Two Weeks In Italy Itinerary: Best Italy Itinerary 14 Days

Starting a two-week adventure across Italy for two weeks is no ordinary trip, and this two weeks in Italy itinerary has you covered. Visiting Italy is like stepping right into the pages of a storybook that unfolds with captivating history, awe-inspiring art, and breathtakingly beautiful destinations. If you ask me, one of the reasons I visit Italy is to watch volleyball in Italy.

Picture yourself exploring the vibrant city of Rome, discovering hidden treasures in enchanting Perugia, immersing in the artistic wonders of Florence, embracing the modern charm of Milan, and unraveling the mysteries of historical Turin. This thoughtfully planned itinerary guarantees an experience that goes beyond a mere vacation. There are plenty of travel experiences in Italy that you should consider, and this itinerary will help you channel them. Let’s plunge into the very heart of Italy, where every city has a tale to share, and every street whispers its unique story.

Enthusiastic wanderers and intrepid adventurers alike are irresistibly drawn to the enchanting allure of Italy. It’s a place that tantalizes your senses, leaving you yearning for more. From its profound historical legacy and rich cultural heritage to its awe-inspiring landscapes and delectable cuisine, Italy offers a sensory feast that is simply unmatched. Look no further if you’re searching for the perfect two weeks in Italy itinerary. This article presents the ultimate Italy guide in 14 unforgettable days, carefully crafted to ensure your journey is extraordinary.

How to Book Your 14 Days in Italy Trip

The best way to book your two weeks in Italy itinerary is using a tool where you can check your costs, plan your flights, book your stays, and check trains. I will help you a bit with this:

Check Your Hotel Stays for Your Two Weeks in Italy

Check Your Trains in Italy for Two Week Trip

What to Pack for Two Weeks in Italy

What to pack for this two weeks in Italy itinerary will depend on the season you are visiting. If you are visiting in mid-July, the list will change compared to visiting in December or Winter. Here, I’ll try to cover some general stuff you’ll need.

Clothing:

• Comfortable Attire: Pack lightweight, breathable clothes for the warm Italian weather. Think cotton shirts, shorts, and sundresses. This will change if you are traveling in Winter
• Layers: Evenings can be cooler, especially in the north, so include a light jacket or sweater. This is required if you are traveling in Winter.
• Modest Outfits: For visits to churches and religious sites, it’s wise to pack outfits that cover shoulders and knees.

Footwear:

• Comfortable Walking Shoes: Expect to explore charming cobblestone streets; comfortable shoes are a must.
• Sandals: A pair of comfy sandals for warmer days or beach visits.

Accessories:

• Sun Protection: Sunglasses, a wide-brimmed hat, and sunscreen to shield from the Italian sun.
• Daypack or Tote: A handy bag for daily explorations, carrying water, snacks, and essentials.

Tech and Gadgets:

• Adapter: Ensure your electronics can plug into Italian outlets.
• Camera or Smartphone: Capture those picturesque moments.
• Portable Charger: Keep devices charged for on-the-go navigation and photos.

Toiletries:

• Travel-sized Essentials: Shampoo, conditioner, toothpaste, and other personal care items. Be aware of check tips for carrying liquids in carry-on bags.
• Prescription Medications: Ensure you have an adequate supply for the trip, but do not overpack; there are pharmacies all around Italy.
• First Aid Kit: Band-aids, pain relievers, and any personal medications.

Documents and Money:

• Passport and Copy: Keep your passport safe, along with a photocopy.
• Travel Insurance: Carry your insurance details. Remember to check insurance like Safetywings Travel Insurance.
• Credit Card and Cash: Notify your bank, and carry some Euros for places that might not accept cards.

Miscellaneous:

• Reusable Water Bottle: Stay hydrated during sightseeing.
• Travel Guides or Maps: Navigate with ease.
• Small Umbrella or Poncho: Be prepared for unexpected rain.

Extras:

• Snacks: A few granola bars or nuts for quick energy boosts.
• Language Guidebook: A basic guide for common Italian phrases.
• Foldable Tote Bag: Useful for impromptu shopping or carrying souvenirs.

Packing light and smart ensures a hassle-free Italian adventure. Check the weather forecast for your specific destinations and tailor your packing accordingly.

Recommended Guidebook:

Rick Steves Italian Phrase Book
Considering this is a Phrase Book made by a traveler for travelers, it could be the best option to get it for your two weeks in Italy itinerary.

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Basic Italian for 14 days

For a smooth 14-day Italy itinerary, travelers should acquaint themselves with some basic Italian words to enhance their experience.

