From the tranquil turquoise sea to white sugar-cube houses to blue-domed churches, the Greek Isles are magnificent – and a superb destination for a 10-day island-hopping trip!
We recently spent four weeks bouncing around the Cyclades. We explored inviting villages, hiked ancient trails, swam in the Aegean Sea and indulged in the spectacular local cuisine.
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Of course, we know that not everyone has a full month to go on vacation in Greece. So, we’ve condensed our adventures into an incredible 10-Day Greek Island Hopping Itinerary!
About Our 10-Day Greek Island-Hopping Itinerary
Planning a vacation to the Greek Islands may feel like a monumental task. Which ones to visit? How long should you stay? How will you get around?
Well, our Greek Island 10-Day Itinerary features four stops: Santorini, Paros, Sifnos and Milos. We specifically chose these for their proximity and diversity; each is distinctive and memorable.
For this trip, we allotted 2 days in Santorini, 3 days in each Paros and Sifnos and 2 days in Milos. It does not include time in Athens or travel days to and from Greece.
We completely detail what to do in the outline below, but you can read these in-depth travel guides for even more information.
If you are apprehensive about driving, don’t worry. Our itinerary for the Greek Islands was specifically designed without a car. Instead, you will use buses, taxis or your own two feet to get around.
Planning a longer getaway? Check out our 2-Week Greece Itinerary for more inspiration. On that trip, we visit Athens, spend time in Chania (Crete), see more of Santorini and go to Naxos.
Greek Island-Hopping Itinerary: 10 Days
Our 10-Day Greek Island Itinerary is an active adventure that focuses on unique experiences while maximizing value. There’s a lot to discover, so we better get started!
DAY 1: Ease into Santorini
There is no better place to begin 10 days island hopping in Greece than Santorini. It’s the most famous Greek island to visit…and for good reason. It’s stunning.
It’s also crowded and expensive – so be sure to read our Need-To-Know Santorini Travel Tips before you go!
MORNING: Arrive and Check In
There’s frequent connections to Santorini by plane or ferry from Athens year-round. Additionally, from April – October, there are direct flights from other cities in Europe. We flew to Santorini from London Gatwick.
Once there, get checked into your hotel straight away. We suggest staying in Fira, the island’s main town and transit hub.
For a clean, budget-friendly hotel, we recommend Villa Rose. The well-decorated rooms are clean, have kitchenettes and there’s even a pool to refresh in after a long day of sightseeing!
AFTERNOON: Fira, Imerovigli and Skaros Rock
Start off in the heart of Fira at the bustling Theotokopoulos Main Square. Grab a fast-food souvlaki pita from Lucky’s for lunch and then step into the tangle of narrow lanes lined with shops.
Stop by churches or pop into museums (the Museum of Prehistoric Thera is our top pick) before navigating north along the pedestrian lane toward Imerovigli.
As you walk along the rim of the caldera, take in the expansive views, the perfectly perched churches and the striking white abodes.
Once you get to Imerovigli, scurry down to Skaros Rock – the craggy headland that protrudes into the sea. Keep following the trail past the peak and down to a hidden church!
EVENING: Santorini Sunset and Dinner
Watch the sun sink into the sea from Skaros Rock or enjoy the spectacle with a beverage in hand at Volkan on the Rocks. (The drinks are pricey, but the view is hard to beat.)
End your day with a delightful dinner at family-owned Taverna Simos. Order meze – small plates to share – so that you can get a taste of multiple dishes!
DAY 2: Sightsee in Oia
Today, head north to the village of Oia, the most recognizable place in the Cycladic Islands.
MORNING: Fira to Oia Walking Path
Lace up your shoes and set off on the walk to Oia. You will retrace your steps from the previous day to Imerovigli (but notice how different it looks in the morning light).
From there, follow the trail markers until you reach the iconic town of Oia. In total, it’s a 6-mile trek – and one of the best things to do in Santorini!
The trail follows the curve of the coastline, offering staggering views of the shimmering sea and rocky landscape.
