italy and greece in 3 weeks + tips for planning a trip from scratch

Hey there!

If my personal instagram is any indication, I just got back in May from an incredible 20 day journey around Italy and Greece. I had so much fun exploring the cobblestone streets, sailing on the most gorgeous blue waters, and eating a ton of gelato. I loved meeting so many people that had so much to share about their homes, their travels, and their experiences. One of the most important things I learned from this trip though?? - hands own the skill, detail, and discipline it takes to plan an epic trip from scratch. One of my best friends from home and I decided to go to Italy and Greece last summer, so over the course of about a year we saved money, pinned a lot on Pinterest, researched about money and transportation, look up the yummiest restaurants, and plan a detailed itinerary. Many people have asked me what my itinerary was, what I would recommend, and how to travel from place to place. I want to go more in depth for each place in further blog posts, but today I am focusing on the overall gist and itinerary for my trip! There are so many ways you can rearrange this itinerary, as Italy and Greece are easy to get around and have a lot to offer depending on what you are looking for. So let's dive right in!!

// flights //

We decided to go to Italy first because the flights were significantly cheaper. There are cheap flights from ATL- Paris/Rome (connect to any destination in Italy from Paris!) as well as from other major US travel hubs. For several weeks we searched a variety of start options, airlines, and connections. Eventually we found the cheapest route (on a reputable airline that we have miles for) to be ATL - Paris CDG - Venice Marco Polo. This was on AirFrance and Delta. However, I recommend searching multiple airlines through Google Flights, Expedia, and a variety of other flight deal websites. You can even sign up for emails to get alerts when the flights you are eyeing drop in price!

Budget air is the best option to get around Europe quickly and efficiently. However, it can get pricey if you don't pay attention to baggage rules (aka bringing an American-sized carry-on and being charged that it was oversized to actually carry-on "HOW RUDE!"). If you are willing to brave the tiny baggage and cramped planes for a cheap price- hit up these budget airlines. We flew from Rome to Athens for a great deal. The best way to get from Italy to Greece and vice versa is by flying, so keep this trip saved in your flights so you can find the cheapest deal!

We also went to Santorini while in Greece. If you want to island hop, flying or taking a ferry are your options! We personally chose to take a flight because the dates we were looking at were about the same price for flying and taking a boat. And to me, a 45 min plane ride at 6:00 am is worth it more than an 8 hour ferry for maybe $10 cheaper. If you want to get to multiple islands in a short time span, look into those flights. But if you book well enough in advance and want to only go to one or two islands, you can definitely score some deals on ferry rides. Just compare your options before ultimately booking!!

To get home, we flew from Athens- JFK New York. JFK has frequent flights to and from Athens through Delta (and I'm sure through other airlines) so once again keep an eye out for those flights to score some deals!

**overall tip about flights: be flexible. In order to score on some good deals, you might need to rearrange a departure date, change your departure city, or pick a different city to fly into. Keep multiple options in mind so that you don't get easily frustrated!

// traveling within the countries //


Italy has an incredible high speed train system. Just be sure to book well in advance and not miss your train (if you do, you might not get refunded aka me). There are large high-speed inner city trains (Trenitalia) as well as regional trains to get ya around. These were so fun to take, and they can get you places a lot quicker than you might expect! The train websites can also help you form an itinerary, so try not to stress about the specifics of each train and connection!


Greece is a bit more difficult to navigate between cities. Luckily, we only stayed on mainland Greece in Athens, which has a great subway system. To get to the islands, ferry and plane are your options. I can't speak much about transportation on mainland Greece, so do some digging on that if you are interested in going anywhere else within the country! Several websites check ferry prices, so check out these places for some deals!

// overview of itinerary //

We left May 9 and returned on May 28. So in total, we were gone 19 days, but count two of those as travel days. So not necessarily three weeks for me (but if you add in a couple extra days, you can add in a new location within one of those countries- which I would have loved to do! We spent

// inspiration and beginning stages //

Two words: Google Docs. If you are traveling with friends, this is your go-to. We put everything we needed in this gigantic document on our gmail accounts. From flights, budget, to day-by-day itineraries, this place was my lifeline while planning. I also created a calendar on my doc with the tables feature, and highlighted days we were traveling, days we were staying put, and days we had reservations. It was a great way to see the overview of the trip and not stress while over there! I printed out a copy to take with me and also screenshot it on my phone. Highly recommend.

Where should I go?? you might ask. First, pick the one destination that is drawing you to the country (or countries) you want to go to. For me, Positano and Santorini were what put these two countries at the top of my bucket list. Maybe you start with a country you want to go to. Draw from your bucket list here. You can go anywhere in the world- just remember that. But pick the place that is pulling you towards it!!

From there, search on Pinterest, read some travel blogs (The Blonde Abroad, The Petite Suitcase, Katie's Bliss and Kara & Nate were super helpful!!) and get some inspiration. Create a Pinterest board with itineraries, places to go, things to do and see, and more. Get inspired. Another tip: if you are staying in an Airbnb, ask your Airbnb host for recommendations! They usually are very well-versed in the area and would love to introduce you to the local sights, food, and culture. Just get the conversation flowing and you can find some great things from them!!

// overall itinerary //

Day 1: Overnight Flight to Venice, Italy

Day 2: Arrive in Venice, Italy

Day 3: Full Day in Venice, Italy
A full day in Venice with two half days from travel is the perfect amount of time. We were able to see everything we wanted to and also visit the islands of Murano and Burano (which I HIGHLY recommend!!)

