What to Do in Greece: Two-Week Island Hopping Edition

I cannot even put into words how beautiful the Greek Islands are. From the food to the white and pastel buildings to the glistening, unbelievable blue water, you’re sure to be in love. In this post, I will share everything you need to know to plan the perfect Greece island hopping itinerary! You’ll get tips for where to stay, how to get there, the best places to go (including a map with locations), and a done-for-you two week itinerary including Santorini, Milos, Zakynthos, and Athens. Let’s jump in!

TABLE OF CONTENTS

• The Basics for Planning Your Trip
  • How to Get to the Greek Islands
  • Tips for Flying with Points + Miles
  • When to Visit
  • How Long to Stay
  • Getting Around
• Things to Do and See
  • Santorini
  • Milos
  • Zakynthos
  • Athens
• Itinerary

The Basics for Planning Your Trip to Greece

It’s probably not a question of if you WANT to visit the Greek islands but whether or not you are up for sorting through all the logistics of bouncing around to multiple places. I’m here to help make all of that seamless for you because you absolutely have to experience this incredible place!

How to Get to The Cyclades

The Cyclades are a group of Greek islands in the Aegean Sea, southeast of the mainland and home to two of the islands that I will cover in this post: Santorini and Milos. If you’re visiting from the US, you have two options. You can fly into Athens then take the ferry to the islands, or you can fly and layover in Europe before hopping on a connecting flight to the islands.

The price for the two options will likely be similar if you visit in high season. Ferries aren’t always cheaper, especially if you take the express ferry which I would recommend. The slower (and cheaper) ferry typically takes at least double the time to get to your destination. I would recommend looking into both options and picking the one that fits your budget and time schedule best!

You can easily book your ferry on the FerryHopper app ahead of time. If you’re looking to fly, Aegean and Olympic Air typically have flights to and from Athens.

I personally flew into London then flew to Santorini from there! I’ll explain my rationale for that in the section below!

Tips for Flying with Points + Miles

As always, I like to minimize costs when traveling by leveraging points and miles! I earn these points with my favorite travel credit card. The points hold the most value when transferred to partners instead of booking straight through the Chase portal. I typically will search for reward flights within the list of Chase’s travel partners then transfer the points to cover the flight once I find the deal that I’m after.

For this trip, Virgin Atlantic had flights from New York to London for 10K points which is a steal. I booked a “positioning flight” from Birmingham to New York with Southwest with points, and I used my companion pass for by husband to fly with me for the cost of fees ($5.60). On the way home, we flew from Athens to Boston with AirFrance. At the time of booking, Chase was offering a 25% bonus when transferring points to FlyingBlue which is the rewards program for AirFrance and KLM. We ended up only needing 11.5K points per person on the trip home.

As always, you do still have to pay the fees when booking flights with points, but this is something you would be responsible for when booking with cash also. In total, we paid ~$600 in fees for my husband and I to fly round trip from Alabama to Europe and back. These flights would have easily cost us $3,000 if we were paying in cash, so I’ll call that a win!

When to Visit

Spring: March to May. A great time to visit to avoid crowds and to visit historical sites with mild weather. Temperatures range from 59-68 degrees Fahrenheit. It’s not always a great time for swimming, though, as the water is still very cold. You can also expect some spring showers.

Summer: June to mid-September. This is high season but for good reason. All of the restaurants are open in the islands, it’s warm, and the water is perfect for swimming. Perfect weather also means larger crowds, but after having visited during this time, I’d say it’s worth it!

Fall: mid-September to November. This is considered shoulder season which could be a good time to visit! Restaurants and accommodations typically start to close in October, though, so be mindful of that. September would be a perfect month to visit to enjoy warm weather, swimming, lower costs, and smaller crowds.

Winter: December-February. You can expect winter to be mild and wet. There’s not a lot open in the islands during this time, but you’d be sure to have a serene experience without the hustle of the busy summer season. I do think that a trip to the islands would be best during a time where you could enjoy the beautiful water though!

How Long to Spend in Greece

Once you get there, you won’t want to ever leave, trust me. That’s not an option for most of us unfortunately, so I’ll settle for two dreamy weeks in paradise! You can absolutely visit Greece with less or more time, but two weeks gives you enough time to see a few Islands and to visit Athens which I think is perfect!

