Start your trip in exciting Rome, where I’ll guide you to through major sites at a leisurely pace, so that you have plenty of time to wander through the city’s offbeat neighborhoods and gorgeous gardens, take in stunning views over the skyline, and savor long meals.

Speaking of food, I’ll tell you about Rome’s bustling markets, its alimentari complete with wine tastings, cozy cappuccino spots, the best gelateria, and osterias where you can sample classic city dishes like cacio e pepe. Continue on to Florence where the art, scenery, and food only get better. In this compact city, you’ll easily be able see all of the major sites on your list, with plenty of time left over for relaxed strolls through inviting piazzas and manicured terraces. Go beyond The David and the Duomo, and explore secret Renaissance passageways, bohemian neighborhoods, underground tombs, and old Italian-family treasure troves before settling into meals of prosciutto, pasta, and Chianti. Round out your Tuscany time in a charming villa, highlighted by some languid vineyard hopping and day trips to towns like Sienna and Lucca. Finally, it’s time for some true beachside R&R! There are many great coastlines in Italy, including glamorous Amalfi, the colorful Italian Riviera, and offbeat and relaxed Puglia. I’ll help you choose between these options by providing the pros, cons, and highlights of each spot.

Where it all Began

Start exploring the city by taking in its stunning skyline. From your apartment in the charming Trastevere neighborhood, walk up Via Garibaldi, and go through the gates to reach Piazza Garibaldi from which you’ll marvel at the best view of Rome.

Once you’ve seen Rome from above, you’ll be eager to immerse yourself in this stunning city. Cross over to the East Bank of the Fiume Tevere by way of Ponte Sisto, and take a stroll along the river until you reach Tiber Island.

Take some time here to explore the heart of Rome before picking up lunch at one of the city’s many delis or, alimentari. Nearby Roscioli is one of the best and also offers private wine tastings. Though pricey, it’s a fun and intimate experience.

Another good lunch option is the open-air market at Campo de’Fiori. Both of these spots are great places to pick up picnic foods, which you can enjoy in an inviting piazza of your choice. Before trekking to Rome’s most famous ruins, a gelato break at Alberto Pica is a must.

The afternoon will be spent touring the city’s most recognizable sights: the Colosseum, and the Roman Forum and Palatine Hill. For a more offbeat experience, visit the Basilica di San Clemente and its underground, excavated church.

Head towards home via the Testaccio district, a neighborhood said to embody today’s “real” Rome. Back in Trastevere, settle into a cozy meal at Meridionale. But before heading there, make a stop at the Michelangelo-designed Piazza del Campidoglio for beautiful views of Rome’s landmarks at night or sunset.

Leave the Country, Immediately

You just got to Italy, but it’s already time to do some border crossing. Head to the world’s smallest country, Vatican City, and spend the day exploring its famous sites. St. Peter’s Square and Basilica, as well as the Vatican Museum with its Sistine Chapel are must-sees, but the Castel Sant’Angelo is also intriguing. It also offers amazing views and hosts a fraction of the crowds that swarm the other Vatican sites during the high tourist season.

Refuel in between sites just across the border at Pizzarium, a pizza joint that creates one-of-a-kind pies using truly unique topping combinations. The rule here is, if it sounds super weird, just try it – somehow it will magically taste perfect.

Once you’re finished exploring the tiny Vatican, travel back to Italy for dinner and drinks. One of the best wine bars in the city is Mimi e Coco, located on a charming side street near the Piazza Navonna. With its incredibly fresh ingredients and atmospheric patio, this spot embodies the quintessential Roman dining experience. This place is so comfortable and charming, you might want to stay for a nightcap – good thing they’re open til 2!

Stairway to Rome

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Today you’ll explore the famous Spanish Steps neighborhood, where you can experience modern Roman life amidst an ancient backdrop.

Ensure your future return to the city by throwing a coin over your left shoulder into the stunning Trevi Fountain, and then perch yourselves on a Spanish Step where you can sit and enjoy watching tourists co-mingle with locals in the Piazza di Spagna.