Greetings and Politeness:

• Buongiorno (Bwon-jor-no): Good morning.
• Buonasera (Bwon-a-say-ra): Good evening.
• Per favore (Pair fa-vor-ray): Please.
• Grazie (Gra-tsi-eh): Thank you.
• Prego (Preh-go): You’re welcome.

Common Phrases:

• Ciao (Chow): Hello/Goodbye.
• Mi scusi (Mee skoo-zi): Excuse me.
• Mi dispiace (Mee dee-spya-chay): I’m sorry.
• Posso avere il conto? (Po-so a-ver-re eel con-to): Can I have the bill?

Directions and Navigation:

• Dove? (Do-veh): Where?
• Sinistra (See-nees-tra): Left.
• Destra (Des-tra): Right.
• Dritto (Dreet-to): Straight.
• Stazione (Sta-tsi-o-ne): Station.

Food and Dining:

• Menu (May-no): Menu.
• Acqua (Ah-kwa): Water.
• Vino (Vee-no): Wine.
• Gelato (Jeh-la-to): Ice cream.
• Pizza (Peet-sa): Pizza.
• Grazie, il conto (Gra-tsi-eh, eel con-to): Thank you, the bill.

Numbers:

• Uno (Oo-no): One.
• Due (Doo-eh): Two.
• Tre (Trey): Three.
• Dieci (Dee-eh-chee): Ten.
• Cinquanta (Cheen-kwan-ta): Fifty.

Emergencies:

• Aiuto (Ah-yoo-to): Help.
• Polizia (Po-leet-sya): Police.
• Ospedale (Os-pe-da-le): Hospital.

Transportation:

• Stazione ferroviaria (Sta-tsi-o-ne fer-ro-vee-ar-ya): Train station.
• Autobus (Ow-to-boos): Bus.

Shopping:

• Quanto costa? (Kwan-to kos-ta): How much does it cost?
• Negozio (Ne-go-tsyo): Shop.

Day 1: Arrival in Rome

As you step off the plane and breathe in the Italian air, Rome welcomes you with open arms. Check-in at your hotel; we know you have chosen the best place to stay in Rome. This city, steeped in history and ancient wonders, sets the stage for an awe-inspiring journey.

Begin your Italian escapade by choosing one of the most unique tours in Rome. Visit the iconic Colosseum, where the echoes of gladiator battles still linger. Explore the ancient Roman Forum, a time capsule that transports you back to the heart of the Roman Empire. Stand beneath the celestial dome of the Pantheon, a testament to engineering genius. Conclude the day with a stroll through the vibrant streets of Trastevere, indulging in traditional Roman delicacies along the way.

Day 2: Exploring the Eternal City

On your second day in Rome for this two weeks in Italy itinerary, dive deeper into its rich cultural heritage. Pay a visit to the Vatican City, the spiritual and administrative heart of the Catholic Church. Marvel at the grandeur of St. Peter’s Basilica, home to masterpieces by Michelangelo and Bernini. Immerse yourself in the artistic wonders of the Vatican Museums, where each corridor reveals a treasure trove of artistic brilliance.

Remember to get into the timeless tradition of tossing a coin into the Trevi Fountain, sealing a promise to return. Ascend the Spanish Steps, a monumental stairway that offers a climb and a journey through elegance and history. End the day with a relaxing walk along the picturesque Tiber River, enjoying the enchanting sunset views.

Day 3: Take a Bus to Perugia

Leave Rome behind and embark on a Flixbus to the Etruscan wonders of Perugia. Make sure you stay in Perugia at the Chocohotel. Indulge in the Chocohotel experience across three unique floors: the Milk floor, the Gianduia floor, and the Dark floor. Each of the 94 rooms offers a chocolate-infused ambiance, from Choco Lamps inspired by hot chocolate hues to a headboard shaped like a chocolate bar. Enjoy your day at the Chocohotel, and start your next day with one of its best features.

Chocohotel Perugia

Ready for a chocolate-infused-themed adventure? Book your spot at Chocohotel now and make it part of your two weeks in Italy itinerary.

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Day 4: Breakfast at the Chocohotel and Visit the Baci Perugina Chocolate Factory

Start your day with the ChocoBreakfast, a buffet extravaganza featuring a variety of chocolates, artisanal cakes, and delicious tarts. The buffet caters to sweet and savory preferences, offering cold cuts and cheeses from Umbria. During the Eurochocolate event, experience an extra dose of chocolate delight. Embark on a sweet journey at the Baci Perugina Factory, where the art of chocolate-making unfolds. Taste more than flavors; savor the history of Torta al Testo, a culinary delight embodying Perugia’s essence.

