The Ultimate 10 Day Greek Islands Itinerary for First Timers

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

---

The first time I visited the Greek Isles was actually the very first trip I planned, which set off my love for travel and researching destinations. I read dozens of blogs and made sure every detail was perfect, but not over-planned. I’m surprised that everything from flights to ferries went exactly as planned. We had the best time and after now visiting over 20 different countries, it’s still one of my favorite trips.

I know how hard it is to plan a trip like this, especially if it is your first. You have limited vacation days and want to spend your time and money wisely. That’s why I want to help!

I’m really excited to share this 10 Greek Island itinerary from our real life trip. I’m confident you’ll love it if you enjoy intimate boutique hotels, amazing restaurants, a little history, and soaking up the sun in picturesque destinations! Read on to begin planning your Greece itinerary for 10 days!

---

10 Day Greek Islands Itinerary Overview

First, here is an overview of the itinerary you can expect. I’ll go into further detail for each day below and include a few customization options with alternate islands at the end. Finally, I’ll answer the most common questions for planning a trip to Greece.

---

Greek Islands Itinerary Day 1 – Athens

Depending on flight and ferry schedules, you will likely spend at least one night in Athens which can work on the front or back end of your holiday. 

PRO TIP: I recommend checking with Seajets and Ferry Hopper to determine when the ferries run before booking anything else. I had to swap our hotels around after booking because I didn’t realize they aren’t always daily between the islands.

Arrive to Athens International Airport and Check in to The Hotel in Athens

You will fly into Athens International Airport, the gateway to Greece. Some islands do have airports, but require a connection in Athens if arriving direct from the US.

Best Hotels in Athens for one night:

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. We stayed here on our first visit to 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. We have also stayed here – it’s definitely more formal and luxury.

If staying 2 nights in Athens. I would go for one of these luxury hotels in the Athenian Riviera:

Four Seasons Astir Place Athens| Four Seasons Astir Place is located closer to the airport along the Athenian Riviera. If you plan to spend a few days in Athens, this is a great spot located on the beach so you can relax before heading to the islands. It’s located about 20-30 minutes from downtown, historic Athens.

One&Only Aesthesis | One&Only Aesthesis is a luxury hotel located along the beach in Athens. It features 3 outdoor pools, beach access, and onsite restaurants. If you prefer to bask in the sun, this is the spot for you! Enjoy relaxing here after a long flight away from the hustle of the city.

If you have babies or toddlers, the riviera would be a better choice if you are okay with skipping the Acropolis and city. They can decompress a bit and enjoy the resort amenities.

Grab a Drink at GB Rooftop

Once settled in to your hotel, head over to GB Rooftop, the restaurant atop the Grand Bretagne Hotel near Syntagma Square. It’s a lively atmosphere with rooftop bar overlooking the entire city with Acropolis views.

Explore Ermou Street

Before dinner, stroll down this large pedestrian street window shopping at major and local retail stores.

Dinner at Nolan

My favorite spot for dinner in Athens is always 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! Be sure to make a reservation in advance.

After dinner drinks at By the Glass Athens

After dinner, grab a drink and a cheese plate at By the Glass Athens. It’s near Plaka and next to the Inn Athens Hotel. I love it for the local vibe and quaint space perfect for a night cap!

When jet-lagged, you want to stay up as late as possible to start acclimating so a night cap will help keep you going!

---

Greek Islands Itinerary Day 2 – Athens to Sifnos

On this day, you’ll spend the morning exploring Athens most iconic sites and ancient ruins. Later, we’ll board the ferry to the Cycladic Islands to begin our Greek island hopping itinerary!

Have Breakfast Smoothies in Athens

Pop into Happy Blender for a healthy breakfast option with smoothies, bowls, avocado toast, and more! Save room for the gyros later.

Wake up Early to explore the Acropolis and Parthenon

The Acropolis of Athens is one of the most important ancient archaeological sites in the world and today remains a popular tourist attraction and UNESCO World Heritage Site.

The Acropolis is the heart of ancient Greek civilization. It contains several ancient temples and structures, including the famous Parthenon and Temple of Athena Nike, which are iconic examples of classical Greek architecture. Notable figures like Socrates, Plato, and Aristotle walked its streets.

Walk Around Plaka

Plaka is the oldest neighborhood in Athens with charming shops and cafes along Adrianou Street and Kydatheneon Street.

Grab a Gyro for Lunch

I highly suggest having lunch at any hole in the wall gyro place! You will see plenty of street food options in Athens.

Taxi to Piraeus to catch a Ferry to Sifnos

Next, you will taxi to the ferry port in Piraeus (1 hour from Athens) where you will board your ferry to Sifnos, Greece. There are no airports on this lesser known island so a ferry is the only way to reach it!

