Joey and I took a 20 day trip to Greece and Italy and it was the absolute best. Below is our itinerary and a brief summary of what we did each day. We are thrilled to share it with you and hope you find ideas you can use for your own trip.
Day 1: Depart for Milan
Day 2: Milan
Depending on where you are flying from, you will be a bit jet lagged; however, after a quick break at your hotel, we recommend you a grab a coffee and go enjoy Milan. While in Milan, the main two things to do (in our opinion) is walking around The Galleria and taking a tour of The Duomo! For the Duomo, make sure to swing by their first to get your tickets as time slots do fill up.
Recommended hotel: Rosa Grand Milano because, not only is it stunning, but it’s a block away from the Duomo and The Galleria.
Day 3: Venice
We took an early morning train to Venice so we could enjoy a full day and a half there. The train ride is about 2.5 hours from Milan and is very fun to experience; you will see beautiful landscapes and go over the water to get this “Floating City”. Our top recommendation is to take a Gondola ride through the back canals. We suggest arranging a gondolier by Saint Mark’s Square.
Recommended hotel: Hotel L’ Orologio. A quirky boutique hotel in a quieter part of Venice, but still central to exploring Venice.
Day 4: Venice and Athens
We spent a second day exploring Venice and eating at cute canal-side restaurants. We recommend doing the same as there is plenty to explore! Our flight to Athens was 5:50 pm. To fly out of Venice, you’ll need to take a boat to the airport (it’s an experience in itself!) – be sure to check the water taxi departure times.
Day 5: Athens
Our day in Athens was spent walking and exploring. It is a jam-packed day, but one day here was enough time for us to see everything we wanted. While in Athens, visit the Agora and the Acropolis. At the Acropolis (the ancient city on a rocky cliff), you will be able to see the Parthenon, the Erechtheion, the Ancient Theater of Dionysus and the Temple of Athena. We also walked to the original Olympic Stadium and visited the Temple of Zeus; both of these aren’t must-sees in our opinion, but if you enjoy history and walking the city, it’s always fun to explore.
Recommended hotel: Grecotel Pallas Athena. This hotel was a good price point and had a wonderful breakfast; however, our room itself was a little outdated, but that can always be changed. We do recommend staying within walking distance of Monastiraki Square where there are lots of street restaurants and souvenir shops. This Square is also near other major tourist and historical sites.
Day 6: Naxos
We used Ferryhopper to book a ferry from Athens to Naxos. After a busy day in Athens the day before, we actually decided to take off early in the morning to enjoy a full, relaxing day on the beach in Naxos, instead of another full day in Athens. Changing tickets from an afternoon ferry to a morning ferry was very simple and inexpensive at the ticket kiosk outside the ferry terminal.
Recommended hotel: Galaxy Hotel. This boutique hotel was incredible, we are itching to go back. It is a great location, steps from Agios Georgios Beach. It is also just a 10-minute walk to Naxos Town (Chora), which is the the busier, tourist area where you’ll find plenty to do at night.
Day 7: Naxos
We bought bus tickets from a local bakery near our hotel to go visit Agios Prokopios, known for being the the most beautiful beach on Naxos. The bus ride itself was a fun way to see Naxos and experience some of the local culture. Once at the beach, all we did this day (and we wouldn’t change it for the world) was soak up the sun, ordered drinks on the beach and ate delicious Greek food. This part of the island had plenty of restaurants and small shops to visit too.
Day 8: Naxos
For our last day in Naxos, we spent time at the beach right outside our hotel. In the evening we went up to the Apollo Temple for the sunset views. The temple is right outside Naxos Town and an easy hike. Be sure to bring your selfie stick!
Day 9: Santorini
We took a 1-hour ferry from Naxos to Santorini on Day 9. The big decision you’ll have to make when visiting Santorini is if you want to stay in Fira or Oia. After our own research, we chose to stay in Fira because it was within walking distance to nightlife, but a little less busy and more affordable than Oia. On this first day in Santorini, we just got our bearings and walked around Fira. It was incredibly hot so we spent time in the afternoon at our hotel pool.
Recommended hotel: Adamant Suites. Like most hotels in Oia and Fira, this hotel is a cave hotel, built into the cliff overlooking the caldera. We chose the Sapphire Suite to enjoy our own outdoor jacuzzi. The staff at Adamant was amazing, and we had fresh breakfast delivered outside our room each morning.
