Embark on a captivating 14-day cultural journey across Italy, exploring iconic cities like Rome, Florence, and Venice, alongside charming Pienza, picturesque Cinque Terre, and the breathtaking Dolomites. This moderate-budget adventure for two emphasizes authentic experiences, from delving into ancient cultural sites and vibrant local markets to indulging in delicious food, scenic nature walks, and stunning photography opportunities, all while staying in cozy Airbnb homestays.

Depart from New Delhi and fly to Naples International Airport (NAP).
This flight includes 2 stops. Remember to account for time zone changes.
After landing, proceed to the train station for your onward journey to Rome.
Take a high-speed train from Naples Centrale to Rome Termini station.
Enjoy the scenic Italian countryside as you travel north.
Trains depart frequently. Book tickets in advance, especially for high-speed services.
Arrive at your pre-booked Airbnb in Rome.
Settle in and prepare for your Roman exploration.
Confirm check-in procedures and key collection with your host prior to arrival.
Enjoy a late dinner in the charming Monti neighborhood, known for its bohemian vibe and excellent restaurants.
Monti is full of trattorias and wine bars. Try local Roman pasta dishes like Cacio e Pepe or Carbonara.
Step back in time with a visit to the iconic Colosseum, followed by an exploration of the ancient Roman Forum and Palatine Hill, the heart of ancient Rome.
Book skip-the-line tickets online well in advance. Wear comfortable shoes as there is a lot of walking.
Visit the magnificent Pantheon, an architectural marvel, then toss a coin into the Trevi Fountain for good luck.
The Pantheon is free to enter, but may require timed entry during peak seasons. Be prepared for crowds at the Trevi Fountain.
Join a hands-on cooking class to master making fresh fettuccine, ravioli, and tiramisu, followed by enjoying your creations for dinner.
Learn authentic Italian cooking techniques from a local chef. Perfect for food lovers!
Explore St.
Peter's Basilica, the Vatican Museums, and the Sistine Chapel, home to Michelangelo's masterpieces.
Dress code strictly enforced: shoulders and knees must be covered. Book tickets online well in advance to avoid long queues.
Travel by high-speed train from Rome Termini to Florence Santa Maria Novella.
This journey offers comfortable and efficient travel.
Book train tickets in advance for better prices. Major providers are Trenitalia and Italo.
Arrive at your booked Airbnb in Florence and settle in.
Florence's city center is very walkable.
Confirm check-in procedures with your host. Consider an Airbnb close to the train station for convenience.
Take a leisurely walk across the iconic Ponte Vecchio bridge, browse the unique shops, and enjoy a stroll along the Arno River.
This historic bridge is known for its shops built along its edges. Great spot for photos, especially at sunset.
Enjoy dinner in the Oltrarno district, known for its artisan workshops and authentic Florentine cuisine.
Try Florentine steak (Bistecca alla Fiorentina) or traditional Tuscan pasta dishes.
Visit the iconic Florence Cathedral (Duomo), climb Brunelleschi's Dome or Giotto's Bell Tower for panoramic city views.
Booking tickets for the Dome climb or Bell Tower is essential and should be done far in advance as slots sell out quickly.
Participate in a hands-on ceramics masterclass in Montelupo Fiorentino, learning traditional Tuscan pottery techniques from a master potter.
This experience offers a unique insight into local craftsmanship. Plan for travel time to/from Montelupo by train.
Take a train from Florence to Chiusi-Chianciano Terme, then a bus or taxi to Pienza, immersing yourself in the heart of Tuscany.
The train portion is about 1.5 hours, followed by a local bus or taxi (approx. 30 minutes) to Pienza. Ensure you check bus schedules or pre-book a taxi.
Arrive at your homestay in Pienza, a UNESCO World Heritage site known as the 'ideal Renaissance town'.
Enjoy the tranquility and stunning views of the Val d'Orcia from your Pienza base.
Savor a delightful Tuscan dinner at a local restaurant in Pienza, perhaps with views overlooking the Val d'Orcia.
Pienza is famous for its Pecorino cheese. Try dishes featuring this local specialty.
Wander through the historic center of Pienza, visiting its Renaissance cathedral, Palazzo Piccolomini, and charming streets.
Pienza is small and easily explored on foot. Enjoy the unique urban planning and stunning viewpoints.
Take a leisurely drive or walk through the rolling hills of Val d'Orcia, famous for its cypress-lined roads, vineyards, and picturesque farms.
Enjoy lunch at a local agriturismo.
Consider renting a car for the day to fully explore the countryside, or book a local tour. This region is a photographer's dream.
Indulge in a tasting of Pienza's renowned Pecorino cheese at a local shop or farm.
Learn about its production and different aging stages.
Many shops offer free tastings; guided tastings might have a small fee. A perfect souvenir to take home!
Enjoy free time to relax at your Airbnb, take an evening stroll, or simply soak in the peaceful ambiance of the Tuscan countryside.
