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Trip Report

2 Weeks of Sailing & Historical Sites in Greece

Two wonderful weeks in Greece with a group of friends. Our goal was to get sun, do some sailing in Greece, visit historical sites, and eat great food.

  • The views really are amazing.+ 13
  • Santorini
  • Santorini
  • 2 Weeks of Sailing & Historical Sites in Greece
About Me:"The world is big and I want to have a look at it before it gets dark" -John Muir read more

EuropeGreece13 days / September 2019

Highs & Lows

Private sail off the island of Crete

Driving in Santorini

Itinerary Overview

  • 4 Nights: Santorini
    Relaxing and time in the sun
  • 6 Nights: Chania
    History, beaches, sailing
  • 3 Nights: Athens
    Historic tour of the city
Santorini - Relaxing and time in the sun

Santorini Relaxing and time in the sun

Santorini - Relaxing and time in the sun - The views really are amazing.
The views really are amazing.
Santorini - Relaxing and time in the sun - null
Santorini - Relaxing and time in the sun - null4+

I was concerned that Santorini would have throngs of tourists and I was hesitate to book time on the island. Yes-it is filled with tourists. At least 4 cruise ships took over and the town of Thira during the day and was packed. That said, the island itself and the views are really worth it. 

Before the trip I couldn't figure out where to stay:  Oia, Imerovigli, or Thera. Honestly, all have amazing views so you can't go wrong with any of them. Oia is at the far end so it would be a pretty long drive if you wan to get out an explore. 

I highly recommend renting a car to explore and get out of the main towns. Careful driving- there are very tight steep roads and some parts have lots of traffic and pedestrians.  Many rented 4 wheelers, but frankly this seems more dangerous and being exposed in the sun would be uncomfortable.

During our stay, we visited the pool / beach at the new Nikki Beach Hotel. The food was great (expensive) and the pool was very nice. Fun people watching, although the beach is rocky.  The hotel itself is very pretty but in a remote part of the island and doesn't have great views. I learned that Santorini is not about the beaches. 

We also wondered a small local village, Meggalochori which had almost not tourists. There seemed to have a few pretty boutique hotels which could be a nice option. They probably don't have the same dramatic cliff views as many of the other towns do. 

The hotel also arranged free transportation for us to visit their spa, A.Spa located in Oia about 15 minutes away which was fantastic.

Chania - History, beaches, sailing

Chania History, beaches, sailing

Chania - History, beaches, sailing - null
Chania - History, beaches, sailing - null
Chania - History, beaches, sailing - null

We took a ferry from Santorini over to Heraklion Crete. We then rented a car near the port and drove the 2 hours to Chania.  There were no direct flights from Santorini to Chania so the ferry was our only option. 

A group of us rented a house for a week just outside the town of Chania. 

Our activities included: touring the charming town of Chania, which used to be a Venation port, beach time, and visiting nearby ruins.

A highlight of our time on Crete was a lazy day on a sailboat.  We swam in the warm water and sailed to a few tiny beaches including one nude beach! 

Athens - Historic tour of the city

Athens Historic tour of the city

Athens - Historic tour of the city - null
Athens - Historic tour of the city - null
Athens - Historic tour of the city - null3+

On the first day we wondered, with gelato in hand, the neighborhood of Plaka which is the oldest part of the city. 

The following day we hit up all the major sites: The Acropolis (get there before 10 am as it's a madhouse of people), Panathenaic Stadium (Olympic stadium), Temple of Zeus, and we watched the changing of the guard at the Presidents residence. 

On our last day, our friends all split up - some went to the archaeology museum for a private tour, some shopped and I went to the GB spa at the Grande Bretagne Hotel which was absolutely beautiful. 


Q & A

  • What would you have changed?

    We kept the pace pretty easy but I could see possibly trimming down to three nights in Santorini and five nights in Crete to squeeze in another island. It's just nice to not have the schlep to new locations ever few days!
  • Tips you would give a friend?

    If anyone in your party has mobility issues, I would check the steps at your hotel in Santorini. We saw some elderly folks really struggling with the steep steps and no handrails.
  • Transportation Tips?

    I'm glad we rented a car in Santorini to explore outside of the main towns which are very crowded. The rental car office in Heraklio's port, where our ferry landed, was about a 15 minute walk outside of the port area (Motorclub.gr). Driving in Crete was pretty easy.
  • Sailing in Crete was lovely.
  • Packing tips?

    Don't bother bringing heels as walking is tricky with the hills, stairs, and cobblestones and make sure you wear a high SPF sunscreen.
  • Restaurant recommendations?

    Santorini: Metxis Mas - located in the center of the island, this small outdoor restaurant gets busy so book ahead. The food here I thought was the best we had on the island (2nd was at our hotel). Feggera (located in the village of Meggalochori) - had a lovely lunch here. Make sure to head upstairs to the patio. Crete: Portes - located in town, on the water. Blue - Wonderful spot to see the sunset. Located just outside of the main part of town. Chrisostomos - popular with locals featuring traditional Creatian food. My carnivore friends loved the food here. Food was good but light on vegetables! Athens: Mani Mani - sophisticated and great quality food. Fabrica tou Efrosynou - Casual family restaurant with excellent food located a little off the main part of town. Falafellas - GREAT falafel street food. Very popular with long lines late at night. For $3 it was one of my favorite meals. City Zen - Rooftop bar for the absolutely best view of the Acropolis. Lively and fun spot for drinks.
  • Any surprises?

    Many said "skip Athens" but we loved the history, charming neighborhoods, and the lively streets at night. We stayed 3 nights which I thought was the perfect about of time.
  • Booking details?

    Hotels: Expedia-- SunRocks in Santorini, Perianth in Athens Flight from Athens to Santorini: Olympic Air Ferry from Santorini to Crete: FerryHopper.com, SeaJets Day Sailing in Crete: Notos Sailing www.notos-sailing.com Flights from Crete to Athens: Sky Express Car Rentals: Santorini, Budget; Crete - Motor Club (motorclub.gr)


  • Sun Rocks - Highly reccomend. This is a small boutique hotel with perfect views. The service was outstanding and the rooms are very nice (try to request room 10 which has a bigger private patio). Don't overlook the restaurant -- the food was some of the best we had in Santorini.

  • Airbnb-Alianthos Villa https://www.airbnb.com/rooms/13288105?guests=1&adults=1&s=67&unique_share_id=ed917570-aa14-4247-bd57-09aaba00e905

  • Perianth hotel - hip boutique hotel in a lively neighborhood. The beds were very comfortable, and the free breakfast was great. We especially loved sitting outside, people watching at their cafe/bar at night. The location was perfect - easy to walk to the old neighborhood, Plaka and lots of fun restaurants nearby.