I would recommend 3-4 days per island except for Santorini. I believe 2 days is plenty here for someone who doesn’t love crowds.

How to Get Around Greece

When visiting the islands, you’ll want a way to get around easily. There’s so much to see!

Santorini: I recommend staying in Oia so you can walk most places then renting a car for a day to explore other parts of the island. An ATV or motorcycle would be fun as well!

Milos: the island is small, so you can rent an ATV and explore the island! I highly recommend this! It’s so fun and adds to the adventure. If you’re not quite up for an ATV, definitely rent a car!

Zakynthos: I would absolutely get a car here! It’s a much larger island, so it takes longer to get from place to place. As much fun as the ATV was in Milos, I’m not sure I’d be down for a 45 minute drive each day without a car.

Athens: The city is very walkable, and there are trains and busses that can get you from place to place if you’re going a little further. Skip the stress of a rental here!

What to Do in Greece

There are so many great islands to explore throughout Greece, and there’s just no way to see them all. After lots of research deciding which islands to visit, I landed on Santorini, Milos, and Zakynthos! I feel like I was able to experience a great variety of what the Greek Islands have to offer with these three!

Here is a Google Map full of all the best things to do in Greece! I will discuss each of the places in length below. Make sure to save the map for offline use!

What to Do in Santorini

Catch the Famous Sunset in Oia

You can’t visit Santorini without seeing the sunset over Oia. If you’re planning a trip to Greece, you’ve definitely seen the famous photos of the sun casting orange and yellow hues onto the perfectly white buildings on the cliff of Oia. Yes, it’s touristy and crowded. Yes, it’s worth it to add this spot to your Greece itinerary!

If you know me, you know I avoid crowded areas as much as possible. This is why my husband and I spent less time on this island than the others, but if it’s your first time in Greece, I still believe it’s worth visiting Santorini for a short time. It’s famous for a reason!

The place everyone flocks to at sunset is the Oia Castle! It does have the best view over the cliffs of Oia and down into Amoudi Bay. You need to arrive 1-2 hours before sunset in high season to get a spot, though. Otherwise, you may not have a view at all.

I have heard that the Byzantine Castle Ruins (just below the castle and down a side road) is a good and less crowded alternative. Additionally, there are great views from restaurants and hotels in Oia. Either way you go, make sure to arrive early! I promise the show will be worth it!

Explore the Streets of Oia

Get up early for sunrise and walk around Oia! This is the best time of the day to explore the beautiful city without all of the other tourists. Your experience between 7-9AM will be wildly different than any other time of the day. Tour busses and cruise ships begin to show up around 9:30-10AM which leads to large crowds and much less charm.

You can’t drive around the streets of Oia. There is parking just outside the town, and the only way to see everything is on foot.

I’ll list out some places you need to check out while you walk around. These spots are great if you’re looking to take some cool photos! Exact locations are pinned in the Google Map near the top of the post.

• Kastro Oia Houses
• Castle of Oia
• Blue Dome Church
• Charisma Suites Windmill of Oia
• Three Blue Domes Viewpoint

Walk Down to Ammoudi Bay

You can get to Amoudi Bay by walking through Oia. You take a left to get to the castle or a right to walk down the 300 steps to the bay. It’s a steep one, so bring plenty of water! Once you’re at the bottom, there are lots of great restaurants right on the water. We ate dinner at Amoudi Fish Tavern then grabbed a smoothie as a dessert to keep us cool on our walk back up the stairs.

Rent a Car and Explore the Island

There are many other beautiful towns and beaches to explore around the island. To see them, it’s best to get a car or ATV to get around. We rented from Vaezos in Oia for 65 euros/day in high season. They were very kind and accommodating, and even let us leave some cash in the car for gas so that we wouldn’t have to worry with finding a place to refuel. This was nice because we were able to leave the car in their parking lot, located as close to Oia as you can get with a car, then walk over to our hotel in which made things much easier than struggling to find parking each day!

Here’s a list of some places to check out:

• Fira: the capital of Santorini perched on a cliff with whitewashed buildings. This is another busy area that is known for its restaurants and bars.

• Imerovigli: charming village with panoramic views of the caldera. Check out the Church of the Resurrection of the Lord for a stunning view of the blue dome church and an unbelievable backdrop. If you’re looking for a hike, check out Skaros Rock!