Enjoy the quiet evening and perhaps catch a beautiful sunset over the Val d'Orcia.
Embark on a scenic journey from Pienza to Vernazza in Cinque Terre.
This will involve a combination of bus and train travel, likely through Siena or Florence to La Spezia, then a regional train to Vernazza.
Train travel is the most efficient way to reach Cinque Terre. Consider purchasing a Cinque Terre Card for unlimited regional train travel and access to hiking paths between villages.
From Pienza, take a local bus to Siena or Florence, then a regional train to La Spezia Centrale. From La Spezia, catch a local Cinque Terre Express train directly to Vernazza. Check Trenitalia for schedules.
Arrive in Vernazza, settle into your Airbnb homestay and refresh after your journey.
Many homestays in Vernazza are a short walk from the train station, but some might involve stairs. Pack light!
Wander through the colorful streets of Vernazza, visit the picturesque harbor, and climb to Doria Castle for panoramic views of the village and coastline.
Doria Castle offers one of the best viewpoints. There's a small entrance fee.
Enjoy a traditional Italian aperitivo with local wine and snacks at a bar overlooking Vernazza's harbor.
Try the local Sciacchetrà wine, a sweet dessert wine unique to Cinque Terre.
Savor fresh seafood and local Ligurian pasta dishes at a restaurant in Vernazza.
Pesto Genovese, focaccia, and fresh anchovies are local specialties.
Take the scenic coastal path from Vernazza to Monterosso al Mare.
Enjoy breathtaking views of the rugged coastline and terraced vineyards. (Verify trail status, as paths can close due to weather).
The path is relatively challenging in sections. Wear comfortable shoes and bring water. If the trail is closed, take the train between villages.
Enjoy lunch in Monterosso, the largest of the Cinque Terre villages, known for its beautiful beach.
Many restaurants near the beach offer fresh seafood.
Take the train to Manarola, famous for its colorful houses clinging to the cliffs.
Explore the village, walk along the harbor, and capture iconic photos. Afterwards, take a short train ride to Riomaggiore, the southernmost village, known for its charming marina.
The train connection between villages is frequent and quick. Manarola is particularly beautiful at sunset.
Use your Cinque Terre Treno Card for easy train travel between villages.
Find a perfect spot in Manarola to watch the sunset paint the colorful houses in warm hues, perhaps with a glass of local wine.
Nessun Dorma is a famous spot for aperitivo and sunset views, but expect queues.
Return to Vernazza by train and enjoy a relaxed dinner at a local trattoria.
Begin a full-day journey from Vernazza to the Dolomites region.
This will involve multiple train connections (e.g., Vernazza to La Spezia, then a high-speed train towards Verona or Bolzano) and potentially a final bus or rental car to your chosen Dolomites base town.
This is a long travel day. Consider booking train tickets in advance for better prices. A rental car offers flexibility for exploring the Dolomites.
Take a regional train from Vernazza to La Spezia Centrale. From La Spezia, take a high-speed train (Frecciarossa/Italo) to Verona Porta Nuova or Bolzano (Bozen). From there, local trains or buses connect to specific towns like Ortisei, Cortina d'Ampezzo, or Val Gardena. Alternatively, pick up a rental car in Verona or Bolzano.
Arrive in your chosen Dolomites town (e.
g., Ortisei, Bolzano, or a town in Val Gardena) and check into your homestay. Take some time to settle in and enjoy the fresh mountain air.
Dolomites towns are generally quiet and charming. Enjoy the change of scenery from the coast.
Take a leisurely walk around your Dolomites town to get acquainted with your surroundings.
Admire the Alpine architecture and mountain views.
Many towns have pedestrian zones perfect for an evening stroll.
Enjoy your first dinner in the Dolomites, sampling regional specialties such as canederli (dumplings), speck, or Schlutzkrapfen (spinach ravioli).
The cuisine here is a mix of Italian and Austrian influences.
Travel to Lago di Braies (Pragser Wildsee), one of the most stunning lakes in the Dolomites.
Enjoy a gentle walk around the lake or rent a rowboat for a unique experience on the turquoise waters.
Access to the lake area might require a shuttle bus or parking fee during peak season. May is still shoulder season, so it should be less crowded. Check specific transport options from your base town.
If you have a rental car, drive. Otherwise, check local bus schedules from your Dolomites town to Lago di Braies. This may require a connection.
Have lunch at a nearby mountain hut (Rifugio) or a local restaurant, enjoying regional dishes with beautiful views.
Many rifugios offer hearty, traditional meals.
Embark on a scenic drive through one of the Dolomites' famous mountain passes, such as Passo Gardena or Passo Sella, marveling at the towering peaks and dramatic landscapes.
If you don't have a rental car, consider a local bus tour or taxi service for this activity.
Best enjoyed with a rental car for flexibility to stop at viewpoints. Alternatively, some local bus routes traverse passes, offering scenic journeys.
