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  • Writer's pictureRay Cheselka



For anyone that loves to travel, Rome and the Amalfi Coast are probably on your list. Great food, a warmer climate, mountains, volcanos, history...Italy has it all. You would probably need a full month in Italy to cover the whole country, so our strategy has been to do it by region.

Another hot spot, Santorini, absolutely wowed us. It's on our minds frequently. A tiny island with different color beaches, surrounded by dark blue water and a volcano caldera. It's a place you can truly relax.

Our trip was planned for 4, we went with some family-Jordan and Frank. To accommodate a different number of people, just consider the size of Airbnb’s/hotels when choosing. Outside of our NYC hotel, both of the Airbnb's were suitable for 6 people.

We saved for a year ahead of this trip and established a budget. We like to spend a good portion of that money on food and drinks-which will probably be evident throughout this post. Restaurants and excursions can be substituted if you’d like to make the trip more cost-effective.

Let's go!


Day 1/2: Travel to New York City, then to Rome. Drive to Amalfi Coast

Day 3: Amalfi Coast

Day 4: Positano + Capri

Day 5: Path of the Gods Hike + Driving and stopping periodically along the coast

Day 6: Drive to Rome, fly to Santorini. Settle in

Day 7: Rent 4 wheelers and drive to all of the different colored sand beaches + around the island

Day 8: Hiking + Oia

Day 9: Wineries + Breweries, riding to the highest point on the island

Day 10: Fly to Rome. Explore Rome + Vatican City. Fly to Newark. Stay in Newark

Day 11: Explore NYC. Fly home



There really isn't anything more exciting than knowing you're about to go abroad for a bit.

You're going to be seeing a lot of new things, you're off work, life is good.

A long day of travel is exhausting and can seem daunting, but make the most of it! We flew from Denver to NYC, and then to Rome overnight. We flew Norwegian Airlines. The food was really good and they give you a lot, along with free drinks. Once we landed in Rome, we headed down toward the Amalfi Coast in our rental car.

Pro Tip: Be sure to allow adequate time for car rentals in Europe as they tend to take a bit longer than what we're used to in the states It ended up taking us longer than expected which resulted in us checking into our Airbnb late, and the host was frustrated.

On the way, we stopped at a rest area. We were greeted by a happy Italian man who served us "champagne" and pizza. The champagne was actually coca-cola haha...The pizza was really good!

We ended up getting to the Airbnb (in Praiano) later than expected so it was already dark, but it was part of a small complex that was literally sitting on the side of the Amalfi coast. The driveway down was steep and narrow. It was a relief to arrive, and we could hear the water crashing on the rocks right below us, breathing in the fresh Amalfi Air.

We popped a bottle of champagne and listened to the coast below us, discussing what we'd do tomorrow. We were all exhausted, and shortly after went to bed, excited for the view we would wake up to.


After a great sleep, we woke up and were in awe of the view off of our back patio. Absolutely incredible.

We also found that there was a path that takes you down to the water where you can sit on the rocks and listen to the waves crash.

The day couldn't have started any better. We were officially on vacation.

We decided to drive along the coast, and stop in a little harbor town to grab some lunch. We ended up at SAVO in Atrani. Really good. At the table we had: lemon risotto, bolognese, gnocchi, and a margherita pizza. A very satisfying start.

While driving around, Ray ran through a traffic circle and the polizia instantly knew we were tourists haha. Sometimes it's hard to not be a tourist, and driving in Amalfi is one of those cases.

We drove through Atrani, Ravello, Amalfi, and found a town that sat inside/on a small beach surrounded by rocky cliffs. There was a restaurant called Il Pirata where we got Aperol Spritz with a view of the coast.

Then we stopped at a ceramic store (ceramic is all over the Amalfi coast), where we had espresso while shopping, picked up some gifts, and a guy named Mario checked us out. Really great. It was so cool that you could be shopping in a lot of places and they would have bars for coffee or fun drinks in the shops.

We took a breather and hung out at the Airbnb down on the water for a bit, having a couple of drinks and great conversations.

We capped off the night by going to Che Bonta for dinner in town. It sits in a really cool, small stairway alley and has a great vibe. Really good people, the servers were so nice and provided great service. The pizza there was amazing, we ended up getting it again later on in the trip because it was that good. We did some pistachio shots and drank wine on the patio until we felt like walking home.

Incredible first day in Italy!


Right outside of our Airbnb, there was a bus stop. They are all along the coast. You can buy tickets (SITA) at local stores, cafes, convenience stores, and train stops. They're fairly inexpensive and easy to find.

