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How to Plan Your Greek Island Hopping Trip

Greece › Island Hopping
By Santorini Dave

See Also

Beach on Greek Island.

The wonderful beaches of Mykonos are a highlight of Greek island hopping.

Island Hopping Guides

My wife and I in Santorini.

My wife and I in stunning Santorini.

Island Hopping Essentials

Where to Stay

Greek Island Hopping – Tips and Information

Greece is the best place on earth for island hopping, but a great trip requires smart planning. The key is to minimize your travel time so you can maximize your beach time. Forget trying to see everything at once; focus on a single island group for a more relaxed and rewarding journey.

My wife and I boarding a Greek ferry as we island hop around the Cyclades.

My wife and I waiting for a ferry in Naxos.

Here are my eight essential tips for planning a Greek island-hopping adventure.

1. Book Ferries and Hotels Well in Advance
This is the most important tip, especially if you are traveling in high season (June to September). The best Santorini hotels, Mykonos hotels, Crete hotels, Paros hotels, and Athens hotels get booked up 6 to 9 months in advance. Popular high-speed ferries can also sell out. I recommend booking your ferries on ferryhopper.com a few months ahead. This locks in your transport, allows you to build a reliable schedule, and prevents the stress of arriving at a port to find your ferry is full.

2. Pick One Island Group and Stick to It
Do not try to visit Mykonos (Cyclades), Crete, and Corfu (Ionian) on the same trip. You will spend all of your time on long, overnight ferries or dealing with airports. The secret to a great island-hopping trip is to choose one island group and explore it well. The Cyclades (Mykonos, Naxos, Paros, Santorini) are the most popular and have the best ferry connections. The Dodecanese (Rhodes, Kos, Symi), Ionian, and Sporades islands are also fantastic choices.

3. Follow the Ferry Routes (Don’t Fight Them)
Greek ferries are like a train system; they operate on logical, well-established lines. Plan your itinerary along these main routes to avoid long, backtracking journeys. For the Cyclades, a classic route is from Athens to Mykonos, then Naxos or Paros, then Ios, and finishing in Santorini (or the reverse). This follows the main ferry line and ensures frequent, easy connections. Trying to go from a small island like Amorgos directly to a far-flung one like Milos will be difficult and waste a precious vacation day.

4. Pack Light: The Carry-On is Your Best Friend
You will be hauling your luggage on and off ferries, up and down cobblestone streets, and into small hotel rooms. Packing light is not a suggestion; it is a necessity. A rolling carry-on suitcase or a travel backpack is ideal. Trying to manage a huge, heavy suitcase is a nightmare on crowded ferries and narrow village paths. Remember, you will be in shorts, t-shirts, and swimsuits 90% of the time.

5. Always Have Some Cash (Euros) on Hand
While hotels, upscale restaurants, and shops in popular towns will all accept credit cards, cash is still king in many situations. You will need it for buses, taxis, small family-run tavernas, buying a bottle of water at a kiosk, or tipping your tour guide. Don’t rely on being able to use a card everywhere, especially on smaller islands or in less-touristy villages. Get some Euros at an ATM at the Athens airport when you arrive.

6. Less is More: Don’t Rush Your Trip
The biggest mistake first-timers make is trying to see too many islands in too little time. Every time you change islands, you lose at least half a day to packing, checking out, waiting for the ferry, sailing, and checking into your new hotel. My rule of thumb is a minimum of three nights for a major island (like Naxos or Santorini) and two nights for a very small one. A 10-day trip is perfect for three islands; it is not enough for five.

7. Be a Little Flexible
While booking ahead is key, you must also maintain a degree of flexibility. The infamous Greek Meltemi wind can sometimes, though rarely, be strong enough to cause ferry cancellations, especially for the smaller high-speed catamarans. It’s wise not to schedule your final island-to-Athens ferry for the same day as your international flight home. Give yourself a buffer day in Athens at the end of your trip just in case.

