Greece is more than just a destination – it’s a place where ancient history meets breathtaking landscapes, delicious food, and an atmosphere that makes you feel like you’ve stepped into a dream. From the sun-soaked beaches to the stunning whitewashed villages clinging to cliffs, Greece is a picture perfect dream. If you’re planning your own Greek island hopping itinerary, the Cyclades is the place to be.
The Cyclades offers the kind of scenery you’ve seen in countless postcards and movies. Think white-washed cobblestone streets covered in pink bougainvillea, side-by-side with some of the brightest waters you’ve ever seen.
This 12-day Greek island hopping itinerary will take you through Athens, where you can walk in the footsteps of ancient philosophers, and then set sail to Paros, Milos, and Santorini – three iconic islands that showcase the best of Greek island life.
While this guide is built for a perfect 12-day timeline, it’s flexible enough to adjust based on your schedule. Have less time? You can shorten it. Want to stay longer? Feel free to add a few extra days of relaxation and exploration.
Planning your own Greek island trip? Check out my complete Greece Travel Guide for island pairings, travel tips, and how to make the most of your time.
Table of Contents
Quick Snapshot of the Timeline
- Athens, 2 Nights: Start your journey in Athens, where you’ll immerse yourself in ancient history and explore vibrant neighborhoods.
- Paros, 3 Nights: Discover picturesque villages, relax on stunning beaches, and enjoy seaside dining at charming local restaurants.
- Milos, 4 Nights: Unwind on secluded beaches, take a boat tour of the island’s dramatic coastline, and explore its stunning natural landscapes.
- Santorini, 1 Night: Experience the iconic blue domes, breathtaking sunsets, and panoramic views that make Santorini a must-see.
- London, 1 Night: Wrap up your trip with a relaxing night in London before heading back to the US.
When’s the Best Time to Visit the Cyclades?
While the Greek islands you see in photos are often bustling during peak summer, each season offers a different vibe. Whether you’re after lively crowds and sun-soaked beaches or a quieter, more laid-back experience, choosing the right time to visit will help you get the most out of your Greek island getaway.
- High Season (June – August): If you enjoy a lively atmosphere with plenty of sun, this is the time to visit. However, keep in mind that the islands will be busy. You’ll need to book ferries and accommodations early to avoid higher prices and overcrowding.
- Shoulder Season (April – May & September – October): For more mild weather and fewer crowds, aim for the shoulder season. The weather is still warm, but you’ll have a more relaxed experience, and you’ll find better deals on accommodations and ferries.
- We ended up visiting in May and found the weather to be perfect! It was still busy but not overwhelmingly so. And, the water was cool, but still swimmable!
- Low Season (November – March): The islands are quiet, with cooler temperatures, fewer activities, and some closures. If you’re looking for peace and quiet, this would be your best bet, but be prepared for a lot of the islands to have limited services.
Travel Tips & Local Etiquette
When visiting Greece, it’s important to be aware of local customs to make your trip even more enjoyable. Here are a few tips:
- Greetings: Greeks are some of the warmest and friendliest people! While on the islands, most people do speak English but learning a few key words really goes a long way. Try to learn a few simple words like “Kalimera” (Good Morning) or “Kalispera” (Good Evening) – it will be beyond appreciated!
- Tipping: Tipping is not mandatory but is still appreciated. But unlike in the US, a 20% tip is not the standard. For meals, you can leave around 5-10% if the service is good. And, in cafes and smaller restaurants, rounding up the bill is totally fine. For taxi drivers, rounding up the fare or leaving a couple of euros is the standard.
Transportation & Getting Around
Getting around Greece is relatively easy with plenty of transportation options available.
- Athens: Athens has an extensive public transportation network, including a metro, buses, and trams. The Athens Metro is super easy to work, and is also the fastest and most convenient way to get to the main attractions like the Acropolis. You can also take taxis, which are easy to find, or even Ubers if needed.
