10 day greek isles & italy from rome civitavecchia

Today, I am sharing my 10 day Greek Islands itinerary perfect for friends, couples, or your honeymoon! Greece is a magical place full of history, incredible beaches, and amazing chefs. The Greek isles are the perfect destination for your next vacation.

First, I will share some important details for planning your trip, then get into the detailed 10 Day Greek Islands itinerary. It will include a quick guide to each of my suggested island destinations with the daily itinerary intertwined throughout. It is a super detailed itinerary, but not to worry, it is very relaxed with many leisurely days of beach hopping and eating great food! Take what works best for you and leave the rest 🙂

Table of Contents

How to Get to Greece & the Islands

First things first, the best way to reach the Greek Islands is to fly into Athens International Airport. This is a major airport with flights from many different carriers.

Some of the islands have airports and some have only ferries. It depends on which island you are going to. For the purpose of this 10 Day Greek Island itinerary, you would fly into ATH and take the ferry to your first island! On the return trip, you will fly from the islands to Athens.

There are many different ferry companies, but I have used Sea Jets and recommend them. There will be options for the regular ferry or high speed. Honestly, the high speed is worth the extra cost in my opinion to maximize your limited PTO days!

Basics for Traveling to Greek Isles

Language: The official language is Greek, but almost everyone we encountered spoke English as well. The islands are tourist destinations so you will generally find English speakers.

Adapter: You will need a typical European adapter in the islands.

Currency: Greece uses the euro so make sure to exchange some dollars at the airport or use an ATM to have some cash on hand.

Cars: You will need a form of transportation, but I suggest an ATV over a rental car on the islands! It is easier to drive and park.

How Many Days Do You Need in the Greek Islands?

You can never have enough days in the Greek Islands! However, I suggest a 10 day trip with at least 7 of those nights in the islands. You will want to have 3-4 days on each island to feel relaxed and not spend all of your time traveling.

For example, the islands can be hours apart so you don’t want to spend time at airports and on ferries. My best advice is to pick 2 islands to enjoy instead of trying to see 4-5 in one trip. You need more than a day to really soak up the culture and relax. After all, it is a vacation!

When is the Best Time of Year to Visit the Greek Islands?

The best time of year to visit Greece is May or September when the islands are less crowded and the weather is comfortable.

The islands are typically open from April through September. Summer is super busy in Europe as you would imagine. It’s when parents take off and kids are out of school. Likewise, peak months are June, July, and August with weather temperatures in the 80-90s. However, the islands have a nice sea breeze making it sometimes cooler.

Where Should I Go for the First Time in Greece?

For your first visit to Greece, I recommend spending a day in Athens to see the historical sites and learn about ancient civilizations. Then, spend the rest of your time in the famed Cycladic Islands known for their postcard perfect, whitewashed homes!

There are so many to choose from, but my favorites are Milos and Sifnos. They are a little off the beaten path and won’t be as touristy as Santorini and Mykonos. Everyone defaults to Santorini, but there is so much more than that. I promise, you will get your fix of whitewash buildings and blue domed churches in the other Cycladic Islands!

Here is a breakdown of some islands:

Sifnos – the foodie island. Home to over 360 churches, more than any other island(love those blue domes)
Milos – known for its 80+ different beaches
Santorini – known for the famed sunsets over the caldera and white washed building of Oia.
Mykonos – the party island
Paros – more family friendly
Naxos – lush landscape and mountain villages
Crete – the largest Greek Island and southernmost island
Rhodes – medieval history and UNESCO World Heritage site

What Is a Good Itinerary for Greece?

The best itinerary for your first time in Greece starts with a little history in Athens, then a relaxing foodie adventure in the Greek Isles, and ending with a few days beach hopping around a Cycladic Island gem! Here is my itinerary for your perfect, laid back vacation to the Greek islands. I will start with a brief guide for each destination, then intertwine the daily 10 Day Greek Islands Itinerary throughout.

Athens Travel Guide

First, you will arrive in Athens AKA the home of the gods! Based on your flight schedules, you will likely spend at least one night in Athens which can work on the front or back end of your holiday.

Best Hotels in Athens

I have been to the ancient city of Athens twice so have two great hotel suggestions for you.

