Best Cyclades Island Hopping Itinerary (2024)
Are you planning an island hopping trip in the Cyclades and looking for the ultimate Cyclades Island hopping itinerary? With over 220 islands waiting to be explored, choosing the best Cyclades Islands to visit can feel overwhelming – but you’re in the right place!
The Greek islands are among my absolute favorite summer destinations in Europe and I’ve done several Greek island hopping trips over the last years. That’s why I’m thrilled to share the perfect 3-week Cyclades Island hopping itinerary with you, featuring the absolute highlights and the must-visit islands you won’t want to miss, along with some alternative routes for 7, 10, and 14 days if you’re short on time!
Believe me when I tell you, it’s such a dream to explore the Cyclades Islands – they hold a special place in my heart! I hope our comprehensive Cyclades travel guide will help you plan the perfect island hopping trip and make the most of your time in the Cyclades. Keep reading for our personal insider tips and recommendations, and get ready to discover iconic islands like Santorini and Mykonos, as well as underrated gems such as Naxos, Paros, and Antiparos.
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How to Get to the Cyclades Islands
If you’re traveling internationally, flying to Athens is often the most convenient starting point. From Athens, you can easily connect to the Cyclades Islands via domestic flights or ferries.
💡 I highly recommend adding a 2-day visit to Athens to your Greece itinerary if you haven’t explored the capital city yet.
Additionally, several Cyclades Islands, such as Mykonos and Santorini, have their own airports, allowing for direct flights from major European cities. Flying directly to Mykonos is ideal if you’re short on time, as this is the first stop on our itinerary.
Alternatively, taking a ferry from Athens’ Port of Piraeus offers a scenic route and allows you to experience the beauty of the Aegean Sea while saving some money, as ferry tickets from Athens are often more economical compared to flight tickets.
How to Travel Between the Cyclades Islands?
When it comes to traveling between the Cyclades Islands, ferries are undoubtedly the best choice. With their frequent schedules and routes connecting all Cycladic islands, ferries offer the best flexibility and convenience.
Tip: I recommend booking your ferry tickets in advance, especially during the peak tourist season. This way, you can secure the best departure times and prices, plus avoid any last-minute hassles, ensuring a stress-free island hopping experience in the Cyclades.
We absolutely enjoyed traveling by ferry in Greece because the ferries are very comfortable, provide scenic views, and offer a seamless way to hop from one island to another. Despite being slightly more expensive, we always opt for speed ferries, as they allow us to maximize our time on the islands.
⛴️ BOOK YOUR FERRY TICKETS WITH FERRYHOPPER
Effortlessly plan your ferry trips and island hopping in Greece with Ferryhopper. Get all ferry schedules, including direct and indirect connections between islands, and book your tickets at the lowest prices with no hidden fees. You can also compare schedules, ferry companies, and prices to choose the best route.
How to Get Around on the Cyclades Islands
While public transportation options such as buses are available on most Cyclades Islands, I highly recommend renting a car for the ultimate freedom and flexibility. A rental car allows you to explore the islands at your own pace and maximize your time.
During our visits, we rented a car on every islands and found it to be the perfect way to navigate the diverse landscapes and attractions – especially considering the Cyclades’ sometimes windy conditions, which may not always be ideal for alternatives like scooters or ATVs.
Renting a car is very easy and straightforward on the Cyclades Islands, and gives you easy access to even the most remote areas of the islands. This way you can discover off-the-beaten-path places, authentic local towns, and secluded beaches, which you often cannot easily reach by public transportation.
🚘 MY GO-TO CAR RENTAL COMPANY: DISCOVER CARS
When booking a rental car online, I personally recommend and always use Discover Cars. They search not only for international car rental companies but also for small, local agencies to find the best deal for you. Plus, there are no hidden costs and they offer free cancellation. I always opt for full coverage because of their comepetitive rates!
Best Time to Visit the Cyclades Islands
The best time to visit the Cyclades largely depends on your preferences and the islands you plan to visit. While the peak summer months of July and August offer warm weather and a bustling atmosphere, they also bring along large crowds and higher prices.
