TABLE OF CONTENTS
Trip Highlights
Tour details
Itinerary
What's included
Itinerary Changes
Terrain
Condition Grading
Starting point and getting there
Food, Weather
Gear checklist
Currency & Banking
Passports, Visas
Tucked in the Aegean west of Athens, this journey takes you through a quieter, lesser-traveled corner of the Cyclades—where whitewashed villages, ancient stone paths, and vivid blue seas shape the landscape. Sailing aboard a comfortable catamaran, the most iconic way to experience the Greek islands, we visit a different destination each day, exploring on foot the historic trails that have linked communities for centuries. From the terraced hills of Sifnos to the myth-laced peaks of Serifos and the otherworldly, lunar landscapes of Milos, we immerse ourselves in the natural beauty and cultural depth of each place we land. This trip strikes a perfect rhythm between activity and rest: after morning hikes through chapels, ruins, and wild coastal scenery, afternoons are for swimming in hidden coves, soaking in thermal springs, and simply drifting with the Aegean breeze. Along the way, we explore lesser-known gems like Kimolos and Kythnos—places where authentic island life and age-old traditions still thrive. On board, life is simple and deeply rewarding: fresh meals, starry skies, and the gentle motion of the sea.
TRIP HIGHLIGHTS
- Sail through the Cyclades —the most iconic and immersive way to experience the Aegean
- Hike ancient trails that link whitewashed villages, chapels, and centuries-old ruins across dramatic island landscapes
- Swim in pristine bays, hidden coves, and thermal springs, balancing adventure with moments of rest and renewal
- Explore lesser-known islands like Kimolos and Serifos, where myth, history, and authentic local life still thrive
TOUR DETAILS
- Dates: May and October
- Days/Nights: 8 days / 7 nights
- Condition grading: Moderate
ITINERARY
DAY 1
From Athens to the Cyclades
We meet in Athens and transfer to Lavrio port, stopping for lunch before setting sail to the island of Kythnos. Our boat becomes our home for the week as we journey into the Cycladic blue. After a four-hour sail, we arrive in Kythnos, where we anchor in the serene bay of Apokrousis. Dinner is served on board, under a sky full of stars.
Overnight in Kythnos
Lunch and dinner included
Driving distance: Athens to Lavrio 60 km / 1 hr
Sailing time: Lavrio to Kythnos 4 hr
DAY 2
Hiking from Dryopida to Kanala and sail to Sifnos
After a hearty breakfast, we set off for the whitewashed village of Dryopida, nestled in the heart of Kythnos. This quiet island, one of the lesser-known gems of the Cyclades, is prized for its thermal springs, unspoiled beaches, and simple island charm. From Dryopida, our scenic hike begins—winding through vineyards, low hills, and small chapels as we make our way toward the seaside village of Kanala. The trail offers sweeping views of the Aegean and leads us to a peaceful cove for a refreshing swim. Back on board, we enjoy a relaxed lunch as we set sail for Sifnos, an island beloved for its harmonious landscapes, stone-paved villages, and strong culinary tradition. Tonight, we dine at a charming local taverna, tasting flavors rooted in the island’s long-standing food culture.
Overnight in Sifnos
Breakfast, lunch and dinner included
Hiking duration: 3 hr
Sailing time: Kythnos to Sifnos 5 hr
DAY 3
The heart of Sifnos and sail to Milos
We begin the day with a hike from Apollonia, following scenic trails through the elegant villages of Artemonas and Kastro —known for their Cycladic charm and well-preserved architecture. Along the way, we visit Panagia Poulati, a striking seaside chapel nestled against the rocks, and continue through the green valley of Erkies toward Kato Petali. After lunch at a local taverna, surrounded by the sounds and smells of village life, we make our way to the coast near Chrissopigi. There, our boat awaits for an afternoon sail to Milos. We arrive in time for a swim in its deep blue waters and a relaxed dinner on deck, as the cliffs of the island glow in the afternoon light.
Overnight in Milos
Breakfast, lunch, and dinner included
Hiking duration: 4 hr
Sailing time: Sifnos to Milos 2 hr
DAY 4
Exploring Milos and sailing to Kimolos or Poliegos
This morning’s hike begins in the colorful village of Klima, with its iconic syrmata—boat garages painted in cheerful hues—and climbs through Tripiti to the ruins of ancient Milos. Here, we explore early Christian catacombs and a hillside Roman theater with sweeping Aegean views. Famous for the Venus de Milo, the island’s layers of history and surreal volcanic terrain continue to inspire. We stop for lunch in the hilltop village of Plaka before heading to the port. In the afternoon, we sail to Kimolos or the uninhabited shores of Poliegos—home to some of Greece’s clearest waters and quietest coves. The rest of the day is all about the sea: swimming, sunbathing, and soaking in the calm beauty of the Aegean.
