Greek Islands Itinerary

When you think of Greece, I bet you think of whitewashed buildings, windmills, and creeping bougainvillea. While you’re not going to see that in Athens, you will see it in spades all throughout the Greek Islands. While Santorini is probably the most famous of the Greek Isles, there are actually hundreds of small islands dotted throughout the Aegean Sea, each with something new and different to share. While I absolutely recommend visiting Athens, you should spend the bulk of your trip exploring the islands.

Day 1: Aegina

This island is only about 45 minutes from the ferry port in Piraeus, which is easily accessible by metro from Athens proper. Aegina is known for their pistachios, and has some extremely well preserved temple ruins open to visitors. It’s an easy “starter island” to explore, and if you only have time for a day trip, it’s well worth it. Some recommendations for things to do include:

  • Visit the Temple of Athena Aphaia, and take in the sweeping views of the coastline with Athens in the distance.
  • Catch a fishing boat out of Perdika village over to Moni Islet. The beaches are beautiful, and the nature is unspoiled since it’s uninhabited by humans. Make sure to take food and potable water with you though.

Day 2: Paros

Paros is not one of the more well-known islands frequented by tourists, but it’s actually the largest island in the Cyclades chain. It’s about a 5 hour ferry ride from Piraeus, and, in my opinion, a must visit for a more authentic experience.

When you arrive, you will dock in a village called Parikia. There are a whole bunch of shops near the ferry dock where you can rent ATVs, motorbikes, or even cars. I highly recommend arranging some sort of transportation because you’re going to want to visit different areas. While they may not be quite as fast, I actually prefer ATVs for Paros because you can go off road and explore areas off the beaten path. Some highlights on the island include:

  • A Pirate Fort built while Paros was under Venetian control
  • Visit the Parian Marble Quarries where they sourced the marble used for the Acropolis
  • Grab a fresh seafood lunch in the small fishing village of Aliki
  • Make a reservation to do a wine tasting Moraitis Winery

Day 3: Paros

  • If you’re visiting “in season”, which is approximately May-September, take a sailing day tour. There are also places where you can book more adrenaline fueled activities, like waterskiing and parasailing if that’s more your speed.
    • Another boat trip you could take would be to the slighter smaller Antiparos, where celebrities like Tom Hanks and Rita Wilson have homes
  • If that’s not an option due to the weather, you can always buy some inexpensive wine and local cheese and find somewhere to picnic
  • Head up to the village of Marpissa in the hills, which has picturesque scenery, historic churches, and family-run tavernas which are worth checking out.

Day 4: Travel from Paros to Santorini

  • Re-board the ferry in Parikia (and grab a gyro for lunch before you go), then settle in for the 3-ish hour journey to Santorini
  • The ferry will drop you off in the caldera at the bottom of the cliffs. Make sure transportation is arranged to take you to your hotel because it is not somewhere you can just walk from.
  • Once you get settled in your accommodations, you can look into one of the many boat tours around the caldera, most of which will take you to the small (active) volcano in the middle of the caldera, let you swim in a geothermal pool in the caldera, and then drop you off for a donkey ride up the hundreds of steps into Oia.
  • Oia is breathtaking. It is everything you’d ever want out of white-washed Greek village. But it is TOURISTY. Food is pricier, the streets are busier, and it’s nearly impossible to get a taxi from Oia to anywhere else on the island after sunset. You have to go there, but go there with those caveats in mind.

Day 5: Santorini

  • Take a Santorini Wine Tour; most Greek wines you see in the US are going to be Santorini whites called Assyrtiko. It’s a dryer white, somewhat akin to a pinot grigio. It’s crazy to see how the grapes are grown on the volcanic soil of the island.
  • If you’re into archeology at all, Akrotiri is a very cool excavation of a Pompeii-like city that was buried under the ash when the volcano erupted, creating the caldera. Buses to Akrotiri leave from Fira regularly.

Day 6: Santorini

  • Visit the Black Sand Beach in Perissa. Located on the opposite side of the island from the famous caldera, the black “sand” beach is a great place to relax and drink some beverages in a lounge chair. Be forewarned, though, that the sand is gritty and rocky, so sandals or water shoes are a good idea.
  • After re-energizing in Perissa, you should try this hike from Fira to Oia. The views are incredible, but be prepared for some very sketchy trails and bring plenty of water.

Day 7: Travel from Santorini back to Athens

  • Either fly or take a ferry back to Athens. Ferries take about 8 hours, so settle in for a full day at sea. There are options for “speed ferries,” which cut about 3 hours off the trip. Don’t do the speed ferry if you in any way get motion sick. You will regret it.
  • Santorini also has it’s own small airport with daily flights back to Athens and some other destinations. The flight is only about an hour long, so well worth it if you want to spend as much time as possible soaking in Santorini.

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