It took us about 3 hours to get to Oia – and that included time for taking photos, popping into churches and detouring onto various side paths.
Travel Tip: Hiking isn’t the only way to get to Oia. You can also take a taxi or ride the bus.
AFTERNOON: Tour Oia
When you arrive in Oia, enjoy lunch with a view at Skiza Café – then go explore. Wind through the alleys and up to the windmills and out to the remains of the Oia Castle.
Snap photos over the famous blue church domes. Seek out the Atlantis Bookshop. Grab a gelato from Lolito’s. Then…just wander.
The main lanes get crazy congested, but a few twists and turns later, you could find yourself nearly alone (except for the cats, of course).
EVENING: Santorini Cruise for Sunset
In the late afternoon, make your way down to Amoudi Bay and hop aboard a sailboat. This Santorini Catamaran Cruise was an absolute highlight from my first trip to Santorini with my family.
From the fun swimming stops to the gorgeous vantage points to the incredible on-board meal and bottomless drinks, it was a magical experience!
DAY 3: Get a Peek at Paros
Next on your Greek Island-Hopping 10-Day Itinerary, head over to Paros. Unpretentious yet alluring, it boasts beautiful towns, sandy shorelines and an opportunity for adventure.
MORNING: Ferry and Introduction
Be on a morning ferry from Santorini to Paros so that you can make the most of your time here.
Ferries to Paros dock in the town of Parikia – and that’s where we suggest you base yourself. It’s the capital and transportation hub; the main bus station is just a short walk from the ferry terminal.
Get checked into your Paros hotel. We recommend finding a place right in the heart of the town, like the traditional (and wallet-friendly) Hotel Dina.
For our weeklong stay, we rented an Airbnb that was on the edge of town. It was great for us, but with just three days, we believe it would be better to stay in the center.
Top Tip: Use our Guide for Booking Top Hotels for Cheap!
AFTERNOON: Discover Parikia
By now you are probably getting hungry – and Ragoussis Bakery is our favorite place in Parikia for a quick and delicious lunch. Try the flaky spanakopita, made-to-order sandwiches or a hot meal.
Now, start exploring Parikia. Get lost in the twisting lanes – but don’t miss the Byzantine-era Panagia Ekatontapyliani (aka the Church of 100 Doors), the 13th century Frankish Castle and the windmills.
Spend the rest of the afternoon on the shoreline. Follow the coast to the small beaches north of town. If you are up for a short hike, follow the path all the way to the lighthouse.
EVENING: Sunset and Traditional Tavern for Dinner
As the sun begins to set, make your way to the Archaic Temple of Athena. The elevated perch is, hands down, the best place to watch sunset in Parikia.
Then feast on a traditional meal at Bountaraki. A classic Greek taverna, they don’t take reservations, so there will likely be a line – but it’s worth the wait!
DAY 4: Explore Around Paros
Today is full of fun things to do! Start off with a visit to neighboring Antiparos Island – then head to the north side of Paros and the lovely town of Naousa.
MORNING: Antiparos
Sitting less than one nautical mile from Paros – and well-connected by ferry boats – Antiparos is a fabulous place to spend the morning of day 4 of your Greece island hopping trip.
The main attractions are natural wonders, like its remote beaches and the Cave of Agios Ioanni. (During our springtime visit, when the island was still waking up from its off-season slumber, the legendary cave was closed.)
Chora – the main town where the ferries dock – is a quaint place to discover on foot, but what we loved most about Antiparos was the rustic coastal path that traces the shoreline of the northern headland.
Find a place to eat a leisurely lunch along the town’s main thoroughfare (Epestrefe is our preferred pick) – then make your way back to Paros.
Pro Tip: Ferries depart from Paros at the Pounda Port year-round – but you will need to take a bus to get there. In the summertime, boats to Antiparos depart right from Parikia.
AFTERNOON: Naousa
On your return from Antiparos, pause in Parikia only long enough to hop aboard a northbound bus to Naousa.