8. Don’t Do a Greek Island Cruise
Greek cruises suck. Don’t do them. It’s much better to island hop on your own. The best websites for booking a Greek holiday are Booking.com (for hotels) • Kayak.com (for flights) • Ferryhopper.com (for ferries). It’s fun and easy to book your own trip – and much more rewarding.

Island Hopping Itineraries

My wife and I on a ferry in Paros, Greece.

Taking the ferry from Paros to nearby Antiparos makes for a great day trip.

Crafting the perfect Greek island-hopping itinerary is about finding the right balance between travel and relaxation. The key is to stick to one island group – and for first-timers, the Cyclades are the best choice, with frequent and reliable ferry connections.

Here are three sample itineraries based on the most common trip lengths.

Important Note: These itineraries are designed to be efficient. I highly recommend flying into the first island and out of the last island (an “open-jaw” ticket) to save a huge amount of time and avoid backtracking to Athens. Book all ferries and hotels months in advance, especially for a summer trip.

The 7-Day Greek Island Itinerary: Santorini & Naxos

With only one week, the key is to pick two incredible but contrasting islands. This itinerary gives you the jaw-dropping views of Santorini and the fantastic, family-friendly beaches and authentic culture of Naxos.

• Day 1: Arrive in Santorini. Fly into Santorini, pick up your pre-booked rental car or transfer, and check into your hotel in Oia, Imerovigli, or Firostefani. Catch your first incredible caldera sunset.
• Day 2: Santorini: Fira to Oia Hike. Walk the spectacular caldera path from Fira to Oia (allow 3-4 hours). Explore the beautiful alleys of Oia in the afternoon before taking a bus or taxi back.
• Day 3: Santorini: Volcano Boat Tour. Take a boat tour of the caldera, where you can hike on the volcano, swim in the hot springs, and watch the sunset from the water.
• Day 4: Ferry to Naxos. Take a morning high-speed ferry to Naxos (approx. 1.5 hours). Settle into your hotel at one of the west coast beaches like Agios Georgios, Agia Anna, or Plaka.
• Day 5: Naxos: Explore Chora. Explore the charming main town (Chora), get lost in the alleys of the historic Kastro, and walk out to the iconic Portara for sunset.
• Day 6: Naxos: Beach Day or Island Tour. Relax on the incredible golden sand of Plaka or Agia Anna beach. Alternatively, rent a car and explore the island’s interior, visiting the mountain villages of Halki and Filoti and the ancient Kouros statues.
• Day 7: Depart from Naxos. Fly out of Naxos, or take a short ferry to Mykonos or Santorini for a wider selection of international flights.

The 10-Day Greek Island Itinerary: Mykonos, Paros, & Santorini

Ten days is the perfect amount of time for a “greatest hits” tour of the Cyclades, combining the vibrant energy of Mykonos, the chic charm of Paros, and the epic views of Santorini.

• Day 1: Arrive in Mykonos. Settle into your hotel in Mykonos Town or at a nearby beach like Ornos or Platis Gialos.
• Day 2: Mykonos: Town & Sunset. Spend the day getting lost in the beautiful whitewashed maze of Mykonos Town. In the evening, have a sunset cocktail in Little Venice.
• Day 3: Mykonos: Beaches or Delos. Explore the famous southern beaches via the water taxi from Platis Gialos, or take a morning tour to the incredible archeological site on the sacred island of Delos.
• Day 4: Ferry to Paros. Take a short ferry ride to Paros (approx. 45 minutes). Check into your hotel in the beautiful fishing village of Naoussa.
• Day 5: Paros: Explore Naoussa. Explore the charming alleys and scenic harbor of Naoussa. In the afternoon, take a water taxi from the harbor to the unique rock formations of Kolymbithres Beach.
• Day 6: Paros: Day Trip to Antiparos. Take the short ferry from the port of Pounta to the laid-back and charming island of Antiparos for a relaxing day of exploring and swimming.
• Day 7: Ferry to Santorini. Take the scenic ferry to Santorini (approx. 2 hours). Check into your caldera view hotel.
• Day 8: Santorini: Oia & Sunset. Explore the stunning village of Oia. Find a spot to watch the world-famous sunset.
• Day 9: Santorini: Sailing Tour. A sailing trip around the caldera is a must. Swim in the hot springs and enjoy the incredible views from the water.
• Day 10: Fly out of Santorini.

