Background: My partner, Amy, & I decided a while back that we wanted to spend parts of our summers abroad, as a way to relieve the itch I had been scratching to immerse myself in another country. We decided on Greece because my niece was getting married in Santorini and took advantage of the destination wedding to extend the trip. We ultimately felt like 22 days in Greece was just enough to 1) still be financially responsible, 2) fulfill this desire and 3) test out the idea of working remotely abroad for part of the trip. We also decided we wanted to spend at least 3 days on each island, if not 4, and settled on 5 locations across the 22 days (Athens and 4 islands in the Cyclades).

Our travel tradition is to always bring along a “Lonely Planet Guide” for that country

Cost & Travel Miles:  Fortunately, the majority of our trip was paid for through miles that we had accrued over the last 2 years. Two years ago, I got the coveted Chase Sapphire Reserve card, which had a generous 100,000 point sign-up bonus (worth $1,500 in travel), if you spent $4,000 in the first 3 months (the bonus has since decreased to 50,000 points). I continued to accrue miles throughout this time period, which eventually added up to a total $3,500 in miles.

Amy & I also each had Capital One Venture cards, with about $1,000 worth of miles, for a total of $4,500 that we could apply towards our travels. The total cost of the 22-day trip, including gas, car/quad rental, all flights and ferries (but not including food which we did a poor job of tracking) was $8,300. When we used our travel miles, our total out of pocket costs ended up being $3,800 (or $1,900 per person), which was a little higher than we had hoped to pay, but still pretty impressive a the grand scheme of a 22-day trip across the Atlantic. (If you have questions about travel credit cards, I have lots of thoughts, so feel free to reach out!)

Pre-Travel Prep: To fly from the US to Greece (for less than 90 days), a Visa is not required, which is great, but important to note is that, like much of Europe, travel to Greece requires that your passport be valid for at least three months beyond the intended date of departure. We had a family member get turned away at the airport because her passport expired 2 months from the departure date, which was incredibly heartbreaking for everyone. These requirements apply to both U.S. Citizens and Permanent Residents.

Walking to the Temple of Apollo on the island of Naxos

Packing & Clothing: Amy and I each packed a suitcase full of clothes & shoes that qualified as our “checked bag.” I also packed an additional carry-on with things I couldn’t fit into my suitcase, which given our extensive travel itinerary (hopping from island to island, ferry to ferry, and flight to flight), I immediately regretted. I recommend bringing one checked bag and a small personal item (such as a large purse or backpack). We experienced pretty high temperatures (90 degrees Farenheit +) and weather so our clothing type wasn’t location-specific. Given the heat, flowing dresses, loose-fitting shirts and tops and comfortable shoes were the ones that we ended up wearing the most. As soon as you step outdoors in any part of the country, during the month of July, you can expect to immediately start sweating, so you want to pack comfortably for this. Nights were also warm, but more comfortable. Everywhere we stayed throughout the trip had AC (which I highly recommend looking out for when booking stay).

I had also packed a ton for the wedding, with more heels than I needed (I never wore any of them) and more sandals & formal dresses than were necessary. Your best bet would be to bring along some comfortable Birkenstocks, cute flat sandals for dressy days and nights, and a pair of comfortable sneakers. Sunglasses, a hat or two and plenty of sunblock are must-haves.

Stoa of Attalos in Athens

Exchange Rate & Credit Card Usage: The exchange rate for dollars to euros was pretty stable throughout our trip, hovering around 0.84. I found that despite Greece’s struggling economy and years of recession, because we were traveling during the height of peak season, we didn’t necessarily get the bargain we expected to get and costs were pretty similar to the US. This definitely varied from island to island (Naxos being pretty inexpensive & Santorini being the most expensive), but it all balanced out throughout the trip. I recommend setting a food/spending budget for the trip. Otherwise, things add up pretty quickly and it’s easy not to notice what could end up being a huge expense. Visa credit cards are widely accepted everywhere, so as long as you give your bank a heads up about your travels, you shouldn’t have any issues.

Our itinerary was as follows: Boston -> Athens -> Crete ->Santorini-> Naxos-> Paros-> Athens-> Boston

Athens

The Parthenon in the Acropolis in Athens

Transportation: Travel to Athens from Boston was pretty smooth and the customs process was painless. When we arrived at the airport, there was an incredibly long line to catch a taxi to where we were staying in Artemida (a village outside of Athens where the international airport is located), but despite the 100+ people ahead of us, it moved pretty quickly and we were in a cab in about 10 minutes. From the airport in Artemida, we paid about 60€ to get to Athina (most taxis are metered so the this is pretty average for the distance traveled).