The island’s most stylish settlement is notable for its charming lanes, boutique shops and waterfront restaurants.
Delve deep into the atmospheric streets to admire the doorways draped in bright bougainvillea and make your way to the coast to visit the partially sunken Venetian castle.
On hot days, cool down in the crystal-clear water at Piperi Beach and then find a shady spot at a cafe to relax and take it all in.
EVENING: Seafood Meal
Although Naousa doesn’t face west, it’s still a sensational place to be when the sun goes down, so settle-in for the evening.
Enjoy a dinner of freshly caught seafood at one of the restaurants situated by the quaint fisherman’s port, like Sigi Ikthios.
The entire scene is like the set of a film. Colorful boats bob on the water and heavenly scents float on the breeze.
DAY 5: Trek Paros’ Ancient Trade Route
Today you’ll be visiting postcard-perfect villages, swimming in the Aegean Sea and savoring yet another incredible meal.
MORNING: Lefkes and Byzantine Trail
Experience Paros the old-fashioned way as you walk between five whitewashed enclaves on the Byzantine Path.
Start in the hillside village of Lefkes – and after a whirl around town, embark on a 5-mile journey south toward the coast.
Begin with the well-preserved 2-mile section from Lefkes to Prodromos, then continue through the countryside to Marmara, Marpissa and finish in Piso Livadi.
Celebrate the completion of your excursion with a satisfying pita from Mango Souvlaki for lunch.
AFTERNOON: Paros Beach Time
Paralia Piso Livadi is calm and shallow, as it’s protected by the harbor, which makes it great for splashing in sea. There’s no sun loungers or umbrellas for rent here, so you’ll want to at least bring a towel.
That said, we like Paralia Logaras even better. Even though the sand is pebbly, the cerulean water is also crystal clear.
EVENING: Aliki for Dinner
Located on the southern coast of Paros, the peaceful fishing port of Aliki is a phenomenal place to eat fresh seafood.
There’s a handful of restaurants clustered around the west-facing shore – and To Balconi tou Aki is our favorite. Try to get a table on the sand and go for the whole grilled fish!
DAY 6: Experience Sifnos
Continue your Greek Island-hopping trip on Sifnos. It is mostly known for a network of hiking trails and exceptional gastronomy, so be prepared to earn your meals!
MORNING: Ferry to Sifnos
The Sifnos ferry port is in Kamares, which is a wonderful coastal town with a beach…but it’s not where we recommend staying.
Instead, take a taxi or bus to Apollonia. The beautiful mountain town is the starting point for several hikes and has great dining options, too.
Check into your accommodation at Rose Studio – an absolute gem of a place! Nestled on manicured grounds, each room has a small kitchenette and patio.
AFTERNOON: Apollonia and Artemonas
After getting settled, stretch your legs on a leisurely walk from Apollonia to Artemonas…and be sure to bring your camera!
The stepped pedestrian walkway passes by quintessential Cycladic architecture: white walls, blue domes and brightly painted doors.
Circle back to Apollonia via Trail #7 and 7A. The old path takes you on a short jaunt through the countryside before ending right back where you started. See the highlights in this video.
EVENING: Drinks and Meze in Apollonia
Make your way back to Apollonia for dinner. Walk along To Steno – which translates to Narrow Street – the main pedestrian artery through town.
Lined with shops, restaurants and bars, it’s a lovely place to stroll…and superb place to dine and imbibe!
For a refreshing early evening beverage, find a seat on the patio at Tselementes – then head to Kafeneio Drakakis for food.
With a menu of contemporary meze and tables that spill out onto the walkway, it’s one of our favorite Sifnos restaurants. (Make reservations in the high season.)
DAY 7: Hike Around Sifnos
Lace up and hit the trails today as you explore some of the most beautiful landscapes on the island of Sifnos.
MORNING: Hike to Kastro
Some of the best hiking trails here depart from Apollonia. We recommend routing your way to Kastro, a hilltop village that overlooks the sea.
