Our 11-day Greece Adventure

How We Did It Series

This is the start of a new series where we share the details behind our travel itineraries, including how we covered costs related to accommodations and airfare. We realize that your experience may vary, based on availability of credit card points and airline miles, but our intent is to show what is possible.

There are two days each year that I purposely plan our adventures around. The first is our anniversary in April and the other is Stephanie’s birthday in August. In each case I try to select something new or unique for us.

This year I chose Greece, a country she has never been to before. And specifically Athens and Santorini, two places that most would consider bucket list worthy.

Getting There

For our flight to Athens, we booked business class on American Airlines in January (8 months before our trip), which had us fly Chicago to London, then London to Athens in British Airways. Total cost per person: 57,000 miles + $23.10! This, along with our AA Platinum status, assured us that we could check our 3 bags (we are not #TeamCarryon) for no additional cost.

One of the benefits of flying international business class on AA is access to the Flagship Lounge, which is a bit more upscale than their “regular” lounge. We enjoyed our time there, as our flight didn’t leave until after 11pm that day.

The flights themselves were uneventful, with all of the bells and whistles of business class that encourage a restful journey with top-notch service. Our only surprise was the BA Business Class between London and Athens. They repurposed an all-coach seating plane by blocking the middle seat out. Still, it was nice to have the extra room.

Our Athens Accommodations

We were really torn between a hotel stay or Airbnb, but with the options that centered in the Plaka area (the historic part of Athens) and unobstructed view of the Acropolis, we opted for a highly-rated Airbnb. The accommodations were right off the main street from shopping and restaurants, with a view of the Acropolis that was beautiful during the day but just gorgeous at night. We highly recommend Cris’ place. The cost for our 4d/3nt stay was $714, for which we made a 50% deposit in April and set aside money towards the final payment in July.

Our itinerary called for 4 days, 3 nights in Athens. As with all our adventures, we know we can always return, so there was no need to pack our calendars to the hilt. After a nice breakfast around the corner from our stay, we joined our group walking tour of the Acropolis, Parthenon, and Acropolis Museum. About 4hrs long, it was the best way to experience the historical center of Athens with an experienced guide. This was a Viator package, at a cost of $109 per person.

Afterwards, we returned to our Airbnb for a nap before heading out to dinner.

The next day, we decided to take a food tour- something we’ve added to our Must Do list as it is a fun and exciting way to experience the culinary highlights (or, lowlights) of a city.

We visited about 8 different locations and enjoyed so much food and wine, it was nice that they cautioned us to come with an empty stomach! This too was a Viator package, for $87 per person and included over 15 tastings during the 1/2 walking tour.

Our last day in Athens was spent just relaxing, as by this point we had pretty good bearing for getting around and so it was a mixture of shopping, eating, and talking about how much we looked forward to returning.

Our dinner that evening was a special treat for us, dining at Electra Roof Garden, just a short walk from our stay. The food was incredibly presented and very good, but the view really made our last evening in Athens one to remember.

Getting there: Santorini

The next morning, we had another leisurely breakfast before leaving for Santorini. Now, there are a few options to travel between Athens and the Greek Islands: ferry, high-speed catamaran, and plane. With even the fastest ferry taking 5hrs we chose to fly. We chose to fly on Volotea, purchasing one-way tickets for the 45m flight in their premium class (including 2 carryon bags and 3 checked luggage) was $206 for 2 people, purchased via Chase so that we could use our Chase Ultimate Rewards towards that expense. A few days before our departure, we added Express Pass, which allowed us to go through the Fast Lane at the airport - saving a considerable amount of time.

Where to Stay in Santorini

When people hear of or see pictures of Santorini, most are not aware of the fact that the island is relatively large and has much more to it than the pictures of what is likely of just one area, Oia (pronounced ‘E-ya’). The most photographed area, it is known for it’s picturesque views and architecture, particularly the blue-domed buildings. It is also the most expense area on the island, which is saying alot!

Our intention in deciding where to stay was to prioritize having high-end accommodations with a front-row view of the caldera. Because we don’t travel light, and intended to change clothes at least 2x a day (evening dinners), having enough space for a 5-day stay without climbing over each other (unless we want to!) was also important. Finally, close proximity to a variety of restaurants and shopping.

There are 100s of choices in accommodations across the island, and many offer views of either the sea (the east side of the island) or the caldera. Price points didn’t vary much, but were all what you would expect for a highly prized holiday spot. We considered a hotel, but felt that the room sizes didn’t give us the space we needed. Airbnb’s offered similar views (and in some cases, better views), more options in terms of layout and space, and were priced similarly or less than many of the hotels we considered.

As is normally the case, an exhaustive amount of time was spent researching Airbnbs, eventually paring it down to 25, the 5, then just a couple. At this point, we needed to decide between staying in Oia, Fira, or Imerovigli. Oia wasn’t a strong consideration because of just how busy it gets, and we didn’t feel the higher costs in accommodations and meals were justified. We then looked at Fira, but were quickly turned away because it is the main port for the cruise ships, making a stay in Oia look much better in comparison. But what really pulled our interest was right in the middle, Imerovigli. It had the best of both - the views of the caldera, a multitude of restaurants, shopping, and relatively less expensive accommodations.

