Natural rocky arches with clear transparent waters in Kleftiko, Milos island, Cyclades, GreeceView of Kamares village from the church of Agios Symeon."nWildland Trekking Hikers on Sifnos Path to the village of Kastro in GreeceScenic Klima village (traditional Greek village by the sea, the Cycladic-style) with sirmata - traditional fishermen's houses, Milos island, Cyclades, Greece.Milos island, Greece - June 11, 2018: Sunset scene in Plaka village which is full of shops and restaurants. People are dining in one of the restaurants decorated with bougainvillea flowers.Hiking on Sifnos Path in GreeceFamous Sarakiniko beach on Milos island, Greece."nWildland Trekking Guests Hiking to Faros in GreeceOcean channel and arch in GreeceWalkway down to Greek temple in Greek Islands

Hiking the Greek Islands

Athens, Greece

Trip Highlights

  • World Class Cuisine
  • Island Hiking in the Cylcades: Sifnos, Kimolos, & Milos
  • Aegean Sea Sailing
  • Elegant Mediterranean Accommodations
  • The Acropolis


Our Greek Trekking Adventure is the best way to experience the best of Greece’s outdoors as well as some of the most historical areas and sights in the country. Together we’ll explore the many islands, waterways, chapels, monasteries, and villages of this ancient country. We’ll see up close the wonders of shimmering inlets, stunning geology, and some of Greece’s great treks.

Each night we’ll stay in a wonderful array of hand-picked accommodations in stunning, iconic settings. With a knowledgeable local guide, you’ll have an insider’s experience of these Greek islands. Don’t miss this amazing opportunity to experience the best of Greece!

Read more …
From USD
$4900 Per Person
$1875 Single Supplement

$1875 Single Supplement

Trip Type: Inn-Based Hiking Tour
Difficulty Level:
Solitude Level:
Group Size: 3-12 Guests
Trip Length: 9 Days
Distance: 33MI / 53KM


Scale of 1-5. 1 is least difficult; 5 is most difficult

This trip involves hiking with a light day pack (8-12 lbs) from 3-5 hours a day with elevation gain and loss averaging around 1200 ft. There is little to no height’s exposure. This trip requires transport via ferry and one day on a sailboat. There is an option for swimming and snorkeling.

Hiking Distances:

Up to 7 miles

Backpack Weight:

Up to 12 lbs


Lightly Rugged

Max Daily Elev. ↑↓:

Up to 1500 feet

Heights Exposure:


Please Note: Terrain, Elevation Gain and Heights Exposure ratings reflect the section or day of the trip with the maximum difficulty of each. Much of the trip is at easier levels. See the trip itinerary for more detailed information.


  • Hiking uphill or downhill with an 8-12 lb backpack for 3-5 hours a day
  • Maintaining balance and footing on steep, variable and uneven terrain
  • Boarding a sailboat
* For an official and complete list of physical requirements, please see our Essential Eligibility Criteria.


1 least solitude, 5 most solitude

We rate this Greek Trek a solitude 2. You can expect several hours of solitude at a time.

Minimum of 3 Guests

We require a minimum of 3 guests to confirm this trip. If a trip date is not confirmed yet, you can register and will be notified when the trip is officially confirmed. We recommend not making final travel arrangements until your trip meets the minimum number of guests and is confirmed.

In most cases, if a trip does not reach the minimum number of guests, you may choose to transfer to another trip date or another trip, be refunded your payments in full, or you may have the choice to pay a supplemental fee to run the trip with fewer guests. We make the final determination for these trips 65-60 days before the departure date.

Private Trips

Travel in perfect company by booking a private trip exclusively for your group!

Our sliding scale for private trips is based on the final number of guests in your group. Rates are per person and do not include sales tax, national park fees or guide gratuity. The final rate is based on the actual number of guests on the trip and may adjust based on cancellations or additions.

Please Note: you can also enjoy a private trip at our normal scheduled rates by filling any empty tour to capacity. However, if group members drop from the tour those spots will automatically become available on our website for instant booking. By purchasing a private trip at the rates listed below, your trip will remain exclusive to your group regardless of cancellations. 

Private Rates FOr This Trip

  • 3 people: rate x 2
  • 4-5 people: rate x 1.5
  • 6-10 people: rate x 1.15
  • 11-12 people: standard rate
  • 13+ people: contact us for availability and pricing

*all rates are per person and single supplements apply

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Day 1

  • Drive: 45 minutes

Yassou and welcome to Greece! Travelers will arrive into Athens to be picked up by your guides and transferred to this evening’s hotel in Piraeus. We will meet as a group for our orientation. A sumptuous Greek dinner is how we’ll ring in this first day of our fantastic island adventure!