Inn Athens Hotel

Inn Athens Hotel is a quaint, boutique style hotel located near Plaka and the Acropolis. There is a fabulous courtyard where breakfast is served and also a fun wine bar at the entrance. It’s a great cost effective option for spending one night in Athens, Greece.

Hotel Grande Bretagne

Hotel Grande Bretagne is a 5-star luxury property located in the heart of Athens at Syntagma Square and Ermou Street. My favorite feature is the super high rooftop views over the city. Additionally, it is a Marriott branded property so you can earn or use points here.

What to Do in Athens

For a quick trip to Athens, you will want to focus on the highlights especially if it is your first trip to Greece.

Acropolis + Parthenon – The acropolis is one of the most important ancient archaeological sites in the world. A former home to the gods, this is now a tourist attraction and UNESCO World Heritage Site.
Walk Around Plaka – the oldest neighborhood in Athens with charming shops and cafes along Adrianou Street and Kydatheneon Street.
Ermou Street – Stroll down this large pedestrian street window shopping at major retail stores and tasting the flavors at local restaurants.

Where to Eat in Athens

Breakfast

I recommend having breakfast at your hotel or the following option:

Happy Blender – A healthy option with smoothies, bowls, avocado toast, and more! Save room for the gyros later.

Lunch

Gyros – Highly suggest having lunch at any hole in the wall gyro place! They put french fries in their gyros in Greece so you won’t want to miss this.

Dinner/Drinks

Nolan – My favorite spot for dinner in Athens is Nolan! It’s an Asian-Mediterranean fusion style cuisine with everything from a fried fish sandwich to sun dried mackerel to salmon bowls. It is featured on the Michelin guide so you can’t go wrong at Nolan!
Thea Terrace Bar and Restaurant – Close up stunning view of the Acropolis
GB Rooftop – High rooftop view over the Acropolis located at Hotel Grande Bretagne
By the Glass Athens – located at the entrance of Inn Athens Hotel. Great place for wine and cheese boards!

First, arrive to Athens and check into Inn Athens or Hotel Grande Bretagne
Explore Ermou Street
Drinks at GB Rooftop or Thea Terrace Rooftop to watch the sunset
Later, have dinner at Nolan Greece
After dinner drinks at By the Glass Athens

Greek Islands Itinerary Day 2 – Athens/Sifnos

Start your morning with breakfast at your hotel or at Happy Blender
Visit the Acropolis of Athens to admire the Parthenon
Then, shower and get ready to head for the islands!
You will depart Athens for Sifnos, Greece – the foodie island
- Taxi to the ferry port in Piraeus (1 hour from Athens) where you will pick up ferry tickets
- There are no airports on this lesser known island so a ferry is the only way to reach it!

Guide to Sifnos: The Foodie Island

Sifnos is a hidden gem often referred to as the foodie island for its renowned chefs and their culinary creations. Some of these restaurants have become my favorites around the world. Read my full guide to Sifnos, Greece if you want further details.

Best Hotels in Sifnos

Verina Astra Sifnos

Verina Astra Hotel is hands down the most magical resort in Sifnos and maybe all of the Greek Isles! The rooms feature spacious suites to accommodate couples or families. There is a fabulous infinity pool overlooking the Aegean Sea and the onsite restaurant is one of the best! Make sure to have authentic greek yogurt and fruit for breakfast – it is truly different in Greece. For dinner, make sure to include a meal here too for the amazing mussels, fish, and cinnamon ice cream! 🙂

What to Do in Sifnos

Besides eating, there is much to explore around the island including local shops, beaches, fishing villages, churches, and charming coastal towns.

Spend a day on the beach at Platis Gialos
Beach Hop to Vathi and Chernossis Fishing Village
Stroll along the Pedestrian Street in Appollonia, the capital
Church of the Seven Martyrs – You MUST see this iconic church located in Kastro. After, stroll around the quaint town.

