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Sailing the Greece Islands
12 days/11 nights  
September 16-27, 2025

 
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$5575

based on double occupancy
($1195 optional single supplement)


$100 per person extra hotel night before the start of the tour based on double occupancy, $185 per person for single occupancy

NOTE: There are two larger VIP cabins offered for an extra $400/person based on double occupancy.


What's included
•   10 breakfasts,
•  11 lunches or dinners (wine included)
•  Transfers from Athens airport and to Athens airport 
•  All accommodations from start to end of tour
•  All transportation during the tour (air-conditioned bus or minivans)
•  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



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
•  Tips for local guides, drivers and sailboat crew
•  Gratuities for chambermaids or personal porters
•  Gratuities for your Tour Dog Travel tour director (at your discretion)
•  Single supplement if not sharing a room

Tour Director - Joey Edwards

Minimum: 8 
Maximum: 10 

NOTE: Would you like to visit the sites in Athens or perhaps a few extra days in another part of Greece? Let Two Dog Travel know your interests and we can make the arrangements.   

Day 1 - Overnight in Rafina, Avra Hotel
Welcome to Greece!  After your overnight flight to Athens you will be met at the airport and transferred to our conveniently located hotel 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. Our tour will begin with a welcome dinner at a local restaurant. 

Day 2
 - Overnight on Syros, Hotel Hermes - B, D
After breakfast, we’ll check out of the hotel and catch our ferry to the beautiful island of Syros, the capital of the Cyclades.  After checking into the hotel you'll have the afternoon to explore the town on your own or head to a local beach. In the evening we’ll have dinner at a local restaurant. 

Day 3 - Overnight on Syros, Hotel Hermes - B, D
Today we will enjoy a walking tour of Hermoupolis, the main town of Syros. We'll visit one of the Neoclassical mansions, the town hall - one of the largest and most impressive ones in all of Greece, the Archaeological Museum, the Apollon Theatre - a symbol of the islands rich cultural heritage, and the Church of St. Nicholas. After the tour, you will have the rest of the day to spend at a local beach or explore the town a bit more on your own. 

Day 4 - Overnight on Syros, Hotel Hermes - B, L
Today we’ll head out to explore the island. We’ll start with a visit to the medieval settlement of Ano Syros, sitting high above Hermoupolis. We'll explore its winding streets and visit some of its notable landmarks. Next we'll head to some of the other Neoclassical villages of the island. After our tour, we'll board our private sail boat, home for the next week. We'll enjoy drinks and appetizers while we meet the crew and discuss our route for the next week. 

Day 5-10 - Overnight on the sailboat - B, L or D
Depending on the weather, we’ll spend our time sailing either the western or eastern Cyclades Islands. We’ll spend the days exploring secluded coves and beaches and disembark for the afternoon or evening to explore one of the islands. Depending on our route, some of the islands we may visit could be  Syros, Serifos, Sifnos, KimolosMilos, Paros, Antiparos, Koufinisia, Amorgos, Naxos and Delos. Each day we’ll start with breakfast on the boat and, depending on our schedule, enjoy either lunch or dinner as well. Our crew will cook for us using local ingredients. You'll be amazed by what the chef prepares for us and the wonderful meals we'll get to experience. 

Day 11 - Overnight in Rafina, Avra Hotel - B, D
Unfortunately, it’s time to disembark. We’ll end at the island of Mykonos where catch our ferry back to Rafina. We'll check into the hotel and have some free time before heading to a local winery for our chef-inspired food pairing/tasting and farewell dinner.   

Day 12 - B
Sadly, it’s time to leave this beautiful country. After breakfast, you will be transferred to the airport according to your flight schedule.  

Office/Retail Store

603 Harrison Avenue

Leadville, CO 80461

 

Mailing Address:

P.O. Box 1367

Leadville,  CO 80461

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