Day 2

  • Hiking Mileage: 4 mi (6.7 km)
  • Elevation Gain: 1,443 ft (440 m)
  • Elevation Loss: 820 ft (250 m)
  • Ferry: 3 hours

Today finds us on a ferry to the one of the most beautiful islands in the Cyclades and well known for its hiking. Sifnos is known for its hikes through traditional villages and churches nestled above the seaside. After a seaside lunch in a local taverna we’ll tighten our laces and head to the charming village of Apollonia. Here we’ll walk along stone paved streets, admiring whitewashed houses with domed roofs, and ornate gardening.

Day 3

  • Hiking Mileage: 7 mi (11.3 km)
  • Elevation Gain: 1,475 ft (450 m)
  • Elevation Loss: 1,475 ft (450 m)

Platys Gialos to Fikiada Bay takes us through olive groves, past the abandoned farm of Moussia, and on to an expansive view of the sea. We’ll cast our eyes on the oldest chapel of Sifnos in the islet of Kitriani. From here we’ll hike back down into the bay with magnificent views of the incredible Mediterranean oceanside.

Day 4

  • Hiking Mileage: 7 mi (11.3 km)
  • Elevation Gain: 1,542 ft (470 m)
  • Elevation Loss: 2,165 ft (660 m)
  • Drive: 30 minutes
  • Ferry: 40 minutes then 15-minute shuttle

This morning starts with a short shuttle to Apollonia, the capital of this island. We’ll hike along past numerous chapels to the highest point of the island: Mount Profitis Ilias at 2,237 feet (682m). Here we’ll find the intact and inhabited 12th century monastery of the same name. The few monks who are still on the premises make their own wine and other sundries. On the hike back down, we’ll encounter the Vougnous Cave and the Kalamitsi springs on the way into Vathy Bay.


Day 5

  • Hiking Mileage: 5.5 mi (9km)
  • Elevation Gain: 492 ft (150 m)
  • Elevation Loss: 492 ft (150m)
  • Ferry: 40 minutes then 15-minute shuttle

After a Mediterranean breakfast we’ll take a ferry to the island of Milos. Here we’ll encounter an important archeological site containing artifacts from the Cycladic civilization of this region’s past. You’ll get to stare into the crystal-clear waters of the Papafranga abyss as we continue to our hike’s end at the port of Mandrakia.

Day 6

  • Hiking Mileage: 5 mi (8.5 km)
  • Elevation Gain: 492 ft (150 m)
  • Elevation Loss: 492 ft (150 m)

Haul up the main and grab the sheets, we’re going sailing! From Adamas pier we’ll set sail in style, to the island of Kimolos. As we hike across this beautiful island, we’ll pass by a famous rock formation, and meet our captain on the other side. Once back on the boat you can take a swim or snorkel. We’ll cap this wonderful day on the water as we cruise back to the pier on Milos.


Day 7

  • Hiking Mileage: 4 mi (6.5 km)
  • Elevation Gain: 820 ft (250 m)
  • Elevation Loss: 394 ft (120 m)

Our first stop today will be the fishing village of Klima with its multi-colored boat garages attached to the houses. After Klima we’ll hike to the catacombs and the breathtaking theater where, nearby, the famous Venus de Milo was found. In Plaka one sees the cobbled streets with their whitewashed houses and traditional domed roofs. In the late afternoon you’ll have the chance to explore the streets and shops of Chora, adjacent to our accommodations for the evening.


Day 8

  • Ferry: 3 hours
  • Drive: 45 minutes

Day 8 wraps up our time on these incredible islands. We will ferry back to Piraeus, then take a private transfer to our hotel in the capital of Athens. Depending on the ferry schedule, we’ll have a leisurely final morning on the island, or we’ll have a longer afternoon to explore Athens. Athens, both a historical and cultural mecca, is the largest urban area in the European Union! Here you’ll find one of the world’s oldest cities spanning over 3,400 years of history. Tonight, you’ll be dining in a typical Greek taverna.

Day 9

  • Drive: 40 minutes

Our final day provides us with a trip to the Acropolis where we’ll experience a cultural English-speaking tour. We’ll have lunch in a taverna and prepare for our airport shuttle. Here we’ll say our “antío” or goodbyes – thank you for choosing Wildland!

Please Note: We always do everything in our power to follow the set itinerary, however occasionally trips are subject to itinerary changes based on a variety of circumstances, including but not limited to: lodging/campground availability, extreme weather, political or bureaucratic obstacles, earthquakes, fires, flooding, changing boat schedules, and more. Normal terms and conditions apply to trips with itinerary changes.


Trip Dates & Booking


Click on a date to register. You can also click here to request new dates or book through customer service.

Available to Book


This trip is available and bookable online! Click on the date to register now or contact us online to book through our award-winning customer service team!