Where to Eat in Sifnos

Sifnos is known as the foodie island so you will find no shortage of amazing chefs across the island. I wrote a whole blog post dedicated to the subject, so here I will share my top picks for your 10 day Grecian vacation:

Maiolica – one of my favorites for lunch or dinner. The cuisine is fine dining, but you get to walk steps from the beach in your salty swimsuit to dine! Must try the grilled veggies, sea bass, and hummus.
Omega-3 is one the most famous restaurants on the island. Omega-3 is frequented by celebs like Tom Hanks and Scarlett Johanssen! Amazing seafood like octopus, sea bass, ceviche, and greek tacos! It is located right next to Maiolica
Cheronissos Fish Taverna – located on the opposite end of the island in a quaint fishing village. You will have incredibly fresh fish here straight from the boats!
Cantina is the sister restaurant to Omega-3 and while I have not tried it, I HAVE to recommend you try it! Cantina is located in Seralia, Kastro and is completely sustainable with zero waste and almost all ingredients sourced locally. Think seasonal rotating menu with smoked whole fish, carpaccios, brisket, ceviches, and classic cocktails.
Kafeneio Drakaki – Recommended by a manager at Verina Astra, we made sure to stop at this restaurant tucked away in the pedestrian street of Apollonia. This restaurant absolutely had a local vibe. Try the fried zucchini fritters!

Continued – Greek Islands Itinerary Day 2

On day 2, we will arrive to your next stop: Sifnos, Greece!

You will arrive at the port located in Kamares. We walked off our ferry with only 8 other people as the rest were headed to more popular islands like Santorini and Mykonos.
Check into the Astra Verina Hotel.
- I suggest having them coordinate a taxi in advance to pick you up from the ferry port which is about a 20 minute drive. Be sure to bring Euros for the driver!
- In addition, you can have them arrange an ATV for your stay that will be delivered and picked up from the hotel for you.
Then, open the bottle of wine in your in-room refrigerator and relax on your patio – it’s been a long travel day!
Enjoy dinner at the amazing hotel restaurant overlooking the sea

Greek Islands Itinerary Day 3 – Explore Sifnos

First, wake up early to see the stunning sunrise over the Aegean Sea. Then, go back to sleep for a bit as you are probably still a bit jet lagged.
Next, hop on your ATV and spend the day at Platis Gialos
Have lunch at Maiolica
Return to the hotel and enjoy relaxing at the infinity pool
Get ready and head to dinner at Cantina Sifnos
Finally, check out the pedestrian street of Appollonia on your way back to the hotel

Greek Islands Itinerary Day 4 – Explore Sifnos

Today, you will get to explore the far end of the island and really get to see the sprawling landscapes of Sifnos as well as some of the many little towns.

Start your day with breakfast at the hotel
- I suggest ordering it to your room! They will set up a lovely spread on your patio featuring cereals, pastries, jams, yogurt, fresh squeeze juice, and coffee/tea.
Then, take a drive to the far end of the island to explore Cherronissos. The beach here was one of our favorites as it was great for swimming and not too crowded due to its remote location. Have lunch at Cherronissos Fish Taverna.
On the way back, explore Artemonas and be sure to stop into Sifnos Stoneware for a souvenir! I adore this pottery store so much that we got this a few years later on our wedding registry instead of traditional china.
Next, return to your hotel and walk down to Poulati Monastery. Follow the path down to the beautiful rocky beach at the edge of the cliff. On a calm day, this is a great secret spot to swim and enjoy views of Kastro and the Church of the Seven Martyrs.
Head to dinner in Apollonia along the pedestrian street at Kafeneio Drakakis.
- Our hotel staff suggested this fun local spot! We shared several small plates, my favorites being fried zucchini balls and the mushrooms layered with cheese (saganaki).
Later, grab a bottle of wine at the hotel and stargaze by the pool. It is unbelievable how many stars you can see.

Greek Islands Itinerary Day 5 – Beach Hop

On your last day in Sifnos, enjoy seeing many of the blue-domed churches and spend ample time at some of the best beaches for sunbathing (and eating!)

Have breakfast in the hotel restaurant
- The greek yogurt and fruit is amazing in this country. I don’t ever order yogurt from a restaurant at home because I can usually make it myself. BUT this was so fresh and the local honey….yummm!
Start your day with a drive over to Kastro to admire the stunning Church of the Seven Martyrs. It’s a long walk down the winding staircase, yet SO worth it. Consider it your exercise for the day!
Next, take your ATV to Vathi Beach for the day. Enjoy the water and local shops throughout the day.
Have lunch at Bola Vathi lounge
Then, head back to Platis Gialos for an early dinner at Omega-3 Sifnos. A great beachy bar, where you can have amazing food…in your bikini.
Relax at the hotel and in the infinity pool enjoying sunset.
Finally, grab a late dessert at the hotel restaurant.