Day 10: Santorini
On our second day in Santorini we took a morning bus to Oia. You can always do a hike from Fira to Oia as well, but when we were there in early September it was too hot. Oia was a beautiful little town to wander. We had amazing gyros and explored the charming Atlantis Books bookstore. We left in the afternoon because it gets very busy for sunset. We thought the sunset view in Fira were incredible and went back there to enjoy it during dinner.
Day 11: Santorini
On our last day in Santorini we signed up for a Santorini Volcano Tour where your boat departs at the bottom of the Fira cliffs. You have the option to take a cable car, donkeys or walk the donkey trail; I hate heights and felt too bad for the donkeys in the heat, so Joey and I walked the full 125 floors down and back up after our tour (not recommended). The Volcano Tour was an interesting activity because when else will we get to stand on an active volcano in the middle of the sea?
We recommend eating dinner at least one night at Argo. It was so good we ended up eating there all three nights!
Day 12: Rome
We took an hour and a half morning flight from Santorini to Rome on our 12th day. We had a relaxing first day here. We enjoyed pasta for lunch and for dinner! For dinners, we recommend going over to the Trastevere neighborhood where you will find plenty of restaurants to choose from with both locals and tourists out.
Recommended hotel: iQ Hotel Roma. This hotel is located in the business district, but we wanted to be in a more central area of Rome. We didn’t mind taking a quick bus ride to Trastevere, and longer walks to the Rome tourist attractions like the Colesseum and the Vatican. We had heard great things from friends who had stayed here before as well. They have an incredible breakfast, a beautiful rooftop and clean, comfy and modern rooms. If you need to do laundry, they also have a laundry room which we took advantage of one morning.
Day 13: Rome
The things you can see and do in Rome are endless. For our second day in Rome, we chose to take a tour of The Vatican. This experience was mind blowing. We didn’t realize a three-hour tour could be filled with so much art, long hallways and … other tourists. It was a bit overwhelming, but of course, a must see when you visit Rome.
To book your tour of The Vatican and other Rome tours we recommend using The Roman Guy. For our Vatican Tour, we did the Skip the Line Vatican Tour with Sistine Chapel & St. Peter’s Basilica tour.
Day 14: Rome
On our third day in Rome we signed up for a walking tour of The Colosseum, the Roman Forum, and Pantheon. It was a busy day with lots of walking, but we are glad we saw it all with a guide. If you do the same, be sure to wear good walking shoes and bring water and snacks.
Day 15: Rome
Our fourth and final day in Rome was spent walking the city again; there truly is so much to see. We stopped at the Trevi Fountain to make our wishes and visited the Spanish Steps for more photo opportunities.
Day 16: Lake Como
From Rome, we took a three-hour train ride to Como. After grabbing a quick bite to eat there, we boarded the water taxi to get us to our hotel in Lezzeno. It was a funny experience pulling our two large Away bags off the boat, up the stairs, and through the winding, narrow streets to get to our hotel. A taxi might have been a good idea, but if you’re up for an adventure, it’s possible!
Recommended hotel: Filario. We can’t say enough good things about this luxury design hotel. If we visit Lake Como again, we will definitely be back. The rooms were modern, large, and luxurious, with private balconies overlooking the lake. The property has a quiet beach, pool, kayaks you can borrow, and an incredible restaurant. When researching where to stay, just note that Lezzeno itself is a more quiet town than Bellagio and Varenna.
Day 17: Lake Como
For our first day at Lake Como, we took the boat taxis around the lake to visit Bellagio and Varenna. Bellagio has a more upscale feel with lots of shopping. Varenna feels smaller and more laid back than Bellagio. Both are wonderful and visiting them is a great way to spend a day.
Day 18: Lake Como
As our trip was coming to an end, we wanted to spend the last day fully relaxing. We couldn’t have chosen a better place to do it then on the beach right outside our hotel.
Day 19: Boat to Varenna to catch Train back to Milan
On our last day in Europe, we caught a water taxi from Lezzeno to Varenna. After a quick bite in Varenna, we took a 40-minute train to Milan. This train ride is quite cool as you go around the lake and through mountains. We spent one last evening walking around Milan and enjoying pizza and pasta before an early flight home the next morning.
Day 20: Depart Milan and return home
That’s our 20-day trip itinerary of Greece and Italy. Some days were full and some days were relaxing, in our opinion, it was the best of both worlds and we would do it all again!
CIAO!
We hope you enjoyed this post and that you can use our recommendations to guide your next adventure. If you have any questions, please feel free to email us or message us on social! To stay in touch and to receive updates when new content is added to our blog, be sure to subscribe to our email list. Wishing you safe and happy travels ahead!
Love, Bri & Joey
