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Trails, Tastes and Turquoise Waters

Sifnos and Milos, Greece

September 2027 - Dates TBC
From A$6885 (double/twin share)

Ladies, THIS is the trip you have all asked for - RoamAway Style!

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Discover a different side of the Greek Islands on this thoughtfully designed 10-day journey through Sifnos and Milos. Blending gentle adventure with beautiful accommodation, delicious Mediterranean food and time beside the sea, this small-group experience will reveal the landscapes, flavours and traditions of two distinctive Cycladic islands.

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We’ll explore Sifnos on foot, following ancient trails through whitewashed villages, terraced countryside and along the spectacular coastline. Our hikes will be balanced with time to slow down, wander village laneways and savour the island’s renowned food culture—including an authentic Greek lunch at a seaside taverna and a very special degustation dinner.

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On Milos, we’ll discover the island’s extraordinary volcanic scenery, colourful fishing villages and fascinating history. One of the trip’s highlights will be a private catamaran day cruise to spectacular Kleftiko and its surrounds. We’ll sail past dramatic rock formations and hidden sea caves, swim in clear turquoise waters and enjoy a gourmet Mediterranean lunch served on board, complete with open bar.​

The itinerary will also include a visit to a family-run winery for a relaxed tasting session, a visit to a local pottery studio and plenty of opportunities to enjoy beautiful beaches, local restaurants and the unhurried rhythm of Greek island life.

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Throughout the journey, we’ll stay in carefully selected, beautiful accommodation that complements RoamAway’s style of comfortable adventure.

All scheduled transfers will be included, including ferry travel from Athens to the islands, between Sifnos and Milos, and back to Athens.

TRIP OVERVIEW

  • 1 Night in Athens at the start

  • 4 Nights each in Sifnos and Milos

  • A maximum of just 9 guests

  • 3 or 4 Village-to-village and coastal day hikes along ancient island trails

  • Private catamaran day cruise to Kleftiko and Sykia cove

  • Swimming, snorkeling and SUP in clear turquoise waters

  • Gourmet Mediterranean lunch served aboard the catamaran, including water, soft drinks, local beer and wine from the open bar

  • Visit to a family winery with a tasting session accompanied by a local tasting platter

  • Authentic seaside taverna lunch

  • Special Mediterranean degustation dinner

  • Time for beaches, villages, local food and relaxation

  • Beautiful, carefully selected accommodation

  • All scheduled transfers and inter-island ferries included

A NOTE ABOUT ROOM ARRANGEMENTS

​​Accommodation will be primarily based on double occupancy, with only a small number of twin rooms expected to be available. Travellers will need to be comfortable sharing a double bed with their travel companion if a twin room cannot be secured. This makes the trip particularly well suited to female couples, close friends or family members—so it may be the perfect excuse to invite someone special to join you.

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EXPRESSIONS OF INTEREST NOW OPEN!

This trip is currently in the planning stage, and dates, final itinerary and pricing are yet to be confirmed. At this stage, I am seeking expressions of interest to determine whether there is enough genuine interest to officially launch this exciting adventure.

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If this sounds like the kind of Greek adventure you would seriously consider joining, please complete the expression-of-interest form. With places capped at only nine travellers, submitting the form is the best way to let me know you are interested and to ensure you receive the trip details first if it goes ahead.

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