We took the bus to Positano, where we bought ferry tickets to go to Capri (about $100 roundtrip for 4 of us).

This ferry ride was about 45 minutes across the sea (If you're prone to seasickness bring medication). The boat ride was absolutely beautiful, spectacular views!

We ate at the strip of restaurants on the harbor, a place called Caffe Augosto. They're all crammed next to each other and there are lots of workers trying to reel you in. In true Italian fashion, you sit at small tables overflowing with food. We got lemon spaghetti, carbonara, and seafood pasta.

For any carbonara lovers-carbonara in Italy is different than in the US. Don't expect what you'd get at a restaurant in the US.

We rented scooters for around 30 euros and covered as much ground as we could. The folks we rented the scooters from were just up the stairs from the strip of restaurants, heading uphill. The people were funny and nice, and gave us a good deal. We made our way up through Anacapri, to the Mesola Fort. This route takes you through really cool villages and neighborhoods. Riding around Capri was so much fun. The island and its views beyond it are incredible. Be sure to keep track of time, because ferries back to Positano are limited and on a tight schedule.

Arriving in Positano, we took some pictures and walked around the town, eventually eating and drinking well at La Tre Sorelle (which means "The Three Sisters" in Italian). It's right on the boardwalk behind the main beach. Be aware that sometimes restaurants close for a couple of hours in between lunch and dinner. We ate at an odd time, but the servers were really nice about it and encouraged us to stay. We had pizza, gnocchi, calamari, a meat and cheese board, 2 or 3 bottles of wine, and some espresso. Needless to say, our bellies were full.

After our meal we walked around the town, took some photos on the beachfront, shopped, and enjoyed taking in the quaint Italian culture. We hiked up the hills of the town to a bus stop and went back to the Airbnb for a nightcap and some rest.



We woke up late and drove to the top of the Amalfi coast to hike the Path of the Gods.

At the start of the path there was a small cafe (Bar Naclerio Giuseppe). At this point we were getting used to having our daily doses of espresso. It's just natural there. The guy that ran the cafe was one of the nicest people we came across. The small town up there was clearly tight-knit, and you could feel the sense of community.

We probably hiked for a few miles in total, and the views were beautiful. It felt great to get some exercise and get a view of the coast from above.

Afterward, we went into town to get some food. We came across L'Angolo dei Sapori, where we had a phenomenal meal. They served pitchers of wine grown behind the restaurant for 10 euros. We ate arancini, unique local styles of pasta, and fresh seafood pasta. The food in Italy was living up to the hype.

After lunch, we drove along the coast for a while to the beach town of Maiori. We just enjoyed cruising along the coast with the windows down, seeing each town.

After a long day, we came back to the Airbnb to enjoy a final sunset down by the water and on our patio. Frank and I went to grab some wine and pizza, Che Bonta again! Then we drank, relaxed, and prepared to go to Santorini early the next morning!


As sad as we were to leave Amalfi, we were unbelievably excited to get to Santorini. The weather was supposed to be a little bit warmer, and we would have 4 full days there.

We left really early to make sure we'd get to Rome with plenty of time for more international travel. It was really clear when we left and the stars were some of the best we'd ever seen. As we drove through the towns they were all silent. We made our way off of the coast and the sunrise started. We could see a silhouette of Mt. Vesuvius in Naples, and then we made our way up to Rome. At one point, we had to get gas. We had no idea how the gas pumps worked. There was a guy at the gas station who happily helped. We dealt with some terrible traffic but made it to the airport with some time to spare.

Rome airport is really nice. We had some good food and got on a really clean Vueling airplane to head to Santorini. We flew west, and then south, passing the islands of Corse and Sardegna. Then we took a turn southeast over the heel of Italy's boot. Before we knew it we were crossing the Ionian and Mediterranean sea, heading into the Aegean Sea, and descending upon Santorini.

As you descend you fly over numerous islands, some so tiny they're uninhabited. Then, you end up landing on the backside of Santorini island to one of the smallest airports you'll ever be in.

When we were there, they were beginning construction on the airport to be able to be more accommodating. We got our bags, and were picked up by "Cristof". It was a really nice Mercedes sprinter, and you could feel the joy and enthusiasm Cristof had about being on Santorini island. He gave us some great history and tips, and after a short 10-minute drive we were pulling into a little roundabout to head to our Airbnb.

At this point, you could see the cliffside, and excitement was peaking. We were welcomed by a local woman, Vanda. She gave us a tour of our place and described each part of the island to us before wishing us a good trip and heading out. Vanda was the cutest little Greek woman, absolutely wonderful!

