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The Perfect First Trip to Italy Rome, Florence, Tuscany, Amalfi Coast

This is the perfect introduction to Italy for those who are limited on time yet want to make the most of their visit. We have planned epic, once-in-a-lifetime experiences for you every day. Explore the history and culture of Rome, Florence, Tuscany & the Amalfi Coast. We've included all the "must-see" attractions - The Vatican, Colosseum, Ponte Vecchio, David, and the dreamy Isle of Capri, and added some surprising extras that will leave you wanting to come back for more!

Day 1 - Arrive in Rome

Upon arrival, you will be met and transferred to your hotel. We'll provide you with Hop-on, Hop-off bus tickets so you can easily make your way around Rome. Take some time to ride the HoHo bus through Rome to become familiar with the surroundings, enjoy a scrumptious lunch in Piazza Novaona or mix and mingle with the locals for aperativo (happy hour) before embarking on an exciting twilight walking tour of the Eternal City.

Welcome twilight tour of Rome!

See Rome’s historic center top sights and get an orientation of the Eternal City with an expert tour guide. Our evening stroll through the historic center includes the Spanish Steps, Trevi Fountain & Pantheon plus a free gelato!

Travel Tip:

Many Roman shops still partake in the afternoon siesta. To be safe, don't plan your shopping between 1:30 p.m. and 5 p.m (though some shops take shorter breaks). Stores are typically open daily until 8 p.m. and closed on Sunday.

Not only in Rome but everywhere in Italy, restaurants are usually open for lunch and dinner. Restaurants tend to start serving dinner around 7:30 p.m. to accommodate visitors' dining habits. Romans usually won't sit down at the table at 9 p.m or later.

Day 2 - The Colosseum

Take some time to relax this morning as your body will be adjusting to the time change. Later, step inside the Colosseum after it closes and enjoy it with only a handful of other people on this very special tour. Special access means you'll have a chance to explore the Colosseum underground, where men and beasts were kept before they took to the Colosseum floor. You'll experience this vantage point too when you walk onto the arena floor to see the amphitheater lit up and looming above you.

Bucket List Ideas

  • Throw three coins into the Trevi Fountain
  • Join a Cooking Class
  • Visit the Fountain of Four Rivers
  • Drink from the water fountains
  • Get a hand-drawn portrait or a caricature at Piazza Navona
  • Don't skip the Roman street food
Roman Forum

Day 3 - The Vatican

Skip the line and go straight to Michelangelo's Sistine Chapel with this guided tour. See the Vatican Museums' best galleries and tour St. Peter's Basilica with a professional English-speaking guide. Our Privileged Entrance guided Vatican Museums and Sistine Chapel tour starts at 7:30 a.m. and doors open shortly after 8 a.m. (a full hour before general admission opens). Visit the Sistine Chapel before it opens to the general public and admire Michelangelo’s works in peace before embarking on a thorough guided tour of the Vatican Museums and St. Peter’s Basilica. There is simply no better way to see the highlights of the Vatican without the crowds that can overrun the galleries later in the day.

Available Monday through Saturday

Tipping in Italy

Tipping at restaurants throughout Italy is not required, but it is a kind gesture that is appreciated as an acknowledgment of good service. A good rule of thumb in a typical restaurant is to tip about 1 euro per person. Alternatively, you can round up the bill, but it need not exceed more than 10%.

Tipping tour guides, on the other hand, is common and expected. The typical amount is anywhere from 5 Euro to 10% of the cost of the tour. And it is standard to tip hotel housekeeping 1-2 Euro per day, and the luggage porter 1 Euro per bag.

Trevi Fountain

Day 4 - Private transportation to Cortona with a stop in Orvieto

Your private, English-speaking guide will greet you at your hotel, and drive you to your Tuscan hotel with some sightseeing along the way. After passing through Lazio, you will arrive in Umbria. The journey will be relaxing and comfortable; in the meantime, you will have the chance to admire valleys, towns, and small medieval towers along the way.

Once arrived in Orvieto, your guide will lead you along the picturesque alleys, full of pottery small shops; then, a visit at Cathedral Square and the Clock Square, and, if you want, there will be the chance to visit also the underground cells where in the past oil and wine used to be preserved.

Lunch is a short 15-minute drive away, in order to reach a farm overlooking the valley, with vineyards and fruit trees. Here, you can taste local products, good wine and get tempted by truffle dishes in fabulous scenery.

