Greek Island Hopping: Crete & Cyclades

Greece is a fantastic place. It surprised me in many ways, both good and bad. After some experience, exploration and research, I’d like to share some of my favorite things about the islands I visited in Greece. These ideas will be especially helpful to “flashpackers,” those of you who (like us) like to travel somewhere in between budget and luxury and who like to visit both “must-see” touristy places and hidden gems. Hopefully this will help you plan the best trip possible!

My suggestion: if you’ll be traveling less than 2 weeks, choose four of the five islands below to explore.  Otherwise, you’ll spend more time traveling than enjoying your vacation; instead, spend your energy/budget on activities!


Known for: Great food and wine

Do: Rent a car & drive to Elafonisi beach (the best in Greece); the drive itself is gorgeous. Hike Samaria Gorge: go early, wear gym or hiking shoes, bring a water bottle to fill up at the springs along the way. Note: the gorge is a fairly expensive experience – you’ll have to pay for the bus ride (~15 euro roundtrip from Chania), the entrance fee (5 euro), and the ferry that takes you to the bus stop after the hike (~15 euro). Check out Knossos (oldest city in Europe) and wineries (Peze and Arhanes are good) near Heraklion.

Elafonisi Beach – worth the trip
Samaria Gorge: beginning of the hike
Samaria Gorge: beginning of the hike

Eat: Literally anywhere! Portes in Chania was probably our favorite meal all trip. Located in an adorable alley, this place has great food, ambiance, and service – don’t miss the sheep cheese. We also liked Kastella in Heraklion since it was right next to our hotel (Kronos) – has a great, waterfront view and the owner is adorable and very passionate about his food. Don’t miss the house salad for a huge, healthy portion.

Portes - Chania
Portes – Chania
Not so patiently waiting to eat at Kastella – Heraklion

Stay: Chania – we had a fantastic airbnb with Nikos; he arranged our rental cars and even dropped them off/picked them up at our door!

Touristy level: 2/5

Budget: $$

Insider tip: Stay as long as you can here. I highly underestimated this island with its natural beauty, friendly people and fantastic food. Also, the bus prices have increased dramatically, jumping from under 3 euro to 15 euro a piece. Keep this in mind when planning your visit to Crete. Unless you’re there for an extended amount of time, stick to one side of the island (east or west) since it’s very large; I chose west and didn’t regret it!


Known for: Party scene, great hotels, people-watching

Do: Paradise or Super Paradise beach for parties after 4:30pm; Ornos beach for a more “family-friendly” scene. Try Scandinavian bar (go early to avoid an expensive cover) or Tropicana bar. If you’re into archaeology, take a day trip to Delos.

Eat: Anywhere near Little Venice.

Little Venice – Mykonos

If by Ornos Beach, try Lefteris for cheap & delicious souvlaki/gyros (eat-in or take-away)

Stay: If you want to party and/or have convenient access to public transportation, stay in Mykonos town. Check out airbnb for cheaper accommodation options. We loved our airbnb by Ornos beach – a place called Mare Mare in the Mimosa complex; it was clean, quiet, and had great amenities, including a wonderful terrace and swimming pool.

Pondering life in our AirBnb's terrace. Rosé all day!
Pondering life in our AirBnb’s terrace. Rosé all day!

Touristy level: 4/5

Budget: $$$$

Insider tip: Cabs are extremely hard to get. When we failed to hail a cab after an hour of trying, I went in the nearest bakery and talked to a young guy working there about our options. He said, “just a moment;” he got his friend (not a cab) to drive us! We ended up driving around the entire island for only $20; it was a great experience, too. Moral of the story: be friendly to the locals and ask for help/advice; you’ll probably have better luck than trying to get a cab!


Known for: Beaches, archaeological sites

Temple of Apollo
Temple of Apollo & Naxos Town

Do: Rent a scooter or ATV and check out some of the sites and the Villindras distillery for some Kitron, a traditional Naxos drink. Go to Plaka or Agios Prokopios white sand beaches, or check out Mikri Vigla. Hike from Melanes to Jesuit Monastery of Kalamitsia.

Eat: Kozi – one of the best meals I had in Greece with a great view of the Temple of Apollo. Don’t miss the baked feta or the Kozi salad. Meze2 – if you’re willing to spend a little more, I’ve been told this place has the best seafood on the island and gives excellent free dessert!

Stay: We adored Pension Sofi in Naxos Town. It’s inexpensive, well-kept with great facilities and a fantastic, family-run staff. We really liked the location, too – central and close to the port & bus station.