Our Stay: WeSense Cave Villa, Imerovigli

In choosing WeSense Cave Villa, we really had the best of everything. Our host helped to arrange transportation to and from the airport, as well as a porter to manage our luggage (important note: getting to/from the cave villas is not for the faint of heart! In our case, it was 80 stairs. We made friends with a couple whose journey was 206 stairs!).

Our place was at the bottom of the developed area, which means our views were unobstructed (read: no tourist taking pictures) and included a heated pool, 1 1/2 baths, a micro-kitchen, lounge area, and king sized bed. We could not have been happier. The cost for our 6d/5nt stay was $4,019, which we reserved in January with a 50% downpayment and set aside money towards the final payment in July.

We Can’t Help Ourselves: The Fira to Oia Hike

For those of you subscribed across our various social channels and watch our YouTube videos, you know we have a penchant for ruining a very relaxing holiday with a long walk or hike! This adventure was no different, choosing a day to tackle the hike around the caldera coastline. Initially, we considered taking the bus from Imerovigli to Fira to start our hike, but opted instead to break it into 2 days.

The first day, we walked south (I say walk, because the path is paved) from Imerovigli to Fira. This is considered the easier of the two, as you are on a pedestrian path with plenty of cafes and restaurants along the way. It took about 45 minutes, and we rewarded ourselves with a nice lunch of a shared club sandwich overlooking the water and people watching (as the cruise ships had been ferrying people all day).

The following day, we geared up and decided to tackle the more arduous hike from Imerovigli to Oia. They advise you to start early in the morning, as we are in the summer season and it is abnormally hot. We started a bit later, but made sure to bring several bottles of water, as there is only 1 cafe along what is typically a 2-3hr journey.

First, the views are incredible. To your left, you get to witness the granduer of the island itself and the caldera the entire way. Frequently, we would just stop to behold how far we had come and smile at the accomplishment.

When we reached Oia, we were definitely not looking our best, dusty and sweaty, but we found a nice little restaurant willing to overlook this and we enjoyed a great lunch while congratulating ourselves on this accomplishment.

Rather than walk back, we decided to take the bus from Oia back to Fira (approximately $2 EUR ea), and then from Fira to Imerovigli. But, being gluttons for punishment, we instead enjoyed a bit of ice cream before deciding instead to walk to to Imerovigli. So, we actually did the complete walk in one day!

Santorini Wine Adventure

On Stephanie’s birthday, I arranged a small group wine adventure through Viator, which included visits to 3 wineries, seemingly all the tapas we could eat, and ending with a sunset view at Gaia, the most established winery & restaurant on the island. The cost for this tour package was $178 per person.

We made new friends, with whom we decided to extend the evening before calling it a “night” about 1am. There was laughter, sharing of stories, and a souvenir that we will refrain from discussing until the statute of limitations has expired!

The next day, we just relaxed in our Villa, enjoying the pool, talking about how much we missed our kids and grandkids, but also just the joy of having so much time together. More than any other adventure, this truly felt like an 11-day date.

For our last meals, we decided to go back to Dear Elie, a favorite of ours on the island, for tapas and to watch the sunset. It confirmed to us that, for the convenience and relative tranquility, Imerovigli beats Oia and Fira, hands-down. After a celebratory toast and promise to return, we then went to Mama Lena for a shared meal that ended with a delicious baklava.

Our Return Home

We’ve found that purchasing one-way tickets is a good way to manage your air travel against your budget, making decisions based on availability of miles and points and strategizing as to the best time to do so. We ultimately chose to book Volotea via Chase Travel, for a cost of $160 for two people, for which we also used Chase Ultimate Rewards.

After a relaxed stay in the SkyLounge (available to us because of our Business Class tickets, but we also could have used our American Express Platinum card benefit), we boarded the first of two return flights. We used American Express Membership Rewards to book on Iberia, Athens to Madrid, with an overnight layover, followed by our flight from Madrid to Chicago. The cost was 72,000 miles + $209 per person.

For our overnight stay, we chose Hilton Madrid Airport, as we have Diamond status.

We had an issue with the airport shuttle, which may have contributed to their upgrading us to their largest suite and ultimately covering the cost of our room against the $56 credit we had on our account.

Final Thoughts

Our out-of-pocket costs for airfare and accommodations was approximately $5,100, which calculates out to ~$250pp per day for a very nice, 9d/8nt holiday in arguably two of most sought-after Greece holiday destinations. It took a considerable amount of discipline to hone our credit card spend to accumulate miles and points, research every aspect of our adventure, and budget accordingly for our meals and entertainment.

One of the questions we were asked, when sharing our intention to stay in Santorini for 6d/5nts was “why?” And this both puzzled and tickled us. Firstly, we are big believers in the idea that, as God continues to bless us, there is no place on earth that we won’t have the chance to visit multiple times, should we wish to. So there’s no reason to feel we have to see everything. Secondly, the idea of island-hopping was too exhausting. This was a celebration of Stephanie’s 29th(?!) birthday; if she wants to spend the time luxuriating in Santorini, who am I to say otherwise? As it happened we met several couples whose Santorini stays were longer than ours, and also had no intention of visiting other islands on this holiday. So, to each their own, but don’t ever feel you have to go with the herd when it comes to planning your own adventures!

As the inaugural post to our new web home and introduction to our newsletter, we hope this hasn’t been too exhaustive of a sharing of our adventure. We really appreciate that you’ve read this far, and hope that it inspires your own adventures.

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Chris & Stephanie