⛴ Book your ferry in advance – compare the best ferry rates here!

Arrival to Sifnos, Greece

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.

Check into 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, honeymoons 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! 🙂

Dinner at Bostani Restaurant and Bar

After a busy day, you’ll enjoy a glass of wine (or 2) and dinner at the amazing hotel restaurant, Bostani which overlooks the Aegean Sea. You’ll dine in the outdoor terrace among olive trees and enjoy the ocean breeze.

✈️ Planning a Greece summer trip can feel overwhelming with so many logistics, but I’ve been there and would love to help you make it easy! I work with you to craft your dream itinerary, from must-see sights to hidden gems, and handle all the logistics so your trip flows seamlessly. You get a stress-free, personalized experience—just show up and enjoy every moment. Inquire here to get started!

---

Greek Islands Itinerary Day 3 – Sifnos

Finally, you have reached the Greek Islands so your first full day will be all about relaxing and enjoying Sifnos. Known as the foodie island, Sifnos is famous for its many restaurants serving fresh seafood and locally grown produce.

Start the Day with Breakfast on Your Hotel Villa Patio

I suggest ordering breakfast to your room! The hotel will set up a lovely spread on your patio featuring cereals, pastries, jams, real Greek yogurt, fresh squeezed juice, and coffee/tea.

Spend the morning at Platis Gialos

Platis Gialos is my favorite sandy beach in Sifnos. It has a quiet lagoon for swimming and charming seaside restaurants after a morning spent soaking up the sun.

Lunch at Mailoica

Maiolica is one of my favorite restaurants in Sifnos 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.

Spend the Afternoon at the Hotel Pool 

Verina Astra has an amazing infinity pool that looks over the Aegean Sea and a blue-domed church. Enjoy a leisurely afternoon at the pool.

Dinner in Apollonia and explore pedestrian streets

Apollonia is the main town in Sifnos known for its charming pedestrian street with great restaurants and shopping. Sitting at the peak of the island, it offers stunning views of the countryside and the Aegean Sea in the distance. The quaint village features traditional whitewashed houses with colorful doors and shutters, narrow alleys, and stone-paved paths.

Kafeneio Drakaki is an authentic restaurant recommended to us by a manager at Verina Astra. We made sure to stop at this restaurant tucked away in the pedestrian street of Apollonia for dinner. This restaurant absolutely had a local vibe. Try the fried zucchini fritters!

Stargaze Before Bed

Grab a bottle of wine at the hotel and stargaze by the pool. It is unbelievable how many stars you can see on this dark island at night.

---

Greek Islands Itinerary Day 4 – Sifnos

Today you will explore the traditional fishing villages and charming towns of Sifnos.

Drive to Cheronissos Beach for the Morning

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.

It’s a super quaint fishing village very off the beaten path. On the way, you’ll see the scenery of the island which is quite desolate in many areas with tons of hiking trails!

Have lunch at Cherronissos Fish Taverna

Lunch at 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!

Wander through Artemonas and Shop for Pottery

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. 

Grab Pastries at Theodorou Sweet Shop

Theodorou is a family run business in the charming village of Artemonas. They produce traditional pastries and other sweets perfect for an afternoon pick me up!

Late Afternoon visit to Kastro Church of the Seven Martyrs

Before dinner, visit the town of Kastro to see the STUNNING Church of the Seven Martyrs. It is a whitewashed church with a blue dome that juts out into the sea. Wear comfortable shoes as you’ll wind down a stone stairway to reach it.

Dinner at Cantina Sifnos

Dinner is at Cantina, the sister restaurant to popular Omega-3. 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. The views are amazing while you dine. It was definitely our favorite restaurant in Sifnos on our last visit! The food in Greece seriously rivals that of the Italian coastline.

---

Greek Islands Itinerary Day 5 – Sifnos

Wake up Early for Sunrise

I know it is tough to wake up early on vacation, but you don’t want to miss this! The sun rises on this side of the island and it is the most serene and peaceful setting. It truly feels so magical as the soft light glows around you that it’s hard to describe.

Morning swim at Poulati and see Pangia Poulati

Follow the path down to the beautiful rocky coastline sitting at the bottom 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 in the distance.

Along the way, you’ll pass Pangia Poulati, a gorgeous monastery.

I will warn you that the climb back up is a bit steep, but so worth it!

Massages at Hotel Spa

After a refreshing swim, head to your spa treatments at Bostani Spa. Located within the Verina Astra Hotel, the spa offers a tranquil setting amidst the Cycladic landscape with stunning views of the Aegean Sea. The spa’s design elements create a peaceful and relaxing ambiance.

