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Rome, Florence & Pienza 14-Day Trip Itinerary

Rome, Florence & Pienza Trip - May 7 to May 20

May 7 - May 20

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.

Rome, Florence & Pienza view
1

Arrival in Rome & First Impressions

Thursday, May 7
1.1
03:00 - 18:50
INR 49140 for 2 people

Flight to Naples

Depart from New Delhi and fly to Naples International Airport (NAP).

This flight includes 2 stops. Remember to account for time zone changes.

New Delhi (DEL) to Naples (NAP)

After landing, proceed to the train station for your onward journey to Rome.

1.2
19:30 - 20:45
EUR 40-70 for 2 people

Train to Rome

Take a high-speed train from Naples Centrale to Rome Termini station.

Enjoy the scenic Italian countryside as you travel north.

Naples Centrale to Rome Termini

Trains depart frequently. Book tickets in advance, especially for high-speed services.

1.3
21:15

Check into Rome Airbnb

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.

1.4
22:15
EUR 60-90 for 2 people

Dinner in Monti

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.

2

Ancient Rome & Culinary Journey

Friday, May 8
2.1
09:00 - 13:00
EUR 32-40 for 2 people

Colosseum & Roman Forum

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.

2.2
14:30 - 16:30

Pantheon & Trevi Fountain

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.

2.3
18:00 - 21:00
USD 142 for 2 people

Fettuccine & Tiramisu Class

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!

3

Vatican City & Travel to Florence

Saturday, May 9
3.1
09:00 - 13:00
EUR 40-50 for 2 people

Vatican City Tour

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.

3.2
14:30 - 16:00
EUR 50-100 for 2 people

High-Speed Train to Florence

Travel by high-speed train from Rome Termini to Florence Santa Maria Novella.

This journey offers comfortable and efficient travel.

Rome Termini to Florence Santa Maria Novella

Book train tickets in advance for better prices. Major providers are Trenitalia and Italo.

3.3
16:30

Check into Florence Airbnb

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.

3.4
17:30 - 19:00

Ponte Vecchio & Arno Stroll

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.

3.5
19:30
EUR 70-100 for 2 people

Dinner in Oltrarno

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.

4

Florentine Art & Tuscan Charm in Pienza

Sunday, May 10
4.1
09:00 - 11:00
EUR 30-40 for 2 people

Florence Duomo Complex

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.

4.2
12:00 - 14:00
USD 260 for 2 people

Tuscan Ceramics Masterclass

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.

4.3
15:30 - 17:30
EUR 40-70 for 2 people

Travel to Pienza

Take a train from Florence to Chiusi-Chianciano Terme, then a bus or taxi to Pienza, immersing yourself in the heart of Tuscany.

Florence to Pienza

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.

4.4
18:00

Check into Pienza Airbnb

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.

4.5
19:30
EUR 60-90 for 2 people

Dinner with Val d'Orcia Views

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.

5

Exploring Pienza & Val d'Orcia

Monday, May 11
5.1
09:30 - 12:00

Explore Pienza Town

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.

5.2
12:30 - 15:30
EUR 50-80 for 2 people

Val d'Orcia Scenic Drive & Lunch

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.

5.3
16:00 - 17:30
EUR 10-30 for 2 people

Pecorino Cheese Tasting

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!

5.4
18:00 - 19:30

Evening Relaxation

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.

6

Travel to Vernazza & Coastal Charm

Tuesday, May 12
6.1
08:00 - 14:00
EUR 50-70 for 2 people

Travel to Vernazza

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.

Pienza to Vernazza

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.

6.2
14:00 - 15:00

Check-in to Homestay

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!

6.3
15:00 - 18:00
EUR 8 for 2 people

Explore Vernazza Village

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.

6.4
18:00 - 19:30
EUR 30-40 for 2 people

Seaside Aperitivo

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.

6.5
20:00 - 21:30
EUR 70-90 for 2 people

Dinner with Ligurian Flavors

Savor fresh seafood and local Ligurian pasta dishes at a restaurant in Vernazza.

Pesto Genovese, focaccia, and fresh anchovies are local specialties.

7

Cinque Terre Coastal Exploration

Wednesday, May 13
7.1
09:00 - 12:00
EUR 16 for 2 people

Hike to Monterosso

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.

7.2
12:30 - 13:30
EUR 50-70 for 2 people

Lunch in Monterosso

Enjoy lunch in Monterosso, the largest of the Cinque Terre villages, known for its beautiful beach.

Many restaurants near the beach offer fresh seafood.

7.3
14:30 - 17:00

Manarola & Riomaggiore

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.

Manarola & Riomaggiore

Use your Cinque Terre Treno Card for easy train travel between villages.

7.4
17:30 - 19:00
EUR 20-30 for 2 people

Manarola Sunset Views

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.

7.5
20:00 - 21:30
EUR 60-80 for 2 people

Dinner in Vernazza

Return to Vernazza by train and enjoy a relaxed dinner at a local trattoria.

8

Journey to the Dolomites

Thursday, May 14
8.1
08:00 - 16:00
EUR 80-120 for 2 people

Travel to the Dolomites

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.