Follow path #3 from Apollonia to Kato Petali, then hike over hills, into valleys and past churches. (Go inside any that have unlocked doors!)
When the trail splits, follow route #1 that meanders through the gorge. As you walk amongst terraced farms, you will get your first peek of Kastro atop the hill in the distance.
Top Tip: Get a preview of the walk in this video and check out more treks in our guide to Hiking on Sifnos Island.
AFTERNOON: Kastro Exploration
When you reach Kastro, pop into the Diporto shop for a take-away lunch (spinach pie is our top choice).
Take your time discovering all the nooks and crannies in the maze-like town – from the crumbling castle remains to the Church of the Seven Martyrs.
When you are ready, continue north through the coastal botanical garden to Panagia Poulati Church. From there, make the long slog up to Artemonas and then back to Apollonia.
EVENING: Traditional Grill
It’s been a big day, so keep dinner simple at Ex Steno. While their moussaka gets high praise, we couldn’t resist the grilled meats. In fact, we stopped here more than once for chicken gyros!
DAY 8: Relax in Sifnos
Slow your pace today and enjoy some time on the coast – then feast on a classic country dinner.
MORNING: Chrisopigi Monastery
After a breakfast of savory pastries (Vegeraki and Threefolds are both great), make your way to Chrisopigi Monastery via the town of Faros.
The 17th century church was built on a rocky cape that is separated from the mainland by a narrow channel. It’s one of the most important landmarks on Sifnos.
You can actually hike to Chrisopigi from Apollonia, but we suggest taking the bus to Faros. From there, it’s a short – and incredibly scenic – 1 mile coastal walk to the monastery. Watch the video highlights!
AFTERNOON: Faros Beach
After visiting the monastery, double back toward Faros. Sit down to a long and leisurely lunch at one of the beachfront restaurants.
Then, settle in for an afternoon of sun and sand. Soak in the warm rays. Swim in the crisp water. Bounce between the beaches.
EVENING: Authentic Sifnos Food
On your last night on Sifnos, get a taste of local island flavors at Kelari, an inconspicuous – but oh-so-popular – restaurant in Kato Petali.
The family-run eatery excels at creating Sifnos farm-style food using a wood-fired oven and traditional recipes.
The house specialties – Mastelo (slow-cooked lamb) and Revithia (chickpea stew) – are the stars of the show, but the atmosphere was a close runner-up!
DAY 9: See the Sights in Milos
It’s time to travel to Milos, the final destination on your 10-day Greek island-hopping vacation. Make the most of your short time here by getting right to some of the best sights!
MORNING: Ferry and Check In
Ferries to Milos dock in Adamantas – also known as Adamas – which is where you should base yourself.
We stayed at Joannes Vacation Rooms, which offers good value for money. The room, while basic, had everything we needed for our longer stay, including a small kitchenette.
That said, it’s situated on the far side of town – and with just two nights, you might want to be more centrally located. Semiramis Guesthouse has decent rates and gets great reviews.
AFTERNOON: Plaka
After getting settled in, stop by Artemis Bakery (the location right next to the main bus stop) and get a slab of Ladenia – Greek-style pizza bread – for a filling lunch.
Then, get on a bus headed for Plaka. Characterized by winding lanes, artisan shops, classic island architecture and mesmerizing vantage points, Plaka is a Milos must-see!
At the top of the town is the 13th century Venetian Kastro – and it’s definitely worth hiking up the stairs to take in the panoramic views. Watch our video reel for highlights.
Milos sights within walking distance of Plaka are the replica statue of Venus de Milo and the colorful Klima fishing village. We outline how to see these and more in our Milos Travel Guide.
EVENING: Traditional Dinner
On your first night in Milos, sit down at a family-run establishment for a traditional meal.
O! Hamos! is one of the island’s most popular restaurants…and for good reason. The atmosphere is jubilant and their signature slow-roasted pork is melt-in-your-mouth delicious!
