2 Weeks in Italy: The First-Timer's Romantic Itinerary

Planning the perfect romantic trip to Italy? Let’s skip the cookie-cutter travel guides and get straight to the good stuff. This 2-week Italy itinerary is based on a real trip I designed for a client—meaning every stop, stay, and experience is curated for maximum romance, effortless luxury, and zero travel stress.

Because let’s be real: Italy is made for love stories, but sorting through endless hotel options, must-see lists, and tourist traps? Not so dreamy. That’s where I come in.

As a travel designer, I craft bespoke itineraries that balance iconic moments with exclusive, under-the-radar experiences—so you can soak up la dolce vita without lifting a finger.

Ready to see what two weeks of pure Italian romance looks like? Let’s dive in.

P.S. If you rather skip to the part where I design your whole trip from start to finish click here to work with me.

Starting Your 2-Week Italy Itinerary by Spending 3 Days in Rome

This is what dreams are made of. Start your Tour di Italy by spending the first 3 days in the "Eternal City".

Like many big cities in Europe, Rome is divided into neighborhoods all with their own unique vibe and varying proximity to local attractions. Here are my top recommendations of where to stay in Rome. This list contains a mixture of local boutique hotels and luxury stays.

Day 1: Introduction to Rome

If you're traveling to the U.S., you'll want to hop on an overnight flight to Rome. When you arrive in Rome in the morning, drop your bags off at your hotel and hit the ground running by visiting Caffe Doria, a posh Italian bistro with historic artwork inside the famed Palazzo Doria Pamphil.

Take a private walking tour with a local to get a feel of the city and discover it's local charm. This private walking tour by City Unscripted is my absolute favorite for a mixture of tourist hotspots and hidden gems. The best part is, it is fully customized to your preferences so you get the experience that matches your interests.

End the night with dinner at Campocorri, an upscale restaurant with a tasting menu that is a mix of Modern European cuisine. The ambience is hip and sexy and the food is to die for.

Day 2: Vatican City & Trastevere

Your next day in Rome, you will want to spend visiting the Vatican Museums, St. Peter's Basilica and Sistine Chapel. The Vatican can be quite crowded and lines can be overbearing, especially in busier months. I highly suggest booking a private or small-group tour and booking a slot for the early morning so that you can experience the magic without being in shoulder to shoulder crowds.

In the afternoon, make a point to explore Trastevere, a beautiful neighborhood in Rome with charming homes, local restaurants and cute little shops to explore. Stop for lunch at Nannarella and take in the sunset at Janiculum Hill.

Day 3: Colosseum & Pasta

No itinerary to Italy for a first-timer is complete without seeing the iconic Colosseum. To beat the crowds I recommend going early in the morning at opening or right before it closes in the evening. During busy season tickets can be hard to come by, especially if you wait until last minute.

Book this small-group tour so you can skip-the-line and have a certified historian take you on a journey through ancient Rome. This tour also includes access to Palentine Hill and Roman Forum to explore on your own after the tour.

End the night with a romantic dinner at Aroma, a Michelin-stared restaurant that overlooks the Colosseum. For something a little more lowkey, try dining at Scuie Scuie for traditional Italian dishes in an intimate eatery.

Next Stop, 6 Days in Tuscany

You could honestly spend months here exploring medieval villages, strolling through vineyards and cafe hopping in Florence. For this 2-week Italian itinerary, you'll spend 6 days in Tuscany with a chance to see a little of it all.

Day 4: Relax in the Tuscany Countryside

There is no better way to decompress from a business of Rome than to explore the Tuscan countryside. Tuscany is known for beautiful villas set amongst rolling vineyards small towns.

Take the high-speed rail from Rome to Florence. Rent a car from Florence and head out to the countryside. Take the first day to relax, get a massage at your villa and enjoy breathtaking view. Sometimes the best plan is no plan at all.

Day 5: Private Tour of Chianti Wineries

The next day you'll want to head out on a private tour of the Chianti region. On this tour, your driver will pick you up from your hotel or villa and take you to 3 different boutique wineries in the Chianti region. You'll also eat a traditional Tuscan lunch and get a guided tours of the vineyards and cellars.

If you prefer a group tour I highly recommend taking this Semi-Private Chianti Wine Tour for a personalized, small-group experience.

Day 6: Day Trip to Siena

On your final day in the countryside you'll drive out to Siena, a medieval village know for its cuisine, art museums and Palio - a horse race help twice annually in Piazza del Campo.

While here, explore the historic old town, take pictures at Fontebranda and see the Duomo di Siena. Before you go, take this super cute cooking class at a cooking school in Siena. Here you'll learn how to make traditional tuscan meats, pasta and tiramisu.

Day 7: Highlights of Florence

Drop off your rental car in Florence and head to your boutique hotel in the city. Begin your day with the Dome Climb at Cathedral of Santa Maria del Fiore. You'll need to purchase tickets in advance and reserve a time slot.