Stay: We spent 3 nights in an Airbnb conveniently-located in the heart of the city, walking distance to most major sites. The Airbnb was upgraded, with all of the modern amenities. A few customs we picked up immediately were 1) put your toilet paper in the trash can and not the toilet 2) only turn the water heater on 20 minutes prior to showering and then turn it off after showering and 3) buy water at the convenience store/market rather than at the restaurants – you will save some € with this one. With the convenience of our place, which had restaurants on every corner, we settled into Athens pretty quickly. Jetlag was a problem at the start of the trip: on the first night we fell asleep around 7pm and woke up at 2am, craving a burger and went hunting for takeout in the wee hours of the morning. It took about a week for our sleep patterns to return to normal.

The Temple of Zeus in Athens

Things to do & sites to see: Here we saw the Acropolis, The Roman Agora, The National Park, The Temple of Zeus, Hadrian’s Arch, while walking around the many markets (Plaka, Monastiraki) along the way. The Acropolis, which houses the Parthenon and is Athen’s most popular site, has a very long ticket line. We were lucky to have been approached by a tour guide who had admission tickets available (20€ each), and was selling a guided tour (30€ each) for a total of 50€ per person. We jumped on the opportunity (and highly recommend a guided tour) and had a fantastic experience. We later learned that we should have purchased an admission ticket for (30€) that would give us access to all of the major historical sites in Greece. We ended up having to pay 5-7€ for each additional site we visited (about 4 more) and quickly shared the lesson with our family making their way to Athens.

Food: The food in Athens was generally pretty good. We were immediately hooked on the Greek salads, which were always refreshing in the hot Athenian sun, and were some of the best we had during the entire trip. The cost of food in Athens was relatively high and adds up pretty quickly when you include breakfast in the mix. If you can stay at a place that provides breakfast, this will help the budget. Street food is also a great (and pretty safe) way to get a taste of authentic Greek food without spending very much.

Crete

Spilia Village Villa in Crete

Transportation: From Athens, we flew to Crete (340€ for 2 tickets). We had heard and read amazing things about it and decided to give it a go even though it was off the path from the rest of our itinerary. We flew on one of those small local airlines where you pay 35€ per checked bag, with very strict weight limits.

Stay: For 5 nights, we stayed at a romantic and private villa in a tiny village of Spilia, in the northern region of Chania, which is known for its old Venetian port and divine seafood. The village was a little more remote than we expected, but we decided to take advantage of the peace & quiet (minus the millions of locusts chirping about) while there. The villa had a private pool, and all the amenities one would need, including complimentary breakfast.

Our private pool in Spilia Village

Things to do & sites to see: Given how big the island of Crete is, how far apart sites are, and the fact that the port we needed to get to for our next leg of the trip was 2 hrs away (in the region of Heraklion), we rented a car for part of our stay here. We realized that driving in Greece was slightly different than in the US: it is customary to pass cars, motor scooters, etc. in the oncoming cars lane, which can be a little dangerous. Our adventures in Crete included driving to the beach town of Falassarna, which was beautiful but with not much else to do but lounge. We also drove to Greece’s renowned Elafonisi Beach, which is known for its pink sand and crystal clear waters. To get to Elafonisi, which was 1.5 hours south of where we were staying, we woke up pretty early and made the trek through winding mountain roads (some paved, some not). We even traveled through a tunnel in the mountain that had a man manually operating a red light.

Port Town of Hania in Crete

Needless to say, this was my least favorite part of the trip. We did our best to navigate the less than ideal route, dodging large tour buses and stopping in areas where roads were too narrow for 2 cars to get through (or where I didn’t like Amy’s fast, nonchalant driving). We arrived around 10am, avoiding the flood of tourists that came in later in the afternoon, but the abnormal winds & cloudy sky made the experience pretty anti-climatic. After a couple of hours of waiting for the sun to come out, we decided to head to the port city of Hania, about 2 hours north of Elafonisi. The port was scenic, filled with restaurants & shops selling everything one can imagine.

