Travel Dreaming

Island Hopping, Greek Style

If I asked you to name some Greek Islands, I bet most of you would kick off your list with the hall of famers. Mykonos. Santorini. Crete. But did you know that there are 227 inhabited islands in Greece? So why does it seem like 95% of vacationers only go to these 3 biggies? Perhaps it’s because that’s where most cruise lines and tour groups decide to stop. Perhaps they get the most press. Maybe they are thought of as the A team. Don’t get me wrong, each of these Grecian gems are well worth the visit but what about the other 224?!

Views like this wait for you at every island
Greek Islands: A bucket list moment for so many!

Getting Our Bearings

Greek Islands are connected by ferry and knowing how the ferry system works can be the key to unlocking other, less touristy islands. These ferries will sure get you to whatever island you are interested in. However, they can be a bit of a time eater. Between boarding schedules and tickets, ferries do the job for the day tripper but might not cut it for the traveler looking to really get away. Good thing there is another choice!

Here’s my thought:

For a true Greek Island experience, may I suggest renting a catamaran with some friends and family? I bet you think that it’s way too much of a splurge to really justify it. Consider this: Let’s say a catamaran costs $12,000 to rent for 7 days. Oosh! That’s way too steep! But what happens if 6 friends can share the cost? Well, your part is now $2,000 inclusive. Better? Now, add in the fact that 2 of your meals and your alcohol tab are included with your room and transportation! Well, well, well. Things are looking up!

Eat, drink, be on island time!
Boat life: Enjoying a drink and a view!

So, you’ve committed to a little island hopping. Exactly which islands will you see? You will quickly find out that islands are grouped together with names like The Cyclades, The Sporades, The Ionian, and more. Focusing on one of these clusters would definitely help. For our purposes, let’s focus on the Cyclades.

Catamarans at Kolona Beach
Famous Kolona Beach

Recalibrate Your Traveling Mind

Sometimes when we travel, we do so to enlighten ourselves; to learn more about another culture. While there are moments that cater to this all over the islands, don’t expect cultural understanding to be the focus. Instead, set your course toward relaxation, food experiences, and local village life. Because that’s what the Greek Islands are made for!

Fresh Food
Locally sourced, super fresh homemade food is on the table every day.

Launching into island mode started in the old port of Lavrion which is opposite the main port of Pireas. Our boat had three staterooms and was manned by a captain, Vasilis, and a host slash chef named Leoni. Once settled, Leoni turned on the music, poured the wine and made us feel right at home in true Greek style.

All aboard!
Our Catamaran!
Our amazing guide!
Leoni from South Africa, our host and chef
Our Captain!
Vasilis from Northern Greece, taking a well deserved break from captain’s duties!

Each day, we would sail to a different island, stopping in small coves along the way, and stay the night in a new port of call. It becomes very easy to get into an island rhythm: breakfast, sail, swim, lunch, swim. dine, repeat. It’s that easy. Have I convinced you yet? Are you ready to go?

Sails up!

In our week, we spent time on the following islands~

  • Kythnos- has plenty of charm and was perfect for a daytime hike up to the top for fabulous views. Stay down by the water for famous Kolona Beach.
Kolona Beach
crystal blue!
  • Syros- home to Ermoupolis, Syros offers a great harbor with plenty of outdoor cafes and bars. The streets are literally paved in marble from Florentine times.
Ermoupolis
Ermoupolis
The Cathedral
Ermoupolis Cathedral
  • Paros- grab a blue chair at a white table and enjoy island life without the over indulgence of cruise ships.
Beach side everything
Beach side everything is ready and waiting!
  • Mykonos- home to those famous white washed winding streets full of bougainvillea and shops. Known for being a party island, it can be overcrowded by day but super fun at night.
Fishing boats in Mykonos
Mykonos Harbor
Lighting a candle at the chapel in Mykonos
Lighting a candle at the harbor side chapel in Mykonos
launches on Mykonos Island
Plenty of launches are ready to help you explore the islands
  • Sifnos- a small but fun spot to enjoy some down time, drink some local wine and take in the salty breeze.
Mykonos
Quiet moments
  • Serifos- with a great harbor, the food here is wonderful and the calm island had plenty of charm.
beach dining
When you sit down with your toes in the water!
  • Sounion Bay- home to Posiedon’s famous temple, there’s a small beach with choppy water but the hike up to the top is bucket list worthy.
The Bay of Sounion
Sounion Bay at the tip of the mainland
Posiedon's Temple
The Temple of Posiedon
  • Athens- We started and ended our trip with a few days in Athens. There we enjoyed the Plaka and climbed up to the top of the Acropolis.
The Acropolis Flag
The national flag waves proudly at the Acropolis
Plaka
Plaka Vibes
Eat, Drink, love life
Greek Food done perfectly…

9 Tips To Make Your Greek Island Adventure Perfect!

  • Be flexible! Our captain did a great job of bringing us to islands where the weather was great. He was able to skirt around storms to keep our sailing smooth. In other words, you may not get to 6 islands in a specific order. Instead, expect to jump in to a group of islands and let your skipper lead the way.
sunset
Sunsets
  • Pack wisely! You won’t need much! A few pairs of tops and shorts, good sandals, your swimsuit, and two or three sundresses or skirts to throw on top of your bathing suit. That’s it!
  • Prepare for chilly water! Contrary to what you may think, some waters are a bit colder than you may expect. Don’t get me wrong, you will still adore it!
perfect water
Crystal blue water waits!
  • Timing is everything! Check the average temperatures before you book so that you will have sunny, warm days and cooler nights to sleep. Most boats don’t have AC.
  • Get sick, fast! This may be a bit gross but the quicker you get over your inevitable sea sickness, the quicker you can get on with your holiday.
hiking in the greek islands
Hiking up to the top!
  • Know your islands! When you book, be sure to ask about the possible islands that you may visit. You can then research each and find your favorite thing to do on each island regardless of where you go.
sunset, greek island style
Sunset moments of a lifetime!
  • Go big! And go small. When you book be sure to let them know that you would like to enjoy all kinds of islands. Cosmopolitan, quaint, Euro-friendly, family-friendly, historic, the list keeps going. Be sure to let your agent know what you want- and that should include at least a day at an icon like Mykonos or Santorini depending on your timing.
Front of the catamaran
Sailing on to the next port of call!
  • Get to Athens! Don’t come this far and not check in with Athens to see this great city!

And Lastly…

  • Leave the kids! While there is no where in the world that you can’t take your kids, some places lend themselves far better to the pint sized set than others. Greece is not one of those places. Yes, there is a ton from the Bible and a ton from ancient times. Yes, you could make an amazing trip to the islands with the kids, I just think there are better places to take them than here. Enjoy yourself as an adult for a while, the kids will be fine!

3 thoughts on “Island Hopping, Greek Style”

  1. Island hopping around Greece is definitely one for the bucket list for me. I love Greek food and Greek history seems really interesting that I just can’t wait to get there, but so far it hasn’t happened. This needs to be my new goal. I love the idea of renting a catamaran like you did. That would be perfect if there were a few people going. Like you said, the food and drink add up quickly so this could end up working out rather cost effective

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