Greek Islands Itinerary Day 6 – The next island: Milos

Today, we are heading to your next stop: Milos!

Have breakfast at the hotel
Pack your bags and taxi to the ferry port
You will take a 1 hour ferry to the nearby island of Milos.

Guide to Milos: The Beach Hopping Island

Next on my specially curated, 10 Day Greek Islands Itinerary I am taking you to Milos! Milos is the perfect island to complement Sifnos with its many opportunities for adventure. It’s close by with only a one hour ferry ride and has dozens of beaches so you can hop from one to the next! Read my full travel guides to Milos, Greece for a deeper dive.

Best Hotels in Milos

Milos Breeze Hotel

We stayed at the trendy, minimalist Milos Breeze Hotel on our trip to Milos. It is located in Pollonia on the far end of the island along a quaint fishing lagoon with tons of shops and restaurants.

The rooms are large and comfortable with spacious balconies overlooking the ocean. I would splurge for a suite with its own plunge pool, but not necessary since it’s an intimate hotel with an infinity pool already.

The hotel has a delicious breakfast buffet each morning and you can sit outside overlooking the pool and lagoon in Pollonia.

What to Do in Milos

Sailing – take a catamaran cruise with Milos Adventures which will take you to the parts of the island that can not be accessed from land. You’ll get to spend time at Kleftiko and legend has it the caves were a pirate hideout once upon a time! They provided snorkel gear, water, beer/wine, plenty of snacks and fresh seafood, too!
Beach Hopping – Milos has over 80 different beaches. From Sarakiniko the famous moon beach, to Tsigrado which is only accessible by ladder, to Mandrakia the old fishing village, and Firiplaka with the red clay cliffs!
Sunset at Plaka and Pedestrian Streets – the most beautiful sunset can be seen from the main town. Be sure to wander the pedestrian street and charming boutiques.
Kostantakis Cave Winery – taste greek wines and enjoy a respite from the harsh sun

Where to Eat in Milos

Milos is a prime destination for fresh seafood prepared with a grecian flare to it! Here are my favorite Milos restaurant recommendations.

Medusa – a fabulous restaurant located near the beach in Mandrakia. Incredible sunset so you must sit outside along the cliff. Try the greek salad with huge block of feta, sun dried mackerel, and baklava.
Armenaki – located in Pollonia, this was a very busy spot! They consider themselves a “wine restaurant” so they clearly had me at that! Enjoy fresh local seafood and veggies from their garden.
Rifaki had the best view of the fishing village along the water in Pollonia. We loved the authentic Greek meal with souvlaki and french fries.
Aqua Loca beach bar – a great beach bar in Paleochori to end a day of beach hopping.
O!Hamos! Tavern is family run using ingredients from their own farm and is located along the beach so you can have waterside drinks if there is a wait.

Continued Greek Islands Itinerary – Day 6

Arrive via ferry to Milos island
- I recommend having a taxi scheduled ahead of time. This port is a bit more hectic with so many travelers! Milos is much more crowded and touristy and it’s evident the second you disembark.
Check into Milos Breeze Boutique Hotel
Have lunch at Enalion
Then, spend the afternoon exploring some nearby beaches like these:
- Papafragas – climb down a cliff to reach this beach with a great lagoon for swimming.
- Kapros – less crowded, great spot for cliff jumping
- Mandrakia – favorite beach with large shallow area for swimming
- Firopotamos – tucked away in a small fishing village – super charming!
Dinner at Armenaki

Greek Islands Itinerary Day 7 – Beach Hopping Day

Get ready for a full day of beach hopping on your ATV!

Breakfast buffet at Milos Breeze Hotel overlooking the pool
Start your day early with a visit to Sarakiniko Beach, the famous moon beach
From there, make stops at the following places:
- Fyriplaka – organized beach with a beach bar and chairs. Fun entry way through some shallow waters and rocks.
- Tsigrado – right next door to Fyriplaka, you climb through a crevice and down a ladder to reach this beach. Great area to swim!
- Paleochori – organized beach with restaurants and plenty of space.
Have a late lunch in Paleochori at Aqua Loca beach bar
Dinner at Medusa Milos

Greek Islands Itinerary Day 8 – Sailing Around Milos

One of my favorites experiences in the islands was sailing for a day. The islands are even more stunning with a view from the water.

