Sailing Greece
September 5 to 12, 2027
7 nights, 8 days | $5450
OVERVIEW
Run, hike and sail through the rugged Dodecanese Islands, discovering crystal-clear waters, traditional villages, ancient trails and a fascinating blend of Greek, Ottoman and Italian influences. Explore volcanic landscapes, abandoned mountain villages, historic monasteries and colorful port towns, while swimming in secluded bays and experiencing island life aboard our traditional gulet. Enjoy fresh island cuisine, Greek cooking, live music and plenty of time on the water, with opportunities to swim, snorkel, SUP or simply relax on deck between adventures
Highlights
Our home for the week!
Beautiful Tersane 8, with comfortable cabins, alfresco dining and spacious decks for sun-soaked or shaded sailing (details below)
Daily cultural experiences
Experience the islands beyond the trails, from live music and dancing, to Greek cooking, a monastery visit, and spa afternoon
All but 1 meal included & Free flow bar onboard
Breakfast and lunch aboard daily, with five dinners ashore discovering local tavernas and authentic island flavors
Time to explore & relax
Swim, snorkel, SUP or explore colorful port towns and boutique shops. Join optional yoga and strength sessions on deck during sailing time
Map
Weather
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September is a beautiful time to explore the Greek Dodecanese Islands, with long sunny days, warm seas and slightly cooler temperatures than the peak of summer. Expect temperatures around 75–85°F during the day, with plenty of sunshine and little rainfall. The sea stays wonderfully warm for swimming and snorkeling, while early mornings are ideal for running before the heat builds. The Aegean breeze brings welcome relief during the day, although seasonal winds can occasionally make the sea more energetic — all part of the adventure!
Itinerary
Day 1
Welcome aboard!
Why are we starting our Greek adventure in Türkiye? Well, finding a beautiful, comfortable vessel large enough for our group in Greece proved surprisingly tricky. Turkish flagged vessel Tersane 8 came highly recommended, and Zoe was lucky enough to spend a week aboard her, checking every detail before giving the escapada seal of approval. Now, we’re delighted to call her home for our week at sea!
Arrive in Bodrum at any time today, then board Tersane 8 from 5:00 PM to settle in, meet your fellow adventurers and get comfortable in your new home on the water. We’ll kick things off with a welcome cocktail and briefing for the week ahead, before sitting down to our first dinner under the stars. As we anchor offshore from Karaada island, watch the glittering lights of Bodrum fade into the distance — then enjoy a peaceful first night as we prepare for the adventure ahead. If you fancy a first dip in the water - why not!
Location : Bodrum, Türkiye
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Meals : Dinner
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Lodging : Tersane 8 - our traditional gulet and home for the whole week!
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Overnight : On anchor offshore of Karaada Island, Türkiye
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Day 2
A castle, historic windmills and crystal clear waters of Leros
Rise with the sun (and the gentle hum of the engine!) as we cruise towards our first Greek island: Leros. Start the morning with an optional yoga and stretching class on the top deck, followed by a fresh Greek breakfast. Then it's your choice — join an optional strength session, grab a coffee and a book, or simply settle in and watch the islands drift by.
We’ll reach Leros in the late morning, then it’s time to stretch our legs with our first run or hike of the week. This is a relaxed introduction to island trails, climbing the steps to Leros Castle for sweeping views before finding the island’s famous windmills and descending towards Panteli Beach, where you can jump right in or enjoy a refreshing beverage or two.
We’ll return to the boat for lunch, then spend the afternoon swimming, soaking up the sun or exploring Panteli’s few boutique shops before our first Greek taverna dinner on shore. Live Greek music & dancing will give us a great introduction to culture on the islands!
Location : Leros island, Greece
Meals : Breakfast, Lunch, Dinner
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Trails : Castle Trail (6-7km)
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Activities : Live Greek music & dancing
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Overnight : On anchor offshore of Panteli, Leros, Greece
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Day 3
Limestone trails and local flavors on Kalymnos
We settle into our daily rhythm of optional yoga and stretching, breakfast and an optional strength class as we make the short sail towards Kalymnos, the island famous for its sponge-diving heritage and rugged limestone landscape - sought after by climbers around the world. After some free time to explore the small shops around the port, we’ll regroup for our second run or hike.