• Megalochori: charming little village known for unique architecture and a less touristy vibe. Take a little time to wander around the cobblestone streets.

• Red Beach: known for its red cliffs and clear waters. It’s worth a stop if you have time!

• Perissa Black Sand Beach: one of the most popular beaches in Santorini but for good reason. It is lined with little beach bars and restaurants making it a great lunch stop. Each restaurant rents out beach chairs that you can lounge in for the afternoon.

What to Do in Milos

Milos is one of my very favorite places that I visited, not just in Greece but ever! It has so much unique beauty and more of a locals vibe which I absolutely love. If you want to see some behind the scenes and follow long as I traveled through Milos, check out my IG stories recap!

Visit Sarakiniko Beach

This place is like something from a dream. It is known for its moon-like landscape, cliff jumping, and unbelievably blue water. I would recommend visiting this beach multiple times on your visit to Milos! We went for sunrise, sunset, and mid-day because we just loved it that much!

Sarakiniko on Film

The best time for photos without people in them is sunrise! Sunset is beautiful as well, but there will be a few more people there than at sunrise. The beach is busy mid-day, but this is the best time for cliff jumping and enjoying the sun! Do not miss this spot!

Explore the Town of Plaka

Plaka is the capital of Milos. It’s not like any capital you’d imagine when you hear the word, though. It’s a charming little town nestled on a hill. It has small streets filled with the most delicious restaurants, cute shops, and colorful flowers. We found ourselves returning here often! My favorite restaurants here were Avli (super cute atmosphere and great food) and Mavros Xoiros (casual lunch spot with 8 euro gyro plates).

Rent an ATV + Go Beach Hopping

There are countless beaches to see while in Milos, Greece. I’ll list the ones I visited and loved below!

• Firopotamos: This area is both a fishing harbor and a beach with stunning blue water! It’s worth a stop!

• Klima: This is a seaside village known for its two-story fishermen houses with colorful doors and windows.

• Tsigrado: this beach is so unique. It’s a bit of an adventure to get there. You’ll climb down on two separate ladders and squeeze between rock walls to get down to the beach. It’s small and gets busy mid-morning, but if you go early in the morning, you’ll have it mostly to yourself!

• Fyriplaka: This is a popular stretch of beach just across from Tsigrado. It can get crowded mid-day, but it’s very large, so there’s lots of space to spread out. This spot is great for sun bathing and swimming in calm water. There’s a stand where you can rent kayaks as well.

• Papafragas Caves: This area is a cove surrounded by cliffs and natural caves! There’s a couple of small beaches that you can visit as well as a cool rock arch.

Eat Lunch at Medusa

Yes, eating lunch here is deserving of an entire section in this post! This food is so delicious. There is an incredible view from the restaurant, and the staff is so nice. Will was taking a photo of me, and our waiter asked to join! It’s extremely popular, so I recommend calling to make reservations (especially if you’re looking to eat dinner here). Another option is to arrive and put your name on the list then explore Mandrakia while you wait which is what we did! Try the sun-dried octopus–just trust me. Yum.

Explore Pollonia

Pollonia is a fishing village in north-eastern Milos. It’s dotted with seaside restaurants and beautiful churches. I recommend checking out the Saint Nicholas Holy Orthodox Chapel pictured above!

What to Do in Zakynthos

The island of Zakynthos lies in the Ionian sea around 12 miles west of mainland Greece. You can take a ferry from the Cyclades, but we decided to fly to save time! The views you can experience in Zakynthos are incredible!

Visit the Myzithres Scenic Viewpoint

This place blew me away. It’s one of the most impressive views on the island. It’s located on the southwest coast of the island and boasts an incredible view of the Myzithres emerging from the dreamy blue water.

You can get there by driving up a paved road then continuing to the viewpoint on foot. Please be careful here! There’s nothing stopping you from falling off of the very steep cliff, and it can get pretty windy. Please do not try to stand close to the edge!

Interested in getting down to that beautiful, secluded beach you see hundreds of feet below? Access to the Myzithres beach is by boat only! You can read more about how to get there in the South Island Tour section below!

Go Beach Hopping

Zakynthos is full of beautiful and unique beaches where you can relax, swim, snorkel, and cliff jump into the bluest water you can imagine. Some of my favorites are listed below!