Overnight near Kimolos or Poliegos
Breakfast, lunch and dinner included
Hiking duration: 4 hr
DAY 5
Hiking in Sifnos and onward to Serifos
As we begin our journey northward through the Aegean, gradually sailing back toward Lavrio, we return to Sifnos for one final hike—one of its most scenic. The trail leads from the lively village of Apollonia down to the tranquil bay of Vathi. Along the way, ancient stone walls, hillside chapels, and sweeping sea views frame our descent. After a refreshing swim and lunch by the water, we sail to Serifos. We arrive in the afternoon and make our way up to its striking Chora, perched dramatically on a rocky peak. With its narrow alleys, whitewashed houses, and breathtaking views over the sea, it’s one of the most captivating villages in the Cyclades. Tonight, we’ll enjoy dinner at a traditional local taverna.
Overnight in Serifos
Breakfast, lunch and dinner included
Hiking duration: 4 hr
Sailing time:
Kimolos to Sifnos 2 hr
Sifnos to Serifos 2 hr
DAY 6
Loop hike around Serifos Chora and return to Kythnos
Today we hike a loop trail that explores the untamed hinterland of Serifos. Passing through ruined farmsteads, Byzantine chapels, and windswept hillsides, we get a true taste of wild Cycladic beauty. Serifos is steeped in myth—according to legend, it was here that Perseus returned with the head of Medusa, turning the island's tyrant king to stone and freeing his mother from captivity. In later centuries, Serifos became known for its rich deposits of iron and copper, and remnants of its mining heritage still mark the landscape. After the hike, we head back to the boat and sail to Kythnos for a refreshing swim in its warm waters.
Overnight in Kythnos
Breakfast, lunch and dinner included
Hiking duration: 4 hr
Sailing time: Serifos to Kythnos 3 hr
DAY 7
Temple of Poseidon and farewell dinner
We start the day with a final swim in the warm, mineral-rich waters of Loutra Bay, long valued by locals for their soothing, healing qualities. Then we set sail across the northern Aegean, slowly making our way back toward the mainland. Before reaching port, we pause at Cape Sounion to visit the majestic Temple of Poseidon, standing watch over the sea since the 5th century BCE. This ancient sanctuary once marked the last sight of home for sailors leaving Attica and the first welcome for those returning. With sweeping sea views framed by its marble columns, it offers a quiet moment to reflect on our journey. Our final dinner is in the harbor town of Lavrio, a place steeped in maritime history and the perfect ending to our time in the Aegean.
Overnight in Lavrio (onboard)
Breakfast, lunch and dinner included
Sailing time: Kythnos to Lavrio 4.5 hr
DAY 8
Departure day
After breakfast, we transfer to the airport or continue your journey independently. Wherever you go next, may the wind stay at your back and may the memories of the Cyclades carry you forward.
Breakfast included
Driving distance: Lavrio to Athens airport 36km / 45
WHATS INCLUDED
Price includes:
Seven nights’ accommodation on a catamaran, with a crew of two to look after every need
All costs related to the boat charter and operation, such as fuel, port fees, and custom fees
All transportation during the trip
All activities mentioned in the program
Services of a guide throughout the tour
Transport and handling of one reasonably sized suitcase and one carry-on per person
Included meals:
Breakfast, lunches and dinners as indicated in the itinerary
Not Included:
International air fare
Transfer to and from the airport/port
Medical expenses
Travel or emergency evacuation insurance
Gratuities for leader/guide and the members of the boat
Alcoholic beverages and meals other than outlined in itinerary
Extra boat provisions (beer, wine, soft drinks etc)
Visas if needed
Other items of a personal nature
Anything not mentioned in above program
ITINERARY CHANGES
We are constantly updating our unique itineraries based on new information and experiences available. The walks, accommodations, and visits listed may be adjusted. The itineraries presented are subject to modification and change by Tripin Adventures. We reserve the right, without penalty, to make changes in the published itinerary whenever, in our judgment, conditions warrant, or if we deem it necessary for the comfort, convenience, or safety of participants, anything not mentioned in above program.
TERRAIN
This trip Level is Moderate and is suitable for most people that are in fairly good physical condition. The itinerary includes walking tours in cities and villages and four days with moderate hikes of 3-4 hours. Although the paths are quite well-kept the terrain often tends to be very stony and rocky. You will mostly be walking on footpaths and on some tarmac roads.