Day 5: Eat Gelato and Take a Bus or Train to Florence

Conclude your Perugian escapade by eating gelato at Lick, where gelato is not just a dessert but a symphony of flavors echoing the city’s spirit. Then, go either to the Train Station or the bus stop and go to your next city: Florence. Is it better to take the bus or the train? The best one is the cheapest when you search on Omio. If I had to add a pro for the trains, specifically the train from Perugia to Florence, that would be the scenic route.

Day 6: Renaissance Art at Uffizi and Accademia

Lose yourself in the timeless beauty of the city’s historic center, a UNESCO World Heritage site. Admire the intricate marble façade of the Florence Cathedral, affectionately known as the Duomo. Discover the wonders of the Uffizi Gallery, home to masterpieces by Botticelli, Leonardo da Vinci, and Raphael. Move to the Accademia Gallery, where Michelangelo’s David is a silent sentinel of artistic brilliance. Finish the day in traditional Florentine cuisine, savoring the flavors of melt-in-your-mouth bistecca alla Fiorentina and creamy gelato at Gelateria dei Neri, one of the best gelato in Italy.

Day 7: Duomo and Ponte Vecchio

Ascend the Duomo, not just for panoramic views but to witness Florence from a perspective that transcends the ordinary. Traverse the iconic Ponte Vecchio, a bridge adorned with charming jewelry shops that span the Arno River. Explore the historic Palazzo Pitti, a Renaissance palace showcasing remarkable art collections. Wander through the enchanting Boboli Gardens, a verdant oasis offering breathtaking city views. As evening falls, savor a traditional Tuscan dinner at a local trattoria, relishing the harmonious blend of flavors.

Day 8: Take a Short Trip to Pisa

Embark on a brief journey to Pisa, a city that challenges the laws of physics with its iconic leaning tower. For less than 10€ and 50 minutes on trains, you will get from Florence to Pisa. The Square of Miracles unfolds before you, a testament to architectural wonder and human determination. After an afternoon in Pisa, take the bus or the train to your next destination: Milano!

Day 9: Milanese Elegance at Galleria Vittorio Emanuele II

Milan, the epitome of Italian sophistication and one of the safest cities in Italy for solo female travelers invites you into its chic embrace, starting your day at the iconic Galleria Vittorio Emanuele II. This 19th-century shopping gallery is a retail haven and an architectural masterpiece that breathes Milanese opulence. Stroll beneath the glass roof, marveling at mosaic tales of Milan’s history underfoot. Pause at historic cafés like Zucca and Biffi for an espresso, absorbing the vibrant Milanese energy. Explore luxury boutiques and immerse yourself in the craftsmanship of brands like Prada and Gucci.

Venture into modern Milan at Porta Nuova, a district flaunting sleek skyscrapers and contemporary design. Witness sustainable architecture at the Vertical Forest towers and delve into avant-garde boutiques on Corso Como. Discover modern art at Fondazione Prada, a testament to Milan’s evolving identity.

Day 10: Milan’s Artistic Haven and Nightcap Views

As the sun rises on Day 10, continue your Milanese odyssey in the historic Brera district. Explore the Pinacoteca di Brera, showcasing Italian masterpieces and setting the tone for a day infused with artistry. Wander through Brera’s narrow streets, where each corner tells a story of Milan’s rich cultural tapestry.

Indulge in a leisurely lunch at a local trattoria, savoring delights like creamy risotto and succulent meats. As the afternoon unfolds, let Brera’s artistic charm captivate you. The district’s vibrant atmosphere and cultural landmarks, including the historic Brera Academy, provide a captivating backdrop for exploration.

As evening approaches, head to a rooftop bar, allowing Milan’s glittering skyline to unfold before you. The panoramic views provide a spectacular backdrop for reflection. Milan, with its fusion of history and modernity, becomes a canvas of possibilities, promising another night of discovery in this dynamic metropolis.

Day 11: Turin’s Architectural Brilliance and Culinary Treasures

As you bid farewell to Milan by taking a train or bus, Day 11 unfolds in Turin, a city synonymous with architectural marvels and gastronomic delights. Begin your adventure by checking Turin’s skyline, which is dominated by the iconic La Mole Antonelliana. Originally conceived as a synagogue, this architectural masterpiece stands tall, offering panoramic views of the Piedmontese landscape. Ascend to its observation deck for a breathtaking vista that captures the essence of Turin.

