Rome to Tuscany Your 9-Day Honeymoon Itinerary

With fairytale villages, picturesque rolling hills, fabulous food and world-renowned wine, Italy is an enchanting country full of romance and wonder. For a classic honeymoon destination that checks all the boxes, look no further than this romantic 9-day Rome to Tuscany itinerary.

Day 1 of your Rome to Tuscany Honeymoon

Upon arrival in the Eternal City, check into your hotel and drop off your luggage. For a decidedly romantic stay, opt for the honeymoon-worthy Rome Cavalieri. This 5-star Waldorf Astoria hotel sits atop Rome’s highest hilltop and offers panoramic views of the city below. With gorgeous accommodations boasting private balconies, room service, upscale dining and a full-service spa, this elegant property is the quintessential Italian honeymoon indulgence.

After settling in, taxi to the Pantheon, where you’ll begin your Roman adventure with a step back in time. Built in approximately 25 BD by Roman architect Agrippa, the Pantheon is the best-preserved building from ancient Rome.

Afterward, meander the cobblestoned streets at your leisure, heading toward Piazza di Spagna. Climb the iconic Spanish Steps and stroll arm-in-arm down via Condotti – the most fashionable street in Rome – where you’ll find upscale shopping from Bvlgari to Armani.

Return to your hotel and enjoy the view from your private balcony as you prepare for a magical meal at Rome’s most celebrated restaurant. Conveniently located within the Rome Cavalieri, Pergola is the only restaurant in Rome to claim a 3-Michelin Star rating. Prepare to splurge, but the exceptional gourmet cuisine and incredible views are worth every euro. Make your reservation far in advance and request a table on the terrace.

What is the Best Time of Year to Visit Rome?

There’s no bad time to visit Rome! Spring and fall offer the most temperate weather, but they’re also Rome’s busiest and most expensive months. While temperatures soar in the summer, heat-tolerant travelers will find lower crowds and an exciting calendar of events from June through August. If lower prices are a priority, opt for a winter visit. Even in the coldest months, Rome sees an average temperature of about 55°F. 

Day 2: Rome

On your first full day in Rome, get an early start with a classic Roman breakfast of cappuccino and cornetto. Then, head for the iconic Trevi Fountain, where an early arrival will allow for your own (almost!) private viewing of this magical romantic landmark.

Toss in a coin and make a wish before hailing a taxi for Vatican City. Home to the Sistine Chapel, St. Peter’s Basilica, and of course, the Pope himself, this iconic Roman experience is not to be missed. For the most efficient use of your time, book a guided tour for skip-the-line, no-wait access. Most tours last about 3.5 hours and will offer the highlights but allow extra time if you plan to explore the Raphael Rooms or climb the dome at St. Peter’s Basilica.

Rome to Tuscany is worth it for the Food!

Hungry? Treat yourself to Rome’s favorite street food, pizza al taglio (“pizza by the cut”), typically served in rectangular slices and sold by weight. You’ll find countless options, but for an especially memorable experience, try Gabriel Bonci’s Pizzarium, located behind the Vatican in the upscale neighborhood of Prati. Featured on Anthony Bourdain’s Travel Channel series The Layover, this tiny pizza shop offers over 1,500 different takes on pizza! After lunch, explore the elegance of Prati at your leisure, or head back for some downtime at your hotel.

This evening, enjoy a candlelit dinner and magical views at Mater Terrae, located on the rooftop of Bio Hotel Raphael. Divided into two levels, the terrace offers a lower-level lounge serving cocktails and small plates as well as a full-service restaurant on the upper level. Whichever you choose, you’ll enjoy gourmet organic, vegetarian and vegan cuisine as well as a breathtaking 360-degree view of Rome. This sophisticated and intimate gem is a Roman honeymoon essential you won’t want to miss.

Looking for an Italian romance with a twist? Hold each other tight as you brave the thrills and chills of a Haunted Rome Ghost Tour. Join a local guide for a moonlit stroll through Rome’s cobblestoned streets where you’ll learn about the historic legends, ghosts and dark lore of Rome’s mottled – and fascinating – past.

Day 3-Rome

On your last full day in Rome, make like Audrey Hepburn and ride a Vespa clear across the city to the Colosseum! To guarantee Vespa availability, reserve your scooter in advance. You’ll need a valid driver’s license and an international driver’s permit, which you can procure online from your home country.

To optimize your time at the Colosseum, book a guided tour that includes skip-the-line access to the Roman Forum, Palatine Hill and of course, the Colosseum itself. One of the New Seven Wonders of the World, the iconic ancient amphitheater is over 1,900 years old. You’ll need two to three hours, so plan to spend your morning exploring these breathtaking archaeological sites.

Afterward, hop on your Vespa and zip across the Tiber to the bohemian neighborhood of Trastavere. Dine al fresco, stroll winding medieval alleyways and soak up the romantic ambiance as you explore local wine bars, boutiques and craft shops.

For your last dinner in Rome, make it a night to remember at the unparalleled Le Jardin de Russie. Located at its namesake, Hotel de Russie, this elegant eatery is inarguably one of the most beautiful restaurants in Rome. Don’t let the French name fool you – Le Jardin de Russie is known for Roman cuisine in a magical, secret garden-like setting.

Day 4- Rome to Tuscany

On your last morning in Rome, board a high-speed train to Florence. In just over an hour and a half, you’ll arrive in the heart of Tuscany, home to romantic Renaissance villages, iconic works of art and of course, some of the best wine in the world.

