6 days, 5 nights · Best for First-time couples seeking Rome, the Vatican and Tuscan hill towns
Romance in Rome & Tuscany
Begin your forever together in romantic Rome and Tuscany, where cobblestone streets, candlelit dinners, and unforgettable moments create the perfect honeymoon.
Your Adventure Starts Here
This is a starting point. Change the nights, choose the style of hotel, add the experiences you want. Your planner takes it from there.
Stop 1Rome, Lazio
Rome
Ancient monuments, Vatican treasures and centro storico strolls
We meet you at the airport and drive to a four-star hotel between the Spanish Steps and Piazza Navona, where narrow cobbled lanes open onto Renaissance squares and fountains lit after dark. You walk to the Trevi Fountain, toss your coins, then settle into a candlelit table at a nearby trattoria. The next morning we arrange a guided visit to basilicas including Santa Maria Maggiore and San Giovanni in Laterano, their mosaics and Baroque chapels less crowded than the Vatican but no less grand.
On your third day you choose between a reserved-entry tour of the Colosseum and Forum or the Borghese Gallery (we book either one weeks ahead), then meet your guide at the Vatican for the museums, Sistine Chapel and St. Peter's. Between monuments you stop for supplì at a counter near Campo de' Fiori and lunch at tables under awnings in Trastevere.
Arranged for you: Three nights premium four-star accommodation in the historic center, airport arrival transfer, private guided Vatican tour, private guided basilica tour, optional Colosseum or Borghese Gallery entry, candlelit dinners at partner restaurants.
Your hotel
Styles, not names. We name the property once we know your dates and your party.
Interests in Rome
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Trastevere food walk with tastings Day Trips · Half day
An evening walk through cobbled Trastevere with a local guide, stopping at five family-run shops for supplì, porchetta, maritozzo and Roman white wine.
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Private Appian Way and catacombs tour Day Trips · Half day
Your guide and driver take you along the ancient Via Appia Antica to visit early Christian catacombs and the Circus of Maxentius outside the city walls.
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Palazzo cooking class with market visit Day Trips · Full day
You shop for vegetables and cheese at Campo de' Fiori, then prepare four courses in a seventeenth-century kitchen and dine at a long table with other couples.
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Ancient and Old Rome Walking Tour, Skipping the line at Colosseum Guided Tours and Sightseeing · Tour in a DayUnlock the secrets of the Eternal City, skip the lines and step into the world of emperors, gladiators, and gods on this lively, story-filled Roman adventure.
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Full Day Rome Tour Guided Tours and Sightseeing · Tour in a DaySee Rome your way in one unforgettable day. Vatican treasures, Imperial ruins, and iconic monuments with the ease of a dedicated tour escort.
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Papal Audience in Saint Peter’s, Vatican City Guided Tours and Sightseeing · Tour in a DayWitness a truly unforgettable moment in Rome, attend a Papal Audience and receive the Pope’s blessing.
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Rome by Bicycles Tour with English Speaking Guide Guided Tours and Sightseeing · Tour in a DaySee more of Rome with less effort, cruise past iconic landmarks on a fun, guided bike ride made for everyone.
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Rome by Night Guided Tour Guided Tours and Sightseeing · Tour in a Day
See Rome at its most magical, an evening stroll through illuminated fountains, grand piazzas, and ancient ruins.
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Rome by Night guided Tour with Dinner & Show Guided Tours and Sightseeing · Tour in a Day
Fall for Rome after dark. Glowing landmarks, a romantic evening stroll, and dinner with live music to seal the moment.
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Rome: The Eternal & Ancient Rome Tour Combo Guided Tours and Sightseeing · Tour in a DayExperience the magic of the Eternal City with a full-day tour showcasing Rome’s most iconic historical sites.
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Rome: The Eternal City Tour Guided Tours and Sightseeing · Tour in a Day
Discover Rome’s most iconic monuments in comfort on this tour.
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Skip the Line: Vatican Museums and Sistine Chapel Guided tours Guided Tours and Sightseeing · Tour in a Day
Skip the lines and step straight into the Vatican’s greatest masterpieces. Museums, Sistine Chapel, and St. Peter’s Basilica with an expert guide.