The 14-Day Greek Island Itinerary: Mykonos, Naxos, Paros, & Santorini

Two weeks is the ideal amount of time to see the “Big Four” of the Cyclades without feeling rushed. This itinerary gives you a fantastic mix of nightlife, beautiful beaches, authentic villages, and epic views.

• Days 1-3: Mykonos (3 nights). Spend one day exploring Mykonos Town, one day on a tour of the ancient ruins on Delos, and one day exploring the famous south coast beaches (Platis Gialos, Paradise, etc.).
• Days 4-6: Paros (3 nights). Take the ferry to Paros. Base yourself in the chic village of Naoussa. Spend your time exploring its charming harbor, taking water taxis to nearby beaches like Kolymbithres, and taking a day trip to the laid-back island of Antiparos.
• Days 7-10: Naxos (4 nights). Take the short ferry to Naxos. I recommend four nights here as it’s a large island perfect for exploring. Spend one day in the historic Chora and at the Portara, two days exploring the incredible west coast beaches (Agia Anna, Plaka), and one day with a rental car visiting the mountain villages of Halki and Filoti.
• Days 11-13: Santorini (3 nights). Take the ferry to Santorini. Spend your three nights soaking in the epic caldera views. Hike the scenic trail from Fira to Oia, take a volcano boat tour, and enjoy a romantic sunset dinner.
• Day 14: Fly out of Santorini.

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About Santorini Dave

Santorini Dave in Athens, Greece Santorini Dave was started in 2011 when I posted a short guide to visiting Santorini with kids. Now, my site publishes regularly updated guides to Santorini, Naxos, Paros, Mykonos, Crete, Athens, and all of Greece.

Questions? Email me at dave@santorinidave.com.

  1. Family Greek Island Trip

    Hi Dave
    Looking at approximately 17 nights dedicated to the Cyclades for me, my Mum, and 16-year-old twin daughters. What are your thoughts on:
    Paros/Anitparos 3 / 4 nights
    Milos 3 / 4 nights
    Syros 3 nights
    Santorini 3 nights
    Crete 4 nights
    If we fly out from Crete back to Athens for our departure to Australia all on the same day, is that too risky?
    Would love your advice.
    Michelle

    1. Santorini Dave The Hotel Expert

      I think that’s a great itinerary. I would check ferry schedules and likely make Syros my first stop, otherwise looks great. One night in Athens before the flight home would be what I recommend. Lots to see in central Athens too!

  2. Which Island to Fly Into?

    Hi Dave, My wife and I are flying in from London & planning 1 month island hopping from mid August. Which is best island to fly into to start? Which islands do you suggest? We would like to visit one of the smaller remoter islands too while we are there. Hoping to do mix of self catering and hotel. Like to do some mild hiking mixed with beach days and lots of historic sightseeing.
    Thanks in advance
    Joe & Kay

    1. Santorini Dave The Hotel Expert

      I would fly into Mykonos and out of Crete or vice versa. In between there are popular islands like Santorini, Paros, and Naxos and less popular islands like Milos, Folegandros, Sifnos, and Serifos (most of these in the Western Cyclades). If you wanted a shorter trip you could arrive and depart from Santorini and Mykonos and save Crete for a visit of its own.

  3. 14 Day Itinerary for Greek Islands

    Hi Dave!

    I am planning my honeymoon and flying from Los Angeles, CA. We have 14 days and we want to do Santorini, Mykonos, Paros, & Milos. Do you think this is enough time for all 4 islands? What’s the best route/order to do for these?

    1. Santorini Dave The Hotel Expert

      With 14 days I typically recommend visiting 3 or 4 islands. So, you’ll be moving around a bit but it’s completely doable. There are so many different routes for those 4 islands that there is no “best order”. You’ll just have to do the research on ferry schedules and see what works with your dates.