- Paros & Milos: Renting a car or an ATV is the best way to explore these islands. Paros and Milos have a mix of narrow streets and rough terrain, so an ATV is perfect for getting to some of the more remote beaches. Make sure to book your rental car or ATV in advance during the high season.
- Santorini: The individual cities on the island are small enough to explore by foot, but taxis and buses are also available for longer trips, especially for getting from Oia to Fira. Be prepared for a lot of traffic in Oia, especially around sunset.
- Ferries: Ferries are the most popular way to travel between islands. It’s definitely better to book your ferry tickets in advance, especially during the summer. Ferries between islands like Athens to Paros (4 – 5 hours) and Paros to Milos (1.5 – 2 hours) run regularly in the peak months, but always check schedules ahead of time.
Booking Ferries & Island Hopping Tips
Island hopping is one of the best parts of a Greek island adventure, and ferries are the best way to get between islands. Greece has one of its most extensive and serviced ferry system in the Cyclades, so it’s quite easy to hop around. Here’s everything you need to know:
- How to Book: Ferryhopper is my go-to platform for booking ferries across the islands. It’s simple to use, and you can compare prices and schedules in one place. We booked all of our ferries at once on the site. They also have an app where you can view your tickets and track your ferry. Just be sure to book in advance, especially during high season (May – September).
- Travel Times: You’ll have the option of high-speed ferries (faster, 2 – 3 hours, but more expensive and sometimes bumpier) or traditional ferries (slower, 4 – 5 hours, more affordable, and relaxed). The high-speed ones tend to be more popular, especially for shorter trips.
- Upgrading Your Seat: We opted to upgrade our seats and it made a big difference. For a small extra cost (typically €10 – 15 each), you get more space, quieter areas, and better views. It’s definitely more relaxing, especially on longer rides. The downside? It costs a little more, and not every ferry offers the upgrade, but if you can, it’s worth it for a comfy ride.
- Luggage: When you get on the ferry, you’ll be ushered through the luggage storage on the bottom level. You can leave your bags there, as you’ll be exiting this way, too. Make sure to keep your valuables on you, though! Since we only traveled with cary-ons, we actually were able to just bring ours up, but you will have to climb stairs with them.
- Tips: Be sure to arrive at the port 30 – 45 minutes before departure to avoid any last-minute stress. It’s also easier to travel with light luggage, especially during busy months when ferries can get crowded.
Budgeting & Costs
You can definitely do a Greek island vacation on the high end of the budget, but it’s also possible to keep it more budget-friendly. It’s just helpful to know what to expect when it comes to costs ahead of time.
- Accommodations: Budget accommodations like hostels or guesthouses will cost around €40-70 per night for a double room. Mid-range hotels range from €80-150 per night, while luxury stays can be €200+ per night.
- Meals: You can find affordable meals for €10-15 in local tavernas. A meal at a mid-range restaurant will cost around €20-40 per person. And for upscale dining, expect to pay €50+ per person.
- Transportation: Ferries between islands can range from €40-150 per person, depending on the route. Public transport in Athens is very affordable, with a single metro ticket costing around €1.20.
- Activities: Entrance fees to popular historical sites like the Acropolis cost around €10-20. Boat tours in places like Milos or Santorini can cost around €40-150 depending on the type of tour.
- Overall Approximate Cost: On average, you can expect to spend around $2,000 – $3,500 per person for a 12-day trip, depending on how luxurious you want to go. This includes flights, accommodation, meals, ferry rides, and activities. If you’re looking to stay on the more affordable side, you can definitely find options that bring it closer to the lower end of the range, especially with careful planning.
Packing Tips
Here’s what to pack to make your trip to the Cyclades comfortable and stress-free:
- Clothing: Pack light, breathable clothing for warm weather, including flowy dresses, shorts, and tank tops. Bring a light jacket or sweater for cooler evenings.
- Swimwear: You’ll be spending a lot of time by the sea, so pack a couple of swimsuits. A beach cover-up is essential when you’re not in the water!