Going Fast


This trip has 1 or 2 spots remaining and is bookable online! Click on the date to book now or contact us online to book through customer service.

Request a Reservation


This trip is exclusively booked through customer service due to logistics with lodging, permits, staffing, availability, or something else. Please contact us online or call us at 800-715-HIKE (4453) to request a reservation.

Permitted and Confirmed Trip Dates

These trip dates are permitted and confirmed. Click on a date to book!

Don't see your dates? Call us! We may be able to add new trip dates.

800-715-HIKE (4453)

Trip Details

Trip Details

What's Included

  • A detailed trip packet that takes the guesswork out of your travel, training, packing, and preparing for the trip
  • Trained hiking guide(s) with years of personal wilderness and hiking experience, medical certifications, and a passion for leading people into breathtaking landscapes. See Guide Bios.
  • Lodging for the duration of the tour
  • Airport pick up and drop off
  • Transportation via ferry, sailboat, taxi, and private transfer
  • All meals from Dinner Day 1 to lunch on Day 9
  • Admission and guide to the Acropolis
  • Emergency equipment including a company-issued first-aid kit and communication device

What's Not Included

  • Transportation to Athens, Greece
  • Trip insurance that includes medical coverage and at least $200,000 in evacuation and repatriation coverage (required)
  • All expenses due to unavoidable events e.g. flight cancellation, personal illness, strikes, etc. (we recommend trip insurance coverage for these variables)
  • Hiking backpack (required) and trekking poles (recommended). See recommendations
  • Clothes, rain gear, and footwear (see recommendations) should have ankle support as terrain can be uneven
  • Bar bills, drink bills, extra snacks, telephone bills, Wi-Fi bills and other personal expenses (shopping/laundry/spa or sauna)
  • Sunscreen, toiletries and personal items
  • Water bottles
  • Guide gratuities are optional and at the discretion of each customer. A suggested guideline is to reward outstanding service with a tip of 5-10% of the total trip cost. Please tip your lead guide and they will distribute responsibly to the crew. Local currency is preferred, or USD is also appreciated.

Click here to see a printable, downloadable trip information packet with more detailed guidance about what to pack.

Meals: What To Expect

We might be a little biased here at Wildland but in our opinion there is no better cuisine than what one finds in Greece. With a diverse palette of olive oil, wine, seafood, vegetables, grains, pork, poultry, beef, lamb, and rabbit, Greek cuisine is one of the most mouth-watering of all the European cultures. From tasty Thessaloniki salads, marinated lamb Kleftiko, Gyros to Baklava and Filo pastries there is something for us all. Greek cuisine leans heavily on oil, oregano, mint, basil, thyme, garlic, dill, cumin, and bay leaves.

We can often accommodate vegan, vegetarian and non-gluten diets and make adjustments for food allergies. These and other special dietary requests may require an additional fee, and in some countries may be more difficult to accommodate than others. Please inquire with us for more information about the specific trip you’re interested in.

Lodging: What to Expect

Our Greek Island adventure offers the opportunity to enjoy our hand-picked, locally owned lodges set in idyllic locations. These unique lodges are a major highlight of these trips for many guests!

There are some unique elements to the accommodations that are important for guests to understand:

  • Twin rooms in much of Europe often have the twin beds set very close together. Your rooming companion may be closer than you are accustomed to at hotels in the US, with only a couple inches between the beds.
  • Most beds are twin-sized; queen- and king-sized beds are not available. Sometimes the twins are pushed together to form a double, but sometimes they must remain separated. If you would like to share a bed, it may not always be available.

Please see the Accommodations section for more information.

Gear We Provide

We provide all group gear which includes the following:

  • Company-issued first-aid kit
  • Emergency Communication Device(s)

Guest Packing List

When you register for this tour you’ll receive access to a printable, downloadable trip information packet with a detailed packing list specific to this trip (click here to see it now.) All trips require a sturdy pair of hiking shoes or hiking boots, rain gear, a recommended clothing system, a headlamp or flashlight, a hydration system (water bottles and/or bladder) and other items specific to each trip.

Trip Logistics

Trip Logistics

How Do I Register?

Reserve your spot today! In the Trip Dates & Booking section of this page, the green and red dates are bookable online by simply clicking on the date, and blue dates must be booked through our customer service team for a variety of possible reasons. To email our customer service team, you can click here to get the ball rolling. Our adventure consultants will confirm availability, and if you’re ready to register we’ll email you a link to a registration profile. You’ll have 72 hours to complete your profile (and that of any dependents) and pay the deposit.

Feel free to call us for more info – we’re here 7 days a week!

Where Do We Meet?

You will meet your guide at the Athens Airport on the first day of the trip. Please plan for your flight to arrive by 3 pm on Day 1.