Delve into Turin’s cultural legacy with visits to the Egyptian Museum, home to one of the most extensive collections of Egyptian artifacts outside Cairo. Immerse yourself in the fascinating history of ancient Egypt. Next, explore the Cinema Museum housed in the Mole Antonelliana, tracing the evolution of cinematic art. Turin, the birthplace of Italian cinema, unfolds its contribution to the seventh art.

Turin is a culinary haven, and your evening is reserved for savoring Piedmontese cuisine. Tantalize your taste buds with dishes like Agnolotti del Plin, rich in flavor and history. Pair your meal with wines from the renowned Piedmont region, known for its Barolo and Barbera varieties. Allow the evening to unfold amidst the gastronomic treasures of Turin as part of this two weeks in Italy itinerary.

Day 12: Museums, Gardens, and Culinary Delights

Day 12 invites you to embrace Turin’s green oasis — Valentino Park and Gardens. Wander through manicured lawns, discover hidden corners, and admire the medieval-style Valentino Castle. The Po River provides a picturesque backdrop, creating a serene setting for your morning explorations.

Turin’s culinary journey continues in the afternoon. Indulge in a delightful lunch at a traditional trattoria, savoring regional specialties like Brasato al Barolo (beef braised in Barolo wine) and Bichierin, a chocolatey treat synonymous with Turin. The city’s culinary prowess becomes a sensory delight, blending tradition with innovation.

Wrap up your Turin experience with an evening dedicated to gastronomy. Join a Taste Turin tour, where local guides lead you through the city’s vibrant markets and quaint food shops. Sample local cheeses, truffles, and chocolates, gaining insights into the flavors that define Turin’s culinary identity. This immersive experience satisfies your palate and provides a deeper understanding of Piedmontese gastronomy.

Day 12-14: Bonus Options

As you have already taken a trip to diverse Italian regions and indulged most of the Italian culinary and historical experiences in this two weeks in Italy itinerary, these would be the options I would choose as bonuses (or as replacements) if you are following this Italy itinerary day by day. Depending on whether they are north or south, these plans can be fit on your two weeks in Italy itinerary between any other cities mentioned.

Bologna and Modena: Discover Parmesan Culinary Wonders

In the middle of the two weeks in Italy itinerary, consider adding a flavorful detour to Bologna and Modena, renowned for their Parmesan culinary wonders.

Begin the day by exploring Bologna’s vibrant markets, where the aroma of fresh Parmesan wafts through the air. Visit local food shops to savor Parmesan in various forms, from young and mild to aged and intense. Tagliatelle al Ragu is a must-try pasta dish where Parmesan shines as a key ingredient. Stroll through Bologna’s medieval streets and stop at traditional trattorias for a taste of Tortellini en Brodo, a comforting soup featuring Parmesan-filled pasta. End the day with a visit to a gelateria for a unique Parmesan-infused gelato.

Embark on a guided tour to discover the art of balsamic vinegar production, often paired with Parmesan. Visit local acetaie (vinegar houses) to understand the aging process and enjoy tastings of this tangy complement to Parmesan’s richness. In Modena’s charming piazzas, indulge in Parmesan-focused meals. Every bite celebrates this iconic cheese, from Gnocchi Fritti with a Parmesan dip to Risotto with Parmesan shavings. Don’t miss the chance to taste traditional balsamic vinegar drizzled over Parmesan as a unique dessert.

Venice: Captivating Charm

Embrace the magic of Venice, which you might be surprised I did not include as a fixed plan on a two weeks in Italy itinerary, but I’ll expand on that. Explore the enchanting Doge’s Palace, which symbolizes Venetian power and opulence. Cross the Bridge of Sighs, steeped in romantic lore, and imagine the bittersweet sighs of prisoners as they catch their final glimpse of the outside world. Discover the captivating art at the Gallerie dell’Accademia, showcasing masterpieces by Titian, Veronese, and Tintoretto. Indulge in cicchetti, traditional Venetian tapas, and a glass of Prosecco at a local bacaro.

Why this is a bonus and not a fixed plan? The truth is Venice is attacked by massive tourism; meanwhile, Italy is still an amazing place filled with many other plans and things to do that do not suffer as much as Venice. I would fit this either after Milan or Turin.

Serene Beauty of Lake Como

Nestled amidst the majestic Italian Alps, Lake Como captivates visitors with its idyllic charm. Take a boat tour around the lake, marveling at the elegant villas and lush gardens adorn its shores. Explore the charming town of Bellagio, known as the “Pearl of Lake Como,” with its narrow alleys and vibrant flower-filled squares. Ascend to the village of Brunate by funicular for breathtaking panoramic views of the lake and surrounding mountains. I would fit Lake Como in this two weeks in Italy itinerary between Milan and Turin due to its proximity to Milan.

