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Greece Islands Active  |  11 days/10 nights  
September 13-23, 2022

This tour is sold out. If you'd like to be on a waiting list in the case of a cancellation, please let us know. 


($975 single supplement)


Additional hotel night before start of tour: $245 per room. Airport transfer and breakfast included


What's included

•   11 breakfasts,

•  5 lunches (wine included)

•  4 dinners (wine included)
•  Transfers to and from the Athens airport
•  All accommodations from start to end of tour
•  All transportation during the tour including interisland flight and ferry included
•  All included group activities, wine tastings, entry fees as per itinerary
•  A full-time Two Dog Travel tour director with you and available 24/7
•  A local professional bi-lingual guide for some local sights and activities
•  All local guide, driver and restaurant tips are included per itinerary



What's not included
•  Airfare, airport taxes and other transportation to and from the pickup location
•  Personal charges such as laundry, telephone calls, rooms service, mini-bar, souvenirs
•  Private excursions not mentioned in the itinerary
•  Gratuities for chambermaids or personal porters
•  Gratuities for your Tour Dog Travel tour director (at your discretion)
•  Single supplement of $975 if not sharing a room


Tour Director - Becky Edwards
Minimum: 6
Maximum: 16
Day 1 - Overnight in Athens - D - Herodion Hotel
After your overnight flight to Athens you will be met at the airport and transferred to our conveniently located hotel, with rooftop views of the Acropolis, where your Two Dog Travel tour director will be waiting to greet you. If you arrive early in the day, your room may not be ready but the hotel will be happy to store your luggage. Your tour leader will be available to make suggestions on things to do and help get you acquainted with the area. We will all meet in the afternoon and join our local archaeologist/guide for a short walking tour of Athens. Our tour will end at a local restaurant where we will enjoy a welcome dinner, toast to our upcoming Greek adventure and marvel at our incredible view of the Acropolis.
Day 2 - Overnight in Santorini - B, D - Strogili Traditional Cave Houses
After breakfast, we will again be joined by our archaeologist/guide for a half day tour of the crowning glory of Athens, the Acropolis and the ancient Agora. After our tour, we will have time for lunch (not included) before being transferred to the airport for our short flight to the picturesque island of Santorini. Upon arrival on Santorini, we will transfer to the beautiful village of Oia where we will check into our private cave houses, all with their own terrace overlooking the famous caldera. After toasting to the glory of Santorini from our terraces, we will head to dinner as a group and enjoy our first evening on Santorini.
Day 3 - Overnight in Santorini - B, L - Strogili Traditional Cave Houses
Today we live like royalty. After breakfast, we meet at for our private catamaran sail around the island. We will stop for a swim at the hot springs and another stop for snorkeling. The crew will prepare an incredible bbq lunch onboard as well as serve wine, ouzo, beer, water and soft drinks all day. After an amazing day on the water, we will arrive back in Oia late afternoon and your evening will be free to enjoy as you'd like.
Day 4 - Overnight in Santorini - B - Strogili Traditional Cave Houses
Today it’s time for a hike. After breakfast we will begin our hike along the caldera where the trail offers legendary views along the way. We will end our hike in Fira around lunch time where we will have the rest of the afternoon and evening free. A few options would be to shop in Fira (or Oia); take a taxi or bus to one of the beaches; rent a car for the afternoon and visit the island beaches and sights; head back to Oia and take the path down to Ammoudi where you can swim from the rocks to a small island. 
Day 5 - Overnight in Santorini - B, L, D - Strogili Traditional Cave Houses
This morning we will be met by our private bus which will take us to our wine tastings and tour of the island. You will have the opportunity to learn the unique vine growing technique of the island and enjoy some local wines. We'll visit a special place that was once an ancient winery and distillery and now has been turned into a beautiful art gallery. We'll learn about their new modern winery and taste some of their wines. We'll also visit the beautiful Holy Monastery of Prophet Elias and learn a bit about the lives of the monks and enjoy the breathtaking views from this high vantage point. Next we'll head to Perissa Beach where we'll sit by the water and enjoy lunch with a view. After our tour of the island you'll have some free time to relax by the pool at our accommodations before meeting back for dinner. We'll have the prime spot for the famous Oia sunset as eat our meal.
Day 6 - Overnight in Milos - B, L - Villa Tania
After breakfast, we will check out of our cave houses, load our luggage onto the bus and join our private guide. We will visit the hilltop fortress village of Pyrgos with its castle, quaint winding streets and panoramic views. We will then visit the ancient ruins of the city of Akrotiri (some say this is the lost city of Atlantis). We'll make a stop for lunch at a local taverna before being dropped off at the port where we pick up our afternoon ferry to Milos. After being transferred to our seaside hotel in the small fishing village of Pollonia, you'll have the rest of the evening free to spend as you'd like.
Day 7 - Overnight in Milos - B, L (light snack) - Villa Tania
Today we enjoy the water on kayaks. After breakfast we will meet for a half day kayaking excursion around Milos where we will have a stop for snorkeling and swimming and enjoy light snacks on the beach. You will be astounded by the incredible geography and the crystal clear water as we enjoy this day. After some free time at the hotel, we'll meet back up to visit the quaint fishing village of Klima where we'll have time to take some photos before enjoying a glass of wine as we watch the sunset by the water. Next we'll be transferred to Plaka, the oldest and highest town on Milos. Here you'll have free time to explore the town, perhaps walk up to the castle for the wonderful view and enjoy dinner on your own in one of the many tavernas in town. 
Day 8 - Overnight in Milos - B - Villa Tania
Today is a hiking and beach day! Grab your swimsuit and walking shoes as we set out to explore the amazing beaches of Milos. We'll first visit Papafragas beach, with its unique rock formations and caves. Next stop is Sarakiniko beach, and its white moonlike landscape. We'll also include Tsigrado beach, where we have to climb down a ladder to reach the sand and the beautiful Paliochori beach and its pastel colored cliffs. Here we'll stop for lunch and some time to relax. Next we'll continue to make our way around the island exploring many of its hidden gems and enjoy some hiking along the paths. After our full day exploring Milos, you'll have the evening free to do as you'd like. 
Day 9 - Overnight in Milos - B, L - Villa Tania
Today, once again, we live like royalty as we board our private sailing boat and enjoy a leisurely day on the water. We'll sail around the island stopping to swim in an area with some of the clearest bluest water you've ever seen. We'll then sail by some of the famous caves along the coast. We'll have the chance to enter some of these caves by dinghy and also swim among these amazing rock formations. We'll be served drinks and snacks on board before enjoying a feast of a lunch prepared for us right on board. It will be the perfect way to spend our last full day on the beautiful island of Milos.
Day 10 - Overnight in Athens - B, D - Herodion Hotel
After breakfast, and checking out of the hotel, time permitting, we'll visit the catacombs, said to be the most important early Christian monument in Greece. Next we'll see the ancient Roman Theater, with its beautiful setting overlooking the Aegean and close to the site where the famous Venus of Milos was found. After some free time for lunch we'll head to the airport for our afternoon flight to Athens. After checking into our Athens hotel, we'll walk to a local restaurant where we'll enjoy our farewell dinner with a view of the Acropolis. What a great way to end an amazing Greece vacation!
Day 11 - After breakfast, transfer to the airport to catch your flight home.

Note: The itinerary is descriptive, not definitive and is subject to change. In particular our actual itinerary will depend on the ferry and flight schedules, which vary from year to year. There also may be modifications due to weather and availability of local activities and guides.

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