For a more relaxed experience, I recommend visiting during the shoulder seasons – either at the beginning or the end of the peak travel season. In my opinion, the best months to visit the Cyclades are May, June, and September. During these times, the weather remains pleasant, the tourist crowds are smaller, and accommodation prices are more affordable.
This allows for a more authentic experience, where you can fully immerse yourself in the local culture and enjoy the stunning landscapes without the hustle and bustle of peak season. Plus, you’ll have more flexibility in booking accommodations and activities, making it easier to create your ideal Cyclades adventure.
Please keep in mind that the off-season, typically between mid-October and mid-April, isn’t ideal for island hopping in the Cyclades. During this time, ferries run less frequently or may even be suspended on some routes. Additionally, it’s more challenging to find accommodations, restaurants, and shops, as many of them are closed during the off-season.
3-Week Cyclades Island Hopping Itinerary Overview
Below, you can find a breakdown of the perfect 3-week Cyclades Island hopping itinerary for first-time visitors, which includes the absolute highlights and the best Cyclades Islands you can’t miss!
- Day 1 – 4: Mykonos & Delos
- Day 4 – 8: Paros & Antiparos
- Day 8 – 12: Naxos
- Day 12 – 16: Santorini
- Day 16 – 21: Milos
In the following, you’ll find more information about our 3-week island hopping route, including helpful insights into each of the islands featured in our itinerary. Explore the best of the Greek islands with our ultimate guide!
Complete 3-Week Cyclades Island Hopping Itinerary
Day 1 – 4: Mykonos & Delos
The Cyclades Island of Mykonos is known for its lively atmosphere, traditional Cycladic architecture, beautiful beaches, and cosmopolitan charm. It’s one of the most popular islands in the Aegean Sea and offers a perfect blend of history, culture, and relaxation.
In the Old Town of Mykonos, also known as Chora, you can wander through narrow alleys lined with whitewashed buildings, small boutiques, and vibrant bougainvillea, while soaking in the quintessential Greek atmosphere.
Must-visit spots include the Old Port, Little Venice, with its colorful balconies overlooking the sea, the famous windmills of Mykonos, and the iconic Panagia Paraportiani Church.
Mykonos is also renowned for its stunning beaches and lively beach bars, so make sure to include some relaxation time at the beach during your time in Mykonos.
As evening falls, Mykonos comes alive with its legendary nightlife. I recommend indulging in a dinner at a seafront restaurant, embarking on a sunset boat cruise, and experiencing the vibrant club scene.
For a cultural excursion, you shouldn’t miss a day trip to Delos, a nearby island and UNESCO World Heritage Site steeped in history and mythology.
Mykonos: Quick Tips
🛏️ Accommodation: Stay at Myconian Avaton
🚘 Car Rental: Find the best Car Rental Companies in Mykonos
📌 Top Places to Visit: Chora, Little Venice, Kato Mili Windmills, Old Port, Delos Island
📲 Stay Connected: Get your Europe eSIM
⛵ Best Experiences & Tours:
• Mykonos Sunset Boat Cruise (my top tip!)
• Delos Guided Day Trip (a must-do!)
• Mykonos Wine Tasting and Vineyard Tour (perfect for wine lovers)
• Mykonos Greek Cooking Class (the best Mykonos food experience)
• Delos and Rhenia Islands Cruise with BBQ Lunch (great alternative to a standard Delos tour)
➡️ Check out my complete Mykonos Travel Guide for our detailed Mykonos itinerary, including the best things to do, must-visit places, and my top insider tips!
Day 4 – 8: Paros & Antiparos
Paros, a gem in the heart of the Cyclades, is famous for its traditional villages, beautiful landscapes, and crystal-clear waters. The island boasts some of the best beaches in the Cyclades. Paros is hands down one of my favorite islands in Greece!