Touristy level: 1/5

Budget: $$

Insider tip: Plaka beach is just a bit farther than the other, more crowded beaches, and much more serene. It’s worth the extra $0.20 for the bus ticket! Don’t be surprised if you find nudists far down the beach like we did 😮

Plaka beach – paradise!


Known for: Beaches, parties (mainly in Parikia)

Do: If you stay in Naoussa, you can take a small boat to some nearby beaches. We really enjoyed Monastiri with its extremely clear, calm waters and nearby hiking. My younger sister & friend (20 years old) loved Pounda beach, a spot known for partying that’s easier to access from Parikia. You could also take a small ferry to Antiparos from Pounda.

Eat: Yemeni in Naoussa – a fresh, fantastic meal.

Stay: Naoussa for a quieter, picturesque stay; Parikia for convenience and parties. We stayed at Alea Apartments in Naoussa – very affordable and cute owners with hundreds of board games for you to use.

Naoussa - were we caught the small boat to the beach
Naoussa – where we caught the small boat to Monastiri

Touristy level: 2/5

Budget: $$

Insider tip: If you’re only staying a short time (2 days or less) and plan to be active, I’d recommend staying in Parikia, since you’ll be able to get around the island easier & cheaper. If you’re looking for a more tranquil, relaxing experience, stay in Naoussa – it’s an adorable town, only a quick bus ride from Parikia.

Santorini (a.k.a. Thira)

Known for: Incredible sunset views; wine

Do: sunset boat tour (~$65) – these usually include the volcano hike, hot springs, dinner and the Oia sunset. Make sure your tour includes dinner; the volcano hike kinda sucks in my opinion! Also – after your tour, do not miss riding donkeys up the hill. After some sun and some boxed Santorini wine, riding a donkey in the dark was an absolute riot and probably my favorite part of Santorini. We heard the hike from Fira to Oia is good (~3 hours), but it was way too hot for us. You could also check out the many wineries.

Our beauty
Our beauty
The blur accurately reflects this moment
View of Oia from the boat

Eat: We liked our gyro places in Fira for lunch. For dinner in Oia, check out Karma for a great ambiance and reasonably priced food.

Stay: We stayed at Kykladonisia Hotel in Fira, a cute budget place with helpful staff and a small, refreshing pool. If you can afford to stay in Oia, go for it! Those places looked so sick, but unfortunately were out of our price range. I may be the only one with this opinion, but I liked Fira better than Oia anyway. Firostefani is another good option; ~10 walk from Fira.

Kykladonisia Hotel
Kykladonisia Hotel

Touristy level: 5/5

Budget: $$$

Insider tips:

  • I may offend some people by saying this, but – Santorini disappointed me. It was way too touristy; I felt like cattle being herded most of the time. The streets were packed with tourists, the restaurants in Oia were very pricey, I had to battle for a good view of the sunset and a spot on the bus back to Fira, and it all felt a little bit ruined by commercialism. I’d recommend staying for a night or 2 at most, unless you’re dead set on visiting wineries, beaches, or Akrotiri. I definitely preferred Crete, Naxos and Paros.

    The reality – wading through the crowds in Oia
  • The catamaran tours are way more expensive than the other tours; try to get on a big pirate-ship-like boat.
  • For the hot springs, bring a swim suit & cover up that you don’t care about. If you want to enjoy the full experience (swim over the bubbling, orange water; cover yourself in mud), your suit will get stained (and so will the clothes that you wear afterwards).
  • If you decide to do the volcano hike, wear hiking/gym shoes and bring a water bottle. However, if you decide not to partake, rest assured you’re not missing much.


If I were to revisit these islands, I’d spend more time in Crete and Naxos and I would skip Santorini and Mykonos altogether. Both of these places have so much to be explored and have something for everyone; they haven’t been overrun by tourism, and they’ve maintained their culture and history. However, if you absolutely love to party, I would suggest staying in Mykonos Town, Parikia (Paros) and Fira (Santorini) for the best nightlife.

Look out for more travel guides on mainland Greece and other island groups.

Want more details? Disagree with my assessments? Comment below or shoot me an email!

4 Comment

  1. Craig says: Reply

    Thank you for sharing the beautiful pictures and your extensive notes and tips!!

  2. Grandma says: Reply

    Love seeing both of you looking great! So happy that all your doing now
    needs energy and a lot of know how to see all those wonderful places,
    and you have both.

  3. Caren says: Reply

    This is so much fun “travelling” with you to all these beautiful places. You have done an amazing job describing this incredible journey. Thank you so much and ENJOY!!!
    Auntie Caren

    1. Brittany says: Reply

      Thanks Auntie Caren! So glad you’re enjoying following along with our journey 🙂

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