Half day tour with Milos Adventures for a cruise on their catamaran.
- You will see the section of the island that is not accessible to cars. You’ll have ample time to enjoy Kleftiko – an old pirate hangout with tons of caves to explore.
Relax at the infinity pool the rest of the afternoon
Dinner is at Rifaki, steps from the hotel

Greek Islands Itinerary Day 9 – Winery Day

Interested in a little wine tasting? Greek wines are absolutely delicious – my favorite type is assyrtiko – a crisp white!

Spend the morning at your infinity pool + order lunch
Kostantakis Cave Winery for a break from the sun and wine tastings!
Leisurely explore the pedestrian streets and shops of Plaka
Catch sunset in Plaka before dinner with drinks at Utopia Cafe
After, have dinner at O!Hamos!

Depart Milos Greece – Greek Islands Itinerary Day 10

Depart Milos for Athens via the Milos Island National Airport to make your journey home 🙁

10 Day Greek Islands Itinerary Recap

Day 1: Athens – explore the Acropolis and ancient history
Days 2-5: Sifnos – eat your way around the foodie island
Days 5-9: Milos – beach hop around 80+ different beaches
Day 10: Return Home 🙁

Frequently Asked Questions about the Greek Islands

What is the best way to see the Greek islands?

The best way to see the Greek islands is to enjoy spending ample time on each island. I do not recommend sailing from one island to the next for a 10 day trip. I believe in a relaxing vacation where you can truly take in the culture of an island. That’s not to say I will never sail around, though! It would be perfect if you have several weeks or a whole month!

Where should I go first time in Greece?

For your first time in Greece, skip the touristy islands and head off the beaten path to more unique places! Visit Sifnos known as the foodie island to taste the flavors and visit the many blue-domed churches. Then, ferry over to Milos where you can beach hop around the 80+ different beaches and spend a day sailing!

How long do you need on each Greek island?

I could easily spend an entire summer on one island alone! Unfortunately, we don’t all have that kind of time with limited vacation days. I suggest at least 3 nights per island to truly experience what it has to offer. Read this post for my full 10 Day Greek Islands Itinerary!

Which Greek island is best to visit?

The best Greek islands to visit in my opinion are Sifnos and Milos, together. However, it depends what you like to do! They are all SO different. If you are anything like me, I value a luxury hotel and a leisurely experience getting to adventure around an island soaking up the culture and of course, trying alllllll the cuisine!

Which Greek island is the least touristy?

Let’s be honest, the Greek Islands are all touristy at this point. Sifnos is pretty undiscovered as there is no airport on the island making it more limited who can visit. It felt very authentic being on the island with only a few other tourists. We were able to chat with so many locals and learn about their lives because of this.

Which Greek Island is the quietest?

Sifnos was a super quiet and relaxed Greek Cycladic Island. In fact, it does not have an airport so that means less people and less cars on the roads. Staying at Verina Astra Hotel was like being on a private island as it is tucked away from the main towns.

Which Greek island has the best beaches?

In my opinion, Milos is the Greek Island with the best beaches. To illustrate, they have over 80 different beaches, some featuring red clay cliffs, pebbles, sand or volcanic rocks. We spent days beach hopping around Milos sometimes climbing through crevices and down ladders to reach them.

Is 10 days enough to visit Greece?

Yes, 10 days is enough to visit Greece. However, it is the minimum I would spend on a trip to Greece. You will have enough time to get a taste of Athens and also spend 7 days on two different islands. Conveniently, the perfect 10 Day Greek Islands Itinerary is outlined above so all you need to do is book!

How do you spend 10 days in the cyclades?

I would spend your 10 days in the cyclades split between two different islands. This will give you enough time to thoroughly explore the islands and learn more about them! You don’t want to spend all your time traveling between islands which is why I suggest limiting it to two unique Greek Islands.

Do I need a car in the Greek isles?

I do not recommend a car, but it is best to have your own transportation. In fact, have the hotel arrange an ATV for your stay. It will be dropped off and picked up from the hotel for you. I prefer an ATV because it is easier to park in the narrow streets and way more fun!

Google Map for Greek Island Hopping

Finally, this is my Google Map with all of this pinned so you can get a lay of the land before your 10 Day Greek Islands Itinerary comes to fruition!