One of the highlights of Paros is the charming fishing village of Naoussa, with its picturesque harbor and vibrant waterfront lined with lovely tavernas and cafes. I especially loved getting lost in the labyrinthine alleyways of Naoussa. The small town exudes a laid-back atmosphere that’s truly captivating!
Make sure to also visit Parikia, the capital of Paros, as well as the picturesque mountain villages of Lefkes, Kostos, Prodromos, and Marpissa for a glimpse into authentic island life.
If you are a beach lover, I recommend exploring Paros’ magnificent beaches, such as Golden Beach, Monastiri Beach, or Kolymbithres Beach. Kolymbithres Beach is known for its crystal-clear waters and unique rock formations and belongs to my favorite beaches in the Cyclades.
No trip to Paros would be complete without visiting Antiparos, the small sister island of Paros. Accessible via a quick 10-minute ferry ride, Antiparos features a charming Old Town and a breathtaking coastline with the most stunning, untouched beaches.
Paros: Quick Tips
🛏️ Accommodation: Stay at Mr & Mrs White Paros
🚘 Car Rental: Find the best Car Rental Companies in Paros
📌 Top Places to Visit: Naoussa, Parikia, Lefkes, Antiparos, Kolymbithres Beach
📲 Stay Connected: Get your Europe eSIM
⛵ Best Experiences & Tours: Sailing Cruise with Greek Lunch & Wine (my top tip!)
➡️ Check out my complete Paros Travel Guide for our detailed Paros itinerary, including the best things to do, must-visit places, and my top insider tips!
Day 8 – 12: Naxos
Naxos, the largest island in the Cyclades, captivates with its rich history, ancient archaeological sites, beautiful beaches, and charming villages.
Chora, the main town of Naxos, features a picturesque labyrinth of narrow alleys, whitewashed houses, and Venetian architecture. Here, you can stroll through the enchanting streets, visit the iconic Kastro (Naxos Castle), and marvel at the ancient Portara, the monumental entrance to the Temple of Apollo.
For history enthusiasts, Naxos boasts several archaeological sites worth exploring, including the Dionysus Temple and the Temple of Demeter in Sangri. Meanwhile, the charming villages of Halki and Filoti offer a glimpse into traditional island life with their quaint tavernas and cobblestone streets.
Don’t miss out on Naxos’ pristine beaches! From the golden sands of Agios Georgios, Agia Anna, and Agios Prokopios to the secluded coves of Alyko Beach, Hawaii Beach, and Mikri Vigla Beach, the island is home to some of the best beaches I’ve ever seen in Greece.
💡 Insider Tip: Close to Naxos are the Small Cyclades. I recommend reserving one full day for a Small Cyclades Island Hopping Tour to the picturesque Greek islands of Kato Koufonisi and Ano Koufonisi. They are one of the best-kept secrets of the Cyclades!
Naxos: Quick Tips
🛏️ Accommodation: Stay at Naxos DownTown Apartments & Suites
🚘 Car Rental: Find the best Car Rental Companies in Naxos
📌 Top Places to Visit: Chora, Portara, Agia Anna, Demeter Temple, Halki, Filoti, Apeiranthos
📲 Stay Connected: Get your Europe eSIM
⛵ Best Experiences & Tours:
• Koufonisi Cruise (my top tip!)
• Naxos Highlights Tour (see all of Naxos’ highlights in one day)
• Naxos Town Food Tour Including Tastings and Wine (try Naxos’ famous cheeses)
• Naxos Half-Day Cooking Class (perfect for food lovers)
• Naxos Luxury Catamaran Cruise with Lunch (an unforgettable experience)
➡️ Check out my complete Naxos Travel Guide for our detailed Naxos itinerary, including the best things to do, must-visit places, and my top insider tips!
Day 12 – 16: Santorini
An island hopping trip in the Cyclades wouldn’t be complete without visiting Santorini! It’s probably the most iconic island in the Cyclades and an absolute must-visit destination!
