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Greece and Italy Itinerary: 3 Best Weeks of Your Life

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Natasha Weiss

What takes an eternity to get to but only seconds to fall in love with? Italy and Greece. For many, a trip to these two countries may take years of careful planning to realize. While Italy is renowned for scrumptious pasta, stupendous opera and magnificent architecture, Greece is a fitting place for soul-searching and finding peace. Legend has it that you are a fortunate human if you are able to sail the Aegean Sea during your years of inhabiting the Earth. 

To make the most of your time in Greece and Italy, spend a minimum of seven days in each country. Traveling to Italy is best done during spring (March-May) because the weather is getting warm and Easter festivities begin to swarm the country. Late April also marks the travel season for Greece. Considered as shoulder season, April is ideal because the weather is not as sweltering as June to August, allowing you to carry out more outdoor activities such as hiking. We round up the best itinerary for Greece and Italy consisting of activities, places, hotels and food to make sure your journey is nothing short of stellar. 

Day 1-2: Athens

It is only fair and logical to start your journey in Athens. Not only is Athens the place where the main international airport is situated, it is also the country’s capital where modern civilization was born. This city is full of historical sites to get you well-acquainted with Greece. 

1. Ramble the Acropolis of Athens

For historical highlights, Acropolis sends you off to a good start. This particular place dedicated to the worship of Goddess Athena is ancient, complex and striking in the sun. It is best to arrive early to avoid crowds as this site opens as early as 8AM. 

2. Wander the streets of Plaka and Anafiotika

The streets of Plaka and Anafiotika ensure a well-spent afternoon. One of the oldest parts of Athens, the street of Plaka played an important role during the reign of the Ottoman Empire. If the street of Plaka is rife with pastel houses and Islamic structures, Anafiotika reflects the true taste of a Greek island with their whitewashed houses and blue roofs. 

3. Run a full lap in the Panathenaic Stadium

For your second day, don’t miss out on the cultural highlights of the city by stepping foot on the Panathenaic Stadium or widely known by locals as “Kallimarmaro” where the first Olympics was held in 1896. To complete the cultural highlights, the Temple of Olympian Zeus will be worth your time and energy.

More great things to do in Athens:

  • Sip cocktails with the view of Acropolis
  • Go south of the city center and enjoy the Athenian Riviera
  • Savor a fancy brunch in the posh and elegant area of Kolonaki

Athens’ best accommodations:

  • Four Seasons Astir Palace (⭐⭐⭐⭐⭐)
  • Coco-Mat Hotel Athens (⭐⭐⭐⭐)
  • Moon & Stars Boutique Hotel (⭐⭐⭐)

Athens’ best restaurants:

  • Dinner in the Sky (fine dining)
  • Cinque Wine & Deli Bar (great wine)
  • To Kyklamino (authentic Greek cuisine)

Day 3-5: Santorini

If we were to sum up Santorini in just a few words, they would be: perfect sunset, picturesque villages and breathtaking caldera views. Fira and Oia are two most popular areas of Santorini, with Fira being the capital of the island and the largest settlement and Oia being dubbed the most picturesque village. 

1. Hike from Fira to Oia

The hike from Fira to Oia will probably be one of the most rewarding highlights while in Santorini. Santorini is known for its active volcanic activities and this 10KM hike will take you tracing volcanic landscapes and the villages of Imerovigli, Firostefani and Fira. The hike itself is fairly easy as the trail is similar to a sidewalk. 

2. Marvel at the Oia sunset

The Oia sunset is one experience that you will continue to treasure for the rest of your life. This picturesque village is blessed with scenery and panorama found in postcards. You can catch the sunset before ending the day with a perfect meal. The Oia Castle is the most sought-after spot to enjoy the sunset, but it can get too crowded. If you are looking for an alternative for a photo spot, the terrace next to the three blue domes of Oia can save you from fighting the crowd. 

3. Cliff-jumping and fresh seafood at Ammoudi Bay

Spending an afternoon in Ammoudi Bay and cliff-jumping sound like a treat that is hard to beat. Ammoudi Bay is a small port and beautiful bay surrounded by flashy red cliffs and whitewashed buildings. Located 300 steps below Oia, you can indulge yourself in mouthwatering and fresh seafood after a hearty afternoon swim.

4. Visit the Ancient Akrotiri and admire the contrasting colors of the Red Beach

Although Santorini is not especially famous for its beaches, the Red Beach near Akrotiri is worth your time of the day. The striking red sand, volcanic rocks and hills combined with the dark blue sea water make for an amusing view to the eyes. You can kill two birds with one stone before visiting this beach. Since the Red Beach is located in the Akrotiri village, this means that a visit to the Ancient Akrotiri (prehistoric Bronze Age settlement demolished by volcanic eruption and the most important archaeological site in Santorini) would be ideal. 