Make your way to Villa Borghese via the Piazza del Popolo to tour the Villa and adjoining Galleria with its magnificent sculpture collection. Whether or not you have an interest in seeing the art, go here to explore the surrounding gardens, which are considered some of the most beautiful in Rome.

Lunch with the locals at Osteria Barberini, a great place to try the classic Roman dish, cacio e pepe. Take a post-meal stroll down Rome’s most famous and upscale shopping street, Via Veneto, even if just to window shop.

With time before dinner, take your pick of the city’s famous sights that you may have missed. Standouts include the iconic Pantheon, the more offbeat San Luigi dei Francesi, which is home to some of Caravaggio’s most powerful paintings, and the ornate Palazzo Doria Pamphilj, a palace in the heart of the city that is nearly tourist-free.

Settle into Crispi 19 for an imaginative and modern take on seafood. For your nightcap, take a trip to the rooftop bar at Il Palazzetto where you can sip prosecco and take in an after-dark view of the Spanish Steps.

The Cinque Terre Trail

Today you’ll be tackling the breathtakingly beautiful terraced vineyards of Cinque Terre’s Sentiero No. 2, or blue trail. A trail pass is needed, and it can be bought at any one of the five towns’ train stations.

Take the local train to Riomaggiore, the southernmost of the five towns, and begin your hike north to your destination of Monterosso. Make sure to check the local train schedule before setting out so you don’t miss the last one of the day back to Vernazza!

Along the way, you’ll enjoy incredible views, lush vineyards, hidden swimming holes, and the crooked alleyways of the rainbow-colored towns; take mental notes, and save more in-depth exploration for another day, as you’ll want to finish the trail before sundown.

Ristorante Belforte in the mid-point town of Vernazza is a great place for a lunch break. Reward yourself at the end of your hike with a Cinque Terre white wine and local food tasting at the Cantina du Sciacchetra in Monterosso.

Uncovering the Secrets of the Cinque Terre

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For a guaranteed-to-be-tourist-free experience, spend an afternoon relaxing on a secret beach near the town of Corniglia. Guvano is a clothing-optional slice of coast that is as fun to find as it is to relax on.

Take the train to Corniglia; above and to the right of the rail platform, you’ll find a narrow flight of stairs. Go down them, walk along a brick coastal wall, turn right, and continue until you come to an industrial tunnel with a metal gate. Ring the bell to the left to get buzzed in, and then take the path for 10 minutes until you reach a private vineyard overlooking two beaches. A paltry 5 euros will grant you entrance to this hidden, heavenly spot.

If you’re more interested in further exploring some of the charming towns you saw on your hike, spend some time riding the rails and getting a more in-depth look at the Cinque Terre.

Once on the move, you’ll uncover plenty of surprises: Peek into charming churches, climb ancient lookout towers, relax with wine and pasta on restaurant terraces, and consider a sunset boat cruise with Angelo, leaving from Monterosso. Your best dining bets in this region are Enoteca Dau Cila in Riomaggiore, Gastronomia San Martino in Monterosso, and Trattoria dal Billy, in the hills above Manarola.

Just Wander

Lucky you! Four days to explore one of the world’s most beautiful cities. Get yourself oriented by wandering the historic city center, relaxing in some lovely piazzas and gardens, and enjoying some of the city’s best vino.

Start in the halls of the Mercato Centrale, an indoor farmer’s market on steroids. Here, you can choose the most enticing items for lunch. Take a stroll through the nearby leather markets on your way to finding a picnic spot; a good option for do-it-yourself al fresco dining is the Piazza di Santa Maria Novella, where benches are bountiful.

After lunch, cross over the famous Ponte Vecchio to the river’s relaxed left bank, and enjoy gelato at Gelateria Santa Trinita. For a more adult dessert, stop at the nearby Enoteca Pitti Gola e Cantina, said to be one of the best wine bars in Florence.

If you’re in the mood for a tour, go next door to the Pitti Palace and gawk at the trove of Medici family treasures, which are housed within the building’s ornate interior. Before leaving, wander the adjoining Boboli Gardens, which provide beautiful views over the city.