Today’s trail follows the Italian Path, an old route built during the Italian occupation that climbs from Pothia before winding through the mountains and descending into the lush Vathy valley. It’s a beautiful mix of rugged hills, panoramic Aegean views and fragrant Mediterranean landscape.
We’ll finish in Vathy, a peaceful, fjord-like valley surrounded by citrus groves and dramatic limestone cliffs. After lunch aboard and a chance to swim in the crystal-clear water, we’ll head ashore for a hands-on Greek cooking experience, learning to prepare a few local dishes before enjoying the fruits of our labor — with something local to wash it all down. We return to our vessel for another peaceful rest on anchor.
Location : Kalymnos island, Greece
Meals : Breakfast, Lunch, Dinner
Trails : Italian Trail (8-9km)
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Activities : Greek cooking experience
Overnight : On anchor offshore of Vathys, Kalymnos, Greece
Day 4
Into the Volcano on Nisyros!
Ease into the morning as we sail towards Nisyros — a small volcanic island unlike anywhere else on our journey. We’ll have lunch aboard before heading ashore in Mandraki to visit Panagia Spiliani, a monastery built into a cave high above the town. From here, it’s time to head uphill by bus to the tiny village of Nikia, perched right on the edge of the volcanic caldera with views across the craters.
Then we run straight into the volcano! Our third trail descends from Nikia into the Lakki caldera, eventually reaching the steaming Stefanos crater — one of the best-preserved hydrothermal craters in the world. This is not the Greece you imagined! We’ve timed our run for later in the day, hopefully leaving the crater and its dramatic volcanic landscape largely to ourselves free from day-trippers.
As the sun starts to drop, we’ll cross the caldera before making our final climb into Emporios village, where a cold drink and some grilled snacks will be waiting at The Balcony, overlooking the volcanic landscape we’ve just crossed. Then it’s a short bus ride back to the port, time for a shower, and an optional sunset drink by the sea before dinner at a local taverna.
Location : Nisyros island, Greece
Meals : Breakfast, Lunch,
Dinner on your own today!
Trails : Volcano Trail (9-10km)
Activities : Visit Panagia Spiliani clifftop monastery & Stefanos crater
Overnight : In port - Mandraki, Nisyros, Greece
Day 5
A ghost village and crystal bays on Tilos
We’ll make the short sail to Tilos, one of the quieter and more unspoiled islands in the Dodecanese. Our fourth trail takes us through the hills to Mikro Chorio, a fascinating abandoned village whose stone houses and winding lanes have been slowly reclaimed by nature. Once home to hundreds of islanders, the village was gradually deserted after World War II, leaving behind a hauntingly beautiful glimpse into Tilos’ past.
From the village, we’ll continue and above the coastline before descending towards Livadia, with spectacular views over the island and some of the clearest waters of the week. We’ll finish at Livadia beach, where a cold drink and refreshing swim await.
Tenders will take us back aboard for a shower and lunch, before we set sail again to explore some of Tilos’ more remote bays. Spend the afternoon swimming, snorkeling, SUPing or simply relaxing on deck as we discover a few different beaches and crystal-clear corners of the island.
We’ll head ashore for dinner. And if we’re lucky, perhaps some more live music to round out another island evening!
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Location : Tilos island, Greece
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Meals : Breakfast, Lunch, Dinner
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Trails : Ghost village Trail (8-9km)
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Activities : Swimming, snorkeling, SUPing
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Overnight : On anchor offshore of Livadia, Tilos, Greece
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Day 6
Our final trail and Symi from the water
This morning we sail into Symi’s breathtaking harbor, where colorful neoclassical houses climb the steep hillsides above the water. Our fifth and final trail is a little gentler, winding through the backstreets of Gialos, up the famous Kali Strata steps and into Chorio, with plenty of opportunities to stop for views and take in village life. We’ll then descend back towards the harbor for a flatter final stretch along the waterfront — the perfect way to finish our week of running.
Back aboard for showers and lunch, we’ll swap trail shoes for swimwear and head out on a private boat cruise to explore some of Symi’s beautiful bays and beaches. Swim, snorkel or simply relax on board as we discover the island from the water.
Back in Gialos, there’s time to wander the boutiques,
explore the colorful streets or enjoy a waterfront drink before dinner ashore. And if you still have energy left, Symi has a livelier evening atmosphere — so tonight is your chance to stay out a little later!
