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- A 9 day Italy itinerary to quench your wanderlust
Why choose Pickyourtrail?
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Awarded The Best Holiday Brand in IndiaItinerary
Florence
3 Nights Stay
Florence — 3 Nights
Day 01
Full Day
Arrive in Florence airport. Get transferred to your hotel.
Day 02
Morning
ponte vecchio bridge
Noon
At leisure. Add Activity
Evening
Florence Cathedral
Day 03
Full Day
Highlights of Tuscany: Siena, San Gimignano, Chianti, and Pisa with Lunch in a Chianti Winery
Train ride to Positano
Positano
3 Nights Stay
Positano — 3 Nights
Day 04
Morning
Check out of your hotel. Take your train from Florence to Positano. Check-in to your new hotel
Noon to Evening
At leisure. Add Activity
Day 05
Full Day
At leisure. Add Activity
Day 06
Full Day
At leisure. Add Activity
Train ride to Rome
Rome
2 Nights Stay
Rome — 2 Nights
Day 07
Morning
At leisure. Add Activity
Noon
Check out of your hotel. Take your train from Positano to Rome. Check-in to your new hotel
Evening
Colosseum or Colosseo Skip-the-line Ticket
Day 08
Morning
Skip the Line: Vatican Museum St Peter's Basilica and Sistine Chapel Tour
Noon
At leisure. Add Activity
Evening
Spanish Steps
Day 09
Full Day
Time to head home with a full camera roll, a few souvenirs, and that Sooper hit holiday glow. The next journey awaits.
Add trip details
₹200,266/ person
Excluding Applicable Taxes
Exceptional Europe Trip & Incredible Support! I want to express my heartfelt appreciation to Pick Your Trail for customizing my dream trip to Europe. From the meticulously planned itinerary and reasonable pricing to the smooth post-trip refund process, everything was top-notch. What truly sets them apart is their phenomenal 24x7 support during critical moments. When a national train strike in Italy cancelled our train from Milan to Venice, and subsequently affected our scheduled gondola ride, the support team stepped up immediately, offering to cover 50% of the replacement tickets and activities. They also went above and beyond when we faced ticketing issues with our BB train transit from Venice, completely reimbursing our travel to Portonova. A massive special thanks to Pranjal for handling our booking and pre-post support, and to Jayalakshmi, Vaishnavi, Janani, Anith, Aashwin George, and the entire 24x7 support crew for being there for us every single step of the way. Any company can sell you a vacation package, but Pick Your Trail delivers unmatched crisis management, peace of mind, and genuine care. Thank you for making our holiday so memorablewe will definitely book our next international trip with you guys!Avdesh Chauhan, Trip to Italy
See what’s included in this tripCost your itinerary to see the hotels, flights, and activities included in your trip
4.7From 8250 reviews
Verified ReviewsPhotos from Travellers
Pickyourtrail's Original Reviews
Avdesh Chauhan Reviewed on :24 Jul 2026
Exceptional Europe Trip & Incredible Support! I want to express my heartfelt appreciation to Pick Your Trail for customizing my dream trip to Europe. From the meticulously planned itinerary and reasonable pricing to the smooth post-trip refund process, everything was top-notch. What truly sets them apart is their phenomenal 24x7 support during critical moments. When a national train strike in Italy cancelled our train from Milan to Venice, and subsequently affected our scheduled gondola ride, the support team stepped up immediately, offering to cover 50% of the replacement tickets and activities. They also went above and beyond when we faced ticketing issues with our BB train transit from Venice, completely reimbursing our travel to Portonova. A massive special thanks to Pranjal for handling our booking and pre-post support, and to Jayalakshmi, Vaishnavi, Janani, Anith, Aashwin George, and the entire 24x7 support crew for being there for us every single step of the way. Any company can sell you a vacation package, but Pick Your Trail delivers unmatched crisis management, peace of mind, and genuine care. Thank you for making our holiday so memorablewe will definitely book our next international trip with you guys!