  4. Santorini Mykonos in November

    Hi Dave,
    Do ferries run from Santorini to Mykonos in November? Couldn’t find one on Ferryhopper.
    Thanks!

    1. Santorini Dave The Hotel Expert

      Ferries between Santorini and Mykonos run until the end of October (for sure) and sometimes into the first week of November. After that you’ll need to travel via Naxos, Paros, or Syros.

  5. Greek Island Itinerary

    Hi!!!! This page is AMAZING!!! I have some questions since I’m building my first trip to Greece.

    I think I could do 10-12 days last 2 weeks of August and would love to visit Athens, Santorini, Mykonos, Zakynthos, Naxos and/or Corfu or Milos, not sure if this is possible. From there then fly to Croatia.

    My question is what would be the best routes/island for this?

    Thank you!

    1. Santorini Dave The Hotel Expert

      I recommend dropping Zakynthos and Corfu as they’re a long ways from Athens and the Cyclades. I think you’re better to focus on Santorini, Mykonos, Naxos, and Milos with only 10 to 12 days. Try flying directly into Santorini from a large airport in western Europe, then ferry to Milos or Naxos (you won’t have time to do both), ferry to Mykonos, and ferry to Athens. From Athens, you’ll be able to fly to Croatia.

  6. Greek Island Itinerary

    Hi Dave, we have 9 nights for island hopping and will be leaving from Athens. Can you suggest a good itinerary ending with our last night in Santorini, as we will fly out from there. I have been to Santorini and Ios before and want to steer clear of Mykonos as we are more into the less touristy islands. Thinking of 2 nights per island. Thanks

    1. Santorini Dave The Hotel Expert

      I recommend Paros to Naxos to Santorini. Milos if you want to do a boat tour (similar to a Santorini caldera boat tour but with more snorkeling). Or Sifnos if you want something off the beaten track.

  7. Greece All Inclusive Resort

    Hi Dave. Such a great website, thanks. We’re coming from London I’m looking for two weeks in Greece with kids 6 and 8. I really want to see the white-washed buildings against bright blue seas and skies. We’re thinking of doing an inclusive resort for 1 week so the kids can make friends and have kids club, then looking for hotels/villas for a little island hopping. We’re not really sure where to start. Any recommendations? Is Crete a good base for the resort week?

    1. Santorini Dave The Hotel Expert

      There are very few all-inclusive resorts on the Greek islands. Crete might have a few, but Santorini, Mykonos, Naxos, and Paros have none that I know of. All the Cycladic islands are great for kids and families. Check out Antiparos if you’re looking for something smaller and quieter where you’ll almost know everyone on the island after a week.

  8. Which Greek Islands for First Time Visitors

    For first-timers, would you recommend Naxos, Paros, Crete, or Corfu? We are definitely flying into Athens to explore and then Mykonos and Santorini.

    1. Santorini Dave The Hotel Expert

      I find Paros to be the most like Mykonos. Crete really deserves a week or more (and I’m assuming you just have a few more days to fill). Corfu is a long way from Mykonos and Santorini (and would require flying via Athens). So I would go with Naxos. Great beaches, local food, and small traditional villages.

  9. Best Greek Islands for Island Hopping with Kids

    Hello,
    We are planning an ‘island hopping’ trip next year with our three young (Ranging 2-12) , but well travelled children. We’re after a mix of beaches, nice hotels with pools, and a few days exploring towns. Would you please be able to recommend the islands best suited to this. We’re after a duration of around two weeks, probably staying 3/4 nights most places and would be flying from London.
    Many thanks 🙏- this site has been such a source of travel inspiration!

    1. Santorini Dave The Hotel Expert

      My favorite islands for kids and island hopping: Naxos, Paros, Milos, Sifnos, Serifos. Santorini and Mykonos are also good but busier and more expensive. Both Santorini and Mykonos have direct flights from western Europe which makes them great bookends to your trip. Fly into one. Island hop through a few other islands. Then finish at the other and fly home.