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The Ancient Rome Tour Guided Tours and Sightseeing · Tour in a Day
Walk in the footsteps of emperors and gladiators, discover the power, passion, and innovation that shaped the world in Ancient Rome.
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The Ancient Rome Walking Tour, Skipping the line at Colosseum Guided Tours and Sightseeing · Tour in a Day
Experience the ancient highlights of the Eternal City with a guided walking tour that takes you through Rome’s most iconic landmarks.
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The Christian Rome & Catacombs Tour with Hotel Pick Up Guided Tours and Sightseeing · Tour in a DayJourney through Rome’s spiritual heart, explore ancient basilicas, sacred relics, and the origins of Christianity in the Eternal City.
Day by day in Rome
Arrive in the Eternal City and settle into your elegant 4-star hotel located in the heart of Rome. After check-in, take some time to relax and refresh before heading out to experience the city’s enchanting atmosphere. Start your Roman adventure with a leisurely stroll around the Spanish Steps and nearby attractions, soaking in the vibrant street life and iconic architecture. As evening falls, treat yourselves to a romantic candlelit dinner at one of Rome’s renowned restaurants, setting the tone for a memorable stay. Return to your hotel for a restful first night in Rome.
Start your day with breakfast at the hotel before heading out to explore Rome’s iconic city center at your own pace. Visit must-see sites such as the Spanish Steps, the stunning fountains of Piazza Navona, and the legendary Trevi Fountain, don’t forget to toss in a coin for luck. Enjoy lunch at a local spot, sampling delicious Roman street food like supplì. In the afternoon, embark on a guided excursion to discover the city’s religious heritage, including visits to the Basilica of Santa Maria Maggiore, the Basilica of St. John Lateran, and a fascinating tour of the ancient Catacombs. After returning to the city center, unwind at your hotel or head straight to a cozy trattoria for dinner, where you can savor classic Roman dishes like cacio e pepe. Cap off the evening with a romantic walk and a scoop of authentic Italian gelato.
Enjoy a relaxed breakfast with your spouse before spending the morning as you wish, either joining a guided tour of the Colosseum and Roman Forum to relive the glory of ancient Rome, or visiting the Borghese Gallery to admire Renaissance masterpieces (advance reservations recommended for both). Pause for lunch at a local eatery, then head to the Vatican area for an in-depth guided tour of the Vatican Museums, including the Sistine Chapel and Raphael Rooms, followed by a visit to the awe-inspiring St. Peter’s Basilica. If you’re feeling adventurous, climb to the top of the dome for breathtaking views over Rome. Return to your hotel to unwind, then enjoy another delicious dinner at a nearby restaurant.
Stop 2Cortona, Tuscany
Cortona
Medieval lanes, Etruscan walls and Val di Chiana views
After breakfast we drive north into Lazio's hill country, stopping in Tarquinia to see painted Etruscan tombs and in Tuscania to walk the empty lanes around twin Romanesque churches. At Caprarola your guide unlocks the Renaissance Villa Farnese, its frescoed salons and spiral staircase among the finest of the period, then you continue across the border into Tuscany and climb to Cortona, perched on a slope above the valley.
Your hotel sits within the medieval walls, and from your window you look over vineyards and farmhouses to Lake Trasimeno in the distance. The next day you walk the steep streets at your own pace, visiting the duomo, the Etruscan museum and artisan workshops tucked under stone arches. We can arrange a half-day wine tasting at a nearby estate or a cooking lesson in a restored farmhouse (your planner holds the options). On your last evening you dine at a family-run osteria where the pasta is rolled that afternoon and the bistecca comes from cattle raised in the Chiana below.
Arranged for you: Private transfer from Rome with stops in Tarquinia, Tuscania and Villa Farnese, two nights four-star accommodation in Cortona's historic center, farewell dinner, private transfer to Florence or Rome.
Your hotel
Styles, not names. We name the property once we know your dates and your party.
Interests in Cortona
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Private wine tasting in Montepulciano Day Trips · Half day
Your driver takes you twenty minutes south to a historic cantina where you taste Vino Nobile in barrel cellars, then tour the Renaissance town center.