We all got unpacked and were stoked about this place. It was a Cycladic home, so very traditional white, Greek, and cave-like. It felt like a spa. Then you go up some stairs, and we had a private patio overlooking the caldera. We picked up some wine from a local shop (Iama) nearby and headed back up to our rooftop to sip and enjoy the views.

We didn't think the day could get much better, but then we went to 1500 B.C. Resto Wine Bar. WOW. Do yourself a favor and eat here. George was our server and I don't think we've ever had better service. He told us how he dreamed of going to New York City and was thankful for our business.

We found this to be a theme across the island. We heard of how the island has a busy season, and that's really when everyone on the island makes all of their money for the year. With the recent economic hardships in Greece, things have been tough on locals.

We shared a couple of bottles of wine, and ate fresh seafood. Maddie and I shared Red grouper (catch of the day) with veggies. He carved the fish tableside and poured a lemon olive oil mixture over it. Then Jordan and Frank got Salmon squid ink pasta. It was our most expensive meal of the trip, but well worth it.

After a long day, it was time for some rest.


Santorini is small, the entire island is about 11 miles long. The best way to get around is by 4 wheeler. You can rent one for $30-$40 per day. You can negotiate. We drove around the island and saw black (Perissa), red (Akrotiri), and white (Kambia) sand beaches.

At one point we were at the tip of the island (opposite of Oia), and we got souvlaki from a food truck. The vendor was giving a stray dog hot dogs, and another local was making and selling jewelry in front of a lighthouse. The souvlaki was good-it's basically a pita with french fries, bbq sauce and chicken in it. We also had a local Greek Beer. We drank alpha beer, and Mythos throughout the trip.

We brought a backpack with wine and some plastic cups, and at the black sand beach we sat in the sun drinking wine, looking at the island of Anafi in the distance, and truly relaxing.

We got home-rested and cleaned up. Then we walked along the cliffs to the main part of Thira, and got some dinner at Zafora. We could see the caldera with the moonlight shining on it, and overlooking the white houses on the cliffs of Thira. There are a lot of restaurant options to choose from in Thira.

We ordered seafood pasta, saganaki, and lamb shanks. After dinner we got gelato and shopped. Maddie and Jordan bought handmade purses. We also got a drink at a little dive bar, and truly felt like one of the locals.

We hung out for a bit, and then headed home for the night. What a day!


Maddie and I woke up early and did a 6-mile hike (took us about 3 hours) along the rim of the island that leads to Oia. We got to walk through a lot of towns, and see the different vibe of each area. We hope to visit again someday and stay in one of these areas. We also got a chance to see the backside of the island where more of the locals live. It's more of spaced out houses and countryside. The hike was a great workout, the views were out of this world, and we worked up an appetite.

​In Oia we ate at Mezzo and had a few drinks before Frank and Jordan came into town. The restaurant had a beautiful view, so we just sat, ate, drank and enjoyed for a bit.

Then we all walked around the town and its little alleyways. Oia was a bit more touristy but had a lot of culture and charm. We shopped around and eventually grabbed some food and drinks at a rooftop bar Pelekanos. It seemed like pretty much everywhere in Santorini had a 10/10 view. It was so soothing.

From there we took a nice long 4 wheeler ride back to our Airbnb, cleaned up, and grabbed a low-key dinner nearby.


For our last day in Santorini, we decided to ride around to wineries. We went on our way towards Kamari to see a new part of the island. It seemed less populated, there were vineyards all over, and you could see Anafi in the distance. The view of that island in the distance is a surreal thing to see.

We ended up stopping at the only brewery in Santorini, Santorini Brewing Company. Great beer, and really cheap to get a tour and then sit outside for a drink. They have some weird law where you have to sit outside and can't drink on the premises.

After our tour and beers, we continued onto Kamari to check it out really quickly, and then started venturing up a cool looking road. We stumbled upon this hidden winery that was made of smooth stone, very modern, and a friendly puppy greeted us. This particular winery was a bit pricey and you needed to make reservations, so we headed on to the next one. It would be cool to do if you planned ahead! It was called Volcanic Slopes.

We rode up to the highest point on the island and soaked up some views. On our way up we drove through some really cool towns looking over the Perissa side of the island. We came back down and stopped at Santo Winery. This place is set at a high point overlooking the caldera, and the views are simply incredible. They have big tastings with cheese platters, olives, and more. We did a 10 wine tasting, everything from Santorini's white wine Assyrtico to dessert wine, Vin santo. It was so relaxing to sit in the shade, drink, and spend time together.

We grabbed a bottle of wine, and sat on the patio until it was time to pack up. Tomorrow was going to be a long travel day.