  10. Greece Turkey Itinerary

    My friend and I would like to do 10 days in Greece on our way to Turkey in May. We will fly into Athens and would like to do Mykonos, Santorini, Crete, and Sifnos if possible. Which route would you recommend?

    1. Santorini Dave The Hotel Expert

      I recommend ferrying from Athens to Sifnos to Mykonos to Santorini to Crete. Could also fly to Crete to start and then ferry back to Athens in reverse order as above. (Most likely you’ll need to fly from Athens to Turkey.)

  11. Crete to Paros Ferry

    HELP!!!
    We are a family of four in need of island transfer from Crete, preferably Chania but at this point any port will do, to Paros on May 2nd. I prefer to ferry rather than fly but am having difficulty finding a company that does this route. Is it too early, perhaps they don’t start until June ?? We’d also be up for going to Santorini, spending the day, and ferry to Paros in the evening.
    Can you point me in the right direction?
    Thanks so much for your help.

    1. Santorini Dave The Hotel Expert

      There should be a daily Heraklion to Paros ferry (with stops in Santorini and Naxos) in early May. I would check Ferryhopper.com for details. You would need to spend the night in Santorini to have time to see the island (as there is no evening ferry on this route).

  12. Greek Island Itinerary for Family

    I have found your information so helpful! Starting with 4 days in Athens, and then 10 nights in the Cyclades. Travelling with 2 adults and well traveled 9yo. For the “islands” portion of our trip (10 nights), I am wondering if just Naxos/Santorini will be a little too long at 5 days each. Maybe cut down to 4 nights each with two nights somewhere else. Plan is to fly back to Athens from Santorini. Any insight very much appreciated!

    1. Santorini Dave The Hotel Expert

      I don’t think that’s too long on Naxos and Santorini. But yes, you could easily add a two-day stop in Paros, Mykonos, or Ios. Or if you’re wanting to do a boat tour then Milos and do the full day boat tour around the island.

  13. 7 Day Itinerary for Greek Islands

    We are taking a short trip for my big 4-0 birthday. It is on my bucket list to see the Greek islands. Santorini is too on the list. What itinerary would you recommend from Chicago for 7 days in Greece?

    1. Santorini Dave The Hotel Expert

      I recommend Santorini for 3 days, Naxos (beaches and traditional villages), or Mykonos (beaches and trendy nightlife and restaurants) for 3 days, and 1 day in Athens.

  14. Athens to Hydra to Spetses

    Hi Dave
    We have set our hearts on Athens to Hydra for 2 days then Spetses for 2 days then back to Athens for our flight home. But can’t find any ferries, is that because its not doable.
    Karen

    1. Santorini Dave The Hotel Expert

      The Athens/Hydra/Spetses ferries run year round. If you’re looking too far in advance they might not be listed yet. But there will definitely be ferries running that route. I recommend booking tickets a month or two in advance just to be safe but there are many daily ferries and they rarely sell out.

  15. Honeymoon in Greek Islands

    Hi Dave,

    We’re planning a honeymoon in Greece through Athens (1-2 Nights), Santorini (3 Nights), Mykonos (3 Nights), and Kreta or Rhodos (3-4 Nights), but we’re not sure which island is better and which island has more beautiful beaches: Kreta or Rhodos? How would you divide and plan the route from Germany ?

    Thanks

    1. Santorini Dave The Hotel Expert

      Both Rhodes and Crete have great beaches and interesting towns. The biggest difference (for your itinerary) is that Crete is a short daily ferry ride from Santorini and Rhodes is a long 2/weekly ferry ride from Santorini. So I would definitely do Crete (ferry to Heraklion and then spend most of your time in Chania). Then fly home from either Heraklion or Chania airports – hopefully without having to fly via Athens.

  16. Itinerary for Athens, Santorini, and Mykonos

    Hi Dave, We are a family of 6 going to Greece for the first time. I am flying into Athens. I want to see Santorini and Mykonos. What do you recommend as far as which Island to go first and what means of transportation to use, Ferry or fly. We have 8-9 days to spend in Athens, Santorini and Mykonos. We will be flying back to U.S. after vacation. We have kids as young as 6.
    Thank you.

