The Italy Experience

Rome + Venice + Sicily

There aren’t many places in the world where you can indulge in mouth-watering cuisine, immerse yourself in centuries-old culture, and witness stunning architecture.

Join us on our 10-day luxury adventure in Italy, where we’ll take you on a journey through the best that this enchanting country has to offer. From exploring the historic landmarks of Rome to indulging in the flavorful cuisine of Sicily and experiencing the romance of Venice, our journey will immerse you in the rich culture and traditions of Italy. Check out our client photos at #UITALItaly.

Can you hear it? The sounds of the bustling streets of Rome, the breathtaking views of Sicilian beaches, and the romantic ambiance of Venice’s canals. Our journey through Italy will take you on a magical adventure through this ancient land.

Indulge in mouth-watering cuisine as you explore the historic landmarks of Rome, marveling at their rich history and cultural significance. Then, head to the picturesque island of Sicily, where you’ll indulge in the flavorful cuisine and explore the island’s stunning natural wonders.

Finally, experience the romance of Venice, where you’ll cruise along the canals and marvel at the stunning architecture of the city. Whether you’re savoring a delicious gelato or exploring the hidden gems of Venice, the breathtaking scenery will leave you feeling grateful for the opportunity to experience the beauty of Italy.

Priceless moments with new friends, cultural immersion, and pampered relaxation await you on your Up in the Air Life journey through Italy.

Love the trip but not the dates?



Here's your trip at a glance.

Screenshot 2023-05-15 at 10.56.17 AM


Prepare yourself for a captivating journey through Italy's most enchanting cities: Venice, Rome, and Palermo. Your trip will take you through the romantic canals of Venice, the awe-inspiring historical sites of Rome, and the vibrant streets of Palermo. Get your camera ready, as the picturesque scenes and unforgettable memories await you in every corner of this magical country.

IMG_1954 (1)


Your Italian adventure is a perfect blend of culture, history, and indulgence. You'll cruise through the iconic canals of Venice, uncover the ancient wonders of Rome, and immerse yourself in the rich heritage of Palermo. Along the way, you'll savor the exquisite flavors of Italy by dining at the finest restaurants, indulging in local delicacies, and sampling the country's world-renowned wines.

IMG_1917 (1)


Indulge in carefully selected luxurious accommodations throughout your Italian journey. In Venice, experience the opulence and charm of the Metropole Hotel, adorned with a private collection of antiques. In Palermo, find sanctuary at the majestic Villa Igiea, with breathtaking sea views. Finally, in Rome, immerse yourself in the heart of the Eternal City at a boutique hotel reflecting its essence. These exquisite accommodations promise an unforgettable stay as you explore Italy's timeless wonders.

Explore the day-by-day itinerary.



Day 1

Welcome to Rome, Italy!

Get ready to be embraced by the undeniable magic of this ancient city.

We’ll kick off our journey with a lavish multicourse welcome dinner that will transport your taste buds to the heart of Italian cuisine.

Indulge in exquisite flavors paired with the finest wines and bubbly, setting the stage for a trip filled with opulence.

Day 2

Today, we’re taking on Rome in true OG style, gliding through the historic streets in our golf carts.

Feel like royalty as we explore iconic landmarks like the majestic Colosseum, where the stories of strength and resilience echo through time.

Prepare to be amazed as we venture to the Vatican City, where the artistry of Michelangelo and the spirituality of the Sistine Chapel will leave you breathless.

And of course, we’ll treat ourselves to a picturesque lunch at a hidden gem, indulging in flavors that make our souls sing.

Day 3

Take a day to revel in the beauty of Rome at your own pace.

Whether you choose to wander through the colorful streets of Trastevere, discover hidden gems off the beaten path, or simply bask in the warmth of an Italian café, this is your time to shine.

Immerse yourself in the magic of the Eternal City, capturing moments of joy, fashion, and the essence of la dolce vita.

Day 4

It’s time to fly high as we make our way to the romantic city of Venice.

Prepare to be bewitched by the charm of the canals and the beauty that dances on water.

Tonight, we’ll explore the city under a moonlit sky, sipping on signature cocktails at a trendy bar that embodies the essence of the floating city.

Dinner will be a feast fit for royalty, celebrating the richness of the Italian flavors.

Day 5

Lace up your designer shoes, because today we’re taking a fabulous walking tour of Venice.

Prepare to be serenaded by the rhythm of the gondolas, as we glide through the canals in true Venetian style.

Along the way, we’ll make stops at our favorite shops, where you can indulge in luxurious Venetian glassware, designer fashion, and exquisite culinary delights.

Let the enchanting spirit of Venice ignite your senses.

Day 6

Today is all about rummaging through the ancient city of masks in your own way.

