Join Ainsley Arment from Wild+Free on a pilgrimage to Italy. This trip will visit Rome, San Gimignano, Siena, Florence and much more.
Ainsley Arment is the founder of Wild + Free, host of the Wild + Free podcast, and author of books encouraging families to cultivate wonder and connection. She brings that same spirit to pilgrimages designed for Wild + Free mothers, pairing sacred destinations with community, beauty, and reflection.
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We depart on an overnight flight to Rome. Dinner and breakfast is served on the flights. Quotes for add-on flights from different airports, optional Premium Economy, and Business Class upgrades are available upon request and will be provided starting 120 days before departure. Group air restrictions (for ten passengers traveling together) do not permit specific seating requests on flights. We recommend purchasing your own airline tickets and land-only packages with us if seat confirmation is an important part of your trip. Should you require any additional information, please do not hesitate to contact your trip Account Manager, who will be happy to assist you.
Welcome to Italy! We arrive in Rome, where our professional tour manager greets us at the airport. We board our private coach and make our first stop on the city’s outskirts at the ancient underground Roman Catacombs, exploring the fascinating miles of subterranean tunnels and centuries-old frescoes. Following lunch we check into our hotel, leaving the rest of the afternoon at our leisure to relax, unpack, and rest after the long flight. Overnight in Rome. Meals: Welcome Dinner with wine
Today is completely dedicated to Rome’s beautiful historic center. We take a leisurely walking tour to see the iconic Trevi Fountain, the Spanish Steps, and the architectural marvel of the Pantheon (the best-preserved building from ancient Rome). Our guided walk ends at the vibrant Piazza Navona, leaving us with a completely free afternoon and evening for shopping, exploring at our own pace, and local dining. Overnight in Rome. Meals: B.L
Today is dedicated entirely to world-class art and architecture. We begin with a visit to the Vatican Gardens with an open bus tour, followed by a visit to the Vatican Museums to walk through the magnificent Raphael Rooms and stand beneath Michelangelo’s legendary ceiling in the Sistine Chapel. Afterward, we tour St. Peter’s Basilica from an architectural and art-history perspective to appreciate its scale, massive dome, and masterworks like Michelangelo’s Pietà. The evening is ours to enjoy at leisure. Overnight in Rome. Meals: B
This morning, we depart Rome and head to the nearby town of Tivoli to visit the Villa d’Este, a magnificent 16th-century Renaissance estate famous for its breathtaking, gravity-powered water fountains and terraced gardens. After lunch, we drive into the heart of Tuscany to check into our Tuscan villa, our beautiful base for the next five nights. Settle into the countryside, take in the views, and enjoy a relaxed evening. Overnight in Tuscany. Meals: B.D
After breakfast, we visit San Gimignano, the epitome of a Tuscan hilltop town, famous for its 14 medieval towers and beautiful stone piazzas. Enjoy a leisurely morning exploring the ancient streets, shopping for local crafts, and sampling world-champion gelato at Piazza della Cisterna. This evening, we head to a local estate for a hands-on pasta-making class, channeling the wonderful energy of Italy. We enjoy our homemade culinary creations for dinner. Overnight in Tuscany. Meals: B.Special Dinner
Today we immerse ourselves in the classic, postcard-perfect Tuscan landscape. We take a scenic drive through the rolling hills of the Val d’Orcia, stopping in the Renaissance town of Pienza, famous for its architectural symmetry and world-class Pecorino cheese. Our stop includes a local cheese tasting! Tonight features a major highlight: a magical outdoor dining experience in a Tuscan vineyard, dining al fresco among the grapevines as the sun sets. Overnight in Tuscany. Meals: B.Special Dinner
Today we visit the gorgeous Gothic city of Siena. We take a guided city tour through its distinct historical districts (contrade), learning about the city’s fierce neighborhood traditions and visiting the magnificent shell-shaped Piazza del Campo. In the afternoon, we head into the countryside to visit a traditional, working Tuscan agriturismo. We tour the property, see how their estate olive oil and wine are produced, and relax on the beautiful grounds before enjoying a rustic, farm-to-table dinner made entirely with ingredients grown right on the property. Overnight at the villa. Meals: B.Special Dinner
Florence awaits us today! Upon arrival, we stop at Piazzale Michelangelo for the absolute best panoramic view of the Florentine skyline. We then head to the Accademia Gallery, where we stand together before Michelangelo’s original masterpiece, David. Afterward, enjoy a walking tour including the historic Ponte Vecchio stone bridge and the Piazza della Signoria, followed by free time at the bustling Mercato Centrale food market. Dinner is at leisure. Overnight in Florence. Meals: B
Enjoy a full day at leisure in Florence to explore the city entirely at your own pace. You might choose to visit the world-famous Uffizi Gallery (to see Botticelli’s Birth of Venus), stroll through the Boboli Gardens, or shop for Florence’s famous leather goods. Tonight, we gather for a celebratory farewell dinner in a local restaurant with excellent Tuscan wine to toast an incredible journey. Overnight in Florence. Meals: B.Special Dinner
Today marks the end of our Italian adventure. We transfer to the Florence airport for our return flight home, taking with us memories to last a lifetime. Meals: B
Base Price. Main trip package.
Base Price and Group Airfare from Newark. Main trip package.
Solo Room (Additional Charge). Additional supplement.
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