DAY 10: Milos Sea Adventures
Wrap up your Greece 10-day vacation by discovering some of the best Milos Island seascapes.
MORNING: Sarakiniko Beach
Milos is marked with staggering scenes formed long ago by explosive volcanoes – and nowhere is that more evident than at Sarakiniko.
Featuring moon-like terrain, the otherworldly beach is a fun place to explore. Just be sure to wear durable shoes and don’t forget your travel camera!
After clambering on the rocks and into the caves, take a refreshing dip in the cove of sparkling blue water. Watch our Sarakiniko reel!
Transit Tip: The beach is only about 2 miles from Adamas, but there is a convenient public bus that goes right to Sarakiniko. It runs during the summer and shoulder season.
AFTERNOON: Milos Sunset Cruise
Be back in Parikia by mid-afternoon so that you can set off on this sailboat cruise. We absolutely loved this boat trip and feel it’s the perfect way to cap off your island-hopping adventures!
Marvel at the fascinating coastline, enjoy a delicious on-board meal and swim around astounding Kleftiko Bay. As you sail back toward Adamas, watch as the sun fades towards the horizon. Watch our video.
EVENING: Last Look at Milos
Back on land by twilight, stroll along the harbor while admiring the twinkling lights and floating boats as you bid Greece a final farewell.
If you are not quite ready to call it a night, snag a seat at Egoist for a Greek mojito – and if you want a late-night snack (like we did), satisfy your cravings at Gyros de Milos!
Greek Island Hopping Travel Tips and Logistics
Our detailed itinerary outlines what to do and where to stay and eat – but there is a lot more that goes into planning your Cycladic holiday in Greece!
Best Time To Go to the Greek Islands
This largely depends on your desired activities. For us – as we were more interested in hikes and exploring villages vs beaches and nightlife – visiting in the spring was optimal.
The weather can be a bit unpredictable, however most days are sunny and temperatures are just right for enjoying the outdoors (but perhaps too cold for swimming). Spring is also an ideal time for budget travelers, like us!
A downside to visiting Greece in the spring is that things are not fully up and running. Bus routes are reduced, some restaurants are still closed and the sounds renovations may echo across the islands.
How To Get to the Islands in Greece
Our outlined 10-day Greece Itinerary showcases what to do on the islands – but you will still need to figure out how to get there!
Flying is a popular option – but you don’t have to use Athens International Airport (ATH). There are seasonal flights to Santorini (JTR) from major European cities in the UK, France, Italy and Germany (among others).
Before purchasing plane tickets, read our Tips for Finding Cheap Flights – then use Skyscanner to find the best routes for your trip.
Once you’ve got that sorted, check out Ferryhopper to compare schedules and prices for getting between the islands.
How To Get Around the Cyclades
For our trip, we used buses, our own two feet and a couple of taxis to make our way around. Each island’s public transportation system operates a little bit differently.
Here’s the official websites: Santorini Bus Info | Paros Buses | Sifnos Bus Website | Milos Bus Schedule and Fares
What To Pack for a Greek Island-Hopping Itinerary
Okay, it’s time pull out your suitcase (or backpack), so grab our FREE Checklist. and let’s get you to the Greek Isles!
While it might be tempting to only bring your favorite flip flops when island hopping for 10 Days in Greece, you actually will want good walking shoes. Read our guide to the Best Shoes for Travel.
All 4 of these islands are incredibly photogenic! We shoot with a DSLR Canon Rebel. It’s a phenomenal camera at a budget-friendly price.
The sun is strong in Greece! Bring plenty of sunscreen (it’s costs a bundle here) – and a wide-brimmed hat, too. Of course, don’t forget your favorite sunglasses.
Travel Planner
When traveling to multiple islands in Greece, it can be a real struggle to keep all the details organized. That’s why we rely on our Printable Travel Planner!
Start planning your trip to Greece! Search for the lowest airfares, the best accommodations and fun things to do…then start packing! Want additional advice? Head over to our Travel Planning Page and for country-specific information, take a look at our Travel Guides Page!
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