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Truffle hunt and lunch in the Casentino Day Trips · Full day
A local hunter and his trained dog lead you through oak woods in search of autumn truffles, followed by a farmhouse lunch prepared with the morning's find.
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Cooking class at a Cortona farmhouse Day Trips · Half day
You prepare pici, ravioli and cantucci with a home cook in her restored stone kitchen, then sit down to the meal with house wine and olive oil.
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Private tour of Arezzo and Piero della Francesca frescoes Day Trips · Half day
Your guide drives you to Arezzo to see the True Cross fresco cycle in San Francesco, then walk the piazza where Benigni filmed Life Is Beautiful.
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Private Tour Excursion to Cortona & Montepulciano Guided Tours and Sightseeing · Tour in a DayExperience the magic of Tuscany on this all-day tour of two of its most enchanting towns, complete with hotel pick-up for your convenience!
Day by day in Cortona
After breakfast and check-out, depart Rome and journey north through the scenic countryside of Lazio. Your first stops are the charming towns of Tarquinia and Tuscania, where you’ll wander medieval streets and discover fascinating Etruscan history. Continue to Caprarola to tour the magnificent Villa Farnese, a Renaissance gem with exquisite architecture and gardens. In the afternoon, travel into Tuscany and arrive in picturesque Cortona, your base for the remainder of the trip. Settle into your hotel and enjoy a delightful dinner at a local restaurant, sampling traditional Tuscan dishes made with fresh, regional ingredients.
CORTONA
Begin your day with breakfast before setting out to explore the romantic hilltop town of Cortona at your leisure. Meander through its charming streets, discover artisan shops, and take in panoramic views of the Tuscan landscape. Visit notable sites such as the Cathedral, historic churches, or the Etruscan Museum to delve deeper into the town’s rich heritage. For a special experience, consider arranging a half-day food tour or wine tasting, your travel specialist can suggest the best options. In the evening, celebrate your unforgettable honeymoon with a farewell dinner at a traditional trattoria, savoring more regional flavors and local wines.
Day 6
CORTONA, FLORENCE (or ROME)
Enjoy your last breakfast in the beautiful town of Cortona before checking out of your hotel. A private transfer will take you to your chosen destination, either Florence’s city center, Rome’s city center, or Rome’s airport, depending on your onward travel plans. As your romantic Italian adventure comes to an end, depart with cherished memories and a renewed sense of connection.
Why plan with Trips 2 Italy?
Designed around you by Italian-born planners
Guides, drivers and boats for your party alone
Hand-selected hotels in every destination
Local English-speaking guides who know their city
Met at the airport, private transfers throughout
Testimonials
Hear from travelers who have planned Italy with us
They took the time to understand our preferences and designed an itinerary that was comfortable, personalized, and enjoyable. They offered thoughtful recommendations while never being pushy.
We missed our connecting flight in Munich. I had just got through customs and was looking up the number to call when Trips 2 Italy called me. They told me exactly what to do and they already knew what flight we had been rebooked on.
Ready to make it yours?
Send us this adventure with your changes. An Italian-born planner builds the first full draft and calls you to walk through it.
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Questions travelers ask
Where will we travel on this itinerary?
Over 6 days this journey brings you to Rome, Cortona, and Florence. Each stop is woven into the itinerary with time for the landmarks, the views, and the local flavor that make it special.
How will we get around during the vacation?
Transportation is arranged as part of the itinerary, with private vehicle transfers throughout. Every connection is planned for you, so you can focus on the scenery instead of the logistics.
What kind of traveler is this package for?
It is designed for couples, with romantic settings, intimate experiences, and time built in to simply enjoy each other and Italy.
Can we customize this itinerary?
Absolutely. Every Trips 2 Italy itinerary is designed to inspire and can be tailored end to end, from the number of nights and hotel categories to the experiences along the way. A minimum of 2 travelers applies.
What is the best season for this itinerary?
The package is available all year around on request. Spring and fall offer mild walking weather and lighter crowds at the major sights, summer brings long lively evenings, and winter rewards travelers with quieter museums and festive streets.