An amazing seafood dish in Crete

Food: The food is Crete was delicious & fresh across the board. In Spilia Village, we found a wonderful restaurant overlooking the local port, where we got a plate of every type of fresh seafood they had caught that day, and some delicious grilled tuna, topped off with a nice, Cretan rose wine and the most mouth-watering, raspberry cheesecake we’ve ever had. The local wine throughout the trip did not disappoint.

Santorini

Transportation: We took a ferry from the Heraklion, Crete to Santorini. Because it was peak season on Greece’s most popular island, when we arrived at Santorini’s main port, it felt like pure chaos. Once you get off the boat, you immediately get shuffled around, with car shuttles & taxi folks asking you where you want to go and demanding an answer. When we paid our 40€ (for 2 tickets, which seemed pretty standard for the island) to get from the port to the hotel we were staying, the ticketing counter guy points to a sea of people, and says “follow my brother.”

Channeling my inner Greek goddess

We managed to follow the right person who put us in a large van cab and off we went, packed in a van like a bunch of sardines.

Stay: As I mentioned earlier, the impetus for this trip was that my niece and her fiance were getting married in Santorini. We made it to this leg of the trip and joined the family for several days worth of celebrations. For 4 nights, we stayed at a beautiful hotel in the mountains of Santorini, a 2-minute walk from the wedding hotel venue, where most of the guests were staying. Our hotel was (more) reasonably priced, and had a pool overlooking the ocean and mountains. You couldn’t have dreamed of a better view from anywhere you looked. Breakfast was included in the stay and while the food wasn’t anything memorable, wedding excitement overshadowed all else and we couldn’t complain.

Munching on sweet corn in Oia, Santorini

Things to do & sites to see: Most of our days and evenings were spent doing wedding things/hanging with family at the Rocabella Hotel, but we did manage to fit in two excursions. First, we ventured to Oia (the town at the northernmost point of the island where all postcard pictures are taken). A group of us tried to walk there from the hotel, but the sun beat down on us, and the dirt road was a bit daunting with two kids with us. After walking for over an hour, with over an hour to go, we decided to catch a bus, which took us the rest of the way for 1.5€ per person. Oia was as beautiful as you imagine it would be, but crowded. Couple huge crowds of tourists with the hot sun, and it’s very easy to expend all of your energy (and patience) in a given afternoon. The second excursion entailed a big group of us renting ATVs to do some sightseeing. We headed to Santorini’s black beach, which is lined with hip restaurants and shady umbrellas. Amy and I then decided to drive around with the ATV (along the shoreline) for a while and met up with the group in Oia to watch the sunset. We took the long route back to our hotel to avoid the tour buses and the mountainous roads as much as possible.

Our lovely bride & groom

The wedding itself was out of this world, right out of a storybook. The entire family took photoshoots, posing like professional models every chance we got, and with the background of the most memorable sunset over the endless ocean. We danced the night away, shared memories and best wishes for the couple, laughed and cried in the company of those closest to our hearts.

Food: Overall the food in Santorini was decent, but costs were higher on this island compared to any others we visited. At first we were mindful and then eventually threw our hands up and said “F**** it” (I don’t recommend the latter approach).

Naxos

Transportation: We took a short, 2-hour ferry from Santorini to Naxos. The ferry rides were pretty comfortable, smooth and safe. Because of how many people smoke in the country (and in Europe in general), we chose to sacrifice the ocean views and settle indoors during these rides.

A stunning view from the mountaintop in Naxos

Stay: For 4 nights, we stayed at a cute, centrally located hotel in Naxos, in the town of Naxos, which had a pool and included breakfast. We got upgraded to a “superior garden room” which meant a view of corn-stocks and a few tomato plants, which we just had to laugh about. The hotel was a short, 6-minute walk to the port of Naxos, which, like every Greek port, is lined with a ton of good restaurants and shops.

Things to do & sites to see: On our first full day, we decided to walk to the Port and then to the Temple of Apollo (a 20-minute walk from our hotel). The view from the hill where the temple was located was mesmerizing. There was a breeze throughout the day that provided a nice break from the unrelenting sun.

ATV riding in Naxos

We also decided to rent an ATV for 2 days so that we could explore as much of Naxos possible. We were told that the inner part of the island didn’t have well-paved roads and that we should stay along the west coast of the island. We drove up and down the shoreline and checked out a few of the beaches, which were all pristine and warm to touch. The only downside about beaches here is that you have to pay for your umbrella/chair which can range from 5-25€ per set of 2.

