Pyt-logo

4.6/5

8250+ reviews

Customize it the way you want

Italy 5 Nights 6 Days Group Winter Escape Itinerary

Sruthi

Curated by Sruthi, planned 4123+ Italy trips

Helper
Sooper hit holidays
Why choose Pickyourtrail - Trust elements

Your Itinerary

Venice

3 nights

Day01

Arrive in Venice airport. Get transferred to your hotel.
Morning

Arrive in Venice airport. Get transferred to your hotel.

At leisure
Noon to Evening

At leisure

Add Activity

Day02

Venice: Boat Tour and Visit to Murano Glass and Burano Lace - Murano and Burano
Morning to Noon

Venice: Boat Tour and Visit to Murano Glass and Burano Lace - Murano and Burano

Venice?s Best Walking Tour & Gondola Experience - City Center Walking Tour in English
Evening

Venice?s Best Walking Tour & Gondola Experience - City Center Walking Tour in English

Day03

Venice Walking Tour from St. Mark's to Rialto Bridge - Venice Walking Tour from St. Mark's to Rialto Bridge
Morning

Venice Walking Tour from St. Mark's to Rialto Bridge - Venice Walking Tour from St. Mark's to Rialto Bridge

Venice: Murano & Burano Panoramic Boat Tour w/ Glassblowing - Departure at 2:30 PM and Arrival at 7 PM
Noon to Evening

Venice: Murano & Burano Panoramic Boat Tour w/ Glassblowing - Departure at 2:30 PM and Arrival at 7 PM

Train ride to Rome

Rome

2 nights

Day04

Check out of your hotel. Take your train from Venice to Rome. Check-in to your new hotel
Morning to Noon

Check out of your hotel. Take your train from Venice to Rome. Check-in to your new hotel

At leisure
Evening

At leisure

Add Activity

Day05

Rome Hop-On Hop-Off Bus Tour: Full Access to 3 Scenic Routes - 1-Day Bus Ticket Hop-on and Off at 3 Stops
Full Day

Rome Hop-On Hop-Off Bus Tour: Full Access to 3 Scenic Routes - 1-Day Bus Ticket Hop-on and Off at 3 Stops

Day06

At leisure
Morning

At leisure

Add Activity

Time to head home with a full camera roll, a few souvenirs, and that Sooper hit holiday glow. The next journey awaits.
Noon to Evening

Time to head home with a full camera roll, a few souvenirs, and that Sooper hit holiday glow. The next journey awaits.

Your trip includes

Transfers, Visa & Insurance

Tell us your dates, travel group, and departure city to view all inclusion details

Hear from a traveller who chose a similar itinerary has to say

parvesh ranka

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, Italy

Travel Experts

GET ASSISTANCE

Not sure if this plan is right for you? Let our experts fine-tune it to match your style.

  1. Home
  2. Itineraries
  3. Italy 5 Nights 6 Days Group Winter Escape Itinerary

Embark on a breathtaking 5-night winter escapade through Italy, where ancient history meets charming canals and vibrant culture. From the romantic allure of Venice to the historical wonders of Rome, this itinerary is designed for group travel enthusiasts seeking unforgettable experiences. Whether you’re wandering through snow-dusted streets or savoring local delicacies, Italy in winter is sure to enchant you.

Highlights of the Destination

  • Discover Venice’s iconic canals and stunning architecture during a guided walking tour.
  • Enjoy a romantic gondola ride, gliding through serene waters while taking in the city’s illuminating reflections.
  • Experience the exquisite craftsmanship of Murano glass and the vibrant hues of Burano on a panoramic boat tour.
  • Explore the rich tapestry of history in Rome, from the Colosseum to St. Peter’s Basilica, using hop-on hop-off bus services for easy access.

Travel Tips for Italy

  • Dress in layers. Winters can be chilly, especially near the canals and during the evenings.
  • Always book gondola rides in advance to avoid long waits and ensure your spot.
  • Make use of the extensive public transport systems in both Venice and Rome for easy navigation.
  • Learn a few basic Italian phrases to enhance interactions with locals during your travels.

Conclusion

Italy's winter ambiance offers a unique charm that transforms its beauty into a mesmerizing experience. With exquisite landscapes, rich history, and local traditions, your group will create memories that will last a lifetime during this 5-night adventure. Pack your bags, gather your friends, and prepare for a winter escape that celebrates the heart and soul of Italy.

Customer Reviews

4.6

From 65+
countries

5

4

3

2

1

Parvesh Ranka-Profile

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-Profile

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-Profile

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!

Srinivasu K-Profile

Srinivasu K

Reviewed on: 23 May 2023

The journey to Europe started from an inquiry with an amazing person Mr. Avik Shriram of pickyourtrial...and from there onwards its smooth planning and excitement to be there...It was absolutely an amazing experience to Swiss and Italy brilliantly organised and customised according to our taste by pickyourtrial.Their APP was amazing and you will love it once you start experiencing.... they provided 24/7 support for all your queries, and you get quick responses.I should give the entire credit to Avik Shriram as we ended with lots of memories to take away.

Preena Singh-Profile

Preena Singh

Reviewed on: 12 Mar 2020

I booked my Honeymoon for Italy from Pickyourtrail , it was a good experience overall a few hits and misses but these guys did a nice job..Thank you for the amazing experience 😊

Bharath Sukumaran-Profile

Bharath Sukumaran

Reviewed on: 12 Mar 2020

Excellent service for my Italy trip... I would definitely recommend Pickyourtrail for any trips...

Divya Mohan-Profile

Divya Mohan

Reviewed on: 10 Mar 2020

Had used pickyourtrail for my Italy vacation. They offered excellent support although. The live chat option was really helpful. Everyone I interacted with was really professional and helpful. 6 Stars 😊.

Dhivya M-Profile

Dhivya M

Reviewed on: 03 Mar 2020

It was a wonderful experience with Pickyourtrial team. We had a pleasant journey. Online support team was very helpful at the new place when we were stuck and they were responding immediately and was very helpful. The entire trip to Italy went very well with no hassle. We loved it. Thank you guys.

Preena Singh-Profile

Preena Singh

Reviewed on: 13 Feb 2020

I booked my Honeymoon for Italy from Pickyourtrail , it was a good experience overall a few hits and misses but these guys did a nice job..Thank you for the amazing experience 😊

Swarna Achin-Profile

Swarna Achin

Reviewed on: 30 Dec 2019

Our experience with PYT was nothing short of amazing. We had originally planned a vacation to Greece and while we were contemplating on the list of islands to visit in Greece with profound excitement, PYT team shared the same excitement as us and brought up this idea of visiting Italy also, instead of just doing Greece, thereby adding versatility to our vacation. And they came up with this beautiful itinerary for us - Venice -> Santorini -> Athens. They intently paid heed to what our interests were and made all the bookings accordingly. Regardless of the time gap, they even promptly responded to our queries while we were in the midst of our vacation. We are grateful for their seamless customer service and look forward to plan our future trips with PickYourTrail :)

Frequently Asked Questions

travelExpertImg

Need help in planning?

Talk to our Travel Experts