Upon arrival in Florence, head to your hotel to drop off your luggage. For a honeymoon-worthy stay, try Hotel Palazzo Guadagni, located in the charming and historic Oltrarno neighborhood. With a romantic rooftop bar and gorgeous views, this conveniently located hotel offers an authentically Florentine experience. For some extra honeymoon magic, ask for a room with a view of the Duomo!

For lunch, head to 19th-century Mercado Centrale, a popular food market offering a dizzying array of culinary delights. Snack your way around the various stalls before a stroll along the enchanting Arno River, where you’ll pass under the iconic Ponte Vecchio. Built in 1345, the famous landmark has survived everything from floods to bombings and is now home to an assortment of interesting shops and jewelers.

In the evening, indulge at one of Florence’s many incredible restaurants. For traditional Tuscan fare in a historic setting, try Ristorante Buca Lapi, the oldest restaurant in Florence. Cozily situated within the cellars of a Renaissance-era palace, this charming “buche” boasts delicious food and a glamorous past! Buca Lapi has hosted the likes of Grace Kelly and her husband Prince Rainier and served as a filming location for Joan Fontaine’s 1950 classic September Affairs.

What is the Fastest Way to Get from Rome to Tuscany?

For a quick and easy transfer to Tuscany, board a high-speed train at Rome Termini Station. Direct trains to Florence leave every few hours between 5 a.m. and about 9:30 p.m. The scenic ride will last just over an hour and a half.

Is a Day Trip to Tuscany from Rome Worth It?

Absolutely! You could easily pass a week (or a month!) wandering the rolling hills of Tuscany, so we recommend at least a few days to fully experience the area. But if you’re short on time, a Florence day trip is well worth the time and effort. Florence is just 1.5 hours from Rome by high-speed train, so leave early and stay late to maximize your time in beautiful Firenze. One day is enough to see the highlights and experience the Renaissance romance in all its glory.

Day 5-Florence

Today, book a guided walking tour to optimize your time. You’ll experience the highlights of Florence and enjoy skip-the-line access to popular attractions like Michelangelo’s David. Discover the breathtaking architecture of Piazza del Duomo, where you’ll find Giotto’s Bell Tower, the Baptistery of St. John, the Museo dell’Opera del Duomo, and of course, the massive and jaw-droppingly beautiful Cathedral of Santa Maria del Fiore. For an extra dash of Tuscan romance, climb the dome around sunset. You’ll enjoy a dazzling panoramic view of Florence and watch the sunset the Tuscan sky ablaze. 

What Month is Best for Tuscany?

While the hot and sunny days of summer are a popular time to visit Tuscany, wine aficionados should consider the milder autumn months of September and October. While fall is officially considered shoulder season in Tuscany, it’s also the vendemmia, when the region hosts harvest celebrations and restaurants offer seasonal specials incorporating the year’s harvest. Just don’t forget your umbrella, as this time of year can see an increase in rainfall. Pack layers and a raincoat!

How Many Days in Tuscany is Enough?

Tuscany is home to a wealth of culture, history, natural beauty and delicious food and wine. While this itinerary offers a taste of Florence and the surrounding areas, plan on spending a full week to fully experience the region and all it has to offer.

Want More of Florence? Check out our Milan and Florence itinerary here.

Days 8-9: Chianti Region

For the last two days of your getaway, explore the magical rolling hills and charming vineyards of Tuscany. To fully immerse yourself in the romance of the wine region, consider spending these last two nights at a luxurious wine hotel like Borgo Tre Rose in Montepulciano. With resort-like amenities and incredible views, this swoon-worthy resort offers three wineries and includes an impressive breakfast with your stay.

From your home base in the Tuscan hills, use the bus or rail system to visit charming Renaissance towns like Greve, Panzano and Radda, and indulge at top-rated wineries like Poggio Cagnano and Villa Pinciana. The number of local wineries is simply staggering, so do your research in advance to decide which establishments to prioritize.

If all that wine tasting has taken a toll, visit one of Tuscany’s sulfurous hot springs for some rest, relaxation and rejuvenation. You can enjoy many of the region’s hot springs for free, but if you’re feeling a little spendy, indulge at a luxurious private spa-like Albergo le Terme in Bagno Vignoni.

Wondering What to Wear in Tuscany?

In general, Italian style leans away from casual attire like leggings, ripped denim, shorts and sneakers. Instead, opt for smart casual pieces for a sophisticated but comfortable look. Layers will accommodate unpredictable temperatures in the spring and fall, while light, breathable fabrics (like linen) are a popular summertime look.

Extend Your Stay on Elba Island

If your honeymoon isn’t complete without a trip to the beach, add a few days on Elba Island. To get there, you’ll journey by train and ferry for a total travel time of about 4.5 hours. On Elba Island, you’ll soak up the sun on glorious white beaches, snorkel in clear, cobalt waters and enjoy the history and culture you’ve come expect of any Italian destination. Considering Elba? The island is at its best in the early months of summer when the weather is warm, but the tourists are scarce.

Are you ready for your honeymoon from Rome to Florence?

Bursting with beauty, charm and romance, it’s no wonder Italy has earned a reputation as a classic and coveted honeymoon destination. If you’re ready for your own Roman Holiday, contact us below to get started!