We got up around 3 am to get to the airport and fly to Rome (da Vinci airport). Upon arrival, we got our boarding passes back to the USA and paid to put our bags into a luggage storage facility they have at the airport. Verify the hours before you go and have your passport ready. Then we went into Rome on the Da Vinci train that is connected to the terminal. You can buy tickets on your phone or at a kiosk there.

Now it's time to explore Rome! We built a route from the train station that enabled us to visit the Colosseum, the Venetian Plaza, the Trevi fountain, the pantheon, and the Vatican city. If you make a route with key landmarks, you'll stumble upon a lot of cool history.

Along the way, we also stopped in some shops, got some fun gifts, drank espresso, and more. Walking through Rome was like walking through a history book, really really cool. All of the streets are picturesque, unique wooden doors on everyone's homes, and the streets outside of the main ones were relatively quiet where we were.

It was hot and we were pushing it going to the Vatican City, but that place is insane! St. Peter's square and that area is just so vast and unique. A must visit. It has a special aura about it.

Pro Tip: It can be tough to find a bathroom in Rome if you're not eating/drinking coffee somewhere! Something to keep in mind.

At the end of it all, we had time to eat some fresh shaved truffle pasta in the Termini train station before heading on the train back to the airport. They have a food hall in there with a lot of options. Before we knew it we were on the flight back to Newark. With the time change, we got in late that night, and went straight to our hotel to sleep.


With flights in the late afternoon and Frank having never been to NYC, we wanted to explore. We walked around central park, and got Lil Frankies. We had Spaghetti Limone, a Chicken Parm sandwich, Ragu, and some champagne. From there we shopped, saw times square, and one world trade center with the memorials.

Then it was onto the airport, and we were headed for home. What a trip!


List of things to get ahead of the trip:

  • Multiple flights to book/manage

    • Your hometown to NYC (or another hub)​ Estimate: $300

    • NYC to Rome Estimate: $200

    • Rome to Santorini Estimate: $40

    • Santorini to Rome Estimate: $40

    • Rome to NYC (or another hub) $200

    • NYC (or another hub) to your hometown $300

    • Estimated total: $1080 in flights per person

  • Get Euros. There are plenty of places that won’t take cards, especially if it’s a small purchase

  • Hotels/Airbnb’s

    • None Needed for Rome

    • Amalfi (Estimate: $1050)

      • Airbnb​

    • Santorini (Estimate: $1750)-Santoniro Villa

      • Airbnb​

    • NYC (Estimate: $235)-Element Harrison-Newark

      • Staying downtown would be better, but we wanted to be close to the airport flying in so late​ and heading out from there the next day

    • Estimated Total: $3,035

  • Rental Car:

    • What a pain to get a rental car. Hertz Rome Airport-terrible experience. Pay extra to bypass the counter.​

    • We decided to get a rental instead of taking trains or busses, because we considered going down to Calabria, and wanted to drive all over the Amalfi coast. A train would probably be more inexpensive, but you wouldn't have the control

    • If you get a rental, make sure it has insurance. Driving in Italy, Amalfi especially-is insane. We went through Auto Europe and I don't think they even billed us the copay for a scrape I got (thank you! haha)

    • Estimated Total: $300

  • Save some money. We saved estimating we'd spend around $200 per day of the trip. If you have the money ahead of the trip, it really gives you peace of mind. You can do everything you want to, and know that it's essentially paid for.

    • Estimated Total: $​2,000

  • TOTAL ESTIMATED TRIP COST PER PERSON: $2,914 per person (that includes everything)

Some things to pack:

  • Passport

  • International Drivers Permit (some rental car companies require it. It's inexpensive, easy to get.

  • Rain jacket

  • A range of clothes light/warm-weather can change quickly with the mountains/coast

  • A blend of hiking/casual/dressy clothes

  • Reusable water bottle

  • Backpack (we have REI flash 22 pack)

  • Euros/Credit card with no international fees + ATM capabilities

  • Emergen-c (take care of your immune system ahead of and on travel days!)

  • Airplane headphones so you don’t have to buy them

  • Sunglasses

  • Sunblock

  • Hat(s)

  • Neck pillow

Some things to check:

  • Cell service-ours was pretty good throughout both countries. T-Mobile and Verizon. You can just look up if you have international service or if you’ll need a plan. A lot of times you can also pay as you go.

  • Credit card for international ideally with no fees, also notify your cards about travel ahead of time so you don't get flagged

  • Good areas/bad areas of the areas you'll be staying in + visiting

  • How to tip: A lot of times a tip/service fee is included so keep an eye out for that. You can (and should) leave an additional 5-10% if you're happy with the service.

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