Enjoy a free day to explore Venice at your leisure, basking in the beauty of its hidden corners and romantic bridges.

For those craving an extra touch of glamour, an optional tour to the captivating island of Murano awaits.

Witness the mastery of glass artisans as they create breathtaking pieces.

Day 7

Time to fly to the vibrant city of Palermo in Sicily, where history and culture collide.

Tonight, dress to impress and embrace the rhythm of the city during a free night on the town.

Dance to the beats of Afro-Caribbean music, savor mouthwatering Sicilian delicacies, and radiate your inner light on the streets of Palermo.

Day 8

Prepare for a day of exploration as we embark on a journey to Segesta, Erice, and the enchanting Salt Pans.

Marvel at the ancient Greek temple of Segesta, a testament to the power and resilience of our ancestors.

In the medieval town of Erice, let the cobblestone streets guide you to breathtaking vistas that overlook the sea.

Finally, immerse yourself in the wonders of the Salt Pans, a place where nature’s beauty and our connection to the earth intertwine.

Day 9

Embrace the spirit of freedom and self-discovery on this free day in Palermo.

Take the time to explore the city on your own terms.

Dive into the vibrant markets, where the colors and aromas of fresh produce will awaken your senses.

Visit the awe-inspiring Palermo Cathedral or delve into the rich history of the Norman Palace and its exquisite Palatine Chapel.

And as the day comes to a close, we’ll gather for a farewell dinner, where we’ll indulge in delectable cuisine and raise our glasses to the unforgettable moments we’ve shared.

Day 10

It’s time to bid “arrivederci” to Italy as our journey comes to an end.

Enjoy your last morning in the hotel with another scrumptious breakfast, and say your goodbyes to your new friends!

Check out at the hotel and get whisked away by your private transfer to the airport where you will head home or onwards to your next adventure.

No matter where you travel, our standards are the same.


Connect with amazing people.

We provide the opportunity to make friendships with people who share your worldview and won't ask why you wear a bonnet to sleep.

Experience attentive
and authentic hospitality.

Not only is the staff of Up in the Air Life dedicated to making sure your trip is flawlessly executed, but we are also intentional about choosing locales and vendors who celebrate Black travelers.

Be pampered with only the best.

There is no need to take a break from your baller lifestyle when you travel with us. Our lodging, excursions, and dining are pure luxury.

Feel safe and secure.

Our experienced American guides and well-maintained local relationships mean that you will have peace of mind when you travel with us.

Say "goodbye" to FOMO.

Our trips are anything but basic. While we make sure you see well-known main attractions, we also develop itineraries that will give you unique stories to share with your friends back home.


The Italy Experience

What is included:

Our trips get you close to that Beyoncé-on-a-boat lifestyle. Let us handle your travel style glow up.

  • Up In The Air Life On-site Tour Leader
  • Bon Voyage Group Video Call with the Up in the Air Life Team
  • Pre-trip Concierge Support for Room Upgrades and Booking Optional Tours
  • Pre-trip Concierge Support for Spa Appointments
  • Pre-trip Concierge Support for Restaurant Reservations
  • Private Concierge Chat during your trip for Dining and Spa Reservations
  • 3 Nights Stay at a 5-Star Hotel in Rome, Italy
  • 3 Nights Stay at a 5-Star Hotel in Sicily, Italy
  • 3 Nights Stay at a 5-Star Hotel in Venice, Italy
  • Daily Breakfast at the Hotels
  • Welcome Multi-Course Dinner paired with Fine Italian Wines
  • Guided Tour of Rome’s Historic Landmarks, including the Colosseum and Vatican City
  • Flavorful Sicilian Cuisine Experience and Island Exploration
  • Walking Tour of Venice City, Gondola Ride, and Shopping at Local Shops
  • Full-Day Excursion to Segesta, Erice, and Salt Pans from Palermo
  • Free Day to Explore at your Leisure with Farewell Cooking Class
  • Transportation for all Hosted Activities
  • Domestic Flights from Rome to Sicily, and Sicily to Venice
  • VIP Meet + Greet Private Airport Transfers
  • Personalized Hand-selected Gifts in your Swag Bag

What is not included:

We take care of all the details on your itinerary once you land. If you want to further personalize your experience, go off!

  • Round-trip airfare to and from the destination
  • Travel Medical Insurance Insurance (Please note this is required to attend the trip.)
  • Room Upgrades are available for purchase after booking
  • Optional tours are available for purchase after booking
  • Tips for Tour Leader, Guides and Drivers
  • Passport or Visa Processing Fees
  • Your passport must be valid for at least 6 months from the time of travel with at least 2 free visa pages.
  • Expenses for vaccines that may be required

Can you envision yourself on this trip?

Download "The Italy Experience" trip brochure and keep it handy as you continue to explore, or take the plunge and book now.