10 Days in Greece: Itinerary for an amazing anniversary trip

From honeymooners to old marrieds like me, the Greek Islands have long been a bucket list destination for couples. When we started to think about dream destinations to celebrate our 20th anniversary and my 50th birthday, Greece kept floating to the top of the list. While it took an extra year to make that trip a reality, our 10 days in Greece ended up being everything we had possibly hoped for and more.

So for those of you who kept threatening on “steal my itinerary” and do the exact same trip — have at it! I’ve put together our complete 10 day Greece itinerary just for you. Obviously this trip was geared toward couples that are looking to splurge on a bucket list trip, but check this out if you are wondering how much a family trip to Greece costs.

Couple kissing in front of two blue domed churches in Oia Santorini
Photo by Nikola from Flytographer in Santorini

10 Days in Greece Itinerary

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We only had nine nights to spend on our trip to Greece, and we wanted to take time to relax and enjoy the experience, versus being on the go, all the time. To get the most out of the trip, we decided to split our time over two different islands.

The romantic images of Santorini that you see all over Instagram, with those quintessential blue-domed roofs and the white stucco Cycladic architecture, beckoned us and we simply had to spend some time on Santorini. Of course, I’ve heard how over tourism is a problem in Santorini, and the crowds and high prices meant I didn’t want to spend too long there.

To balance out the crowds of Santorini, we decided to spend the bulk of our time on nearby Naxos, the largest of the Cyclades islands, which is known to be quieter and less visited by American tourists. Plus, it is much more affordable!

We had planned on flying in and out of the island and finishing out our visit with one quick night on Mykonos (knowing that the expensive party atmosphere wasn’t our cup of tea). However, our Swiss Air flights that were connecting through Zurich were cancelled and we didn’t want to risk transiting through another European country with changing entrance protocols, so we decided to fly in and out of Athens on Delta, which meant we needed to spend our final night on the mainland in Athens.

Keep reading for our full 10 days in Greece itinerary!

Two blue domes churches and blue water in Oia Santorini

3 Days in Santorini

When I was posting about my trip on Instagram, one of the questions I received was how long to spend in Santorini. My feeling is to spend at least two nights, or three if it is your first day in Greece. But in reality, it is however long you can afford. 🙂

Day One

We flew overnight into Athens and then had a three-hour layover before our short flight to Santorini, getting us to the island around 2:30 pm. You can also take a ferry from Athens to Santorini, but it is long and the departure times didn’t align well with our arrival so it made more sense to fly, to avoid spending a night in Athens as a layover. If we had more time, I would have spent the first two days in Athens and taken some more time to explore and tour the Pantheon and the other historic sites of the Acropolis.

Whether you arrive at the port or the airport, I’d recommend pre-arranging your transfer to the hotel so you don’t get stuck waiting in long taxi lines. While our hotel was happy to arrange a VIP transfer, we decided to save a little money and used Welcome Pickups instead. We were able to book online and every transfer we arranged worked perfectly, with friendly drivers, clean cars, and some amenities like cold water. I would definitely use them again!

Private plunge pool for the honeymoon suite at the Canaves Oia Epitome
Private plunge pool at the Canaves Oia Epitome

For our three nights in Santorini, I booked a honeymoon suite with a private plunge pool at the luxury hotel Canaves Oia Epitome. You can read my full Canaves Oia Epitome hotel review on my sister site YourTimetoFly. This was certainly a huge splurge for this milestone trip, but it was such a wonderful luxury experience that I don’t regret a penny.

The Canaves Oia Epitome is part of the luxury brand of Canaves Oia properties, and is the newest of its hotels. Located right outside of the popular town of Oia, the hotel offers gorgeous sunset views from each luxury villa. We loved the location, the service, the room, the food, the pool…seriously, we loved it all.

After a quick nap on our comfy sun beds by our private plunge pool, we dressed for dinner at Elements, the Canaves Oia Epitome’s fine dining restaurant. We enjoyed stunning sunset views while indulging in a seven-course degustation menu that will long be remembered as one of our top all-time dining experiences.

sunset and table at Elements Santorini
Dinner at Elements

Day Two

On our first full day in Santorini, we decided to explore the gorgeous town of Oia. Just a 10-minute walk (or short hotel shuttle ride) away, we were advised to get an early start to get to experience town before the crowds of day trippers arrived. Luckily, the visitors in 2021 are just a fraction of 2019 numbers, so we had until noon before the streets started getting even a little crowded.