Food: We had one of our favorite meals of the trip in Naxos. I had a whole fried fish drizzled in lemon and olive oil, and Amy had grilled prawns with fresh sautéed vegetables. The owner’s dad was a little old man who walked around making sure everyone was content. The decor couldn’t have been more romantic and we treated ourselves to a lovely bottle of rose.

Paros

Transportation: Paros was a very short, 30-minute ferry ride from Naxos.

Stay: From the port of Paros, we caught a cab to our Airbnb in the port town of Naoussa. The apartment sat atop a hill, overlooking the ocean, a couple hundred feet from our kitchen. If Santorini didn’t have its views, Paros would have been my favorite part of the trip, hands-down. The Airbnb was as wonderful as it gets, with a fully furnished living and dining room, and a patio with magical views of the mountains and ocean. The only downside was that the wifi connection was pretty abysmal at both the Airbnb and throughout the entire island. The silver lining is that this helped us unplug, which is always good for the soul.

Our airbnb balcony in Paros

Things to do & sites to see: At this point, we were obsessed with renting ATVs for exploring because 1) they are relatively cheap to rent (30-40€ per day), and 2) they gave us the flexibility to see and do a lot more than would have been able to otherwise. We spent a full day driving around the entire island, visiting the port towns of Aliki, Piso Livadi and stopping by the island’s famous Golden Beach. A couple of minutes into our first day’s drive, we found a tiny, beach tucked into a corner of the island, which had very few tourists and crystal clear, warm water, and decided to stay awhile. The views along the island were breathtaking, not to mention the roads were paved, and I felt incredibly safe in and around the mountains. On one beautiful, sunny day, we took an all-day boat trip with Captain Ben, which was filled with both lazy lounging and jumping off the boat into the deep turquoise, blue ocean across all parts of Paros and along nearby Antiparos.

On Captain Ben’s Boat Tour in Paros

Including snacks, lunch, alcoholic & non-alcoholic drinks, this boat trip cost us 150€ for two tickets. We also spent a great deal of time exploring the port of Naoussa, walking around and stopping to snack. The majority of the remainder of our stay, we spent in our Airbnb, reading and playing card games, soaking in the serenity of the place as much as possible (and saving money). At this point, we had begun throwing around the idea of investing in a home in Paros in the future – to give you an idea of how much we loved it.

Food: The food in Paros was very good. We ate a lot of gyros from a tiny little cantina and thought they were the best we had yet. We also continued to live by Greek salads. We ate delightful, grilled octopus & even tried out some local pizza. Every meal was appetizing.

Walking around Naoussa in Paros

From Paros, we took a flight from the town of Parikia to Athens, where we stayed in a traditional Greek home (Airbnb) close to Athens International airport. Our host was the sweetest woman we had encountered: she picked us up from the airport, picked up and delivered dinner to us in our rooms, provided a lovely homemade breakfast, and dropped us off at the airport for our flight home to Boston.

Working Remotely: We have our jobs to thank for, for allowing us to be abroad for such an extended period of time: Amy works in the public school system and was able to take the entire time off during her summer break. I work at a startup in Back Bay and am fortunate enough to have a CEO who believes in workplace flexibility and allowed me to work remotely for part of the trip.

For a little over a week of our trip, I worked remotely (the remainder of the trip, I was “on vacation” and tried my best to be unplugged).

Wedding sunset in Santorini

Given the time difference (Greece is 7 hours ahead of Boston), this proved to be challenging but not impossible. On days that I was working, Amy and I would get all of our excursions done during the mornings and afternoons, and head back to where we were staying around 3pm/4pm, at which point it was 8am/9am in Boston and I could be in sync with the rest of my team. We used Slack, Zoom & email for most of our communications and, other than in Paros, didn’t have any trouble with reliable internet. I’d then work until about 12am/1am, which meant that I wasn’t always well rested during those days, but I managed well and felt it was definitely worth the compromise.

All in all, we had a memorable, once in a lifetime kind of experience, and glad we were able to do it at a pretty reasonable cost. We learned a lot along the way and are eager to apply it to our next extended trip abroad, where ever that should be! Hopefully, this was helpful to you as you plan your own Greek adventure!