Dinner is at L’Osteria Di Giovanni, one of the best restaurants in Florence that features classic, Tuscan cuisine. Whether or not you’re into opera, seeing a performance in the intimate setting of St. Mark’s Church is an unforgettable experience. Tonight they’re playing The Marriage of Figaro, and on the 22nd it’s La Boheme.

A Renaissance Classic

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Travel back in time to the Renaissance era as you immerse yourself in the iconic, Florentine classics for which the city is famous. Start your day early at the Bargello Museum, home to an extensive collection of sculptures chiseled by the great Italian masters. Next, enjoy some fun photo ops with Michelangelo’s strapping David at the Galleria dell’Academia.

Lunch with the locals at Mario. You’ll have no trouble finding this popular spot near the San Lorenzo Basilica; it always has a line out the door. But if you like an authentic, hectic experience sharing tables with strangers and chowing down on incredible, local food, you’ll find this place worth the wait!

Whereas you spent your morning amongst marble, the afternoon is all about frescoes. Immerse yourself in the art of the Galleria degli Uffizi, said to have the best collection of Italian paintings in the world.

Stop at Gelateria dei Neri for a snack, and then work it off with a climb to the top of the Duomo dome. Back down in the square, pay special attention to the beautifully bronzed Baptistery doors, said to be the spark for the Renaissance movement.

A good choice for dinner is the old school and afforadable Osteria Il Buongustai; don’t blink, or you might miss this tiny gem wedged into one of the city center’s side streets.

Slightly Offbeat Florence

It’s difficult to find true hidden gems in a compact and classic city like Florence, but there are a few quirky sights and out-of-the-way neighborhoods that are worth visiting.

Start your day with the dead, in the underground tombs of Santa Croce, which serves as the final resting place for Michelangelo, Machiavelli, and many of Florence’s other famous residents. Next, head to the Palazzo Vecchio, and take a tour of the Vasari Corridor, an elevated passageway on top of the Ponte Vecchio, housing a collection of hidden art.

If you feel like you’re on Renaissance overload, catapult yourself back into modern-day Italy with a trip to the Museo Gucci, which displays the chic creations of the iconic fashion house. And if you need a pizza fix, La Bussola serves up a great pie for lunch.

Spend the rest of the afternoon on the Ardo’s left bank. Stroll through the peaceful Giardino Bardini, and then explore the bohemian and tourist-free Oltrarno neighborhood on your way to the Piazzale Michelangeo. Here you can enjoy the best views of the city and then visit the nearby Basilica di San Miniato al Monte, one of the most beautiful churches in Florence.

For dinner head to the Piazza di Santo Spirito, a young neighborhood brimming with hip cafes and outdoor terraces; pick the most inviting one, and then experience the ultra-trendy side of Florence by heading to Volume for a night cap.

Wine Walking Tour

One of the best ways to tour vineyards in any wine region is by foot – it gives you an immersive experience that those riding in cars, and even on bikes, won’t feel. So put on your walking shoes, and start exploring Chianti!

Start your wine walking tour far from town in the morning, and then make your way back home as the day goes on. The Castello di Verrazzano is about five kilometers north of Greve and is the perfect place to begin your day. Consider booking one of the tours with food pairings – those who book the one-hour, wine-only session report feeling very envious once the edibles are laid out on the table.

If you want to squeeze in three tastings, you can stop at Fattoria Viticcio on the way to your next stop. If you want to take a more leisurely pace, scratch it in favor of the Montefioralle Winery. This scenic spot, with its incredible views of the town, offers one of the most celebrated vineyard experiences in the region. It’s also conveniently located just down the road from La Castellana, an incredible restaurant dishing up regional specialties – you know it’s good when the dining room is filled with locals every night.

A word of caution: this walking tour covers about 13 kilometers. If you think that’s a bit much, consider hiring a taxi to shuttle you part or all of the way. Pasquale Pugliese is a great driver; he’s pricey, but prompt. On the other hand, walking goes by quickly when you have a good friend and a recently purchased bottle of wine to keep you company!