More great things to do in Santorini:

  • Visit Santorini’s hot springs in the island of Nea Kameni
  • Go on a winery and microbrewery tour
  • Get the full local experience in the Pyrgos village

Santorini’s best accommodations:

  • Katikies (⭐⭐⭐⭐⭐)
  • Aspaki by Art Maisons (⭐⭐⭐⭐⭐)
  • Noni’s Apartments (⭐⭐⭐)

Santorini’s best restaurants:

  • Avra Santorini (Mediterranean dishes)
  • Metaxi Mas (local cuisine)
  • Ariale Restaurant (Mediterranean and seafood)

Day 6-8: Crete

The largest and most populated island of Greece, Crete is a land rife with ancient sites, amazing beaches and interesting outdoor adventures. There is always something for everyone in Heraklion. 

1. Melt away stress at Elafonisi Beach

They say that great things take time, and it may take you a while to get to Elafonisi Beach, as the location is rather hidden and tucked in the southwest of the island, but the greatness that awaits is worth every second and penny. The crystal clear water, pink sand and beautiful scenery will melt your exhaustion. 

2. Visit Moni Preveli and walk down to the Preveli Beach

Before getting to the Preveli Beach, paying a visit to Moni Preveli, the most treasured monastery that served many functions over the years as a center of resistance during the Turkish occupation and was essential in World War II as a hiding place for Allied soldiers from the Nazis. 

3. Step on the said birthplace of Zeus

What better way to immerse yourself in Greek culture than to visit the birthplace of Zeus? Dikteon Andron Cave is located 48km away from the revered Agios Nikolaos (a famous coastal town) and has an upper and lower cave full of various stalactites and stalagmites. The lower chamber boasts a stupendous stone interior with a pond which people toss coins into.   

4. Enjoy a vibrant evening in Agios Nikolaos

To enjoy the most of the evening, the town of Agios Nikolaos that surrounds Lake Voulismeni will give you the vivacious yet serene vibes of Crete. It is said that the goddess Athena used to come to this lake to bathe. Many open air restaurants dot the town and overlook the water. Agios Nikolaos is popular with young adults and sipping drinks by the lakeside cafes is a sure way to inhale the beauty of this seaside town.

More great things to do in Crete:

  • Marvel at the ruins of Venetian castle in the abandoned Spinalonga Island
  • Experience the true village life in Kritsa
  • Sunbathe in Crete’s most exotic beach, the Vai

Crete’s best accommodations:

  • Domes of Elounda  (⭐⭐⭐⭐⭐)
  • DOM Boutique Hotel (⭐⭐⭐⭐)
  • Artion City Boutique Hotel (⭐⭐⭐)

Crete’s best restaurants:

  • Peskesi (classic local dishes)
  • Pelagos (local and vegetarian cuisine)
  • Chrisofyllis (salads and BBQ)

Day 9-10: Thessaloniki

The second biggest city in Greece might not be popular with tourists, especially if they go down the usual Athens-Santorini-Mykonos route, but who says that this city pales in comparison to the ever popular destinations?

1. Ambles and promenades around the White Tower and waterfront

After spending a good hour strolling around the White Tower that has been around since 1535 which is undoubtedly the most iconic landmark of Thessaloniki, be sure to take leisurely ambles and promenades along the waterfront. This is a truly relaxing experience as you embark on a 5km long walk. Quenching your thirst is the last thing you should worry about, because many bars and restaurants dot the seaside.

2. Museum and archaeological site day

You can also squeeze in a day full of museums and archaeological sites during your stop in Thessaloniki. The Ancient Agora which was the religious center during the Greek and Roman periods and the Archaeological Museum full of remains will definitely satisfy your inner Indiana Jones.

More great things to do in Thessaloniki:

  • Take a stroll in Ana Poli, Thessaloniki’s old town surrounded by heavy Byzantine Walls
  • Visit archaeological sites of Pella and Vergina for history addicts
  • Find serenity and stare at the turquoise waters in the beaches of Chaldiki Peninsula

Thessaloniki’s best accommodations:

  • Makedonia Palace Hotel (⭐⭐⭐⭐⭐)
  • The Modernist Thessaloniki (⭐⭐⭐⭐)
  • Blue Bottle Boutique Hotel (⭐⭐⭐)

Thessaloniki’s best restaurants:

  • Grada Nuevo (Mediterranean and European dishes)
  • Opsopoion Manganeiai (Mediterranean, European & Greek cuisine)
  • Kanoula (Mediterranean & Greek dishes)

Day 11-12: Venice

The Floating City is a dream come true to many. Venice is like a maze in which every corner and nook makes you go “ooh” and “ahh”. The canals are not the only striking aspects of Venice as this city is festive and full of carnivals and romance. 