Avdesh Chauhan Reviewed on :24 Jul 2026
Exceptional Europe Trip & Incredible Support! I want to express my heartfelt appreciation to Pick Your Trail for customizing my dream trip to Europe. From the meticulously planned itinerary and reasonable pricing to the smooth post-trip refund process, everything was top-notch. What truly sets them apart is their phenomenal 24x7 support during critical moments. When a national train strike in Italy cancelled our train from Milan to Venice, and subsequently affected our scheduled gondola ride, the support team stepped up immediately, offering to cover 50% of the replacement tickets and activities. They also went above and beyond when we faced ticketing issues with our BB train transit from Venice, completely reimbursing our travel to Portonova. A massive special thanks to Pranjal for handling our booking and pre-post support, and to Jayalakshmi, Vaishnavi, Janani, Anith, Aashwin George, and the entire 24x7 support crew for being there for us every single step of the way. Any company can sell you a vacation package, but Pick Your Trail delivers unmatched crisis management, peace of mind, and genuine care. Thank you for making our holiday so memorablewe will definitely book our next international trip with you guys!
Parvesh Ranka Reviewed on :04 Jun 2026
Dear Rohit / Somi / Subhash / Srivathsan / Vaishnavi & Entire Pickyourtrail Team I Would Like To Thank You All For Making Our Italy Trip Wonderful & Memorable Your Presence During Our On Going Journey Made Ourself Relaxed & Supportive
Parvesh Ranka Reviewed on :04 Jun 2026
Dear Rohit / Somi / Subhash / Srivathsan / Vaishnavi & Entire Pickyourtrail Team I Would Like To Thank You All For Making Our Italy Trip Wonderful & Memorable Your Presence During Our On Going Journey Made Ourself Relaxed & Supportive
Monisha Borthakur Reviewed on :22 Nov 2025
Experience of my Italy was very good. Gaurav Ramani was very prompt and helpful. Sana guided me well and planned a good trip me. Overall it was a very good experience
Monisha Borthakur Reviewed on :22 Nov 2025
Experience of my Italy was very good. Gaurav Ramani was very prompt and helpful. Sana guided me well and planned a good trip me. Overall it was a very good experience
Vamsi Pradeep Reviewed on :02 Jul 2025
Hey, we just got back from our first Schengen trip to Italy and swiss with PYT, and it was awesome! The whole thing went super smoothly, and a big shoutout to the Visa team they were lifesavers, especially since our visa got rejected at first. Uma helped us plan everything, and Mohasib kept things running perfectly. Plus, the app support was great, with reminders and quick answers to all our questions. Seriously, I totally recommend PYT if you want a stress-free trip!
Vamsi Pradeep Reviewed on :02 Jul 2025
Hey, we just got back from our first Schengen trip to Italy and swiss with PYT, and it was awesome! The whole thing went super smoothly, and a big shoutout to the Visa team they were lifesavers, especially since our visa got rejected at first. Uma helped us plan everything, and Mohasib kept things running perfectly. Plus, the app support was great, with reminders and quick answers to all our questions. Seriously, I totally recommend PYT if you want a stress-free trip!
Prachi Chirania Reviewed on :11 Dec 2024
We had an amazing experience booking our honeymoon trip to Italy planned through Pickyourtrail. From the very start, their team was attentive, helpful, and thorough in understanding our preferences. Every detail, from the accommodations to the activities, was planned well, with 24/7 virtual assistance making our trip stress-free. Highly recommend PickyourTrail for anyone looking to plan a seamless and Special !
+1View all
Prachi Chirania Reviewed on :11 Dec 2024
We had an amazing experience booking our honeymoon trip to Italy planned through Pickyourtrail. From the very start, their team was attentive, helpful, and thorough in understanding our preferences. Every detail, from the accommodations to the activities, was planned well, with 24/7 virtual assistance making our trip stress-free. Highly recommend PickyourTrail for anyone looking to plan a seamless and Special !
+1View all
Bhavana Rao Reviewed on :07 Nov 2024
I am an avid traveller and have taken help from many travel agencies over the years. I haven't seen anyone come close to what PYT provides starting from providing itinerary, working with us on visa, helping us through documentation, changes required and support during the overall journey is incredible. Some folks like Nayanashi and Rinchen here are just amazing. We just finished a 10 day trip to Italy and it was just awesome. Dedicated to providing what we need in terms of travel, sight seeing, transfers required etc
Bhavana Rao Reviewed on :07 Nov 2024
I am an avid traveller and have taken help from many travel agencies over the years. I haven't seen anyone come close to what PYT provides starting from providing itinerary, working with us on visa, helping us through documentation, changes required and support during the overall journey is incredible. Some folks like Nayanashi and Rinchen here are just amazing. We just finished a 10 day trip to Italy and it was just awesome. Dedicated to providing what we need in terms of travel, sight seeing, transfers required etc
4.7From 8250 reviews
Verified ReviewsSimilar Itineraries
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