Santorini is renowned for its breathtaking sunsets, stunning landscapes, and picturesque villages perched atop dramatic cliffs. I can totally understand why Santorini is so popular – I completely fell in love with its unique beauty and romantic atmosphere.
The island’s main towns of Fira, Imerovigli, and Oia offer enchanting experiences, from strolling through picturesque alleys leading along whitewashed buildings and blue-domed churches to admiring panoramic views of the caldera.
Insider tip: For a taste of Santorini’s culinary delights, head to Amoudi Bay for a seafood lunch by the water, or enjoy a wine tasting experience at one of the island’s wineries.
Don’t miss the chance to experience a mesmerizing sunset cruise in Oia, where you can sail along the coast and witness the sun dipping below the horizon in a blaze of colors. Santorini truly promises an unforgettable journey filled with breathtaking memories!
Santorini: Quick Tips
🛏️ Accommodation: Stay at Aqua Luxury Suites
🚘 Car Rental: Find the best Car Rental Companies in Santorini or read my detailed guide about Renting a Car in Santorini
📌 Top Places to Visit: Oia, Imerovigli, Fira, Pyrgos
📲 Stay Connected: Get your Europe eSIM
⛵ Best Experiences & Tours:
• Luxury Sunset Catamaran Cruise (my top tip!)
• Santorini Wine Tasting Tour (perfect for wine lovers)
• Santorini Highlights Tour (private customized Santorini tour)
• Iconic Santorini Flying Dress Photo Shoot (a once in a lifetime experience!)
➡️ Check out my complete Santorini Travel Guide for our detailed Santorini itinerary, including the best things to do, must-visit places, and my top insider tips!
Day 16 – 21: Milos
The Greek island of Milos is celebrated for its stunning landscapes, iconic beaches, laid-back vibes, and dreamy Greek villages. Milos boasts an abundance of natural beauty and cultural treasures that make it a must-visit destination.
The island is steeped in history and mythology, with archaeological sites scattered across the island. You can explore ancient ruins, including the ancient theater and the catacombs of Milos, which offer fascinating insights into the island’s past.
Additionally, Milos is blessed with an array of breathtaking beaches, ranging from secluded coves and hidden bays to expansive stretches of golden sand. Some must-visit beaches include Sarakiniko, with its unique moon-like landscape; Firiplaka, known for its crystal-clear waters and colorful cliffs; and Kleftiko, accessible only by boat and renowned for its dramatic rock formations.
Milos is also a paradise for outdoor enthusiasts, offering opportunities for hiking, snorkeling, and exploring its rugged coastline. With its diverse attractions, you can easily spend one week in Milos, immersing yourself in the island’s charm and beauty.
Milos: Quick Tips
🛏️ Accommodation: Stay at Kedros Milos Suites
🚘 Car Rental: Find the best Car Rental Companies in Milos
📌 Top Places to Visit: Adamas, Plaka, Klima, Mandrakia, Sarakiniko, Firiplaka Beach, Tsigrado Beach, Kleftiko
📲 Stay Connected: Get your Europe eSIM
⛵ Best Experiences & Tours:
• Polyaigos Sailing Tour (including Kleftiko, my top tip!)
• Kleftiko Sailing Cruise (an amazing sailing trip)
• Milos Archaeology and Culture Tour (see the highlights of Milos)
• Milos Kayaking Tour (includes Tsigrado Beach and Gerakas Beach)
• Milos Highlights Tour on an Electric Bike (amazing bike tour)
➡️ My complete Milos Travel Guide, including the best things to do, must-visit places, and my top insider tips will be published soon!
Alternative Cyclades Island Hopping Itineraries
If you find yourself short on time but still eager to experience the magic of the Cyclades, there are plenty of alternative Greek island hopping routes tailored to suit your individual schedule and preferences. Whether you have two weeks, ten days, or only one week to spare, below you’ll find some alternative Cyclades Island hopping routes and suggestions for maximizing your time in the Cyclades.