Following your tour, your driver will escort you to your Cortona hotel, about an hour away.

I think it might be fun to drive in Italy.

It sure is, but keep in mind it can be daunting at times. Here are some things to think about before you tackle driving around Italy.

  • Book car rental well in advance.
  • Smaller car rental offices may be closed at weekends, so plan accordingly, especially if you aren't returning the car to an airport or metropolitan office.
  • Get an international driving permit. Some areas of Italy have more strict driving rules than others, so be prepared with a valid passport, US-issued driver's license, and an international driving permit in the event that you are asked to show them.
  • Expect manual cars – automatic cars are available but usually come at a higher cost. If you prefer an automatic car, it's best to rent it months in advance.
  • Renting Vespas and e-bikes are fun alternatives to renting a car, but it's not the safest means of travel in Italy. We recommend them for the Italian countryside where there is less traffic.
  • Italians drive on the right-hand side of the road.
  • Blue parking lines mean you need to pay to park – bring coins as most parking machines do not accept cards.
  • Be aware of ZTL in small towns – ZTL means ‘Zona Traffico Limitato’, areas only open to traffic of permit holders.

Under the Tuscan Sun in Cortona

Following your scenic tour through the Umbrian countryside, you'll arrive at your hotel in one of the most lovely villages in all of Italy, Cortona! The town was made famous in 1996 when author Frances Mayes published her book, and subsequent movie, "Under the Tuscan Sun." Stroll past Bramasole, the Tuscan villa Frances restored and where she currently spends much of her time.

Day 5 - Private Guided Tour of Tuscany

Travel by luxury minivan with an expert English-speaking driver-escort, explore the idyllic hill towns of Siena, San Gimignano, and Monteriggioni. You'll receive personalized attention, enchanting locations, and free time at all destinations. This day seeing the best of Tuscany is a fantastic experience.

Tuscan Wines to Try

  • Chianti Classico
  • Brunello di Montalcino
  • Nobile di Montepulciano
  • Vernaccia di San Gimignano
  • Bolgheri di Sassicaia
  • Morellino di Scansano
  • Vin Santo, dessert wine

Day 6 - Pasta Making Class in The Chianti Hills, then on to Florence.

Depart Cortona in the morning and enjoy a scenic drive through the Chianti hills to Florence. On the way, immerse yourself in a private pasta-making class at a Cesarina's* home, learn the secrets of the region's most famous pasta dishes and taste the fruit of your labor accompanied by a glass of local wine.

During the lesson, the Cesarina will reveal the tricks of the trade of 3 authentic regional pasta recipes. Have fun putting your cooking skills to the test. Each participant will have a workstation equipped with utensils and all the ingredients to make the dishes. Then, taste everything you have prepared accompanied by a selection of red and white local wines.

*A Cesarina is a member of Italy's first nationwide community of local home cooks whose mission is to safeguard Italy's food culture through home cooking.

Afternoon - Arrive in Florence

Check-in to your hotel right in the center of Florence. Enjoy this afternoon on your own exploring the historic district which is closed to motor vehicles making it very easy to navigate on your own.

Find yourself surrounded by street performers and artisans along the way. A short walk along the Ponte Vecchio Bridge crossing the Arno River leads you to Oltrarno. A lovely neighborhood with antique shops, artisans, and some of Florence's most authentic restaurants.

Enjoy dinner followed by a leisurely stroll back to your hotel with a gelato stop along the way.

Fun things to do in Florence

  • Wander the historic streets in search of wine windows
  • Cross the Ponte Vecchio and shop from Oltrarno Artisans. Their studios and workshops are often hidden away in backstreets, courtyards, and basements where they welcome visitors with open arms. You'll find everything from metal works, leather goods, handmade paper, musical instruments, ceramics, perfumes, jewelry, and more!
  • Shop at Mercato Centrale, a two-story market where local vendors sell products like produce, fish & meats, cheeses, spices, homemade pasta, pastries, nuts, oils, wines, and flowers.
  • Stroll through the historic district and be entertained by artists, musicians and street performers.
  • Ride a gondola on the Arno River
  • Visit The Santa Maria Novella Pharmacy, the oldest still-operating pharmacy in the world, where they continue the traditional preparation methods, and still carry products using the original recipes of monks. A specialty of the pharmacy is Carta D’Armenia (“Armenian Paper”). This is not your average drug store!

