2 Week Itinerary For Greece and Italy: How to See the Best of Both Countries

Does it seem like every person you know goes on vacation to Europe over the summer? Is this finally the year you want to plan an ultimate European adventure for yourself? Greece and Italy are the perfect pair of countries to visit on such a trip, offering a blend of ancient history, breathtaking sites, and delicious food that will make your vacation unforgettable.

I will admit that the title of this post is a little misleading, as you’ll discover that we were actually away for a little more than two weeks (17 days to be exact), but this itinerary is the exact one John and I followed during our “European Summer” vacation in 2024. We designed it to maximize our time while enjoying a mix of relaxation and adventure. This trip was my second time in both countries and John’s first time visiting either, so we made sure to include all of the must-see sites along with a few hidden gems or points of interest I did not get to experience during my first time around. 

We took this trip during the end of July. If you plan your trip for the same time of year, one thing to keep in mind is that summer is the peak season for European travel, which means prices will be higher and places will be busier. Don’t let that deter you – Europe is incredible during the summer, but do plan ahead! The sooner you book experiences and restaurant reservations, the smoother and less stressful your trip will be when you’re there.

This trip will always hold a special place in my heart because it’s the one that John proposed to me during. After we arrived at our hotel on the Amalfi coast, we immediately stepped out onto the balcony, which offered sweeping views of the breathtaking cliffside and blue water below. After snapping a few photos, I turned around to find John down on one knee asking me to marry him. It was all very romantic (when you don’t take into consideration how sweaty and dirty we were after just visiting Pompeii on our way from the airport!). With or without a proposal, this trip is ranked as one of my favorites of all time, and I would be thrilled for you to steal some or all of our itinerary! Keep reading for my Two Week Travel Guide For Greece and Italy. 

Itinerary Overview

Two Week Itinerary For Greece and Italy

Days 1-2: Travel to Athens

Fly into Athens International Airport. It was significantly cheaper for us to fly from Chicago to Athens versus any other city we had on our itinerary, so that’s where we started. Direct flights out of O-Hare International Airport (ORD) cost us approximately $550 USD per person, but flight prices will obviously vary depending on a number of factors, including which day of the week you choose to fly on. We left Chicago on a Monday afternoon and arrived in Athens at approximately 9:00 AM local time the next day. We knew we would be tired after an overnight flight, so we had arranged ahead of time to have a private car to pick us up to transport us to our hotel.

Stay at a hotel in or near Plaka. If you have limited time in a destination, it’s always a good idea to pick an accommodation that is centrally located. Since we only had two days in Athens, we wanted to be close to as many must-see sights as possible. We chose to stay at a more budget-friendly place, Airotel Parthenon, which was centrally located in Plaka and offered a free breakfast included in our room rate.

Explore Plaka. After checking in to your hotel, stroll through the historic heart of Athens. Wander its charming streets, shop for souvenirs, and enjoy a relaxed lunch at The Greco’s Project next to Monastiraki Square. For our first meal in Greece, we ordered dolmades and souvlakis.

Head back to the hotel to nap like we did (the jet lag hit us harder than expected!) or continue exploring Ancient Agora, Panathenaic Stadium (the first modern Olympic stadium from 1896), the National Garden, and try to see the changing of the guards at the Hellenic Parliament building!

Eat dinner at GH Attikos Restaurant. For our first night of our trip, we found a perfect rooftop restaurant that not only had delicious Greek food and exceptional service, but it also offered a stunning view of the Acropolis. Be sure to make a reservation or arrive early to beat the rush – understandably so, this is a very popular spot for sunset and we noticed that they had to turn a lot of people away due to capacity.

Day 3: Athens – Acropolis and Historic Athens

Wake up early to beat the heat. The sun in Greece is intense! You will also want to fuel up for a full day of sightseeing. We grabbed breakfast at the hotel (breakfast was included in our stay) before starting our day.