Day 4: Travel to Cinque Terre, Italy by regional train (anywhere from 4-8 hour journey)

Day 5: Full Day in Cinque Terre, Italy
Give yourself some time to truly experience every aspect of each town- the beaches, the hiking, the regional specialities! This is one of my new favorite places in the world!

Day 6: Full Day in Cinque Terre, Italy
Two full days is perfect in CT if you want to get a good overview of everything and do a hike. However, if you really want to hike all the trails and get some time to relax and lay on the beach, you'll want to stay longer!

Day 7: Cinque Terre to Sorrento, Italy via Naples
Take the train to Naples (through various routes and companies), then transfer to regional Circumenzia train to Sorrento (about an hour more)
This would also be a great point to head to Rome if you don't want to go to Sorrento and the Amalfi region (even though I highly recommend going there!!)

Day 8: Sorrento, Italy
Sorrento is a great hub for going to the coastal towns and islands you dream of visiting! We took a day excursion to Amalfi and Positano, but you could also extend your stay in Sorrento by spending time in the coastal towns and going to Capri! I definitely wish we spent more time here!

Day 9: Sorrento to Rome via Pompeii
-Pompeii is right in between Naples and Sorrento, so we stopped there for a short excursion. There are places to hold your luggage so you can leave it at the train station and walk around Pompeii luggage-free. We then got right back on the regional train to Naples, and then took the high-speed train from Naples to Rome. We arrived in Rome in the early evening and were able to enjoy a nice dinner and walked to the Trevi Fountain.

Day 10: Full Day in Rome
Rome has so much to see, and I loved walking around it. We also booked a super touristy bus tour just to be able to see everything in the short amount of time we had.

Day 11: Full Day in Rome/Vatican
I didn't plan on going to the Vatican, but once I was there I decided I probably should. I bought a skip the line pass, but honestly the Vatican wasn't worth it for me. It was incredibly packed the day I went and was miserable. If you want to visit, try to go in the off season. This was a big miss for me (which is really sad because it is such an important place with so much culture and religious history- but tourists and smelly people cramped into a hot building is not my fave way to spend a trip)

Day 12: Rome to Athens
We flew out in the morning on a budget airline to Athens. Just be careful of those sneaky luggage rules!! Also- there is a super great airport train line that can take you right into the center of the city! Just ask your Airbnb host or hotel what line to take and where to get off at. The trains were easy to navigate and way cheaper than a taxi!

Day 13: Full day in Athens
Take this full day in Athens to explore the Acropolis and all the touristy sites. I loved visiting the Plaka neighborhood, which I highly recommend if you want to get away from the hustle and bustle of the city. I also recommend going to rooftop bars. We didn't get a chance to because we were nervous about being out late, but I really regret not going to them- they have great views of the Acropolis! You really only need one full day in Athens to see all the sites.

Day 14: Athens to Santorini
We took a very very early flight to Santorini (as in I didn't sleep that night). It gave us the full day in Santorini, but honestly we ended up napping the majority of the day. Try to book a little bit later flight or ferry, as I definitely would have done this differently.

Day 15: Full Day in Santorini
Day 16: Full Day in Santorini
Day 17: Full Day in Santorini

Day 18: Santorini to Athens
Late night flight from Santorini to Athens. At this point, we could have taken off a day in Santorini and headed to another island. However, I fully enjoyed having an extended time in Santorini because it is now one of my all time favorite destinations. There is so much to do and it was truly beautiful. I would have been content skipping Athens and staying longer or going to Mykonos or another island. 

Day 19: Full Day in Athens
We could have done without this full day in Athens, but we wanted to make sure we wouldn't miss our flight home if anything happened in Santorini.

Day 20: Fly Home

// planning your itinerary //

I gotta admit it- Rick Steve's Europe, EF Ultimate Breaks, Contiki travel, and Intrepid Travel were SUPER helpful in helping me design an itinerary (granted I could have taken those trips, I wanted to personalize my trip and loosely base mine off of the professionals). I looked at various Italy and Greece (and Italy and Greece combo trips) to figure out things to do, how to get from place to place, and for overall guidelines for my itinerary. Maybe I am cheating the system, but this is a great way to make an itinerary that you  know works and has been done for. Basing your itinerary after a proven-to-work itinerary from the pros is a great way to ensure you will get the most out of your itinerary. So it maybe might not be a COMPLETE itinerary from scratch, looking at the basics from these trips can help you start your own. I added on and deleted things I didn't want, and was able to formulate the ideal itinerary for my travel needs.

At this point I've probably over explained planning this trip, but I truly wanted to give insight into how to plan a trip from scratch. It is so rewarding to see your trip come to fruition after working so hard on it. It seems very challenging, but once you get the main gist of where you want to go, filling in all the little details can be much easier than you would expect. Where are you dying to travel to next? Let me know below!

If you want to see previous travel experiences, check out these posts! Also let me know what travel destination guide you'd like to see first out of all my destinations from my Italy & Greece trip!

also an old throwback- where to take pics in Nashville, TN 



  1. This looks like it will be the best trip! What an incredible experience and opportunity!

  2. I definitely enjoying every little bit of it. It is a great website and nice share. I want to thank you. Good job! You guys do a great blog, and have some great contents. Keep up the good work. I really appreciate this wonderful post that you have provided for us. I assure this would be beneficial for most of the people. Australia road trips

  3. The Tsitouras couple furnished them with carefully chosen antiques and the odd modern, design piece, and then, one by one, turned them into something like a private museum. We specialize in transfers from or to Santorini

  4. Oh wow! These pictures look incredible!

    Amber | The Unpredicted Page

  5. How much was the average total cost? I am looking to follow this itinerary for my trip, just looking for a price so I can get a general idea to save up. Looks like you had fun!

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