When exploring town, make sure to get off the main pedestrian street and poke into the small alleys and wander through the streets that overlook the caldera. If you get hot or hungry, stop in for a cold drink at Terpsi n Oia, which has a rooftop terrace with incredible views.

After we finally worked up an appetite after our decadent meal the night before, we enjoyed another rooftop meal at the gorgeous Oia Gefsis. It was here that I realized I was going to really enjoy dining in Greece. We had considered lunch in the courtyard of nearby Roka or Karma, but I think we made an excellent choice for food and views combined.

Windmill in Oia

Full from lunch, we headed over toward the castle ruins, where people gather to watch the sunset. It is also a great photo spot looking across the buildings built into the cliffs and the few remaining windmills in town. This is a great spot to explore with gorgeous Insta-worthy views.

By afternoon the heat of the summer afternoon set in and it was time to return to Canaves Oia Epitome for some time at the pool. That evening, we headed back to town for another degustation dinner at Lycabettus.

We had reserved a cliffside table for dinner with an unforgettable view. While this may be one of the more unique dining experiences in Oia, the food and service didn’t compare to our previous night at Elements. If you want to enjoy the view, I’d suggest booking a standard table on the terrace and order from the menu a la carte.

Oia town at night

Day Three

Our third day started early, with a photoshoot with Nikola from Flytographer. Nikola did an excellent job finding scenic photo spots, suggesting poses, and capturing our joy in a memorable set of anniversary photos. If you have never tried Flytographer for a vacation shoot, I’d recommend checking it out. We have also used them in Marrakech and it is so wonderful to get professional photos to capture the special memories you make on vacation.

Couple sitting with woman leaning her head on the man's shoulder
Photo by Nikola from Flytographer in Santorini

After our photo shoot, we had time for an outfit change and a delicious breakfast at the hotel before being picked up for our half-day wine tour with Santorini Wine Trails. Over the next four hours, our guide Iliana gave us an education about Santorini wine and agriculture. Despite the challenging growing conditions, there are over 20 small wineries on Santorini, primarily focused on the Assyrtiko grape, with vineyards up to 3,500 years old, as the island wasn’t heavily impacted by the phylloxera that destroyed so many of Europe’s vines.

Our first stop was in a vineyard where we observed the unique “basket” growing method that protects the grapes from the heat and wind. We then proceeded to visit three distinctly different wineries. Our first was at Gavalas in the town of Megalochori. We tried a few wines, including their version of Santorini’s famous Vinsanto, which is entirely different than the Vinsanto you find in Tuscany. The favorite wine here was the Santorini, plus the delicious Santorini tomato paste and Naxos cheese which was served with the wine tasting.

Couple holding wine glasses at wine tasting in Gavalas winery
Wine tasting at Gavalas

The second stop was at Gaia, which is located right on the beach on the east side of the island, in an industrial building that was once used for producing tomato paste and sun-dried tomatoes. Gaia offers such a relaxing and beautiful setting for wine tasting. The final stop on our wine tour was at Domaine Sigalas, which is closer to Oia. With a outdoor tasting area adjacent to the vineyard, this is a popular spot for tourists and they served a beautiful charcuterie board to accompany our tasting.

Octopus hanging under Ammoudi Fish Tavern sign

Full on wine and good food, we returned to the hotel with time to relax at our pool once again. That evening, we walked down to Ammoudi Bay for dinner at the Ammoudi Fish Tavern on the water. The entire bay is a line of fresh fish restaurants next to the docks where the sunset catamarans depart. We considered doing one of these as it is one of the top things to do in Santorini, but we didn’t want to deal with the crowd and I’d already booked a private boat tour in Naxos.

5 Days in Naxos

We were sad to say goodbye to Santorini but it was time to move on to Naxos via ferry.

SeaJet WorldChampion Jet ferry

Day Four

We booked a ferry from Santorini to Naxos, as it is only about an hour and a half boat ride. The ride from Oia to the ferry port takes about 45 minutes, and is a bit of a hair-raising ride if you don’t like heights or cliffside driving, or you get motion sick on the switch backs like me. Another option would be to fly from island to island.