Go on a guided tour of the Acropolis and Parthenon. No trip to Athens is complete without a visit to the Acropolis. If you’re planning on going, I highly recommend booking a guided tour (group or private) so you can more deeply understand and appreciate what you’re observing. We booked our tour through Viator with Athens Walking Tours, and our booking also came with admission into the Acropolis Museum. Our guide was very knowledgeable, passionate, and ALMOST had me convinced to sign up for the Athens Classic Marathon (almost). The tour gave us the perfect amount of time at the historical site – any longer and we would have baked in the hot sun. If you have long hair, do yourself a favor and bring something to tie your hair back with – it’s windy on the top of the Acropolis!

Visit the Acropolis Museum and the Temple of Olympian Zeus. The museum really helps you to really understand what you observed during your visit to the Acropolis. It’s also a great way to get out of the sun for a bit!

Indulge in traditional Greek treats. We stopped for a couple of snacks in between sights, including a cup of fresh greek yogurt from Fresko Yogurt Bar and the most delicious greek donuts, called loukoumades, from a dessert shop, LUKUMAΔΕΣ, around the corner from our hotel!

Enjoy the sunset from the top of Nymphs Hill. This location was less crowded than the popular Mount Lycabettus and the hike to the top offered great views along the way. There are also a lot of neat landmarks and historic sites to see in the park, such as the Prison of Socrates and the Themistoclean Ancient Wall.

After sunset, we made our way back down the hill and ended our night exploring the streets of Plaka one last time before heading back to our hotel to pack up and get some sleep before our early flight to Santorini in the morning. 

Day 4: Travel to Santorini

Catch an early flight to Santorini. The flight only took approximately 45 minutes (you can also ride a ferry to the island, but that takes longer). Once we landed, we opted to take a cab to our hotel instead of waiting for the bus. 

Stay at Santorini Palace. This hotel is right across from the Three Bells of Fira. When we arrived, our room wasn’t quite ready yet, but we were still able to enjoy the free buffet breakfast and lounge by the pool while we waited. And since we booked with American Express Platinum, we received a free room upgrade which came with a private balcony and a gorgeous view of the sunrise.

We chose to stay near Fira because it’s centrally located and is more affordable than other places on the island, like Oia. Santorini’s main bus hub is also located in Fira, making it cheap and easy to get to anywhere else on the island. (All buses go to and from Fira.) On my first trip to Santorini in 2017, I stayed in Kamari, which was another great budget-friendly location. 

Explore Fira’s picturesque streets. Take a scenic stroll into Fira town, stopping in shops along the way. It does take about 10 minutes to walk, but the views are so breathtaking you will easily lose track of time and probably make several stops along the way for pictures.

Enjoy drinks and incredible views at PK Cocktail Bar. The patio is small, so plan ahead and make a reservation if you want to be there for sunset.

Eat a quick bite for dinner at McDaniel’s Snack Bar. This spot has a great variety of traditional Greek plates and gyros. We ate there twice during our stay.

Day 5: Santorini Wine & Sunsets 

Enjoy a winery tour and tasting at Santo Wines. After breakfast, catch the public bus from Fira to Perissa, but make sure to ask the bus driver to stop at Santo Wines (if you don’t ask, they won’t stop). We learned a lot on the tour, and then sat down at the restaurant to enjoy a wine flight while taking in views over the caldera.

Head to Oia in the late afternoon to see the iconic white-washed buildings and blue domes.

Hike down to Amoudi Bay for some delicious seafood. If you’re up for it, make the trek down the 278 steps to Amoudi Bay (just remember you will eventually have to make your way back up!) Relax and fuel up for the journey back up by sitting down and enjoying a delicious meal at Ammoudi Fish Tavern or Dimitris.

Capture the famous Santorini sunset from Oia. The most popular place to view the sunset is from the Castle of Oia. For less of a crowd and a better chance of catching the first bus back to Fira, I suggest standing across from The Virgin Mary of the Akathist Hymn Church. 