Dinner at Omega-3

Omega-3 is the most famous restaurant on the island. It is even frequented by celebs like Tom Hanks when he visits Sifnos! The restaurant is located in Platis Gialos right along the beach where you can dine al fresco on their covered patio or right in the sand. You will have amazing seafood like marinated octopus, fresh sea bass, ceviches, and my favorite greek tacos with Sifnian chickpeas.

---

Greek Islands Itinerary Day 6 – Sifnos to Milos

Next on my specially curated, 10 Day Greek Island hopping 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.

Arrive to Ferry Port and Check into Milos Breeze Hotel

You will take the one hour ferry to Milos where you will arrive to meet your taxi driver. I recommend having transportation coordinated ahead of time as this port is large and a bit hectic. The hotel can help arrange this for you.

We stayed at the trendy, minimalist Milos Breeze Boutique 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 area is more secluded offering a less touristy escape.

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 totally necessary since it’s an intimate hotel with an infinity pool already. 

Have lunch at Enalion

Once checked in, you’ll be ready for lunch. Grab a bite at Enalion located steps away in Pollonia where you can also pick up an ATV or rental car.

Enalion is ideally situated right by the sea creating a charming setting. You can expect a variety of fish and shellfish dishes prepared in traditional Greek and Mediterranean styles. Grilled fish, octopus, shrimp, and seafood pasta are some of the highlights on their menu.

Beach Hop Around Milos

Then, spend the afternoon exploring some of the amazing beach in Milos. With over 80 different beaches, the landscapes are each so unique making it one of the best activities in Milos, Greece. Plan to hit these beaches on your first day:

• Papafragas – climb down a cliff to reach this beach with a great lagoon for swimming.
• Kapros – less crowded, great spot for cliff jumping
• Mandrakia – my favorite beach with large shallow area for swimming (is rocky on the shore, but sandy in the sea!)
• Firopotamos – tucked away in a small fishing village – super charming! 

Dinner at Armenaki

Armenaki is located in Pollonia and 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. Go early to put your name on the list.

---

Greek Islands Itinerary Day 7 – Milos

On day 7, you will visit the famous moon beach and spend the day exploring more of Milos’ natural beauty.

Enjoy Hotel Breakfast Buffet

Milos Breeze Hotel offers a a great breakfast buffet within their open-air lobby and patio. Fuel up for a busy day exploring Milos and soaking up the sun.

Start your day early with a visit to Sarakiniko Beach, the famous moon beach

Sarakiniko is the most famous beach in Milos so we’ll want to go early one morning to beat the crowds (and cruise ships!!). The lunar landscape is truly otherworldly and is a must see in Milos. I would not spend too much time here as it’s not the most comfortable beach and there are plenty of other amazing ones to see.

Spend the Day Beach Hoppping

You will spend the rest of the day hopping around to some of the best beaches in Milos. These are ones I recommend visiting next and in this order!

• 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.

Lunch at Aqua Loca Beach Bar

Aqua Loca is a fun little beachside spot for lunch in Paleochori. You can grab a sandwich and Mythos beer or glass of wine.

Dinner at Medusa

Tonight, you are in for a treat at my very favorite restaurant in Milos, Medusa! It’s located in the charming fishing village of Mandrakia. The stunning views of the Aegean Sea make for a truly unforgettable dining experience. Be sure to make a reservation in advance or arrive early, as this popular spot fills up quickly.

We had the greek salad topped with a huge block of homemade feta, sun dried mackerel, swordfish souvlaki, and finished it off with a little baklava. The sunset here was beautiful so you must sit along the cliff. 

---

Greek Islands Itinerary Day 8 – 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. Today, you are headed out to sea!

Half Day Catamaran Cruise to Kleftiko

Book my favorite experience 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

After a fun morning at sea, kick back with a cocktail at the hotel’s infinity pool which overlooks Pollonia and Antimilos.

Explore Pollonia & Dinner at Rifaki

Tonight, you will have dinner at Rifaki which was my favorite restaurant in Pollonia. It has a charming atmosphere where you can dine along the lagoon and fishing boats.

Our favorite wine of the trip was served here from Moraitis Winery in Paros. I loved their more traditional greek food like chicken souvlaki which was a nice break from so much seafood. They also offer a vegan menu with mushroom risotto and great salads.

---

Greek Islands Itinerary Day 9 – Milos

After a many days in the Greek isles, this day will be leisurely and fun. Relax in the morning to enjoy your hotel then try a winery in the afternoon!

Spend the morning at your infinity pool + order lunch

This morning, relax at the hotel’s amazing infinity pool overlooking Pollonia and have lunch.

Another option if you are up for it, is to tour the Catacombs of Milos. It is the earliest Christian monument and site of worship in all of Greece. This archaeological site is a labryinth of underground caves and pathways to explore.

