Day 1: Rome – Time Travel Through the Eternal City
Arrive in Rome and settle into your elegant boutique hotel in the heart of the city. Spend your afternoon exploring the hidden corners of Trastevere with a local guide who will take you beyond the usual tourist paths — think ivy-covered lanes, ancient artisan workshops, and tucked-away courtyards. In the evening, enjoy an exclusive underground Colosseum tour after hours, followed by a private rooftop aperitivo overlooking the Forum. End with a gourmet dinner at a Michelin-starred restaurant in the historic center.
Highlights: After-hours Colosseum underground experience Private walking tour of Trastevere Rooftop aperitivo + Michelin dining
Day 2: Rome – Icons, Art, and Hidden Gems
Begin the day with a VIP Vatican tour, granting early access before public hours to the Sistine Chapel and St. Peter’s Basilica. Afterwards, explore Campo de’ Fiori and the Jewish Ghetto with a local food historian, sampling Roman-Jewish delicacies like fried artichokes and ricotta pastries. Late afternoon is free for luxury shopping or an optional Vespa sidecar tour around Rome’s iconic sites. Optional Add-On: Spa treatment at a Roman bath-inspired wellness center.
Highlights: Early-access Vatican + Sistine Chapel tour Culinary walk through Rome’s Jewish quarter Optional Vespa sidecar ride or luxury spa
Day 3: Tuscany – Wine Roads & Renaissance Towns
Depart Rome in a private car and drive through the Tuscan countryside to your boutique wine estate. En route, stop in Orvieto for a guided exploration of its hilltop Duomo and secret underground caves. In the afternoon, settle into a luxury agriturismo in Chianti. Take part in a hands-on truffle hunting experience with trained dogs, followed by a rustic outdoor lunch paired with local wines. End the evening with a private vineyard tour and candlelit dinner under the stars.
Highlights: Orvieto underground visit Truffle hunting and countryside lunch Wine tasting and Tuscan farm-to-table dinner
Day 4: Pisa & Offbeat Tuscany
After breakfast, head west to Pisa — but skip the crowds with a back-door entry to the Leaning Tower, including access to the rarely seen cathedral rooftops. Then visit Lucca, a beautifully preserved walled city perfect for a private bike tour on the ramparts. Enjoy a cooking class with a local chef inside a 17th-century Tuscan villa before returning to your countryside retreat.
Highlights: Skip-the-line Pisa Tower + rooftop cathedral access Lucca bike tour and artisan market visit Private cooking class in a historic Tuscan villa
Day 5: Amalfi Coast – Cliffs, Colors & Coastline Luxury
Drive or take a private transfer to the Amalfi Coast and check into a cliffside villa in Positano or Ravello. After arrival, embark on a sunset boat cruise along the coast, visiting hidden coves, sea caves, and swimming spots only accessible by sea. Enjoy prosecco and oysters on board. Evening at leisure — dinner at a clifftop restaurant overlooking the sea.
Highlights: Scenic drive to Amalfi Coast Private sunset yacht experience with prosecco Fine dining in Positano or Ravello
Day 6: Amalfi Coast – Culture, Leisure & Departure
Spend your final day at a relaxed pace. Options include a limoncello-making workshop at a family-run lemon farm in Amalfi, or a private hike along the Path of the Gods, offering some of the most breathtaking views in southern Europe. Wrap up with a beachside lunch before your transfer to Naples or Rome for your flight home.
Highlights: Optional Path of the Gods hike or lemon farm visit Coastal lunch & final swim Private transfer to departure city