Vernazza to 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.

8.2
16:00 - 17:00

Arrive & Check-in

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.

8.3
17:30 - 19:00

Evening Stroll & Orientation

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.

8.4
20:00 - 21:30
EUR 70-90 for 2 people

Dinner with Alpine Flavors

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.

9

Dolomites Lakes & Panoramas

Friday, May 15
9.1
09:00 - 12:00
EUR 20-40 for 2 people

Lago di Braies Excursion

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.

Lago di Braies, South Tyrol

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.

9.2
12:30 - 13:30
EUR 40-60 for 2 people

Mountain Lunch

Have lunch at a nearby mountain hut (Rifugio) or a local restaurant, enjoying regional dishes with beautiful views.

Many rifugios offer hearty, traditional meals.

9.3
14:30 - 17:30

Dolomites Scenic Drive

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.

Dolomites Passes

Best enjoyed with a rental car for flexibility to stop at viewpoints. Alternatively, some local bus routes traverse passes, offering scenic journeys.

9.4
17:30 - 19:00

Relax in Town

Return to your Dolomites town, take some time to relax, perhaps enjoy a coffee or aperitivo.

9.5
20:00 - 21:30
EUR 70-90 for 2 people

Traditional Dinner

Indulge in another delicious dinner, perhaps trying a different local specialty or visiting a highly-rated restaurant.

10

Dolomites Cable Cars & Alpine Views

Saturday, May 16
10.1
09:00 - 12:00
EUR 50-70 for 2 people

Cable Car to Panoramic Views

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.

10.2
12:30 - 13:30
EUR 40-60 for 2 people

Lunch at Altitude

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.

10.3
14:30 - 17:00

Explore Another Dolomites Town

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.

Dolomites Town (e.g., Castelrotto or Corvara)

Use local bus or rental car to reach the next town.

10.4
17:30 - 19:00

Leisure Time & Packing

Enjoy some free time back at your homestay, relax, and start preparing for your departure to Venice tomorrow.

10.5
20:00 - 21:30
EUR 70-90 for 2 people

Farewell Dolomites Dinner

Enjoy a final memorable dinner in the Dolomites, reflecting on the stunning landscapes and experiences.

11

Dolomites Exploration & Leisure

Sunday, May 17
11.1
09:00 - 13:00
EUR 0 for 2 people

Morning Dolomites Hike

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.

11.2
13:30 - 14:30
EUR 50-70 for 2 people

Alpine Lunch

Savor a traditional Alpine lunch at a local 'rifugio' or restaurant, enjoying regional specialties.

11.3
15:00 - 18:00
EUR 0 for 2 people

Leisure & Packing

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.

11.4
19:30 - 21:00
EUR 70-100 for 2 people

Farewell Dolomites Dinner

Enjoy a final dinner in the Dolomites, reflecting on the stunning landscapes and experiences.

Opt for a restaurant offering local Ladin cuisine.

12

Travel to Venice & St. Mark's Square

Monday, May 18
12.1
09:00 - 14:00
EUR 80-150 for 2 people

Travel to Venice

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.

From Dolomites to Venice

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.

12.2
14:30 - 16:00
EUR 40-60 for 2 people

Check-in & Lunch

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.

12.3
16:30 - 18:30
EUR 0 for 2 people

St. Mark's Square Exploration

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).

12.4
18:45 - 19:30
EUR 80-120 for 2 people

Romantic Gondola Ride

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.

12.5
20:00 - 21:30
EUR 80-120 for 2 people

Dinner in Castello

Enjoy a delicious dinner in the less crowded Castello district, savoring fresh seafood or classic Venetian dishes.

13

Doge's Palace & Rialto Charm

Tuesday, May 19
13.1
09:30 - 12:00
EUR 52 for 2 people

Doge's Palace & Bridge of Sighs

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.

13.2
12:30 - 14:00
EUR 0 for 2 people

Rialto Bridge & Market

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.

13.3
14:00 - 15:00
EUR 50-70 for 2 people

Lunch Near Rialto

Enjoy lunch at a trattoria or osteria in the San Polo or San Marco sestiere, near the Rialto Bridge.

13.4
15:30 - 18:00
EUR 0 for 2 people

Cannaregio Exploration

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.

13.5
19:30 - 21:00
EUR 80-120 for 2 people

Farewell Venetian Dinner

Enjoy your final dinner in Venice.

Consider a restaurant with canal views or one recommended by your Airbnb host for an authentic experience.

14

Departure from Italy

Wednesday, May 20
14.1
09:00 - 11:00
EUR 30-50 for 2 people

Last Venetian Breakfast & Souvenirs

Enjoy a final Italian breakfast at a local cafe.

If time permits, do some last-minute souvenir shopping for Murano glass or Venetian masks.

14.2
11:30 - 18:00
EUR 150-250 for 2 people

Travel to Naples Airport (NAP)

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).

From Venice 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.

14.3
20:00
INR 98280 for 2 people

Depart from Naples to New Delhi

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.