Day 7 - Tour Florence in a Day

See the best of Florence in a day with an expert local guide. For 7 hours you'll be immersed in history, art & architecture; skip long lines at precious Renaissance sights like Michelangelo's 'David', the Uffizi Gallery; then take to the streets to experience the endless charm of Florence at Florence Duomo, Ponte Vecchio and the outdoor sculpture gallery of Piazza della Signoria.

Day 8 - Day Trip to Pisa and Lucca

After picking you up from your hotel, a private driver will take you on a journey west to visit two fascinating Tuscan towns rich in architectural wonders: Pisa, Lucca and San Miniato. You will discover that in Pisa there’s much more to explore beyond the iconic Leaning Tower, with a charming historic centre developing along the Arno river and boasting gems like the elegant Piazza dei Cavalieri conceived by Cosimo I de Medici and his architect Giorgio Vasari and the lovely Borgo Stretto lined with porticos and cafes. In Lucca, on the other hand, you can take a delightful stroll along its beautifully preserved medieval walls and enjoy a drink in the unique Piazza Anfiteatro surrounded by pastel-colored buildings. The tour will take you also to San Miniato, an ancient town strategically located along the Via Francigena, which is home to an imposing medieval tower that offers some spectacular views.

Spend about three hours in the elegant and refined town of Lucca. Here you will have a light lunch in an old-fashioned Tuscan Trattoria. You can walk along the famous sixteen-century walls, then entering into the enchanting historical center where you will have the chance to admire the amazing Piazza Anfiteatro, the Torre Giunigi, the Duomo di San Martino and the typical “antique dealers’ street”.

The tour continues with a stop in Pisa, where we will remain for about one hour and a half. Enjoy the view of Piazza dei Miracoli, with the celebrated Leaning Tower, the Baptistery and the Cathedral, an unrivaled masterpiece of Romanesque art constructed between the 11th and 12th centuries. In Piazza dei Cavalieri you can admire the historic Scuola Normale, one of the most famous universities in the world.

Before going home, a shortstop in San Miniato. San Miniato is a medieval town in the province of Pisa, located halfway between Pisa and Florence. Since the Middle Ages, it has been considered strategic because it is situated atop three small hills, where it dominates the lower Arno valley, between the valleys of Egola and Elsa (three rivers that flow in Tuscany).

Prepare to be wowed in for the Amalfi Coast!

Expect to see the most beautiful sunrises, sunsets, and moonbeams over the water that you've ever witnessed! If possible, plan your trip over a full moon and reserve a water view room with a balcony, or choose a hotel with a rooftop bar for ultimate viewing.

Day 9 - High-Speed Rail to the Amalfi Coast

High-speed rail is one of the most efficient and comfortable ways to travel in Italy. The high-speed Florence to Naples bullet train completes its route in around three hours and offers modern amenities, as well as several train classes for your convenience.

When you arrive at Naples Centrale train station, your driver will be waiting to take you to your next destination... The Lost City of Pompeii!

Want the best pizza in Naples?

We can fit a pizza lunch stop into your itinerary, just ask! Even better, learn from the experts during an expert-led pizza-making class.

  • L’antica Pizzeria da Michele Forcella
  • 50 KALO
  • Gino E Toto Sorbillo
  • Antica Pizzaria Port d'Alba
  • Pizzaria Brandi
  • Pizzaria Pellone
  • Starita, Materdei
  • Pizzaria La Notizia (From "Stanley Tucci Searching for Italy")

Pompeii

Seeing Pompeii on your own can be difficult and baffling, so we have designed our Best of Pompeii Tour: Unveiling The Buried City to bring you closer to the amazing history and tragic end of Pompeii than you could ever get on your own (or at least without a degree in archaeology. Led by an official Pompeii tour guide – most of whom are trained archaeologists – you will wander the fully-preserved streets of Pompeii and visit the most interested and heart-wrenching sights from the city that was lost under the massive eruption of Mt. Vesuvius.

Afternoon arrival at your Sorrento hotel

Following your tour of Pompeii, enjoy some authentic Napolese Pizza for lunch before proceeding to your Sorrento hotel.

