2024 Oakwood Italy Cultural Journey

Dear Families, Friends, and Travelers – Welcome to the 2024 Oakwood Italy Cultural Journey! We have created two webpages dedicated to this exciting program so that travelers are as informed as possible throughout the process. The first page, Pre-Enrollment, is meant to share exciting details, highlights and pertinent info that participants will want to know before enrolling. Once enrolled, the Post-Enrollment page, is meant to prepare travelers for participation on the adventure ahead. Please be sure to review the information on the appropriate page thoroughly and we can't wait to start our enriching adventure!
Travel Dates: April 5, 2024 - April 13, 2024
Group Organizer(s):
WTT Contact:
Program Tuition: $3,100 USD
Airfare not included in program tuition
Estimated Airfare: $1,200

Tuition Calculator

There are two options for payment, including an interest-free installment plan.  Follow whichever works best for your family. If we are within 90 days of travel, only the pay in full option is possible.

Program Tuition: $3,100

Pay in Full


due today

All prices in United States Dollars.

Italy Cultural Journey

Italy is a traveler’s dream and an item on everyone’s bucket list. No other country in the world contains as many historical sites and artifacts that provide a glimpse at the very root of western civilization. Where else can you stand and see the place where the basis for modern government was forged? Where else can you see so many timeless and priceless pieces of ancient art and architecture in just a few days?

Natural history, as well as human history, is on full display in the massive peninsular nation with stunning views of the Dolomites and Alps in the north, idyllic Mediterranean countryside along the coast, and broad pastoral landscapes of rolling hills in between. Italians are an incredibly varied and diverse people, but the one constant is their openness and sense of hospitality towards travelers. And, of course, once you have tried true Italian food, there’s no going back to anything else!

Cultural Journeys

Cultural Journeys

Cultural Journeys allow travelers to gain insights into the heritage, history and modern realities of their destination by offering a broad diversity of experience. We rely on the expertise of our local staff to plan itineraries which not only explore the prominent sites but also make time for the lesser-known local gems and are intentional about regular interaction with local people.

Program Highlights

Check out some of the featured experiences of your program!

Wander the streets of Florence, one of the most charming cities in the world!

Explore the world's smallest country, Vatican City!

Have the adventure of a lifetime with your friends

Visit Siena's world-renowned cathedral and crypt

Spend a night on a farm in the Tuscan hills

Tour a local olive farm

Learn to make true Italian food in a private cooking class

Head to Murano Island and witness Venice's famous glass blowing

Wander through the Roman Colosseum

Explore La Basilica di Santa Croce, where greats like Niccola Machiavelli, Galileo Galilei, and Michelangelo are buried

The Itinerary

We do everything possible to run safe, engaging, and immersive programs for our travelers and given the unpredictable nature of international travel we must remain flexible in our planning. Changes to a schedule are uncommon but, we reserve the right to adjust programming in the best interest of the group. 

April 5US - ItalyFly from the US to Italy. Airplane
April 6VeniceUpon arrival, we will meet your programs leaders and start the adventure! We'll head out to see sights like the famous Doges Palace, Canal Grande, the Ponte Rialto and St. Mark's Basilica and Square. Tonight we will have a our first group dinner to enjoy local delicacies. Venice Hotel
April 7VeniceWe will start our day with a gondola ride and take in the amazing canals of Venice. Next, it's off to the Island of Murano where we’ll learn about the unique glass blowing techniques that have been used for centuries by the local craftsmen and even try it ourselves (safely). We will return for a relaxing dinner. Venice Hotel
April 8Venice - FlorenceAfter a ride on one of Italy’s high speed trains we'll arrive in Florence and start our day with a walking tour, visiting the Duomo, Ponte Vecchio and many other piazze and monuments. We'll also make time to visit the Uffizi, one of the most important museums in the entire country.Florence Hotel
April 9FlorenceThis morning we’ll have a walk through town on our way to the "New Market" where we'll explore, shop and have lunch. Afterwards, we’ll head to the Santa Croce church as well as Piazza Michelangelo to take in Florence from above. In the evening, we'll enjoy a cooking class that will culminate in our dinners!Florence Hotel
April 10Florence - Siena Farm StayWe will say goodbye to Florence and take a private bus to Siena where we will have a walking tour of the small but once very powerful city. After that, we will head to an amazing organic farm which produces organic olive oil and wine. We will have a walking tour of the farm and the natural surroundings. In the evening, we will make our own pizza from the farm owners secret recipe using ingredients from the farm! Azienda Agricola Le Vezure
April 11Siena - RomeToday we will take our bus to the eternal city of Rome. We will head straight to the Colosseum and Forum, and have a guided tour of this historic wonder of the world. We will then go up a glass elevator in the Vittoriano, and view the Forum and the Colosseum from one of the most unique positions of Rome! We will then have a Roman pasta dinner and of course a Gelato for dessert. On our way back to the hotel, we will stop by the Trevi fountain and throw our penny into it.Rome Hotel
April 12Rome Today we will have a day to wonder around Rome and visit its highlights. We will visit pizza Navona, piazza di Spagna and its famous steps. We will admire the beautiful park of villa Borghes. We will enter the Pantheon and see its incredible architecture. We will have some time to go shopping and of course to have some gelato! We will then finish the day off with a wonderful pasta dinner. If we have time we will head to the Vatican and see St Peters light up at night.Rome Hotel
April 13Rome - USADepending on the time of departure, we will visit The Vatican before making our way to the airport for our flight home. Your own bed...eventually!