Cyclades Island Hopping Itinerary 7 Days
If you have just one week to explore the Cyclades, I highly recommend visiting the iconic islands of Mykonos, Paros, and Santorini. This itinerary offers a perfect blend of charming Greek towns, stunning landscapes, beautiful beaches, and vibrant culture, allowing you to experience the highlights of the Cyclades in a limited timeframe.
- Day 1 – 3: Mykonos · Skip Day 3 of our Mykonos Itinerary
- Day 3 – 5: Paros · Skip Day 3 and 4 of our Paros Itinerary
- Day 5 – 7 Santorini · Skip Day 3 and 4 of our Santorini Itinerary
Cyclades Island Hopping Itinerary 10 Days
For a 10-day island hopping adventure in the Cyclades, I recommend the following itinerary, which includes visits to Mykonos, Paros, Naxos, and Santorini:
- Day 1 – 3: Mykonos · Skip Day 3 of our Mykonos Itinerary
- Day 3 – 5: Paros · Skip Day 3 and 4 of our Paros Itinerary
- Day 5 – 8: Naxos · Skip Day 4 of our Naxos Itinerary
- Day 8 – 10: Santorini · Skip Day 3 and 4 of our Santorini Itinerary
Cyclades Island Hopping Itinerary 2 Weeks
With 14 days in the Cyclades, you can explore the same islands as suggested in our 3-week itinerary, but with a shorter stay on each island.
- Day 1 – 3: Mykonos · Skip Day 3 of our Mykonos Itinerary
- Day 3 – 6: Paros · Skip Day 4 of our Paros Itinerary
- Day 6 – 9: Naxos · Skip Day 4 of our Naxos Itinerary
- Day 9 – 11: Santorini · Skip Day 3 and 4 of our Santorini Itinerary
- Day 11 – 14: Milos · Skip Day 4 and 5 of our Milos Itinerary (coming soon)
Cyclades Island Hopping Itinerary 1 Month
For an extended stay of one month in the Cyclades Islands, I highly recommend venturing off the beaten path and adding some lesser-known islands and hidden gems to your island hopping itinerary. In addition to the previously mentioned islands, here are my personal recommendations:
Visit Ios
Nestled in the heart of the Cyclades, the charming island of Ios features a lovely main town, picturesque landscapes, vibrant nightlife, and crystal-clear waters. Despite its small size, Ios offers plenty of activities.
One of the island’s main draws is its stunning beaches, such as Mylopotas Beach and Manganari Beach, which boast golden sands and azure waters ideal for swimming and sunbathing.
Additionally, you can explore the island’s rich history at sites like the ancient ruins of Skarkos and the Venetian Castle of Ios, offering insights into the island’s past.
Having explored Ios during our most recent island hopping trip in the Cyclades, I wholeheartedly recommend adding this enchanting island to your itinerary.
Ios: Quick Tips
🛏️ Accommodation: Stay at Liostasi
🚘 Car Rental: Find the best Car Rental Companies in Ios
📌 Top Places to Visit: Chora, Mylopotas, Manganari Beach, Koumbara Beach, Skarkos
📲 Stay Connected: Get your Europe eSIM
⛵ Best Experiences & Tours:
• Ios 4-Hour Cruise of the Best Beaches (my top tip!)
• Ios Snorkeling Cruise (an unforgettable experience)
➡️ Check out my complete Ios Travel Guide for our detailed Ios itinerary, including the best things to do, must-visit places, and my top insider tips!
Visit Syros
Syros, the capital island of the Cyclades, is a true hidden gem! Often overlooked by international tourists, Syros has a unique charm with its blend of traditional Greek culture and relaxed atmosphere.
One of the island’s main attractions is its picturesque main town, Ermoupoli, characterized by its neoclassical architecture, iconic churches, and vibrant waterfront. For a taste of local cuisine and culture, wander through the bustling streets and sample delicious Greek specialties at the tavernas and cafes.
Syros also features beautiful beaches, such as Galissas Beach and Kini Beach, perfect for relaxing and soaking up the Mediterranean sun. With its undeniable charm and rich history, Syros is one of the best-kept secrets in the Aegean and a destination that captured my heart from the moment I arrived.
