Well, it only took me a year to do our Italy and Greece itinerary recap, but here it is! One year in the making 🙂
I am also using this as a reminder of the amazing time we had, the things we did, the places we stayed, and how we put it all togehter so I can do it again someday!
For a few years, my daughter has been obsessed with the “Mamma Mia” movies- singing every song to the top of her lungs, sharing them with me, and even crying like babies when she read the lyrics of “Slipping through my fingers” to me (seriously, I cry every time I hear this song). So when travel opened up after the lockdowns, I asked her to choose a place where she’d like to go on vacation to celebrate her 18th birthday and high school graduation, and without hesitation, she chose Santorini, Greece.
Before I share with you all the details of our Italy and Greece itinerary, let me tell you something: every mom of little girls should plan a vacation for just them when they are older. Grace and I have always been close but this experience took our relationship to the next level. Those late nights playing cards and laughing until our bellies hurt, the deep conversations about life and her future, doing a lot of “first” with her, talking to strangers and making new friends each place we went, discovering new flavors, and sharing a bed and snuggling until she fell asleep (and me tearing up knowing that she was leaving for college 800 miles away from me), all made connect to a whole new level. I even surprised her with a letter I wrote for her when she was 10, and that I sealed, dated, and saved, to give to her on her 18th birthday. I didn’t know we would be in Tuscany when it was time to read it, so that made it 1,000 times more special. I made a reel about it if you want to see her reaction.
Every minute of this vacation is etched in my memory, and I hope I planted the “traveler seed” in her and that she starts planning trips of her own. Like the sticker on my water bottle says… “You don’t always need a plan. Just go.”
Ok, back to the planning.
The hardest part of planning this trip was “where in Italy do we go?” The whole country is a postcard, so I knew I had to be strategic if we wanted to maximize our time there. We chose Rome as our main airport and decided to go everywhere from there. I booked our flights in August of 2021 with Lufthansa for the entire trip, but unfortunately, they have had so many issues that they kept canceling our Rome-Santorini flights and rebooking us on completely different dates, so we decided to get a refund for that portion of the trip and use a greek airline for it. This is probably not the most time-efficient system, but it allowed us to add days to our trip.
We arrived in Rome and took the train to the city center (Termini station), and then a taxi to the hotel. This all costs us 50 euros, so I learned my lesson: book the airport transfer with the hotel. It may cost 10 or 15 more euros, but you don’t have to worry about luggage, train times, etc. We stayed in Rome for a night at a boutique hotel in the city center. Even with the time change, the delayed flights, and the long traveling day, we had to go and explore. We had an amazing Italian dinner nearby and walked to the Trevi Fountains. The location of this hotel was superb – only a 15-minute walk to the Spanish step and the fountains, and about 30 min walk to the Colosseum. The hotel staff is kind to show you how to get places and even though we were there for less than 24 hours, we learned our way pretty easily.
The next day we booked a tour to the Colosseum, and despite the extremely hot day, it is something anyone visiting Rome has to see. The stories alone make it worth it, but it is as impressive as I thought it would be. After our tour, we headed to the train station to catch our train to Florence – our real hub, where we spent the next 6 days.
There are a few things I learned in just 24-hrs:
After experiencing the Italian train system for a few days, I am completely confident that the next time I visit, I won’t be booking private tours. I will feel very comfortable going places using the train and buses because they are super efficient, affordable, fast, and FUN! The train rides are as scenic as they can be and they go everywhere.
The train ride Rome-Florence is about 2.5 hours and it includes a few stops along the way. We arrived at the Santa Maria Novella station in Florence and our hotel was about 10-min walk from it (we took a taxi because of the luggage).
The best thing about Hotel Paris was the location. Just a 10-15 minute walk from every important spot in the city. We walked everywhere – 13 to 15 thousand steps a day! We had incredible restaurants, coffee shops, bakeries, and gelaterias all nearby. Our hotel was not fancy but it was interesting. It’s a 14th-century renaissance palace that became a maze in the first couple of days. The rooms were small and simple, decorated with antique furnishing. It included breakfast (I don’t ever eat breakfast so I don’t really care for this) but Grace surely enjoyed her daily chocolate croissant. Florence became our home for 6 days from which we explored some of the best sights in the region.
On the days that we didn’t have tours planned, we just explored the city. We watched the sunset from Ponte Vecchio one night after an amazing dinner at the White Boar. We went to see Michelangelo’s David at the Uffizi gallery (did you know this is Goliath’s David? I didn’t!). It is a good idea to buy the tickets in advance to avoid the long lines. We shopped until we dropped because they have amazing fashion at great prices. We ate ridiculously good Florentine T-bone steak. We had dinner three times at the same restaurant facing the Santa Maria Novella plaza because everything there is soooo good, especially the eggplant parm and their grilled chicken. We ate gelato. We drank local wine. We ate local meats and cheeses. It was absolutely fantastic and I am so glad this was the hub of choice. Florence made Garce consider studying abroad… that’s how fun this place is.