Grab a late night treat from Svoronos Bakery. Catch the bus back to Fira and treat yourself to some delicious baklava or kataifi from a local bakery.

Day 6: Santorini Beach Day

Spend the day at Kamari Beach. After breakfast at the hotel, we took the public bus from Fira to Kamari. The beach is about a 5 minute walk from the bus stop.

Lounge under an umbrella or take a stroll along the beachfront promenade. Kamari is the perfect location to relax and shop for souvenirs. Most of the beachfront restaurants offer free beach chairs so long as you purchase food or drinks. If you plan on doing any swimming, be sure to bring water shoes to protect your feet on the rocky shore.

Other popular beaches on Santorini include: Perissa Beach, Perivolos Beach, and Red Beach.

Eat one last dinner in Greece. Head back to Fira and freshen up after your day at the beach. If you are looking for a sit-down meal, try Aris Restaurant for great food and equally phenomenal views. If you want something more laid back and casual, get food to-go from McDaniel’s Snack Bar and take it back to the hotel to enjoy.

Day 7: Pompeii & Amalfi 

Fly into Naples. Naples Airport is the closest international airport to the Amalfi Coast. We arranged for a private transfer to pick us up at the airport and take us to Amalfi. This was costly at approximately $300 USD, but we didn’t want to prolong a travel day by navigating the bus routes and we also wanted to make a stop to see Pompeii. We considered the cost as part of our “airfare,” and since plane tickets from Santorini to Naples were so cheap, we felt better about splurging for the private car. 

Go on a tour of Pompeii. Explore Pompeii’s ruins with a guided tour en route to your hotel in Amalfi. You could easily spend an entire day in Pompeii and still only see a fraction of it. We would have loved to stay longer, but we departed after approximately 2.5 hours, which was about all we could tolerate in the heat. If you’re on the fence about visiting Pompeii, I can’t recommend it enough.

Stay at Grand Hotel Excelsior Amalfi. This luxurious cliffside hotel overlooks the stunning Amalfi Coast, offering breathtaking views of the sea and the charming town of Amalfi below. Guests can dine at the hotel restaurant, relax by the pool, or take the private shuttle to the town or the hotel’s private beach club. We splurged a little bit by staying here, but it was my favorite hotel I have ever stayed at!

Eat dinner at the hotel restaurant, TATO’ – Dine on delicious Italian cuisine while overlooking the water. The seafood in the Amalfi Coast is incredibly fresh and well-prepared. We tried their octopus as well as the gnocchi and one of the seafood entrees. During our dinner, we watched a rare full moon, called a Buck Moon, rise into the sky, making for a very memorable and romantic evening – ‘That’s Amore!’

Day 8: Amalfi Town

Eat breakfast at the hotel. Grand Excelsior Hotel Amalfi offers a great a la carte breakfast buffet, including hot items made-to-order. We loved eating our breakfast and sipping on a morning cappuccino while taking in the view from the hotel’s balcony. 

Explore Amalfi’s charming town center. After breakfast, take the hotel’s private shuttle down to the town center. After viewing the Amalfi Cathedral, wander the charming streets, stopping for lemon-flavored treats and browsing for souvenirs as you go.

Spend the afternoon at a beach club. You can’t leave the Amalfi Coast without lounging at a beach club. Mar di Cobalto is a popular spot in Amalfi Town. We loved that Grand Excelsior Hotel Amalfi had their own private beach, the Mare Club, which is where we spent a lot of our downtime when we weren’t exploring. 

Eat dinner at Gerry’s Pub. Just a short (but steep) walk up from Grand Excelsior Hotel Amalfi you will find Gerry’s Pub, a ‘mom and pop’ restaurant serving delicious authentic Italian dishes. When we arrived, a group of locals were playing cards at a table in the corner, and that’s when we knew we had found a good place to eat. We ordered three entrees and dessert to share, and it was one of my favorite meals we ate during our time in Italy! Do yourself a favor and order the tiramisu – it’s vacation after all!