Syros: Quick Tips
🛏️ Accommodation: Stay at Syros Soul Luxury Suites
🚘 Car Rental: Find the best Car Rental Companies in Syros
📌 Top Places to Visit: Ermoupoli, Ano Syros, Kini Beach, Galissas Beach
📲 Stay Connected: Get your Europe eSIM
➡️ Check out my complete Syros Travel Guide for our detailed Syros itinerary, including the best things to do, must-visit places, and my top insider tips!
Visit Tinos
The Cyclades Island of Tinos is known for its religious significance, traditional architecture, authentic atmosphere, and unspoiled beauty. One of the island’s most famous attractions is the Church of Panagia Evangelistria, a major pilgrimage site and home to the miraculous icon of the Virgin Mary. Pilgrims flock to Tinos to pay their respects and seek blessings, especially during the Feast of the Assumption on August 15th.
Beyond its religious sites, Tinos offers plenty of attractions to explore. Make sure to wander through the charming streets of Tinos Town, adorned with marble-paved squares, whitewashed houses, and traditional tavernas serving local delicacies.
Also, don’t miss the chance to visit the picturesque villages of Pyrgos and Volax, known for their marble craftsmanship, and discover the stunning mountain villages of Kardiani and Isternia, offering breathtaking views of the surrounding landscapes.
Additionally, Tinos features beautiful beaches like Agios Fokas Beach and Kolimpithra Beach, perfect for swimming, sunbathing, and water sports.
Tinos: Quick Tips
🛏️ Accommodation: Stay at Orion Suites
🚘 Car Rental: Find the best Car Rental Companies in Tinos
📌 Top Places to Visit: Tinos Town, Pyrgos, Panormos, Volax, Agios Fokas Beach
📲 Stay Connected: Get your Europe eSIM
⛵ Best Experiences & Tours: Tinos Winery Tour & Wine Tasting (my top tip!)
➡️ Check out my complete Tinos Travel Guide for our detailed Tinos itinerary, including the best things to do, must-visit places, and my top insider tips!
I hope you enjoyed reading our comprehensive Cyclades travel guide, filled with different Greek island hopping ideas and itineraries. I’m sure that our insider tips and recommendations will help you plan the perfect Cyclades Island hopping adventure.
Whether you’re drawn to the iconic islands of Santorini and Mykonos or the hidden gems of Syros and Tinos, the Cyclades are the perfect place for creating memories to cherish for a lifetime. It’s one of our favorite destinations in Europe and we already can’t wait to return for our next Greek island hopping trip!
FAQ – Cyclades Island Hopping Itinerary
To fully enjoy the Cyclades, plan for at least 2-3 weeks to explore the islands you visit thoroughly and to immerse yourself in the beauty and culture of each island.
Start by selecting your desired islands, considering factors like transportation, ferry schedules, accommodation, your budget, and your personal interests. I highly recommend booking accommodations, ferries, and tours in advance for smoother planning.
Mykonos and Santorini serve as excellent bases due to their well-connected ports and airports. Plus, both islands offer frequent ferries to nearby Cyclades Islands.
The Cyclades are known for their picturesque towns, beautiful beaches, rich culture & history, and quintessential Greek Island vibes.
In my opinion, the most beautiful towns in the Cyclades are Oia in Santorini, Naoussa in Paros, and Ermoupoli in Syros.
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Want to explore more of Greece? Check out my other Greece travel guides to get the best travel tips!
- 2 Days in Athens Travel Guide
- 4 Days in Santorini Travel Guide
- 4 Days in Naxos Travel Guide
- 4 Days in Paros Travel Guide
- 3 Days in Mykonos Travel Guide
- 3 Days in Ios Travel Guide
- 3 Days in Tinos Travel Guide
- 2 Days in Syros Travel Guide
- 5 Days in Rhodes Itinerary
- Renting a Car in Santorini Guide
- Best Photo Spots in Mykonos
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