1. Gondola ride and walking tour

What is a trip to Venice without a hearty and romantic gondola ride along the Grand Canal? If limited time is one of your concerns, taking a Venice walking tour and gondola ride lets you have your cake and eat it too. Besides relaxing in a gondola and passing through the Grand Canal, you get to pass by and adore important landmarks of the city including Piazza San Marco and Ponte di Rialto. 

2. Get aboard the ferry to Murano and Burano

A trip to Venice cannot be whole without stepping foot on Murano and Burano. Murano is the place where glass workers reside, producing high quality, luxurious and handmade Murano glass. This is a practice and tradition that has been passed down from one generation to another. Burano, on the other hand, is a tiny island and home to approximately 3,000 people. This island is situated 9km north of Venice and is renowned for its colorful houses with vivid colors.

More great things to do in Venice:

  • Walk around and admire the Byzantine Cathedral
  • Browse the personal art collections of Peggy Guggenheim
  • Get away from the touristy spots and relax in the Venice Lido

Venice’s best accommodations:

  • Hilton Molino Stucky (⭐⭐⭐⭐⭐)
  • Palazzo Veneziano (⭐⭐⭐⭐)
  • Rosa Salva Hotel (⭐⭐⭐)

Venices’s best restaurants:

  • Osteria Alle Testiere (fresh daily seafood)
  • GLAM (Italian and Mediterranean cuisine)
  • Estro (contemporary Venetian cuisine)

Day 13-14: Florence

Arguably the most beautiful city in Italy, Florence’s charm remains ever pure and untainted by the hustle and bustle of a big city. No skyscrapers are found here, and if you really want to take your time and inhale every bit of magic that lurks in every corner of the city, you can opt to walk from one destination to another because almost everything is within walking distance. 

1. Adore the Duomo and Michelangelo’s David

For starters, to get the true atmosphere of Florence, circle around Piazza del Duomo, also known as Cathedral of Santa Maria del Fiore. This building is the definitive spot of the city and catches the eyes with its glorious Renaissance dome and gothic style. When in Florence, you simply cannot miss Michelangelo’s David that was masterfully placed in Galleria dell’Accademia.

2. Catch wonderful sunsets at Piazzale Michelangelo

No trip to Florence is complete without a hike to Piazzale Michelangelo. Florence seen and savored from above is a magical experience, especially just before sunset. Although you can drive or take the bus to get to the piazza, we recommend you take a promenade and enjoy every step of the way, because what awaits above is indescribable. 

3. Savor the authentic and juicy Florentine steak

To close a great day, go for the authentic Bistecca alla Fiorentina experience. This t-bone steak weighs over a pound and is good for sharing. Served rare with all its juiciness dripping, enjoy this beauty with a glass of red. 

More great things to do in Florence:

  • Buy scoops of thick and authentic gelato from Gelateria La Carraia 
  • Walk slowly down Ponte Vecchio
  • Spend hours and hours in Uffizi Gallery for art fanatics

Florence’s best accommodations:

  • Four Seasons Firenze (⭐⭐⭐⭐⭐)
  • Arte’ Boutique Hotel (⭐⭐⭐⭐)
  • Hotel Renaissance (⭐⭐⭐)

Florence’s best restaurants:

  • Trattoria dall’Oste (Florentine steak)
  • Ristorante Il Guscio (Tuscan & Italian classics with a great wine selection)
  • Culinaria Bistro (French and Morrocan flavors)

Day 15: Tuscan

The Tuscan countryside is another world. With its green and lush fields, rolling hills and endless rows of cypress trees, the sun truly shines differently in Tuscany. It is also known for winemaking and famous wine regions include San Gimignano, Montalcino, Chianti and Montapulcino. This winemaking region is not far from Florence (approximately 2 hours by car) and you can also opt for a wine tour by bus departing from the city. 

For guided wine tours, you have to secure the spots several weeks before the intended date. If you are having a hard time selecting which winery to go to, we highly suggest you visit Montalcino and Chianti. There is a medium-size winery called Altesino in Montalcino that serves exquisite brunello (a wine variety native to Montalcino). You can enjoy 5 kinds of wine and light bites for around 40 euros. As for chianti, there is a great family-run winery called Montefioralle with their exceptional chianti classico. 

