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Italy with Tiffany Lai Photography

Rome - Florence

2022: May 12 - May 18

Ciao bella ciao! Come on a beautiful gastronomic Italian adventure with me. I have so many exciting activities planned for us including pasta making, a cycling tour, visiting an authentic Tuscan farm - and many many more!

Our Italian fantasies of legendary cuisine, breathtaking architecture, timeless art pieces, wine tastings in vineyards, afternoon espressos and sidewalk cafes are not a myth but a reality. What the Italians call 'La Dolce Vita,' or the 'Sweet Life,' is yours for the taking. Benvenuto in Italia!

  • 7 days

  • 10 - 20 spots

  • Double occupancy in 3-star hotels (single rooms available)

  • 6 breakfasts, 2 lunches & 3 dinners included

  • Fly into Rome–Fiumicino International Airport International Airport (FCO). TrovaTrip will provide 3 transfers between 11am and 5pm.

  • Fly out of Rome–Fiumicino International Airport (FCO). TrovaTrip will provide two transfers on the last day.

Activities Included

  • Content Creation + Photography Workshop
  • Cycle Tour Rome
  • Pasta Making Class
  • Vatican City and the Sistine Chapel Tour
  • Train: Rome - Florence - Rome
  • Florence Walking Tour
  • Tuscan Farm Experience
  • Tuscan Farm Lunch

Other Inclusions

  • Double Occupancy in 3-star Hotels
  • Local Guide throughout Trip
  • All City Transfers
  • Arrival Airport Transfer (until 5pm on first day)
  • Departure Airport Transfer (morning of last day)
  • 6 Breakfasts, 2 Lunches & 3 Dinners


Content Creation + Photography Workshop: As you eat delicious Italian food and gaze at beautiful European architecture, you will learn tips from Content Creator, Model & Youtuber, Tiffany Lai. You’ll have full access to everything she knows, from posing to pitching brands - absolutely nothing is off limits. Schedule some one-on-one time with her for a more personalized session, where you can ask anything from content creation/photography or just life in general.You will also have access to her OG IG Hubby and sister bestie, Lili Lai, to show you tips and tricks she uses to get the picture perfect shot. Together they will assist you in creating content on the trip!

Optional Activities

  • Wine Tasting with an Italian Sommelier
  • Arno Boat Tour


  • International Flights
  • Food & Alcohol (except as noted)
  • Visas & Travel Insurance
  • Airport Transfers Outside of Designated Times

Your Host

Tiffany Lai

Tiffany Lai is a full time Montreal-based content creator and cat-mom. She paints her surroundings with Parisian inspired aesthetics and her Instagram conveys a sense of intimacy and harmony. She applies the strengths of her medium to achieve awareness on Asian Canadian social issues while maintaining a romantic visual of the beauty on earth. When she’s not too busy hunting for mushroom lamps, she can be found napping on her purely-for-aesthetics-uncomfortable couch or inquiring her little sister about trendy internet culture. She has perfected the art of curation through her Instagram page, with a target audience of 20-45 year olds. Her YouTube features beautifully edited lookbooks, tutorials, and vlogs. While being an active promoter for wellness and mental and physical health, she is also an advocate for the LGBTQIA2+ community. Tiffany is also present on Tiktok, despite the younger crowd, her short videos on fashion and beauty regimes are also popular.


Day 1

Benvenuto and welcome to ‘la dolce vita’ or the ‘the good life’ of Italy! Rome awaits you and upon arrival, you will be transferred from the airport and into the Eternal City.

After checking into your hotel and freshening up a bit, you will meet with your new travel buddies and head to a local restaurant for a 3-course welcome dinner where you will toast to adventures to come!

Overnight in Rome

Arrival: Fly into Rome–Fiumicino International Airport International Airport (FCO). TrovaTrip will provide 3 transfers between 11am and 5pm.

Included: Airport Transfer, Welcome Dinner

Day 2

Buongiorno! Wake up to your first morning in the old world. After breakfast, you will head out to the streets of Rome.