CONDITION GRADING
Moderate
Trips designated "Moderate" are more active and require a bit more endurance. Hikes and treks includes occasional steep ascents. Trip members should be experienced hikers in good physical condition, capable of walking 3-5 hours
STARTING POINT AND GETTING THERE
Starting point is: Lavrio Port
Getting There & Away: The port of Lavrio is located about 60 km southeast of Athens and approximately 35 km from Athens International Airport (Eleftherios Venizelos). It's well-connected by road and can be reached by car, taxi, or bus. If you're coming from Athens or the airport, we can arrange a transfer directly to Lavrio port. Alternatively, you can take a taxi (around 1 hour, approx. €50–70 from central Athens or €40–60 from the airport), or use the suburban bus service (KTEL) which runs regularly from Pedion Areos in central Athens to Lavrio (about 2 hours, ~€5–6).
Getting around: Once you're at Lavrio port, everything is within easy walking distance — including shops, cafes, and nearby accommodations. If needed, we can also organize transport from Lavrio to your next destination or hotel.
FOOD
Simple, nutritious and flavorsome, the food is one of the pleasures of travel through Greece. Rustic Greek Cuisine reflects the history and bounty of its diverse regions and relies in the fresh, seasonal home-grown produce and generally simple, unfussy cooking that brings out the rich flavors of the Mediterranean.
Greece's relaxed and hospitable dinning culture makes it easy to get into the local spirit. Greeks love to eat out and share impossibly big meals family style. Given the long summers and mild winters, alfresco dining is central to the dining experience. Service could be slow by Western standards, but why being in rush either way.
As a rule our groups tend to eat together to enable you to taste a larger variety of dishes and enjoy each other's company. There's no obligation to do this though. Wherever possible we will cater for dietary needs for any included meals, but there may be times when those with special requirements may need to provide their own. Note that alcohol and soda are not included.
WEATHER
Spring, summer and fall in Greece are sunny and warm. The daytime temperatures average 25-30 C though temperatures in the 35s are possible in the summer months. Nighttime temperatures cool off slightly to 20 C. Rain showers are rare in the islands, but it's often breezy and rainy on the coast.
GEAR CHECKLIST
Greece has a temperate climate. Base your clothing on the "layering system", if it is hot you can "peel off" layers quickly, if it is cooler and windy you can quickly "dress up". The lighter you travel, the easier you travel. Use your best judgement and pack as lightly as possible. You will appreciate light luggage towards the end of your trip.
Please consider taking along the following items on your trip.
OFFICIAL PAPERS
- Valid passport
- Airline tickets
LUGGAGE
- Duffel bag or rolling luggage
- Daypack to carry camera, water bottle and snacks etc.
- Luggage locks and tags
OUTERWEAR
- Midweight polar fleece sweater
- Rain jacket and rain pants, or poncho
CLOTHING
- Hiking shorts
- Casual clothing made of light-weight fabrics
- T-shirts
- Long-sleeve shirt
- Hiking pants, loose and easy to move in
- Underwear
- Swimsuit
CLOTHING ACCESSORIES
- Sun hat or baseball cap
FOOTWEAR
- Lightweight and supportive hiking boots, broken-in with good ankle support
- Beach sandals
- Casual, comfortable shoes for evening
ACCESSORIES
- Sunscreen and lip protection
- Sunglasses and retainer strap
- Beach towel
OPTIONAL ACCESSORIES
- Security pouch or money belt
- Trekking poles or walking staff
- Camera, memory and batteries
- Reading and writing materials
- Watch with alarm or travel alarm
- Travel pillow
- Motion sickness remedies
- Personal first-aid kit
- Insect repellent (lowrisk)
- Electric adapter plug/converter
This is not a fixed list, but more of a guideline, so feel free to add and remove items as you see fit.
CURRENCY & BANKING
Greece has adopted the Euro as its currency. The easiest way to obtain local cash is from an ATM. Greek ATMs accept cards bearing the Cirrus, EC, Euro card, Visa and Plus symbols. If you take cash, US or Canadian Dollars can be easily exchanged at banks. Most major credit cards, Visa, MasterCard and American Express are accepted. It is advisable to have some Euros with you upon arrival to be used for a taxi if necessary. You may want to check the website www.xe.com for current exchange rates.
PASSPORTS
You must have a passport valid for at least 6 months beyond the conclusion of your trip. Please make sure that you have blank pages in your passport for your visa (if required), entry and exit stamps (one for each). Please make a copy to take with you in the event yours is lost or stolen and keep it separate from your actual passport.
VISAS
Currently a Greek Tourist Visa is not required for citizens of Canada, United States, Britain and Australia. If you hold another passport, please check online http://visacentral.com/visas.php
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