Return to your Dolomites town, take some time to relax, perhaps enjoy a coffee or aperitivo.
Indulge in another delicious dinner, perhaps trying a different local specialty or visiting a highly-rated restaurant.
Take a cable car up to a higher altitude for breathtaking panoramic views of the Dolomites peaks.
Enjoy a leisurely walk on an alpine plateau.
The Dolomites offer numerous cable car options. Popular choices include Alpe di Siusi (Europe's largest high-altitude Alpine meadow) or Seceda (for dramatic jagged peaks). Check which are open in May.
Dine at a mountain restaurant or rifugio at the top of the cable car for an unforgettable lunch experience with stunning views.
Savor local specialties while surrounded by majestic peaks.
Descend back into the valley and explore another charming Dolomites town nearby, perhaps browsing local shops or visiting a church.
Each town has its own unique character and charm.
Use local bus or rental car to reach the next town.
Enjoy some free time back at your homestay, relax, and start preparing for your departure to Venice tomorrow.
Enjoy a final memorable dinner in the Dolomites, reflecting on the stunning landscapes and experiences.
Enjoy a final, refreshing hike in the stunning Dolomites.
Choose a trail suitable for your group's fitness level, soaking in the panoramic mountain views and fresh Alpine air.
Wear comfortable hiking shoes and bring water. Check local trail conditions.
Savor a traditional Alpine lunch at a local 'rifugio' or restaurant, enjoying regional specialties.
Spend the afternoon at leisure, perhaps enjoying a coffee with a view, and begin packing for your journey to Venice tomorrow.
Ensure all belongings are ready for an early start.
Enjoy a final dinner in the Dolomites, reflecting on the stunning landscapes and experiences.
Opt for a restaurant offering local Ladin cuisine.
Depart from the Dolomites (e.
g., Bolzano or Cortina d'Ampezzo) by bus or private transfer to a major train station, then take a scenic train journey to Venezia Santa Lucia station. Enjoy the changing landscapes.
This journey typically involves a bus from your specific Dolomites location to a train station like Bolzano, Belluno, or Trento, followed by a train to Venezia Santa Lucia. Pre-booking train tickets is highly recommended.
From Santa Lucia station, take a Vaporetto (water bus) or water taxi to your Airbnb.
Check in and then find a local spot for a quick Venetian lunch.
Vaporetto tickets can be purchased at the station. Consider a multi-day pass if you plan to use it frequently.
Begin your Venice exploration at the iconic Piazza San Marco, the city's main public square.
Admire St. Mark's Basilica (exterior), Doge's Palace (exterior), and the Campanile.
Be aware of pigeons and potential crowds. Consider visiting St. Mark's Basilica interior if time permits (booking recommended).
Experience the quintessential Venetian gondola ride, drifting through the charming canals.
A perfect way to see Venice from a unique perspective.
Gondola prices are fixed by law. Confirm the price before boarding. Gondola ride prices can be around EUR 80-120 for a private ride, not per person.
Enjoy a delicious dinner in the less crowded Castello district, savoring fresh seafood or classic Venetian dishes.
Explore the majestic Doge's Palace, a symbol of Venetian power and glory.
Walk through its opulent rooms and across the Bridge of Sighs.
Book tickets online in advance to avoid long queues. Allow ample time to explore.
Walk across the iconic Rialto Bridge, enjoying views of the Grand Canal.
Explore the bustling Rialto Market nearby, where locals shop for fresh produce and seafood (morning is best for the market).
The market is most lively in the morning. Be prepared for crowds on the bridge.
Enjoy lunch at a trattoria or osteria in the San Polo or San Marco sestiere, near the Rialto Bridge.
Wander through the quieter, authentic district of Cannaregio, home to the historic Jewish Ghetto.
Discover hidden courtyards, artisan shops, and charming canals.
This area offers a different, more local side of Venice away from the main tourist hubs.
Enjoy your final dinner in Venice.
Consider a restaurant with canal views or one recommended by your Airbnb host for an authentic experience.
Enjoy a final Italian breakfast at a local cafe.
If time permits, do some last-minute souvenir shopping for Murano glass or Venetian masks.
Travel from Venice to Naples for your international departure.
This is a significant journey, best done by high-speed train (approx. 5-6 hours) from Venezia Santa Lucia to Napoli Centrale, followed by a taxi or shuttle to Naples International Airport (NAP).
Book your train tickets from Venice to Naples in advance. Ensure you allow ample time for transfers to and from train stations, and for airport check-in and security.
Check in for your international flight from Naples International Airport (NAP) back to New Delhi (DEL), concluding your Italian adventure.
This 14-day itinerary for Rome, Florence & Pienza can be customized using our AI travel planner. Chat with our AI assistant to modify activities, adjust timings, add personal preferences, and get recommendations for restaurants, hotels, and transportation.