Day 9: Day Trip to Capri

Catch an early-morning ferry to Capri. While cars are an option, one of the best ways to get from one town to the next in the Amalfi Coast is by ferry. We booked the first boat out of Amalfi in order to maximize our time on Capri. 

Go on a boat tour of the caves around the island. One of the best ways to see Capri is by boat! After de-boarding the ferry, climb aboard another (but smaller) boat to discover some of the island’s caves (aka grottos), its gorgeous cliffsides, and the famous Faraglioni rock formations, including the ‘Arch of Love.’

Take the Capri Funicular to the Piazzeta in the center of town. Purchase tickets for the funicular across from the entrance. You can walk up the hill or take a cab, but the funicular is the cheapest and fastest way to go. The center of Capri town is located approximately 150 meters above sea level offering stunning views of the island’s coastline and the Tyrrhenian Sea. Once you arrive at the Piazzeta, you’ll be greeted by the lively atmosphere of cafés, boutiques, and charming streets. It’s a perfect spot to soak in the views, grab a lemon sorbet, or do some high-end shopping.

Stroll through the Gardens of Augustus. This is a beautiful terraced garden offering breathtaking views of the Faraglioni rock formations and the island’s coastline. It’s a perfect spot to relax and take in Capri’s natural beauty. You can buy admission tickets through this website.

Trek down the cliffside to Marina Piccola Beach. Trekking down the cliffside to Marina Piccola Beach is no easy feat – it’s a steep descent that can feel like quite the workout. But once you reach the beach, the stunning views of the shore make it all worth it. Just be prepared for the climb back up, which definitely gets the heart pumping!

Take the Capri Funicular back down and board your ferry back to Amalfi. Grab dinner in town or head back to the hotel and order room service while relaxing on your private balcony.

Day 10: Amalfi Beach Day

Enjoy a relaxing beach day. Spend the day lounging in a beach chair and sipping on aperol spritz. 

Have dinner at La Taverna del Duca. This quaint restaurant emanates Italian ambience and is perfectly located in the town center of Amalfi. We thoroughly enjoyed our lemon-infused pasta and fresh seafood on the patio. And the meatballs were life-changing!

Day 11: Travel to Rome

Take the train from Naples to Rome. This is a breezy train ride that only takes approximately 1.5 hours. I highly recommend buying your train tickets in advance (especially during peak travel season) so that they don’t sell out for your preferred time. We used Italo for our train rides, but I’ve heard the others in Italy, such as Italia Rail and Trenitalia, are just as reliable. Purchase tickets directly with the trainline’s site or use Trainline to help you book.

Stay at a hotel near Piazza Navona. When in Rome (ha!) you will want to be centrally located to many of the must-see attractions, including Trevi Fountain, the Pantheon, and the Colosseum. Staying near the famous Piazza Navona will place you close to sites, restaurants, and entertainment. We stayed at Hotel Navona, which was one of the more budget-friendly accommodations we chose on this trip, but we loved its location and we knew we wouldn’t be in the hotel much with everything we had planned to see and do while in Rome.

Stroll through Piazza Navona. Piazza Navona is one of the city’s most famous open squares. Known for its architecture, it sits on the site of an ancient Roman stadium. The square is home to three fountains, including the iconic Fontana dei Quattro Fiumi by Bernini. Piazza Navona is a lively spot of street performers, artists, and cafes, making it a perfect spot to soak in Rome’s charm while enjoying a gelato or an espresso. Be sure to go inside the 17th-century Baroque church, Sant’Agnese in Agone, which faces the piazza.

Try carbonara at Cantina e Cucina. Carbonara is a pasta dish that originated in Rome and is made with eggs, cured pork, cheese, salt, and pepper. The eggs create a rich and creamy sauce that coats the pasta. It is sinfully delicious, and you can’t go to Rome without trying it! Cantina e Cucina is a cozy, authentic Italian restaurant with welcoming atmosphere. Not only was the staff friendly, but the food was also delicious. The crispy Roman artichoke was to die for!