Location : Symi island, Greece
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Meals : Breakfast, Lunch, Dinner
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Trails : Harbor Trail (6-7km)
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Activities : Swimming and snorkeling in different bays on a private afternoon cruise
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Overnight : In port - Gialos, Symi, Greece
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Day 7
Sail, soak and celebrate - a relaxed final day
Today we sail away from Greece and make our way back towards Bodrum. With no trail to catch, the day is yours to slow down - simply find a spot to sunbathe, or read, reflect on the week and enjoy the final hours at sea.
As we arrive in Bodrum, we’ll head ashore for lunch before spending the afternoon relaxing with a traditional Turkish hammam and spa experience. The perfect way to round off the week!
Tonight, we return to Tersane for our final dinner together onboard. We’ll raise a glass with our crew, watch the lights of Bodrum sparkle across the water and enjoy one last evening under the stars.
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Location : Bodrum, Türkiye
Meals : Breakfast, Lunch, Dinner
Activities : Spa afternoon
Overnight : In port OR anchor - Bodrum, Türkiye
Our Home at sea - Tersane 8
Our home for the week is Tersane 8, a spacious 44m traditional gulet with 14 comfortable cabins accommodating our group of 30 guests (including escapada staff), plus a 9-person sailing crew. With generous indoor and outdoor living spaces, alfresco dining, sunpads and both sunny and shaded decks, there’s plenty of room to relax between our adventures. SUPs and snorkeling equipment are provided (although we recommend bringing your own mask and snorkel if you love spending time underwater!)
All cabins are located on one level below the main deck, with a decent amount of space, portholes for natural light and air conditioning. Each has a private bathroom with a large shower cubicle and reliable hot water, plus sockets for charging your devices. Hairdryers and basic toiletries are provided (although you may want to bring your own if you have particular preferences). Cabins are cleaned daily, with fresh bathroom and swimming towels provided.
There are lines onboard for hanging wet clothes and swimwear, and one laundry (<5kg) service is included during the week.
Start & end location, visas and flights
Start and end location
We’ll start and finish our sailing adventure in Bodrum, Türkiye, spending two nights in Turkish waters and five nights in Greek waters.
Visas
For US passport holders, no visa is required for tourist visits to Türkiye of up to 90 days within any 180-day period. Greece is part of the Schengen Area, where US citizens can also visit visa-free for up to 90 days in any 180-day period.
The necessary exit and entry formalities will be completed smoothly by a customs official who will come aboard to ensure everyone’s passport is checked and correctly stamped.
Flights
These would be our recommended options when looking for flights:
US > London OR other European hub (round trip) + separate London OR European hub > Bodrum (round trip)
Because you can choose your preferred airline or alliance
US > Istanbul (round trip) + separate Istanbul > Bodrum (round trip)
Because multiple low cost airlines operate from Istanbul to Bodrum
US > Bodrum (round trip via Istanbul - eg Turkish Airlines)
This would be the easiest ticket, but probably not most cost-effective. Turkish Airlines are part of the Star Alliance
Extending your trip
Why not add a few extra days before or after your sailing adventure? We’ll share more information before the end of the year on recommended ways to extend your trip, including flight tips and any additional tours or experiences we may offer — so hold off on booking your flights for now!
Explore more of Türkiye (1-4 days): Spend a day or two Istanbul — Türkiye’s vibrant cultural capital, where East meets West. Explore Hagia Sophia, the magnificent former church and mosque; the Blue Mosque, famous for its beautiful blue Iznik tiles; Topkapi Palace, the former home of Ottoman sultans; and the Grand Bazaar, one of the world’s oldest and largest covered markets. Finish with a cruise along the Bosphorus, the saltwater strait separating Europe and Asia, before flying to Cappadocia for its surreal valleys, fairy chimneys, underground cities and iconic hot-air balloons.
Explore more of Greece (1-4 days): Extend your adventure with time in Athens, exploring the Acropolis and Parthenon, ancient landmarks overlooking the city, and the Acropolis Museum, home to an impressive collection of Greek archaeological treasures. Then head to Santorini for dramatic caldera views, whitewashed villages, the iconic blue dome roofs, volcanic landscapes and famous sunsets in Oia.