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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.

by KBennettAbout 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

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!

  • What tips would you 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.

  • Any standout moments?

    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.

  • How was the food?

    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....Read More

  • 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 house

  • 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.