- Packing Cubes: These were the absolute best in helping me stay organized when moving between so many locations on one trip, while also still allowing me to fit SO much more than I thought I could in my carry-on.
- Shoes: Comfortable sandals for walking around the islands and exploring, plus a sturdy pair of sneakers for more rugged hikes or long days exploring towns – there’s plenty of days where you’ll be getting 20,000 steps.
- Accessories: Definitely bring a hat and sunglasses for sun protection, plus a good sized bag for beach days or shopping around towns.
- Extras: Don’t forget sunscreen, a portable charger, a voltage converter, and a reusable water bottle.
Staying Connected While Abroad
When you’re traveling abroad, using an international plan on your US cellular can get pretty expensive. We found Airalo to be the easiest and most affordable option. Their eSIMs for Greece start at $5 USD for 1GB of data valid for 7 days, and go up to $49 USD for 20GB.
How it works: Download the Airalo app, choose the data plan that fits your needs, and activate the eSIM directly from your phone. And, you can monitor your data usage, upgrading if you need.
We ended up purchasing the $15 plan for 5GB, and didn’t even get close to hitting the full 5GBs. Compared to the $10 per day Verizon would have charged, I’d consider that a steal!
12 Day Greek Island Hopping Itinerary Breakdown
Athens (2 Nights)
While Athens is a city known for it’s rich history, it does offer an incredible mix of ancient history and a cool, vibey culture. With two nights here, you can spend a full day seeing the iconic ruins of the Acropolis and other historical sites. And, you’ll also have time to wander through neighborhoods like Plaka and explore Athens’ lively cafes, restaurants, and nightlife. Stay in Psiri or Plaka for the easiest access to all the hot spots.
Where to Stay:
- Luxury: Hotel Grande Bretagne: A classic, high-end hotel offering luxury accommodations with views of the Acropolis, located in the heart of Athens. Perfect for those looking to indulge in style.
- Mid-Range: Plaka Hotel: A comfortable and affordable option located in the charming Plaka neighborhood. Great for those who want to be close to the main attractions and enjoy a welcoming vibe.
- Budget: City Circus Athens: A stylish, budget-friendly boutique hotel in the Psiri area, offering a relaxed atmosphere with a touch of local flair. Ideal for travelers looking for a cool, budget-conscious stay.
What to Do:
Day 1: Arrival Day & Major Historical Sites
- Make your way to the iconic Acropolis at opening hour, 8AM, and check out the Parthenon, Temple of Athena Nike, and the Erechtheion.
- Afterward, walk over to Hadrian’s Arch and the Temple of Zeus for more ancient wonders.
- Stroll through Plaka, shop for souvenirs, and enjoy a leisurely lunch at one of the charming cafés in Anafiotika, the neighboring charming village.
- For dinner, check out a rooftop restaurant in Monastiraki Square for sweeping views of the Acropolis.
Day 2: Explore More & Unwind
- Start the morning at the Ancient Agora and Temple of Hephaestus, two must-see ruins.
- Spend some time wandering through Monastiraki Square for its vibrant market and lively atmosphere.
- For lunch, try a traditional taverna in Psiri, known for its cozy vibe and delicious Greek dishes.
- In the evening, explore the streets of Psiri for dinner and nightlife.
Want to explore more Athens? Dive into my 36 Hours in Athens Itinerary.
Paros (3 Nights)
Paros is the perfect island escape with its serene beaches, traditional villages, and relaxed vibe. It feels like a quintessential Greek island, with the white cobblestone streets, making it the perfect first island to stop at.
Three nights here give you enough time to discover its best spots, including the charming town of Naoussa, the mountain village of Lefkes, and the beaches of Antiparos. You’ll have plenty of time to unwind without feeling rushed, and you’ll experience the true essence of island life. Stay in Naoussa for the best proximity to the action.