One of the best ways to explore the ancient backstreets of Rome is on the saddle of a bicycle. Your guide will help fit you for a bike, pop on a helmet, and go exploring. The Eternal City is teeming with ancient ruins and religious moments but still has a pulsing modern edge that is packed with cafe life, restaurants, shops, and nightlife. Your cycle tour will not only show you the traditional side of the city but will also take you off the beaten path. The tour will conclude in a local restaurant for a rewarding 3-course menu after the morning cycle.

After having some time to relax from cycling and lunch, you will join a local chef for a pasta-making course. Along with pizza, is there any other type of food that is as synonymous with culture as the Italian’s and their pasta? In Italy, there are over 50 varieties of pasta and tonight your chef will lead a workshop on how to prepare a few types by hand.

Overnight in Rome

Included: Breakfast, Lunch, Dinner, Cycle Tour Rome, Pasta Making Class

Day 3

No trip to Rome is complete without visiting the smallest country in the world, the Vatican. At only 19 square miles and a population of just over 800, the tiny city-state easily wins this claim.

Your guide will lead you through a comprehensive tour of the Vatican, beginning with the Vatican Museum. This experience will give you a real insight into Vatican City, from the ancient sculptures to the Raphael Rooms, and of course to the piece de la resistance, the Sistine Chapel.

The afternoon is free and at leisure to sip espressos or wander through the streets. If you’re feeling thirsty, there will be an optional Wine Tasting offered.

The optional wine tasting will be lead by a professional Italian sommelier. They will not only give you a master class on wines but also a bit of geography as you will be tasting wines from the north, central, and south regions of Italy. All paired with snacks of course.

Overnight in Rome

Included: Breakfast, Tour of Vatican City & the Sistine Chapel

Optional: Wine Tasting with an Italian Sommelier

Day 4

This morning, after breakfast, you will hop on a train and head to the cultural heart of Tuscany, the magical city of Florence.

You will check-in to your hotel and drop your bags before meeting with the group and guide for a walking tour of Florence.

The city of Florence is like a giant outdoor museum, bursting with Renaissance masterpieces and stylistically striking with architecture from the Renaissance, Gothic, and Baroque periods. On this tour, you will walk the footsteps of Leonardo da Vinci, Machiavelli, Michelangelo, and the greats.

After getting acclimated to the city, you will have the evening at leisure to meander and discover on your own.

Overnight in Florence

Included: Breakfast, Train - Rome to Florence, Florence Walking Tour

Day 5

Today you will have the opportunity to sample the legendary cuisine of Tuscany directly from the source on a Tuscan Farm Experience.

In the late morning, you will transfer to a local Tuscan farm and visit its vineyards and olive groves. You will have the chance to feed the sheep, visit the wine cellars, and learn about how they produce their olive oil. You will taste their wines and pair them with olives, cheese, and homemade baked bread, all produced directly from the farm to your table.

After lunch, you will head back to Florence where you’ll have the rest of the afternoon and evening to explore this romantic city.

For the optional boat tour you'll hop aboard a ‘barchette’, and your local "barcaiolo" will gently steer you over the Arno River and back in time through Florence’s historical center of majestic palaces, stunning bridges and imposing towers.

Overnight in Florence

Included: Breakfast, Tuscan Farm Experience, Tuscan Farmer’s Lunch

Optional: Arno Boat Tour

Day 6

The morning is free and at leisure to do any last-minute sightseeing or shopping in Florence before heading back to Rome for a free afternoon to wander.

In the evening, you will meet with your travel buddies for a final farewell dinner, Roman style, where you will toast to an extraordinary adventure together.

Overnight in Rome

Included: Breakfast, Train - Florence to Rome, Farewell Dinner

Day 7

All good things must come to an end but only until our next adventure! After breakfast, you will transfer to the airport to wave goodbye to Italy and your travel buddies.

Included: Breakfast, Airport Transfer

Departure: Fly out of Rome–Fiumicino International Airport (FCO). TrovaTrip will provide two transfers on the last day.

Cancellation Policy

25% down payment Additional payments
Spot pending Refundable Refundable
Spot confirmed Non-refundable* Refundable
60 days pre-trip Non-refundable Non-refundable

*If you cancel when your spot is confirmed and outside of 60 days until departure, you can receive a trip credit for your down payment minus the $100 cancellation fee.

For our full cancellation policy, see our Terms & Conditions.

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