In order to provide a safe and memorable experience, we follow strict guidelines when choosing program accommodations. Walking Tree partners with hotels and guest houses which are centrally located, clean and safe.  We vet and inspect the accommodations to ensure they uphold the ethos of our programs, are great values for our travelers and nice places to rest after enriching days of travel.  

Below are the accommodations we anticipate using on your trip, subject to availability. 
Ostello Bello Firenze

Ostello Bello Firenze is ideally located in San Lorenzo neighborhood, in the heart of the Florence. From the hotel, you can easily access the entire city and enjoy the local area. This accommodation has air-conditioned standard rooms and private, in-suite dorms. In addition, the hotel has a beautiful terraces, a shared kitchen and a lounge area. A beautiful Italian breakfast is served to fuel a wonderful day of exploration.

Le Verzure Azienda Biologica

This farm is flanked by olive groves and vineyards, with a wonderful view of Montalcino and the Merse Valley. Located near the Etruscan ruins of Murlo, in the small village of La Befa and surrounded by Mediterranean bush. This farm offers walks in their vineyards, a stop in our small artisanal cellar and the tour of their wine and olive oil production. The farmhouse has two independent apartments furnished in a traditional Tuscan style, as well as the main house, recently renovated paying respect to the original structure, that can accommodate up to nine people. The property also counts with a swimming pool for guests.

Hotel Astoria Garden

This hotel is a 5-minute walk from Rome Termini Station and only 2 metro stops away from both the Coliseum and the Trevi Fountain . It offers air-conditioned rooms with TV and a private bathroom. The private garden is full of exotic plants and palm trees. The restaurant serves a buffet-style breakfast. Free Wi-Fi keeps guests feeling connected at all times. Students will be grouped in their rooms according to gender.

Hotel Alinari

Located just across the square from Florence train station, this hotel offers easy access to the airports and other places in Italy. The sights of the historic center, such as the Accademia Gallery, Uffizi Galleries and the Ponte Vecchio, are all easily reached by foot in less than 15 minutes. All the rooms have private bathroom, air-conditioning, colour tv. Free Wi-Fi keeps guests feeling connected at all times. Students will be grouped in their rooms according to gender.

Il Giglio Rosso

Colorful, spacious, and dedicated to the preservation and appreciation of local art, this bed and breakfast in the heart of Florence provides unique accommodations for our students. Free Wi-Fi access throughout the building keeps everyone feeling connected. Students will be grouped in their rooms according to gender and availability.

Rome Garden Hotel

The Rome Garden Hotel is the perfect accommodation that marries peace and relaxation, characteristic of a reserved and suggestive location, with the commodity of a central position, in the heart of the bustling metropolis of Rome. The hotel is located in the vicinity of Porta Pia on Via Nomentana, in the elegant area of the consular and diplomatic premises. It’s a Patrician villa of the XIX century, entirely modernized and surrounded by a private garden and only a few steps from the splendid frame of Villa Torlonia. It is also the perfect location for art lovers, with the nearby park of Villa Borghese and its prestigious gallery, which houses the famous sculptures of Bernini, being easily reachable on foot from the hotel.

Safety and Support


Thank you for giving my son a memorable lifetime experience. [There was] constant contact with the parents with updates and photos to ensure us about the students’ safety and that they were doing well. [The Program Leader] and the teachers were outstanding. Couldn’t have had anyone else better to do the job than they have done.

Parent of Benjamin, traveler on Costa Rica Service Adventure

Your Adventure Includes

Estimated Airfare

In order to give our travelers the best possible price, we break out airfare from the Program Tuition. We will still handle all booking and ticketing via our flight partner who has access to special fares not available to the general public. Once confirmed, you will be invoiced for the flight roughly 75 days prior to travel. 

Program Tuition Excludes: Travel insurance, baggage fees, passport/visa fees, laundry, souvenirs, and activities not listed on itinerary.


Need to Raise Money? We Have You Covered.

Walking Tree Travel is proud to team up with Equal Exchange, a worker-owned cooperative that distributes organic coffee, tea, sugar, bananas, avocados, cocoa, chocolate bars, and more.  There is no limit to the amount you can earn, so the sooner you can start, the better!

Learn more here.

WTT coffee
Resource center

Resource Center

Why should high school students travel abroad? What happens if a participant gets sick? How quickly do we need to enroll? We’re sure you have plenty of questions and we’ve got you covered! Visit our Resource Center to discover the answers to your most pressing questions and contact us anytime with additional questions.

Learn More