Where to Stay:
- Luxury: Parilio, a Member of Design Hotels: A sophisticated, minimalist hotel offering luxury in a stunning setting, ideal for those looking for a serene retreat with high-end amenities.
- Mid-Range: Saint Andrea Sea Side Resort: Located near Naoussa, this charming resort offers a blend of comfort and modern design, with easy access to beaches and the lively town atmosphere.
- Budget: Lilly’s Residence: A budget-friendly option offering cozy rooms and a welcoming atmosphere. It’s perfect for travelers who want a laid-back stay in Naoussa without breaking the bank.
What to Do:
Day 1: Village Hopping
- Start your day with brunch in Parikia, exploring its charming shops and cafés.
- Afterward, drive to Lefkes, a peaceful hilltop village with narrow streets and breathtaking panoramic views.
- In the evening, head back to Naoussa for dinner at Sigi Ikthios, a cozy seafood spot known for its fresh catch.
Day 2: Paros Park
- Spend the morning hiking or relaxing at Paros Park, where you can explore scenic trails and hidden beaches.
- For lunch, enjoy fresh seafood at Taverna Vigla, a beachfront gem.
- In the afternoon, head to Kolymbithres Beach, famous for its unique granite rock formations and crystal-clear water, perfect for swimming.
- Grab dinner & drinks at Come Back Bar, with a few right on the water, and enjoy the beautiful sunset.
Day 3: Antiparos Adventure
- Rent your own boat or take the ferry to Antiparos, a tranquil island just across the water from Paros. Spend the day exploring its secluded beaches and quaint town.
- After a relaxing day, return to Paros and enjoy dinner at Souvlaki Kargas, the best gyro spot in Naoussa with really affordable prices.
For more tips on Paros, read the check out my 3-Days in Paros Itinerary.
Milos (4 Nights)
Milos is one of Greece’s hidden gems, with rugged landscapes, striking beaches, and spectacular natural formations. It’s a perfect island for more adventurous types, where you can rent ATVs and explore all the beaches & villages. Four nights here allows you to fully experience the island’s unique character, and since the villages & beaches are spread out, it gives you time to see it all. I’d recommend staying in Plaka, Adamantas, or a quaint fisherman village for the true Milos experience.
Where to Stay:
- Luxury: Milos Breeze Boutique Hotel: A beautiful, adults-only hotel with stunning views of the Aegean Sea. Known for its luxurious rooms and excellent service, it’s perfect for a romantic getaway.
- Mid-Range: Terra Mare Milos: A boutique hotel with a beautiful design and a relaxed vibe, offering excellent value for a mid-range option. It’s located near Pollonia, making it a great base for exploring the island.
- We stayed here on our trip, and it was perfection! Check out my Terra Mare Hotel Review for a more in-depth look at our stunning stay.
- Budget: Joannes Vacation Rooms: A simple, budget-friendly option located in the island’s main town. It’s a great pick for those looking for a no-frills stay that’s both affordable and convenient.
What To Do:
Day 1: Evening Arrival & Relax
- Arrive in Adamantas, pick up your rental car, and settle into your accommodation.
- Spend the evening exploring the town and have a chill dinner at Gyros of Milos.
Day 2: Full Day Boat Tour
- Take a full-day boat tour to Kleftiko, a stunning cove with white cliffs and hidden caves, perfect for swimming and snorkeling.
- After the boat tour, check out O! Hamos! Tavern for dinner, a local Greek tavern famous for its seafood and cozy vibes.
Day 3: Beaches & Villages
- Head to Sarakiniko Beach in the morning, one of the most famous beaches on the island, known for its moon-like white rock formations, crystal-clear water and cliff jumping.
- Afterward, head to Mandrakia, a colorful fishing village, for a seafood lunch at Medusa – get the vinegar octopus!
- Spend the evening at Firopotomous village, relaxing on the beach and enjoying the stunning scenery.
- End your day with dinner at Archontoula in the hilltop town of Plaka, where you can check out the view of sunset before sitting down at the street-side tavern.
