italian adventure, beginning and ending in the eternal city of Rome. Your journey will navigate through iconic landmarks in Rome like the Colosseum and Vatican City before whisking you to the medieval wonders of Orvieto and Siena in Tuscany. Savour the picturesque landscapes of Cinque Terre and the idyllic Italian Lakes, and explore the cultural riches of Florence, Verona, and Venice. Experience the allure of Portofino, the historic charm of San Marino, and the vibrant life of Naples with side trips to Capri and Pompeii. This tour brings Italy's diverse landscapes and rich history to life, promising memories to last a lifetime.
14 days
See all Italy 14-Day Summer Deals
Frequently Asked Questions about 14-Day in Italy
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Italy Tour Reviews
Honest insights from past guests on our 14-Day Italy tours
Big guy | Traveled in April
Many highlights every day. A taste of Europe.Days are long often starting 7am on bus, ending after 8 pm. Tiring but worth it for a 70 yr old. Very, very well organized and timed.. Highly recommend.
Julie | Traveled in May
Enjoyed the tour, a wonderful experience. Salvo our tour guide was excellent, very knowledgeable about Sicily, also responded immediately if any issues, recommended the best places to see during our free time, excellent advice on restaurants and where the best granitas and gelato places to go to. Don?t think abut it go and book a tour, it was my first tour and would definitely book another.
Constance F. | Traveled in December
Our tour guide, Davide was exceptional. He made sure we all had a good time and were safe . Also Diego, our bus driver, was great. Everyone had a good time and my trip was unforgettable. I am so glad I went!
Anonymous | Traveled in May
Excellent, interesting tour, amazing scenery and visiting some wonderful places like Lucca my absolutely favourite place on the tour. We stayed in some really nice interesting hotels though I wasn’t that keen on Villa Pitiana in Tuscany. Lots of faded grandeur and an uncomfortable bed. I don’t mind old hotels at all but the bedroom I had at Villa Pitiana was gloomy and most unwelcoming and the bathroom was not great. The Villa was in need of major refurbishment and too far away from anything. I would have preferred three nights in Lucca to explore some more. A few people on the tour felt the same. I also really liked Rapallo and would have enjoyed more time there. Silvia was a wonderful guide.So knowledgeable, helpful and great personality. Our driver Gaetano was friendly and a skilful, safe driver. They made a great team.
Lauren | Traveled in July
Both of my leaders really made our tour exceptional and went above and beyond to build connections and create lasting memories for us. I would consider both of a them a friend, I loved how connected to us they made themselves. Both were very passionate and enthusiastic about the trip and we couldn?t have had such a great time without them. They a were the best tour group leaders I?ve ever had!!
Patti Co | Traveled in October
Absolutely loved this tour! From the tour guide, to the destinations, to the organisation of the tour I can’t fault anything. We will definitely look to do another Back Road Tour in the future. Highly recommend.
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