Visit the Trevi Fountain and Pantheon. No visit to Rome is complete without seeing the Trevi Fountain and the Pantheon, two of the city’s most iconic landmarks. Don’t forget to toss a coin into the Trevi Fountain to ensure your return to Rome! Just a short walk away, the Pantheon features a preserved dome that opens to the sky.

Treat yourself to some gelato. There is no shortage of gelato shops in Rome, Stop into one for a cold late-night dessert before heading back to your hotel room to rest up before another busy day of sightseeing.

Day 12: Rome & Vatican City

Get a cappuccino and pastries from L’Antico Forno di Piazza Trevi. This is a very popular cafe right next to the Trevi Fountain. Get in line early to beat the rush!

Climb The Spanish Steps. Climbing the Spanish Steps is a must-do experience in Rome. This iconic staircase, with 135 steps, connects Piazza di Spagna to the Trinità dei Monti Church. It’s a lively spot!

Tour the Vatican Museums and the Sistine Chapel. Explore the art, history, and architecture of the Vatican Museums and the Sistine Chapel, home to some of the world’s most famous masterpieces, including Michelangelo’s breathtaking ceiling. You can take a guided tour if you prefer or wander through by yourself, which is what we did! Tickets for our preferred time were sold out on the Vatican website, so we got our through Get Your Guide.

Visit St. Peter’s Basilica. Just around the corner from the Vatican Museums, you can discover the grand St. Peter’s Basilica, one of the most iconic landmarks in Vatican City. Be sure to abide by the dress code, including covering your shoulders and knees. 

Eat paninis at Bono Bottega Nostrana – San Pietro. This place, near St. Peter’s Basilica, serves up perfect paninis made with fresh ingredients and authentic flavors.

Day 13: Rome – The Colosseum

Take a tour of the Colosseum. The Colosseum in Rome is one of the world’s most iconic landmarks. Acclaimed as one of the 7 New Wonders of the World, the famous amphitheater once hosted gladiator battles and grand spectacles. Learn about its rich history and marvel at its architectural ingenuity during a guided or self-led tour. We booked a ticket that included admission to the arena floor, which was super cool to see.

Explore Palatine Hill and the Roman Forum. After touring the Colosseum, head to the birthplace of Rome on Palatine Hill and wander through the Roman Forum, once the center of political, religious, and social life in ancient times. 

Eat cacio e pepe at Pub Cuccagna. This dish is a classic Roman pasta made with Pecorino Romano cheese and black pepper. It’s simple yet delicious!

Day 14: Florence & Tuscany

Take the train from Rome to Florence. Take an early train out of Rome to maximize your time in Florence. An express train ride takes approximately 1.5 hours. 

Stay near Piazza di Santa Maria Novella. This location offers easy access to Florence’s historic center. We stayed at Hotel Rosso 23, a stylish boutique hotel with a free buffet breakfast and a prime location just steps from the iconic square.

Visit the Galleria dell’Accademia to see Michelangelo’s David. Admire the work of Michelangelo’s David at the Galleria dell’Accademia in Florence. This world-famous marble masterpiece is a must-see, along with the gallery’s impressive collection of Renaissance art. I highly recommend booking a skip-the-line ticket for the museum ahead of time.

Go inside the Basilica of Santa Maria Novella Step inside the Basilica of Santa Maria Novella to admire its stunning Gothic and Renaissance architecture, including the impressive stained glass windows. 

Take a Chianti wine tour in the Tuscan countryside. Head out to the Tuscan countryside on a Chianti wine tour. Sip on wines while learning about the region’s winemaking traditions. We did a half day tour, which included a visit to two wineries and the tasting of eight wines combined. This was easily one of our favorite parts of the entire trip!

Discover Florence’s unique buchette del vino, or wine windows. These small openings in historic buildings once used to serve wine directly to passersby. Today, many have been restored, offering a fun and quirky way to enjoy a glass of wine in Florence.  