I chose the company “Ciao, Florence” for our organized tours. I am very impressed with how well organized and affordable these tours are, but even more impressed about how much they pack in a day (sometimes too much). The tour hub was only 10 minutes from our hotel, but on the first day, we took a taxi since we hadn’t learned our way yet. Interestingly enough, it took longer via taxi than walking because of the one-way streets. There’s a lot of driving around to get to a particular point, so from that moment on we decided we would walk everywhere.
We used Ciao, Florence for three-day trips:
I cannot say which one was better, because everything was absolutely breathtaking. However, one thing I wish is that we could have spent more time in each place.
Tuscany, especially Siena and San Giminiano, was stunning, and after learning that they are both easily accessible by train and bus transfers, I would travel with less luggage and do an overnight at one of them. There is so much to see and learn that a 45 min stop is just not enough, but at least we got to see a lot in one day. This tour started at 7 am and finished at 8 pm, so it is a very long day full of excitement but also a lot of traveling. This area was about 2 hours from Florence and took us on a loop around different little towns, and it included a wine tasting experience in Chianti. This day was Grace’s 18th birthday so we took advantage of the beautiful scenery for a birthday photoshoot.
Some people are brave enough to rent a car and drive themselves everywhere, but I am a chicken when it comes to driving in foreign places (even inside the US), so these day trips solved that problem for me. If you don’t mind the “follow the leader and stick to a schedule” type of day, then definitely consider this company!
I am still dreaming of this place. Cinque Terre (Five Villages) is one of the most beautiful places my eyes have ever seen. This was also a long, long day, and it included buses, trains, and a boat ride to get to four of the five villages. Again, now that I know of the reliability of the train system, I would come here without a tour and spend all day in just one of the villages. They all look similar, but each one has its own charm. This part of the Italian riviera is simply stunning.
The tour took us to the main train station called La Spezia, and from there we took another train (the one that connects all the villages) to Manarola, the first village. It’s literally one street with a few restaurants. Pretty, but I would skip it.
The next stop by train was Monterroso. Now, this was stunning. This is where I would come and spend the entire day. You can rent a beach umbrella for the day, shop, eat lunch and then go back to Florence without the hustle of a tour. The train that connects the villages runs every 15 min or so, and you pay only one train fare and can hop from village to village.
Next, they took us to Vernazza by boat. This is the town that inspired the Disney movie “Luca” and it’s as beautiful as you would expect. We were not allowed too much time here so spent our time taking a few photos and then sitting down for a glass of wine and focaccia bread pizza. And since there’s no rush service here, well… we spent all of our time here.
From here we took another train to Riomaggiore, the final village. This is the most instagrammable village of all. At this point, Grace was so tired that she decided to go to a restaurant, order a drink and wait for me while I went to see the spot everyone talked about. Just wow. I am so glad I talked myself into walking uphill for this after the long day of walking we had.
This day tour is definitely not suitable for people with mobility issues. There is so much walking, steps, stairs, on and off from trains, buses, and boat, that it would be really taxing on legs and knees. But if you can manage it, it’s a tour that cannot be missed.
The final day tour of our Florence adventures was also a long day but riding a gondola in Venice was on my bucket list. The touristy “must see areas” that you find on Instagram are all walkable from the port where the water taxi drops you off. This tour was $98 a person and it was basically just transportation to and from, there’s no really a “tour” as you are on your own for about 4 hours to walk the city. With the tour company, you don’t have to worry about the logistics because they take care of everything – the bus ride to and from Florence and the water taxi from the bus station to Venice. I know now that when I come back I will certainly plan an overnight stay. I really want to see it at night! I will take the train from whatever city I am in, arrive at the Venezia Santa Lucia station, and from there walk to the water taxis (called vaporettos) at Piazzale Roma and pay about $10 to get to Venice and even other islands like Murano or Lido.
Part 2 of our vacation included a 5-night stay in Santorini. We took a train directly from Florence to the Rome airport (about 2.5 hours) to board our flight to Greece. We used a local airline, Aegean, which I can compare to Spirit airlines. All of our flights with them were delayed between 40 min to an hour, and on our way from Greece back to Italy they lost our luggage (we got them 3 days later, on the day we returned home). It was a decent airline, and the flights are so short that we didn’t care much for comfort. Both ways have a layover in Athens, so that made the day a little longer, and the transfer required going thru security again. No big deal, it’s just an FYI that with a short connection you have to hustle (and risk not getting your luggage, that’s what happened to us).