Day 10 - Tour the Isle of Capri

See Capri & Anacapri with Blue Grotto

No holiday in Sorrento is complete without a trip to the enchanting island of Capri. Spend an unforgettable day in the little treasure of the Mediterranean!

Meet your expert local guide in Sorrento and embark on the high-speed boat toward the Island of Capri. Please note that this is a public ferry and is not exclusive to your tour group.

Once we arrive in Capri, you’ll take a boat ride to the popular and dreamy “Grotta Azzurra” (Blue Grotto), where sunlight passes into an underwater cavity and shines through the seawater, creating a magical blue reflection. After returning to the port you’ll board on a minibus for a scenic drive to Anacapri, 918 feet (280 meters) above the sea level.

You’ll see wonderful views of the bay of Naples before continuing to a local restaurant for lunch. After lunch, you can take advantage of some free time to explore Capri at your leisure or go shopping Then you’ll return to Marina Grande and embark back to Sorrento.

...but the view from the top is amazing!

The best views in all of Capri can be seen from the summit of Monte Solaro. Soaring 589 meters above sea level, it's the highest and most panoramic point on the island. The easiest way to reach the summit is by single-passenger chair lift. The journey to the summit of Capri's mountain takes just 12 minutes and allows an opportunity to enjoy a 360° panorama of Capri.

Day 11 - Amalfi Coast Tour

Explore Positano, Amalfi, and Ravello immersing yourself in the unique atmosphere of the Amalfi Coast on this 8-hour tour. Travel through the scenic roads of the Sorrentine Peninsula overlooking the Gulf of Naples. Do not miss the opportunity to take breathtaking photos and to visit the famous Positano, the ancient Maritime Republic of Amalfi, and the splendid Ravello overlooking the crystal clear waters of the Gulf of Salerno.

A bucket list experience, for sure!

The Path of the Gods, or “Sentiero degli Dei," is a clifftop trail running between the villages of Bomerano (near Agerola) and Nocelle (near Positano) along the Amalfi Coast. The trail starts in the mountains, so you get sweeping views of the amazingly blue Mediterranean and all of the seaside towns that dot the coast. The trail averages at about 1640 feet (500m) above sea level. It is often referred to as the best hike in the world for its breathtaking views of the Tyrrhenian Sea. If you can fit an extra day into your itinerary, this is a must!

Day 12 - Arrivederci!

Today, your private driver will transport you from your hotel in Sorrento to Rome Fiumicino Airport or an overnight hotel, before your flight home.

* Accommodations, transportation, tours, and activities described in this itinerary are based on availability and are subject to change at any time. If something is not available at the time of booking we will do our best to find a suitable alternative. For this reason, rates and availability will vary. We will gladly price this itinerary upon request and will modify it to suit your personal needs.

Summary

  1. Arrive in Rome
  2. Rome - Morning to relax. Twilight Colosseum tour
  3. Rome - VIP Vatican tour
  4. Rome - Orvieto - Cortona
  5. Cortona - Full day tour of Tuscany
  6. Cortona - Chianti Hills - Florence
  7. Florence - See Florence in a Day
  8. Florence - Day trip to Pisa and Lucca
  9. Florence - Pompeii - Sorrento or Positano hotel
  10. Capri - Full day tour
  11. Amalfi Coast - Full day tour
  12. Transfer to Rome airport or overnight hotel before departing for home

Our thoughts about Travel Insurance

Travel should be fun and relaxing. But what if something happens? What if you or a family member becomes sick, your bags are lost or stolen, or you need to cancel a trip due to an emergency?

A travel insurance plan is a package of benefits and services intended to protect your travel investment, your belongings, and most importantly, you. Now more than ever, we have witnessed just how important travel insurance is. No matter what your vaccination status is, if you plan to travel it's important to have a financial safeguard in place for pandemic-related trip problems. This is especially true if you’re traveling abroad, where your U.S. health plan may have limited global coverage. Travel insurance can provide that safety net.

Most plans provide benefits for:

  • Trip Cancellation
  • Trip Interruption
  • Medical Expenses
  • Missed Connection
  • Travel Delays
  • Baggage Loss
  • Reimbursement for missed portions of your trip if you're forced into quarantine due to a positive Covid test.
  • Optional "cancel for any reason" - a benefit of travel insurance coverage that offers the opportunity to cancel travel plans for reasons other than those listed as “covered reasons” on a policy.
Created By
Brenda Ajay
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