• Porto Limnionas: this is a secluded cove with breathtaking, crystal clear water surrounded by cliffs. You can cliff jump, relax on a sunbed, or snorkel. There’s a restaurant that sits just above the cove and is a perfect spot for lunch! I’d spend much more time here on a return trip!

• Filippoi: After a scenic drive down to the water, you can relax on large rocks or swim to a small beach to the right. Don’t miss this place!

• Plakaki: From the parking lot, you’ll walk a couple hundred yards to the “beach” which is a large rock. You’ll find perfect water and a beautiful place to relax and swim away from the crowds!

• Korakonisi: This is small, rocky penninsula surrounded by blue water perfect for snorkeling. From the parking, you will continue on foot and down a series of stairs carved into the rock.

• Xigia: This is one of the most unique beaches in Zakynthos thanks to the sulfur spring that changes the water to a milky hue.

• Porto Roxa: This is a stretch of stone-filled beach on the western coast of the island. You can find sun loungers and beach taverns scattered throughout. The perfect place to spend the afternoon!

Hire a Boat

North Island Tour:

Hire a boat with a skipper to see the Blue Caves and Navagio Beach (famous shipwreck)! We booked a private tour through Luxury. Our skipper was knowledgable and took us to lots of hidden gems in addition to the famous spots you’ve probably already been admiring.

South Island Tour:

Booking a boat on the south side of the island allows you to see places like the Keri Caves, Marathonisi (turtle island), and Myzithres Beach!

To my surprise, you can rent a boat and captain it all by yourself! If you’re like me and my husband who have minimal boating experience (and definitely not in the ocean), this probably sounds a little scary. For this reason, we ended up booking a skipper for the first couple of hours then took the boat out for ourselves after that. We booked through Big Blue, and they teach you everything you need to know to be safe before you head out. Additionally, there are limits to where you can go as well as “lifeguard” boats essentially to police the traffic and ensure everyone stays safe!

You cannot go inside the Keri Caves without a skipper, so if you’re interested in that, consider doing half and half like we did! It was a lot of fun to captain our own boat and find little secluded beaches to anchor. I would absolutely do both the North and South boat tours again!

Visit Ionian Sunset Cafe

There’s just something about a Greek sunset, and this is an insane place to catch one! The property is owned by the cafe, and it’s a really popular spot. In order to get in, you must make a purchase from the cafe. We bought a smoothie to share and enjoyed the view. Parking can get a little crazy, so get there early to grab a spot!

Visit Navagio Beach and Overlook

Navigio Beach (also known as shipwreck beach) is probably the most photographed area of the island of Zakynthos. There’s a very good chance that you have seen photos of this beach in multiple travel promotions while researching your Greece vacation.

While visiting the beach itself is beautiful, the best view of the beach comes from the overlook hundreds of feet above! Unfortunately, during our visit, the road to the overlook was closed due to wind and fire risk. Here’s a link to a blog post that provides lots of details on how to reach the viewpoint. I have read recently that the side trail is now completely closed for safety, but you can still get a view from the designated viewpoint!

If you’re wondering why the ship is there, apparently it was smuggling cigarettes from Turkey for the Italian mafia, and the crew was forced to ditch the boat in the Navagio Cove while running from the Greek Navy. Crazy right? The ship has been rusting and slowly falling apart ever since.

Check out Nobelos

This is a great spot to spend an evening! The food and atmosphere are great. They offer sunbed rentals, so you can spend as much time as you’d like enjoying the sun then grab dinner at the restaurant just steps away! We didn’t need reservations here although they are welcome. Don’t miss this place!

What to do in Athens

Explore the City on Foot

You can’t visit Greece without a trip to Athens, right? We only had 24 hours in Athens, so we opted to stay in the city near the Acropolis and see as much as we could on foot! You will stumble upon some really pretty places just wandering around. We walked by a farmers market and bought some delicious fruit for example! I’ll list out some can’t miss-stops below.

Must-See Stops in Athens

• Philoppapos Hill Panorama: visit this area for sunrise! It’s a bit of a hike through a park that ends at a rock pile with views of the Parthenon and the city of Athens! It’s not so much of a hike though that you would need to change your shoes as long as you’re wearing something comfortable to walk in!

• Odeon of Herodes Atticus: this is an open air theatre that sits just below the Acropolis and was built between 160AD – 174AD!