Get pizza to-go from LiVio Pizzeria. After a long day of exploring Florence and drinking wine, treat yourself to a local favorite. We picked up two pizzas from LiVio Pizzaria to take back to eat in our hotel room for a quick and delicious meal after an action-packed day!

Day 15: Travel to Venice

Take one last stroll around Florence. Go inside of the impressive Santa Maria del Fiore or search the city for one of Florence’s multiple replicas of Michelangelo’s David statue, including a bronze copy in Piazzale Michelangelo and a marble copy in Piazza della Signoria.

Take the train from Florence to Venice. This train ride was the longest of our trip at approximately 2 hours and 15 minutes. Be sure to have a plan for what to do after you arrive in Venice. We had planned to take the water bus from the train station, as that was our cheapest option. However, we ended up waiting over 1.5 hours in line for it and we were packed in like sardines. If you can afford to do so, opt for a water taxi or ask your hotel for help navigating ahead of time. 

Stay at a hotel in either the San Marco or San Polo district. San Marco is where all of the action takes place. San Polo is still close to popular spots and attractions, but with less noise and crowds. We stayed at the historic Antica Locanda Sturion – Residenza D’epoca in San Polo. We loved how it was near the Rialto Bridge, but carrying our luggage up three flights of stairs (there was no elevator in the historic building) was not the most fun thing to do on a hot summer day. If we were to go back, I think we would check out Hotel Rialto.

Go on a traditional gondola ride through Venice’s canals. You almost cannot visit Venice without going on a traditional gondola ride through the city’s canals. Gondolas are not the main form of transportation throughout Venice any longer, but they remain an iconic symbol of the city and offer a unique, romantic way to experience its charm. As you glide through the narrow canals, you’ll pass under historic bridges and stunning architecture.

Eat dinner at Osteria da Carla. Located just steps away from the Piazza San Marco, this restaurant serves up traditional Venetian dishes.

Day 16: Venice – Mask Making & Exploration

Take a Venetian mask making workshop with San Marco 596. Mask-making is a cherished tradition in Venice, rooted in the city’s history of masquerade balls and the iconic Carnevale di Venezia. Unleash your creativity by taking a Venetian mask-making workshop with San Marco 596, where you’ll learn traditional techniques and craft your own unique mask to take home as a souvenir.

Explore Piazza San Marco and Doge’s Palace. Discover the heart of Venice at Piazza San Marco, a bustling square surrounded by stunning architecture, including the iconic St. Mark’s Basilica and the towering Campanile. Nearby, step into history at the Doge’s Palace, a Gathic building that once served as the political and judicial hub of the Venetian Republic. Reserve your admission here.

Wander through Giardini della Biennale. Escape the crowds and wander through the peaceful Giardini della Biennale, a lush garden that’s home to some of Venice’s renowned art and architecture exhibitions.

Have one final Italian dinner at Snack Bar Castello. This restaurant, located just a little bit off the beaten path, is the perfect restaurant to end your time in Italy at. Indulge in fresh seafood, homemade pasta, and local wines as you savor your last evening in Venice.

Treat yourself to a cannoli from Bar Rizzo (Mogo G). Cap the final evening in Venice with a true Italian treat. Known for its crisp shells and sweet, creamy ricotta filling, this dessert is the ideal way to end your final full day in Italy.

Day 17: Depart Venice

Enjoy one last cappuccino and pastry. Wake up, pack your bags, and savor one last cappuccino as you soak in the last bits of Venice before heading to the airport or train station. Take a moment to reflect on your adventures and say “arrivederci” to Italy.

Head home! Depart Venice. If you are an American Express Platinum member, be sure to make your way to the lounge in Venice – it’s one of the best I’ve ever been to!

Final Thoughts

Exploring Greece and Italy for two weeks was the perfect mix of history, stunning landscapes, and delicious cuisine. If you are considering a trip to Europe this summer (or any time of the year), these are two destinations I would highly recommend!

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