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As many chances as I get, I'm going to Greece. It is just amazing there. My first trip to Greece was back in 2011, then I went again in 2013, and again in 2016. I'm already planning another trip for 2019. It's worth it every, damn, time. And what's funny, I've never really spent any significant amount of time in Athens! It's been all about the islands for me, and I plan to keep it that way. I was originally invited by friends to join them on a sailing trip- and it was just such an awesome experience that I decided sailing the Greek islands was, for me, the best way to do Greece. The company I've now used every time I go is Greek Seas boutique sailing company, and I have gone from tagging along on other friends' sailing trips, to organizing my own and having 2 boats worth of friends along for the ride.
The deal with this trip is: your hotel is the boat. There are usually 4 cabins per boat and 2 bathrooms where you sleep and shower. You meet the boat in the marina of Athens, and set sail Saturday-Saturday. You go to a different island each day, usually with about 4-6 hours of sailing time in between (the boats will stop by various coves along the way to break up the sailing time with a little swimming!). By the afternoon you are docked and ready to have some lunch on a new island- explore- have amazing group dinners at island restaurants - nightlife if you wish- and back to the boat for final drinks or just straight crashing. You see so many different islands, and I cannot tell you how much I enjoy swimming in the Aegean Sea.
Also, the islands Greek Seas charters take you to are really cool- some are sleepy little greek islands like Aegina, Erminoni, Kythnos, Serifos, Siros - others have lots of activities like Hydra with it's donkey rides, cliff jumping and beach club "Magic by the Sea", and Spetses with awesome ATVing, shopping, more beach clubs, etc. The last trip I extended my stay in Greece and took a quick side trip from Athens to Santorini- and I was just blown away. Santorini is the shit- it's probably the most beautiful place I've ever been. Definitely a little more expensive than the "off the beaten path" islands that Greek Seas took me too, but worth every penny. On my first trip, Greek Seas tested out a route to Mykonos, where we actually were dropped off, spent a couple nights in a hotel, then took a ferry back to Athens to catch our flight. Mykonos is the party island for sure- tons of nightlife and beach clubs, really a fun spot with a ton going on.
What more can I say about Greece? The food is incredible (think pastries and coffee for breakfast, gyros for lunch and fresh fish, greek salads, bread and olive oil for dinner) and CHEAP, so cheap- we walked away from dinners with endless wine and food paying only $15 a person most times. The weather is fantastic anytime between May and October (it really doesn't rain at all during these months, but it does get very hot, my best trips were in June when also the ocean is pretty mild and it's not very windy.) The sea is so blue, and the houses/architecture on the islands is just so. classic. Greece. If you are thinking about going, do it and do it by boat, here is the boat company's website:
Breakdown of usual trip with Greek Seas Sailing Company (cost is per person):
Visit 5-7 islands with 4-8 hours each day of sailing time in between places
Boat cost estimate (largely depends on your group size): $750-900 for the week
Add in of shuttle transfer/picking up at airport and driving to dock/vice versa: $40
Tip for Captain: $20
Extras (food and drinks on trip): $300-500
Total Estimate for 2 of us 7 night trip on boat: $2900
Any side trip flights to Santorini or Mykonos: usually around $60 round trip on RyanAir from Athens-flight is about 45mins. Ferries are another option but they are much slower and not too much cheaper, can be 4-6 hours.