There are so many options to stay in Santorini, from $3,000 a night resort to $100 AirB&B without views. I did a lot of research and read a lot of reviews, and still it was hard to choose what was perfect for us. We knew we wanted to stay in Oia because that’s where the action is. The blue domes, the shopping and the best caldera views are there. We stayed at Olympic Villas, a hotel located 10 min walk from Oia. While it was not the most luxurious stay (this trip was planned before I became an amateur/expert at points and miles) it had everything we needed and more!
We wanted the “cave experience” because we wanted that Santorini view every day, and we compromised on this one. Caves tend to be small anyways because they are literally holes dug on the mountain, but it checked all the boxes: a comfy queen-size bed with a tiny bathroom, A/C, a tiny kitchenette with a coffee maker, utensils, mini-fridge, and electric stove, a stunning porch facing the caldera where we had at least one homecooked meal a day, a refreshing pool, and the most incredible sunset views.
There is a convenience store 3-min walk from the hotel that opens from 8 am to 11 pm, where you can get anything you need, drinks, fresh produce, cheese, eggs, meats, snacks, ice, and even souvenirs. I loved going there daily to get some local wine for our sunset watch, as well as fresh greek sausages and cheese, to make for breakfast.
One reason why you need a hotel with a pool is that the beaches in Santorini are far from Oia, they are rocky (unless you go to the other side of the island which is far), and the water is cold. During our walks at night, we heard so many people complain that they didn’t have a pool and it was really hot during the day (it truly was!). Our Santorini days were filled with laying in the sun, walks at Sunset Blvd (the main shopping area in Oia), and delicious greek food (moussakas were to die for).
Most restaurants that face the sunset require a reservation. It’s hard to get a place to sit anywhere near a good view without it, therefore we chose to go for early dinners (and one night we took our food home) and we watch the sunset from our hotel. Downtown gets so crowded for sunset – we saw 3 or 4 cruises dock a day, and rivers of tourists heading to the Sophia Castle to wait for it, while we walked the other way to the comfort of our private VIP section. That’s what made this hotel so special.
We couldn’t do Santorini without a photoshoot 🙂
Warning: do not wear high heels in Santorini, or get too drunk that you may stumble. This is not the place for either one. It can be extremely dangerous as the steps do not have railings and the paths are all made of uneven cobblestone. Also, no matter what hotel you choose, book the transfer with the hotel with enough time. Our hotel hires the same drivers all the time and they trust them enough to give them your room key if your check-in is after hours. We got to Santorini at 2 am, and our driver was there with cold water, sanitizing wipes, and mints for the road. The fare was $40 each, each way, but they know exactly where to go and how to get to the hotel since most of the entrances do not face the street but the caldera and they are hard to find! Plus, they take all of your luggage from the car to your room. Again, the paths are narrow, uneven, and dark – so let them guide you!
This part of our vacation was the relaxing part. We got to do a whole lot of nothing while watching sunsets and taking in the views. One thing we knew we had to do was a catamaran sunset trip. It was SO WORTH it, despite the rough seas and the motion sickness Grace suffered towards the end.
There are many sunset cruises available but we chose Santorini Day Tour. This was a 5-hour tour with a fresh-cooked meal and unlimited Greek white wine. They took us around the calderas, some people went swimming (too cold for me!) and it closed the tour with a spectacular sunset from the boat.
Our flight home was out of Rome, so we went back there for the last three nights of our vacation. We had all kinds of plans for those three days, including a visit to Vatican City, but Grace was “toured-out” and begged me to cancel. Well, now I have to go back to Italy to see the Vatican City 🙂
Two of the last three days we went for a beach day. The gorgeus Mediterranean Sea was accesible via train from Rome. We went to Santa Marinella, which was a scenic 45-min ride for $5 each way. To rent the umbrella and chairs was only $20 for the day. It was so easy find our way around that we were excited to repeat the adventure. The beaches look like the movies: rows of umbrellas and chairs, everything so clean and organized, no loud music, and lots of families just enjoying their summer.
This was one of the most “intricate” itineraries I’ve put together by myself. Boats, trains, cars, planes, gondolas and buses were part of this adventure. We stayed at 4 different hotels. We ate a many, many, many restaurants. We drank a lot of wine. And the memories we made will always make us smile and remember the love we share.
Oh, and it wouldn’t be me if I didn’t take advantage of a long layover in Switzerland to go out and explore the old town! Swiss chocolate, schnitzel for lunch, and some cute photos 🙂
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