I talked about our ferry experience on a recent episode of the Vacation Mavens podcast, but here are a few things to keep in mind:

  • There are many different ferry options when traveling between the Greek Islands. You can use FerryHopper to check rates and schedules for the various ferry lines and book tickets online.
  • If you haven’t checked in online and received a mobile boarding pass, stop into the ferry office to print your boarding passes.
  • If you are traveling in 2021, make sure you complete the health form in advance of boarding. If you aren’t vaccinated, you will need to present a negative test result.
  • Note that the SeaJet World Champion Jet ferry to Naxos is a large boat that also stops at Ios first and then other islands after Naxos so it will be a large crowd herding onto the boat together.

On arrival in Naxos, we were picked up by Naxos Luxury Transport for the 15 minute (and 20 euro) ride to our hotel in Agios Prokopios. Our hotel, Virtu Suites, is a newly opened, luxury boutique hotel located right on one of Naxos’ most beautiful beaches. You can read my full Virtu Suites review over on YourTimetoFly, but suffice it to say that it was a perfect choice for what we were looking for.

Virtu Suites pool

This contemporary hotel utilizes gorgeous bohemian and coastal style, while incorporating classic Cycladic architecture. The use of beach-inspired materials like rope, stone, and driftwood are beautifully incorporated into the room design and outdoor restaurant and bar. While there was a small pool right outside of the door of our Seaview Suite, we opted to spend most of our downtime on the beach, which was right across the street, and the hotel offered padded sun loungers and rope umbrellas, with prime seating reserved for guests.

We spent our first afternoon enjoying the beach and a sunset dinner at the hotel restaurant before taking a short stroll through town.

Two wine glasses on table at Virtu Suites restaurant

Day Five

Our first full day in Naxos started with a room service breakfast (included in our stay) before heading out early to meet Captain George of sailing yacht Annabella for a day on the water with Naxos Sailing. I had booked a full day private sailing to Antiparos and Paros, as I thought it would be a fun way to get out on the water, while also getting a chance to explore a neighboring island without having to deal with ferry schedules.

Man snorkeling off Antiparos

As we sailed out of Naxos, some dolphins made a quick appearance as we headed toward some small islets off Antiparos. After some time spent snorkeling, we headed over to the mainland of Paros to snorkel into a sea cave. The next stop was in the small village of Piso Livadi on Paros. We had the option of enjoying the town or beach here but we decided to take a cab to the main village of Naoussa.

Naoussa street

I totally fell in love with this village and it made me want to return and stay on Paros if we get a chance to go back to Greece. After that we sailed back to Naxos Town, and Glenn and I even took turns piloting the boat. It was a lovely day that reminded me a lot of the day we spent boating around Capri.

Tamara, Glenn and Captain George in front of Naxos Sailing yacht Annabella

After a long day at sea, we opted to have dinner near our hotel at Spiros. This family-run taverna offers traditional Greek and Naxian dishes served in the typical huge portions. Seriously, don’t over order! But even if you do, a meal here won’t cost you much (like 40 euros for an appetizer, two entrees, and two drinks!)

Day Six

The next day was definitely one of our favorites of the trip, as we embarked on a full day Cheese, Food, Wine and Island Tour with Eleni from Philema Food Tours. I can’t recommend this tour highly enough (or any tour with Philema Food Tours for that matter) if you really want to understand more about Naxian food, wine, and local culture.

cheese wheels on a shelf

Our first stop was at a family farm of cheesemakers. After meeting the goats whose milk we would be soon turning into cheese, we stepped inside the farm kitchen to a feast of homemade Naxian specialties. Pro tip: don’t eat breakfast if you are taking this tour! We then got hands on and had a chance to help make one of Naxos’ most famous cheeses. This was such a fun experience it was almost hard to say goodbye to continue our tour.

The next stop was in a small village with only seven full-time residents, and a potter whose family has been creating pottery for generations. We explored the town’s olive oil press, watched a pottery demonstration, and browsed through his shop.

Pottery vases and cups

The tour wrapped around the island, winding through the mountains and stopping at a few scenic overlooks for photos. A highlight was a stop in the charming village of Chalki. Most well-known for the Kitron distillery, this town is also a great spot to see artisans in action.

For lunch, we stopped in the village of Apeiranthos. The white streets of this beautiful village are lined with local marble, making it a beautiful place to wander and get lost in the labyrinth of small streets.

We had a delicious lunch at Amorginos Restaurant, where we got to sample two famous dishes in this village — a veal with eggplant, tomato sauce, and cheese baked and topped with yogurt, and roasto. Roasto is pork thigh aged for two months and stuffed with garlic, pepper, and cooked in tomato sauce. While I’m not usually a huge pork fan (unless it is bacon or pancetta), this dish was delicious! If you see it in on a menu be sure to try it!