Day 4: ATV Adventure & More Beaches
- Rent an ATV and explore the southern beaches of Tsigrado and Firiplaka, both offering seclusion and crystal-clear waters.
- In the afternoon, visit the Sulfur Mines after picking up a quick gyro for lunch, and hike down to the beach to explore the abandoned mines and experience the unique landscape.
- End the day with a sunset dinner at Astakas in Klima, another charming seaside fisherman’s village.
For a deeper dive into Milos, read my complete 4-day Milos Itinerary.
Santorini (1 Night)
Santorini is an island that needs little introduction. It’s definitely a bucket-list destination, famous for its stunning sunsets, whitewashed buildings, and blue-domed churches. While one night might seem short, it’s still enough to take in the iconic views and experience the magic of the main town, Oia.
Where to Stay:
- Luxury: Oia Spirit Boutique Residences: Located just steps from the iconic blue domes of Oia, this boutique hotel offers stunning caldera views, private plunge pools, and a serene atmosphere.
- We stayed here and it was absolutely worth the splurge! Check out my review HERE.
- Mid-Range: Old Castle Oia: A charming hotel in Oia with beautiful views and a welcoming atmosphere, offering great value for a mid-range stay in this iconic location.
- Budget: Olympic Villas: Located near Oia, this budget-friendly hotel offers stunning views and comfortable rooms without the hefty price tag, giving you a great Santorini experience on a budget.
What to Do:
Day 1: Arrival & Oia
- Check into your hotel and explore the streets of Oia, known for its iconic whitewashed buildings and narrow, picturesque streets.
- Find a great spot to watch the famous Santorini sunset from Oia Castle, the perfect spot for photos – or if your hotel has a view, stay in and enjoy the colors!
- After the sunset, grab one of the best gyros in town from Pitagyros.
Day 2: Oia & Ammoudi Bay
- Enjoy a leisurely breakfast at your hotel, then head back to Ammoudi Bay for an amazing seafood lunch. The trek to Ammoudi is down a long flight of stairs, so make sure to wear comfy shoes!
- Take one last stroll through Oia for some shopping before heading to the airport.
Want more Santorini tips? Check out my complete 24-Hours in Santorini Itinerary.
London (1 Night)
Our flight back to the US left the following morning out of Heathrow, so we chose to spend a quick night in London to give us enough time to relax and not stress about any delays messing with our big travel day back. While we thought about going into town for the night, staying at the Sofitel, directly connected to Heathrow, was the easiest move after a many days of travel.
The hotel’s chill vibe made it the perfect place to unwind. With everything we needed right there – from a relaxing spa treatment to just kicking back for a quiet night in – it turned out to be the ideal way to end our trip and prepare for the long journey home.
What To Do:
Evening
- After your flight from Santorini, check into Sofitel London Heathrow for a chill stopover.
- Schedule a spa treatment or a couples massage to unwind, and take advantage of their lovely co-ed pools.
- Then head to one of the multiple restaurants onsite for dinner, and relax for the evening.
Morning
- Start your day with breakfast at the hotel or order in room service.
- When it’s time to head back to the airport, it’s a super easy 5-minute walk to connect back. If you need to switch terminals, just hop on the tram, which is only a few minutes’ walk away. Navigating was such a breeze, it really made the night at the hotel worthwhile.
Your Greek Island Hopping Experience Awaits!
This 12-day Greek Island Hopping Itinerary takes you through some of the most beautiful spots in the Cyclades. From the rich history of Athens to the stunning beaches of Paros, Milos, and Santorini, you’ll get the perfect mix of sightseeing, relaxation, and those postcard-worthy moments. Whether you’re new to Greece or coming back for more, this guide helps you make the most of your time on the islands.
You’ll experience the best of Greece without feeling rushed, from Athens’ ancient ruins to the idyllic beaches of Paros, Milos, and Santorini. Plus, a quick stop in London adds a nice touch to wrap up your adventure.
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