Basking in the Beauty of the Cinque Terre

Cinque Terre is a string of five colorful fishing villages perched precariously on the rugged cliffs of the Italian Riviera. Hike along the famous Sentiero Azzurro (Blue Path), which winds its way through vineyards, olive groves, and terraced gardens, connecting the villages of Monterosso al Mare, Vernazza, Corniglia, Manarola, and Riomaggiore. Marvel at the stunning coastal views and immerse yourself in the laid-back atmosphere of these charming towns. Indulge in freshly caught seafood and sip the local Sciacchetrà wine, savoring the region’s flavors. Find yourself the best place to stay in Cinque Terre and make your stay longer to explore these views better.

When is the best time to fit Cinque Terre into your two weeks in Italy itinerary? I would do it after Pisa and before Milano. I think it could be an option to maximize your stay.

The Splendor of the Amalfi Coast

Settle into the coastal town of Sorrento, perched atop dramatic cliffs overlooking the azure waters of the Tyrrhenian Sea. Embark on a scenic drive along the winding Amalfi Coast, stopping at charming towns like Positano and Amalfi. Immerse yourself in the vibrant atmosphere of Positano’s colorful streets and indulge in limoncello, a zesty liqueur made from local lemons. Explore the historic Duomo di Amalfi, an architectural gem that reflects the region’s maritime history. If I have to pick a moment of this two weeks in Italy itinerary to fit the Amalfi Coast, it could be between Rome and Perugia or even before Rome to maximize the time.

The Idyllic Island of Capri

Sail away to the idyllic island of Capri, a jewel in the Gulf of Naples. Hop aboard a boat and cruise the turquoise waters, admiring the rugged coastline and iconic Faraglioni rock formations. Explore the charming town of Capri, with its elegant boutiques and picturesque streets. Take a chairlift ride to the top of Monte Solaro for breathtaking views of the island and the shimmering sea below. Delight in a visit to the mesmerizing Blue Grotto, a sea cave bathed in ethereal blue light. End the day with a relaxing stroll through the tranquil Gardens of Augustus, overlooking the azure waters and the iconic Via Krupp.

This plan could be done when you choose to be by the Amalfi Coast. I wouldn’t advise doing Capri on its own without doing Amalfi.

Discovering Pompeii’s Ancient Ruins

Embark on a journey back in time as you explore the ancient city of Pompeii. Buried under layers of volcanic ash after the eruption of Mount Vesuvius in 79 AD, Pompeii offers a fascinating glimpse into the daily life of a Roman city frozen in time. Wander through the remarkably preserved streets, marvel at the intricately decorated villas, and imagine the bustling atmosphere that once filled the Forum. Visit the haunting plaster casts of the volcano’s victims, a poignant reminder of the city’s tragic fate. You can do this between Rome and Perugia or before Rome.

Day 14: Farewell to Italy’s Magnificence

On your final day in Italy, take a moment to reflect on the incredible experiences and memories you’ve created during this two weeks in Italy itinerary. Indulge in a leisurely breakfast at a charming café, savoring the flavors of freshly brewed Italian coffee and delicate pastries. Take one last stroll through the picturesque streets, soaking in the atmosphere and bidding arrivederci to the beauty of Italy. As you board your flight back home, carry with you the indelible imprint of Italy’s splendor, knowing that this two weeks in Italy itinerary has offered you a taste of the country’s best treasures.

Map of Italy to Plan Your Two Weeks in Italy

To simplify your two weeks in Italy itinerary, we have compiled a map to follow the route. Add it to Google Maps here.

FAQ on 14 Days Italy Itinerary

Final Thoughts on our Two Weeks in Italy Itinerary

The two weeks in Italy itinerary is a dream come true for passionate travelers seeking to immerse themselves in this enchanting country’s rich history, culture, and natural beauty. From the ancient wonders of Rome to the Renaissance masterpieces of Florence, the canal-laden streets of Venice, the idyllic charm of Lake Como, the breathtaking Amalfi Coast, the timeless ruins of Pompeii, the colorful villages of the Cinque Terre, and the modern marvels of Milan, this itinerary encapsulates the essence of Italy’s diverse offerings. Prepare to be captivated as you embark on this 14-day journey, where every moment is filled with unforgettable experiences, and the magic of Italy awaits at every turn.

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