Man walking up steps in town of Apeiranthos
Walking through Apeiranthos

The final stop on our tour was at a vineyard. While Naxos has the most vineyards and vines that go back for millennia, it is not known for its wine making. In fact, most of the wine on Naxos combines all sorts of grapes and ferments them together, producing a very strong house wine. But one winemaker is looking to change that by producing a more refined wine using traditional grapes from Naxos.

Wine tasting bottles

A vineyard tour and tasting was the perfect way to end our tour with Philema Food Tours. That evening we enjoyed another simple, but delicious meal nearby in Agios Prokopios at Giannoulis.

Day Seven

Agios Prokopios beach with Paros in the distance

After a busy few days, we wanted to take a day to just relax and enjoy the beautiful beach at Agios Prokopios. In the evening, we headed into Naxos Town to try out Oinohoros, the wine bar owned by the winemaker we met on our tour the day before. While many people choose to have sunset drinks at a rooftop bar in town, we enjoyed this small wine bar tucked into a side street and focused on small lot Greek wines.

Oinohoros wine bar in Naxos

We then walked over to the Portara, or Apollo’s Temple, for sunset. Of course we arrived too late to get an ideal spot but it wasn’t so crowded that we couldn’t still get a decent view. Dinner that evening was in the romantic courtyard at Doukato, just a short walk from the Temple. The food was just ok but the setting was nice. For something more lively, check out Apostolis in Old Town.

Apollo temple at sunset

Day Eight

Tamara standing on balcony overlooking Apollo temple

We took our last full day in Naxos to explore Chora, or Naxos Town. After getting lost a few times in the labyrinth of the Old Market the night before, we wanted to explore this area and the castle ruins by the light of day. After a few hours of walking around, we had a quick coffee on the rooftop terrace at the 520 Cocktail Bar & Restaurant, which was much more mellow during the day than it was the night before.

Naxos town from Apollo Temple with path across water at sunset

Our meandering also took us over to St. George’s Beach and wrapped back around to the port area before catching a cab back to the hotel. After taking some time to relax on the beach, we headed back to town that evening for a fine dining meal at Barozzi. One of the more upscale restaurants in Naxos, we had a lovely meal and excellent service in a beautiful outdoor dining space.

Day Nine

Beach chairs on Agios Prokopios beach

On our final day in Naxos, I had arranged a fast ferry to Athens. Everything I’d heard about the ferries in Greece led me to believe that I didn’t want to risk taking a ferry to Athens and then heading right to the airport so we booked one night in Athens before flying home. Flying is also an option but the flight times weren’t lining up with our flight back to the USA either so we decided to stick to the ferry. It is a good thing we gave ourselves this extra time because our ferry left about two hours late due to winds slowing them down.

But since we had an afternoon ferry, we were able to enjoy a last morning at the beach before heading into town to catch our ferry. On the way, our driver checked an app to see the status of our ferry and found out it was running 45 minutes late (it ended up being much later), so we walked over to Pikantiko Grill House right in the port for an excellent and inexpensive meal of chicken souvlaki.

1 Day in Athens

After standing around forever, our ferry finally arrived, but unfortunately it got us into Athens too late to visit the Acropolis as I had planned. However, our friendly driver from Welcome Pickups drove us by the Olympic Stadium and told us about the Changing of the Guard, in front of the Parliament building, which we ended up watching from our hotel balcony.

View of Acropolis from Hotel Grand Bretagne

To finish out our trip, we used Marriott points to book a room at the Hotel Grand Bretagne. This luxury collection hotel has a great location, but its special feature is the rooftop restaurant, which has amazing views of the Acropolis. I had booked dinner at the rooftop restaurant, and we also enjoyed the views the next morning with our complimentary breakfast as well.

This trip was so amazing that we weren’t prepared to say goodbye to Greece. After dinner we took our last few hours to walk around the bustling Plaka neighborhood near the hotel and decided that we must return some day soon.

Day Ten

Couple kissing in doorway
Photo by Nikola from Flytographer in Santorini

Sadly, it was eventually time to leave Greece with our hearts full and so many happy memories. The nearly 11-hour flight back to JFK, followed by a three plus hour drive home to Rhode Island was not fun, but it was worth it for our dream trip to Greece.

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10 Days in Greece itinerary

Feature photo by Nikola from Flytographer in Santorini.

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Publish Date: July 28, 2021

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