Leave it to the Experts

Want to samples wines further afield? Today, leave the tasting itinerary to a local expert on a wine tour with Monika Iris.

If you enjoyed your walking tour yesterday, and want to keep it more local, you can walk out to Villa Vignamaggio on the southern side of town. With its manicured gardens, quintessentially Tuscan vineyards, and jaw dropping views over the region, it’s easy to see why this scenic spot was chosen as the filming location for the movie Much Ado About Nothing.

There are more tasting opportunities back in town. Stop by the Castello Di Querceto just outside of the city center, and then wander the winery outposts on the streets surrounding the Piazza Matteotti. A good, albeit pricey, spot for dinner in town is Gallo Nero.

Settle the Age-Old Debate

Did you like Florence? Why not take a day trip to its rival city, Siena, and weigh in on an age-old debate? Check it out, and decide for yourselves which Tuscan beauty has your heart.

What Siena lacks in famous art and must-see sites, it makes up for in intimacy and ambiance. This is the place in Tuscany to just wander and soak in the feel of the Renaissance. Start in its heart at Piazza del Campo, widely regarded as Europe’s finest medieval square.

While taking in your surroundings is the main event in Siena, there are also a couple of attractions to take in if you’re looking for something to “do.” The Duomo is extremely impressive, as are its crypts, Baptistery, and the especially stunning Biblioteca Piccolomini. If you go here, purchase entrance to all of the cathedral facets.

Wander the alleyways before making you way back to the piazza where you can climb the iconic Mangia Tower for incredible views over Siena and the Tuscan countryside. After your short sight-seeing stint, park yourselves at one of the patio bars in the square, enjoy an aperitif, and watch Italian life in this small city go by. Enjoy the view from Bar Il Palio, but move to the side streets when you’re ready to eat; the food here is relatively lackluster. Antica Osteria da Divo on Via Franciosa is a great choice. For dessert, try a Siena specialty from the Nannini bakery; ricciarelli are soft, almond cookies with crunchy vanilla and honey topping

La Grassa

You probably already know that Bologna is the country’s culinary capital – the Italians have even gone so far as to nickname it “La Grassa,” or “the Fat One.” While there are some lovely sites to see in this city, the main purpose of visiting them is to let your food digest before your next meal. So let’s do some eating!

Start your day with the perfect cup at Cafe Terzi, an elegant shop where the baristas truly know the art of coffee making. Stand at the bar, and order a cappuccino and pastry with the locals.

The coffee shop is steps from Piazza Maggiore, the heart of the Bologna. Start your exploration of the city here, at the beautiful sanctuary of Santa Maria della Vita and by climbing to the top of Torri degli Asinelli, the taller of the iconic Due Torri, and taking in the beauty of Bologna’s terra cotta rooftops.

Hungry yet? Go casual for lunch at Tamburini, a deli with cafeteria-style dining in the back. Don’t worry, this isn’t your average buffet – the local dishes are tasty, and you can choose from over 200 varieties of vino.

Speaking of vino, keep the party going after lunch at a spot just down the street. Osteria Del Sole is a wine bar – and that’s it. No food… just spectacular drink from the surrounding area and a whole lot of character. If you like, you can bring your own food in with you and eat it picnic-style. But my guess is you’re still full from your last stop.

Next visit Santa Stefano, a beautiful church that is perhaps Bologna’s premier must-see site. Featuring seven structures in one, the basilica is more of a complex. Enjoy roaming the covered arcades and exploring room after room of intriguing architecture.

In Bologna, even cocktail hours are accompanied by food. Enjoy an aperitif at Bar Pasticceria Gamberini, where you can nibble on delicious snacks laid out on the bar. Bonus: this place is also a bakery, so consider taking some tiramisu to go.

To get the best dinners in Bologna, you have to wander just a little bit outside of the city center. Trattoria Nonna Rosa is a comfortable, local spot with a homey atmosphere and delicious, homemade Bolognaise cuisine. This little offbeat spot is 100% worth the short walk – don’t miss it!