Wine Tasting

Interested in a little wine tasting? Greek wines are absolutely delicious – my favorite type is assyrtiko – a crisp white! Head to Kostantakis Cave Winery for a break from the sun and wine tastings in Milos.

Explore the pedestrian streets and shops of Plaka

Plaka is the picturesque capital of Milos, known for its natural beauty, rich history, and charming villages. It is is located on a hilltop in the northern part of Milos, offering stunning panoramic views of the island and the Aegean Sea. It is about a 10-minute drive from Adamantas, the main port town of Milos.

In the afternoon, head to Plaka to explore the pedestrian streets of this main town. It is home to art galleries, traditional tavernas serving local cuisine, quaint cafes, and boutique shops selling handmade crafts and souvenirs. I’m obsessed with the flowers and sprawling pink bougainvillea everywhere!

Catch sunset in Plaka before dinner with drinks at Utopia Cafe

One of the main draws of Plaka is its stunning vistas making it renowned for its sunset views. There is a great wine bar called Utopia Cafe offering an amazing spot to view it. Be sure to get there early! Alternatively, you can watch from one of the most stunning church settings – Church of Panagia Korfiatissa.

Dinner at O! Hamos! Taverna

After sunset, head to O!Hamos! for dinner. O! Hamos! Taverna is situated in Adamas within the garden of a house lending to its homey atmosphere. It is a farm-to-table restaurant known for its delicious seafood and Greek cuisine. It’s popular for dinner, offering a cozy atmosphere and friendly service.

---

Greek Islands Itinerary Day 10 – Depart

Depart Milos for Athens via the Milos Island National Airport to make your journey home. You will have to connect in Athens then continue to wherever you call home from there.

If you have a later flight, there are plenty more things to do in Milos!

---

Custom Options for Your Greece Itinerary

If you would like to add on another island or swap out one of these, here is where I suggest for a more high end experience and recommend accommodations. I carefully select hotels that are luxury properties and offer an escape from the tourist areas.

Mykonos

Head to Mykonos, known as the party island for its vibrant nightlife and beach clubs. Stay at the ultra luxurious Cali Mykonos which is a bit off the beaten path and away from the party scene – ideal for a romantic honeymoon to Greece. Be sure to see the famous windmills of Mykonos, Little Venice and shop in Mykonos Town!

It is a 2 hour ferry to Sifnos and 3 hours to Milos.

Paros

Paros is a great family friendly option with amazing sandy beaches. Stay at either Cosme or Parilio both with amazing pools, spas, and stylish accommodations.

It is only a 1 hour ferry ride from Sifnos and Milos.

Santorini

If you simply must visit Santorini, stay at my favorite Grace Hotel in Imerovigli. You wont want to miss the famous white washed cliffside village of Oia and you have to plan a sunset sail around the caldera!

The scenery in Santorini is simply breathtaking which is what attracts to so many visitors. It will be crowded with tourists and cruise ships so I recommend visiting in the shoulder season of April or October.

---

How to Get to Greece & the Islands

Let’s talk about logistics. First things first, the best way to reach the Greek Islands is to fly into Athens International Airport. This is a major airport with direct flights from the US on 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, Sifnos. On the return trip, you will fly from Milos 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 time.

---

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 if you are able. It is easier to drive and park. However, if you have kids then a car is the way to go. 

---

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 to Greece 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. Additionally, you will probably have a night in Athens on either end of you trip depending on flights. 

The islands can be hours apart so you don’t want to spend time packing and unpacking and 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 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. However, the summer months are the most popular and you can count on great weather.

You should note that many hotels and restaurants close for the winter season only opening from April – October. Peak months for visiting the Greek Isles are June, July, and August with weather temperatures in the 80-90s.

---

Where to Go for Your 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 islands to choose from, but my favorites are Milos and Sifnos as described throughout this itinerary. 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 whitewashed buildings and blue domed churches in the other Cycladic Islands!

Here is a breakdown of some recommended Greek islands:

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

---

Packing List for the Greek Islands

Greece can be very hot in summer, so pack accordingly with light, breathable clothing. Consider packing light as some islands may have uneven terrain and you’ll have to carry it on/off ferries and small planes. Check out my complete post on packing for the Greek Islands for an in-depth guide.

• Lightweight, breathable clothing (shorts, t-shirts, dresses)
• Swimwear (bikinis/swimsuits)
• Light jacket or sweater for cooler evenings
• Comfortable walking shoes or sandals
• Flip-flops or beach sandals
• Hat and sunglasses for sun protection
• Sunscreen
• Pajamas or comfortable sleepwear
• Adapter for electrical outlets (if necessary)
• Hiking shoes or sturdy footwear (if planning on hiking)
• Casual evening wear (for dinners out)
• Exercise Set
• Beach tote

---