Day 16-17: Roman and Vatican City

The Eternal City is one of Europe’s oldest cities dating back to the times of the Roman Empire. When in Rome, besides making a wish and tossing a coin over your shoulder at the Trevi Fountain for good luck, don’t skip the Colosseum night tour. 

1. Brace yourself for the Colosseum night tour

The Colosseum may get too packed and crowded during the day, but here is one secret: you can book a night tour with just a few other people. The magnificence of this amphitheater that is one of the Seven Wonders of the World at night gives private and intimate vibes. The night tour also lets you see the underground area of the theater. 

2. Explore the Roman Forum and have a wonderful dinner at La Pergola

Before joining the night tour, some mandatory activities when in Rome include marveling at the ruins of ancient buildings at the Roman Forum, tracing the 138-step staircase of the Spanish Steps that connect Piazza di Spagna at the base with Trinità dei Monti at the top and treating yourself at La Pergola, a rooftop restaurant overlooking the astonishing and panoramic views of Rome and the only restaurant with 3 Michelin stars in Rome. 

3. Walk around St. Peter’s Basilica and St. Peter’s Square

Vatican City is more than just the headquarter of Roman Catholic, it is also the smallest country in the world that is situated in Rome. If you happen to visit during Easter, you can celebrate it by attending a mass taking place in St. Peter’s Basilica extending to St. Peter’s Square due to overflowing participants. 

4. Delight in Sistine Chapel’s magnificent ceilings

You cannot speak of St. Peter’s Basilica without mentioning Sistine Chapel as the two places are the most significant landmarks of Vatican City. We suggest you book a skip-the-line group tour for these two places as they tend to get swamped by an influx of tourists. Sistine Chapel is where architectural wonders really materialize: its ceilings are the representation of fine Renaissance art painted by the one and only Michelangelo from 1508 to 1512. This is also the place where important ceremonies such as inaugurating new popes occurs.

More great things to do in Rome & Vatican City:

  • Shopping sprees at the famous shopping street, Via dei Condotti
  • Hop on a train and explore the ruins of Pompeii 
  • Send a postcard to a loved one from the Vatican

Rome’s best accommodations:

  • The First Roma Dolce (⭐⭐⭐⭐⭐)
  • Spanish Diamond Luxury Suites & Jacuzzi (⭐⭐⭐⭐)
  • The Radical Hotel Roma (⭐⭐⭐)

Rome’s best restaurants:

  • La Pergola (Mediterranean cuisine)
  • Zia (seasonal Italian produce)
  • Pipero Roma (Campanian delicacies)

Day 18-20: Amalfi Coast

Located in the Campania region of Italy, Amalfi Coast is one of UNESCO World Heritage Sites with its breathtaking coastal landscape and countless cliffs. Not only is it popular for the many fishing villages, Amalfi coast is a significant producer of lemons and limoncello liqueur. Amalfi Coast is so popular because of the idyllic and panoramic views of the sea meeting the hills. 

1. Trace and hike the Path of the Gods

Nothing beats hiking Sentiero Degli Dei (the Path of the Gods). This path is 4 miles long and will bring you on a 2 to 2,5-hour journey to witness the beautiful views along the coastline of Amalfi. This track is especially preferable because it does not require participants to do ridiculous amounts of climbing stairs. Pack your breakfast and make a few short but meaningful stops to enjoy it with postcard views. Make sure to stop at the Belvedere viewpoint to absorb the best views. 

2. Spend daytime in Positano

Positano gives you the best southern Italy holiday vibes with its cascading houses along the hills in their glorious pink, terracotta and peach hues. The best all-around view of Positano can be savored from Arienzo Beach Club. 

3. Hop on a vespa and explore the coastline

Two is a party, and if you come to the Amalfi Coast with a lover, rent a vespa to circle around the coastline and discover the towns of Amalfi, Positano and Ravello. Other notable spots on this coast include the Atrani, Furore Beach and Villa Cimbrone in Ravello.

More great things to do in Amalfi coast:

  • Take a day trip to Capri
  • Descend to a breathtaking marine cave near Amalfi, the Emerald Grotto
  • Wander to another magnificent coastal town just 1 hour from Amalfi, Sorrento

Amalfi Coast’s best accommodations:

  • Le Sirenuse (⭐⭐⭐⭐⭐)
  • Hotel Santa Caterina (⭐⭐⭐⭐)
  • Albergo L’Antico Convitto  (⭐⭐⭐)

Amalfi Coast’s best restaurants:

  • Arienzo Beach Club (endless peach bellinis)
  • Il Tridente (amazing sunsets and great cocktail bar)
  • Gerry’s Pub (Italian & Mediterranean dishes)
Natasha Weiss

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