Then get oriented in the city with this Sunset Food & Wine Walking Tour (one of my favorite experiences in Italy). On this tour you'll try samples of traditional Tuscan cuisine from local restaurants in the city while sipping wine served from the historic wine windows that are hidden throughout the city.

Day 8: Galleries and Gardens

Spend the next day exploring the cities museums. Start with the Uffizi Gallery - an art gallery of works from the 16th century to modern day. On the Uffizi complex you can also visit Pitti Palace and Boboli Gardens all on one ticket.

End the day with a dinner at La Giostra - an intimate local restaurant frequented by the likes of celebrities like George Clooney. The food is some of the best in the city and the ambience is perfectly romantic. Reservations fill up quick so don't wait!

Day 9: Shopping & Iconic Art

Start day 9 of your Italy itinerary by seeing Michelangelo's "David" statue at the Galleria dell’Accademia. You'll need to book a ticket early in advance and I suggest getting there early as the crowds can be unbearable. Alternatively, You can book a small-group tour, for skip-the-line access and a historical perspective of the museum's works.

After head over to Mercato Centrale for a quick lunch by visiting Gucci Gardens - an complex comprised of a fashion exhibition, restaurant and boutique dedicated to the iconic Italian designer.

If you're into luxury shopping you need to head to Via Tornabuoni for all of your designer goods. When you spend over 100 EUR you can reclaim the VAT (value added tax) at customs when leaving the country essentially saving you money on all your luxury purchases.

Then It's Venice in 2 Days

A 2-hour train ride from Florence you'll meet Italy's most unique city, Venice. Get lost in the narrow calli, sit canalside with cicchetti (Venice’s famous finger food), explore famous sites like St. Mark's and the Rialto Bridge or visit the beautiful islands of Murano and Burano. 

Day 10: Highlights of Venice

Since your time in Venice will be short, I highly suggest taking a walking tour to quickly familiarize yourself with the city and learn some history. For my foodies, I highly suggest this food tour for the best cicchetti.

For a cute, intimate restaurant overlooking the canals try Osteria Al Cantinon to end your night with a romantic dinner.

Day 11: Murano and Burano Islands

The next day, you'll take a half-day trip to the colorful Venetian Islands of Murano and Burano.

Start with a 40 minute vaporetto ride to Murano, most well known as the home of Murano Glass. In medieval times Venice built itself up as the city of pleasure and excess. Some of that was extravagant and artistic glasswork.

45 minutes from Murano you'll find Burano, a small fishing village known for its bright and colorful buildings. The perfect location for an Instagram photo op. Outside of its beautiful buildings, you can witness artisans crafting handmade lace inside one of Burano's many lace shops.

End Your 2-Week Italy Itinerary with 3 Days in Lake Como

Spend the last few days of your romantic Italy itinerary with a trip to Lake Como. For centuries this lake has attracted an elite crowd of villa owners, from famous celebrities through to successful businessmen and women from around the globe. The lake is HUGE, with multiple small towns on either side of the lake. I recommend staying on the westside in a town like Como, Torno or Bellagio.

Day 12: Explore Como Town

With cobbled streets and cozy squares lined with historic buildings, shops, and restaurants, the historic city center of Como is really charming.

The nicest part of the old town is located between the lake and the remains of the old city wall, Porta Torre. It’s in this area that you will find most shops, restaurants, quite a few churches, and several museums.

When you're done exploring, stop by Figli dei Fiori for lunch. The ambience and is chic and a little bohemian with live plants used for decor. The food is amazing and the service is 10/10.

Day 13: Have a Boat Day

No trip to Lake Como is complete without a day on the lake. You can hire a driver and guide for the day. If you want to fully let go, I highly recommend going with the private driver and booking this tour here. You can also join a small-group party boat tour.

Day 14: Explore Bellagio

Bellagio, Italy is one of the most popular towns of anyone who visits the area. Known as the Pearl of Lake Como, it’s a gorgeous town, filled with historic cobblestone streets and local artisans selling keepsakes.  

Bellagio is accessible by ferry from many points of the lake. While here explore the town and ferry hop over to Villa Carlotta - a 20 minute ferry ride from Bellagio to see the stunning villa, gallery and botanical garden in Tremezzo.

And there you have it! The perfect plan for 2 weeks in Italy for lovers. Every moment of this itinerary is designed for romance—but the real flex?

Letting someone else handle the planning while you just show up and live your best life.

Let’s be real—planning a trip these days feels like a full-time job. Endless options, sketchy reviews, and who has time for all that research? That’s where I come in.

At Truly Travl'd, I do the heavy lifting so you don’t have to. Think of me as your personal travel BFF—here to craft epic, stress-free adventures for busy professionals who want more than cookie-cutter vacations.

Here’s what you get when you work with me:

• A custom itinerary built around your vibe (no tourist traps here).

• Insider perks and upgrades you won’t find on Google.

• 24/7 support while you’re jet-setting—because things happen, and I’ve got your back.

Sound like your kind of travel? Click here to start planning the trip you’ve been dreaming about.

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