• Acropolis & Parthenon: The Parthenon is an ancient religious temple that sits on Acropolis Hill. It’s very touristy and often extremely crowded. We opted to view it from the outside given our very short stay here, but here is a tour you could look into if you’re wanting to get a closer look!

• Ancient Agora of Athens: This is a large area at the center of Athens where political gatherings and juries took place. There is an entrance fee of 10 euros per person, but you’ll get to walk around and see lots of ancient ruins!

• Roman Agora: It was constructed in the 1st century BC funded by Julius Ceasar and Augustus. The agora is an open air courtyard that housed a series of shops and was eventually used as a commercial and administrative center.

• Temple of Olympian Zeus: housed the statue of Zeus which was one of the 7 wonders of the ancient world.

• Arch of Hadrian: a triumphal arch whose location was strategically selected to mark the line between the ancient part of Athens and Hadrian’s new city.

• Areopagus Hill: The Apostle Paul delivered his famous sermon from Acts 17 in the Bible.  Near the base of the stairs is a bronze plaque with the Greek text of Paul’s sermon. At the top, you’ll get a great view of the Acropolis! Go for sunset!

• Plaka: a cute area of Athens dotted with delicious restaurants and close to most sights. It’s a great place to grab lunch or dinner.

• Anafiotika: A small district adjacent to Plaka that is quieter and more picturesque. It’s worth a short stroll around to see it!

Two Weeks in Greece Itinerary

I have linked each activity to the details up higher in the post for convenience! Happy planning!

Day One:

Fly to Europe from the US! Highly recommend a stopover to reset and avoid jet lag. We stopped in London for a day to break up the travel! (There was a great deal on flights to London as I mentioned above!)

Day Two:

Spend a day in stopover location! I’ll share a post on how to spend a day in London soon!

Day Three:

Fly to Santorini, get checked in to your hotel, and enjoy a famous sunset in Oia.

Day Four:

Get up early and explore Oia without the crowds. My favorite photo spot is from the steps across from the Kastro Oia Houses. Rent a car for the afternoon to check out the other fun spots on the island. End your day with dinner in Amoudi Bay.

Day Five:

One last chance to catch the sunrise over Oia! Check out the spots you may have missed the day before then take the ferry to Milos! Catch the sunset at Sarakiniko Beach!

Day Six:

Check out Sarakiniko again at sunrise (yes, it’s that good!) then rent an ATV and go beach hopping; don’t try to get to them all though because you’ll have the next day too! We went to Firomopomas, Klima, and Mandrakia. Eat lunch at Medusa, and grab dinner in the cute town of Plaka!

Day Seven:

Check out the beaches you missed the day before! (Hint: plan the order by location on the island and which beaches you want to see without the crowds and go there early). We went to Tsigrado early then relaxed at Fyriplaka. We went back to Sarakiniko in the afternoon (yes, again haha) to cliff jump! Grab dinner again in Plaka (you’ll love this town, promise)!

Day Eight:

Check out Papafragas Caves then explore Pollonia! Hop on a flight to Zakynthos and get checked in to your hotel.

Day Nine:

Visit the Myzithres viewpoint then go beach hopping! We went to Plakaki (unfortunately closed for fire/wind) and spent the whole afternoon and Porto Roxa. Catch the sunset at Ionian Sunset Cafe!

Day Ten:

Go out for a private North Island Boat tour (10/10 recommend)! Check out Fillippoi Beach then head to Nobelos to grab a sunbed for the afternoon. Have dinner there at the restaurant!

Day Eleven:

Rent a boat to explore the south side of the island (again, highly recommend!) then hop on a late flight to Athens!

Day Twelve:

Spend a day in seeing the sights in Athens!

Day Thirteen:

Fly from Athens back to the US (sad tears and all). We landed in Boston and stayed the night here since it was late. We booked our flights with points, so we chose the options that would cost us the least points. If it makes the most sense to you to fly into your home city on this day, of course do that!

Day Fourteen:

Finish making your way home reminiscing on the best trip of your life!

I hope this post has been helpful, and I can’t wait for you to experience Greece for yourself! It’s truly magical between the history, the views, the perfectly blue sea, and the mouthwatering cuisine! Please leave any questions you may have in the comments, or you can reach me on IG here!

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