    1. Santorini Dave The Hotel Expert

      I would ferry from Athens to Mykonos, ferry from Mykonos to Santorini, then either fly Santorini to Athens or (even better) fly Santorini to Western Europe (Paris, London, Amsterdam, or Rome) and fly directly home from there.

  17. Which Greek Islands in January

    Hello. We will be visiting Greece in January. We would like to do some Island Hopping from Athens. What Islands do you recommend at this time of year. We would like to see Santorini, do you think we should? If so, what islands should we stop at along the way? We want to visit islands for about 7 days. We have to finish in Athens because we are flying to Morocco next. Thank you very much for your help.

    1. Santorini Dave The Hotel Expert

      I’d recommend Santorini and Naxos or Paros in January, mainly because of the ferry connections.

  18. Which Greek Island

    Hi Dave,
    We’ve narrowed down our islands to Naxos, Santorini and Milos. We’re able to stay 3-nights on 2 of those islands and 4-nights on 1 off them. Which island would you recommend to spend the 4-nights on? I’m thinking Naxos or Milos. Of those 2, what has more to do where an extra day would be beneficial? Thanks so much.

    1. Santorini Dave The Hotel Expert

      Of Naxos and Milos, I think Naxos has more to see and do. Though Milos has more interesting boat tours.

  19. Best Way To Get from San Francisco to Greece

    Hi Dave.

    Quick question on how would you divide and route flying to Greece from San Francisco? 14 nights in Athens, Santorini, and Mykonos and would it be sufficient time to see most highlights of Greece. Thanks a bunch. Any info is greatly appreciated.

    1. Santorini Dave The Hotel Expert

      It of course depends on what flights are available which varies greatly depending on the time of year. But most likely you’ll need to fly via London, Paris, or Amsterdam. From these western European hubs I would recommend flying to Athens but returning from Mykonos or Santorini – or even Heraklion in Crete. For example, fly SFO to London, fly London to Athens, ferry to Mykonos, ferry to Santorini, fly Santorini to London, fly London to SFO. This does require a fair bit of flight searching to see what’s available on each route – but it’s worth the effort so that you don’t have to retrace your steps to Athens and waste time and money. 14 days is enough time to see some of the highlights of Greece – but all of them? Not even close. I recommend focusing on 3 or 4 destinations so you don’t feel rushed.

  20. Best Greek Islands to Visit

    Hello, I am traveling from New York to Greece for the 2nd time. I traveled to Greece about 5 years ago and split my trip between Athens, Mykonos, and Santorini. This year I’m in between Paros, Ios, and Crete and confused if I should all three or which to do and the order. Was hoping you can provide expert travel advice and let me know what would be ideal for us to do. We are looking to relax on the beach, nightlife, party, and restaurants. Have about 10 days. Thank u

    1. Santorini Dave The Hotel Expert

      I’m thinking you love Greece and will likely make another visit in the coming years. If that’s accurate then visit Paros and Ios on one trip (best for the high season summer months of late May to early September) and Crete on the other trip (great in summer but also fine in the shoulder season of April, early May, late September, October, and early November). Both are good destinations for 10 days but visiting all 3 in ten days would be rushed.

  21. Greek Island Hopping Routes

    We are planning a honeymoon through the Cyclades. Our plan is to stop in Santorini, Mykonos, Naxos, Paros, and Ios. Is there a “best-route” for these 5 islands. We have not booked any flights or ferries yet so are open to any itinerary. We’ll be flying from NYC and visiting London and Paris on the same trip.

    1. Santorini Dave The Hotel Expert

      My recommended route would be
      • Paris fly to Athens
      • Athens ferry to Mykonos
      • Mykonos ferry to Paros
      • Paros ferry to Naxos
      • Naxos ferry to Ios
      • Ios ferry to Santorini
      • Santorini fly to London
      The reverse order is fine too. This has the quickest, most direct ferry routes and the largest choice of flights.

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