Chef Secrets

Learn the secrets of Italian chefs with a cooking lesson today. Bologna has several culinary classes available – some offered by more formal institutes, others by local enthusiasts. Here’s a rundown on the top options:

– The Culinary Institute of Bologna is a pricey establishment, but they’ll give you the most options. You can choose from half- or even multi-day courses and select the type of food you want to learn about, such as meat, cheese, or seafood.

– At Taste of Italy, you are welcomed into the home of a Bologna local and taught the secrets of home cooking. This in-house experience focuses on making fresh pasta, and at the end you get to lunch on the fruits of your labor. They also offer the option of adding on a market tour.

– Cook Italy is run by Carmelita, a local woman with an apartment overlooking the old town. Enjoy the view as you chop and saute tonight’s dinner at the longest-running cooking school in the city. Menus and classes are completely tailored to your desires and skill levels.

Depending on which class you select, you might also have time for a few other culinary experiences. Enoteca Italiana is one of the best wine caves in all of Italy and is great for a stand-up sandwich while sampling some of the country’s best bottles. Satyricon is one of the most celebrated osterias in town, but this incredible dining experience first requires a walk or a taxi ride. For a little bit of nightlife, try Le Stanze, a lounge that was once a 16th-century chapel complete with frescoed ceilings. And don’t leave the city without stocking up on goodies at La Baita Formaggi. The meats, cheeses, and wines sold here are perfect for a gourmet train meal.

Soak in the Sea

Spend at least a day soaking in the gorgeous scenery from your coastal home base, Positano, the most photogenic of the Amalfi Coast towns. The stunning views over the ocean and the coastline’s staggering cliffs are the most notable attraction in this seaside sanctuary. The best place to take in the abundant natural beauty is on the Footpath of the Gods, which takes you into the vineyard-laced hills above town. Or, if you prefer a more relaxed day, just wander the charming streets of the old town.

The Positano harbor is also the meeting point for one of the most unique dining experiences in the region. Head down to the dock around 11:00 a.m., and make a reservation to ride the boat with the red fish on its mast. It will transport you to a secluded cove that hides an amazing seafood restaurant called Da Adolfo.

In the foreground of the rocky inlet are a few rows of tightly packed-in beach chairs, and in the background are several tables scattered under a straw overhang. Enjoy a lounge in the sun or a swim in the sea before ordering a jug of local wine and enjoying plate after plate of freshly caught fish. The boat takes diners back to town between 3:30 and 4:00.

Another incredible dining experience in Positano can be had at La Tagliata. This family-owned restaurant sits precariously on the cliffs above town, serves only locally grown food, and has no menu. The owners will even give you a complimentary, roundtrip lift between the restaurant and your hotel if you book ahead of time.

Captivating Capri

At some point during your time on the Amalfi Coast, consider taking a ferry to the isle of Capri, where you can live in the lap of luxury for a day.

Enjoy the island’s scenic beauty by traversing some of the many walking paths that criss cross the landscape. Or, tour the island by boat. If you decide on this option, it’s recommended that you hire a small boat so that you can easily slip into the many grotto caves and spend as much time as you like swimming in their enticing waters.

There are also a number of interesting villas on the island, including Villa Jorvis, former home to the Emperor Tiberius and Villa San Michele, which has particularly beautiful gardens.

Round out your day with some upscale shopping and a relaxing meal at Da Paolino Lemontrees. Though close to the bustling Marina Grande, the restaurant cannot be reached by car, keeping it relatively secluded. This spot’s most charming feature is its outdoor dining patio, situated in an expansive lemon tree grove.


If you’re comfortable… booking your trains before you get to Italy, you can get some amazing deals on tickets through Trenitalia, Italy’s national rail service.

If you decide… you want to tour the Villa Borghese, you should make reservations to do so before you leave for Italy.

A trail pass… is needed for Cinque Terre’s Sentiero no. 2, or blue trail, and can be bought at any one of the five towns’ train stations. You should also check the trail status before heading out; portions are frequently closed due to impassable conditions.

Reservations are recommended… to see The David and for the Uffizi Gallery; without them, you risk long lines or missing out entirely.

You must book… tastings ahead of time for the Chianti vineyards.

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