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Sailing the Greece Islands
12 days/11 nights
September 17-28, 2025
Only one cabin left and it is a VIP cabin
$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 - Jess Floe
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 - D
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 - Day 3 - Overnight on Andros, Galazio Rooms & Suites- B, D
After breakfast, we’ll check out of the hotel and catch our ferry to the beautiful island of Andros. After checking into the hotel we’ll have the afternoon to relax on the local beach, grabbing some chairs and umbrellas at one of the beach bars and see what island life is all about. In the evening we’ll have dinner at a local restaurant.
Day 3 - Overnight on Andros, Galazio Rooms & Suites- B, L
Today we’ll head out to explore the island. We’ll start with a visit to a local winery where we'll learn about the indigenous grapes of the island. We'll tour the facility and taste their wines. Next we'll visit a couple of the quaint villages of the island where you'll have a chance to explore their streets and learn about the history of the island. We'll stop for lunch before heading back to the hotel. After our tour, you'll have the remainder of the day to spend as you'd like.
Day 4 - Overnight on the sailboat - B, D (appetizers)
Today we’ll have a leisurely morning before we check out and head to the port and catch our ferry to Mykonos. Upon arrival, we’ll store our luggage and have free time to explore the main town. You’ll enjoy getting lost in the maze of streets and alleyways, shopping and exploring this chic island. Early evening we’ll meet back up and 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, Kimolos, Milos, 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.
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