Our Greece communications team will be in contact via email approximately 45 days before your trip to coordinate and confirm your rendezvous and answer any last-minute questions you may have.

Travel To/From Piraeus, Greece


For this Greek Trekking adventure, you will need to fly in and out of the Athens airport located in Piraeus Greece, a port of Athens. Flights should arrive by 3 pm on Day 1. Your guide will pick you up at the airport on Day 1.

On the last day of the trip, guests will be transported to the Athens Airport at about 2 pm, after a tour of the Acropolis. Departing flights should be planned no earlier than 5 pm to utilize our provided airport transportation this day. Any airport transportation needs outside of this will be at the guest’s expense.

Flights to and from the Athens airport are the guest’s responsibility. Multiple airlines operate flights into Greece from many U.S. and European international airports. Some of the primary U.S. departure cities include Atlanta, Denver, Boston, Washington DC, San Francisco, Seattle, New York, Dallas and Minneapolis.

Safety Precautions

Your safety is our top priority. Our hiking tours are led by professional hiking guides, all of whom are wilderness-certified first responders or EMT’s, each with years of guiding and wilderness experience. Guides adhere to standardized risk management protocols in case of any potential or actual incident, and all tours carry an emergency communication device and comprehensive first-aid kit. Additionally we have a “24/7” system through which guides or guests can reach Wildland support personnel at any time.

In the interest of your safety, it’s important to refer to the Center for Disease Control website for up-to-date recommendations on immunizations before your trip.

Essential Eligibility Criteria

Essential Eligibility Criteria (“EEC”) have been specifically identified to help you understand the skills and abilities necessary to participate on each Wildland trip, and they apply uniformly to all potential trip participants, irrespective of the presence or absence of any disability.

Once you identify a trip in which you may be interested, please carefully review the EEC and itinerary details. If after reviewing the EEC that apply to your desired trip, you determine you need an accommodation in order to meet the EEC, please contact us prior to registering to discuss your requested accommodation.

The EEC exist for your own safety and the safety and enjoyment of all participants. If you are unable to meet the EEC for the trip, with or without an accommodation, you are not eligible for that trip. If you register and arrive for a trip for which you do not meet the EEC, you will be disqualified from participation on the trip and will be dismissed or evacuated from the trip without a refund.


Our approach to international travel is to combine the best of two worlds: the dialed-in details, professionalism and consistency Wildland trips are known for; and the cultural immersion and intimate regional knowledge that only locals can provide. To excel with this approach, we vet and hire the best local guides, welcome them into the Wildland family and train them to meet our standard of excellence with every aspect of a trip. But along with managing logistics and safety, your guides will teach you about the area’s history and culture, and provide a level of familiarity and intimate detail only locals can.

Check out our Meet Our Team page for staff bios.

Guide Working Parameters

Guides are required to take 8 hours off each 24-hour period to sleep, recuperate, take personal/down time…etc. In addition, as part of the 8 hours off they must sleep/rest or be in their tents/rooms uninterrupted for a minimum of 5 hours each night. We ask guests to respect these requirements and to not interrupt guides’ off time and sleep time unless there is a true emergency.

Age Restrictions

Age restrictions on this trip are as follows:

  • 12 and older to join scheduled tours (mixed groups)

Trip Insurance

Field evacuation, repatriation, and medical insurance is required on this trip as a condition of partnership terms with our European vendors (field evacuation and repatriation minimum coverage is a combined $200,000 USD).

If you need to purchase field evacuation, repatriation, or medical insurance we recommend IMG/iTravelinsured. They are one of the world’s leading providers of travel insurance and policies meet all requirements.

For information on the recommended IMG/iTravelinsured policies please click here.

For even greater information, or if you simply prefer communicating with a real, live person, feel free to contact our exclusive agent Michael Bennett. Michael will help you identify the best product for your needs, and there is no cost associated with his assistance. You may contact him at:

Email: [email protected]
US by Phone: 877-305-9083
Direct/International by Phone: 702-448-3664

If you already have the required insurance or wish to purchase from anyone other than IMG/iTravelinsured, we recommend careful consultation with the provider to ensure appropriate coverage. This is because many providers have a number of policy exclusions.

Weather In Greece

Given Greece’s advantageous geographical position, it affords mild winters and warm summers uniformly throughout the mainland and islands. Summers are characterized by plenty of sunshine with scant rainfall. The weather in the Aegean islands and Ionian seas is more mild with characteristic Meltemi, or summer winds that blow consistently to afford wonderful sailing.

In the summer and fall you will find temperatures between 90°F (33° C) to 75°F (24°C). Be prepared to have some sun layers or sunscreen as well as a nice insinuative layer for the evenings.





A four star hotel located right at the Port of Piraeus which happens to be one of the largest passenger ports in the world, and the largest in Europe. Mitsis features 103 rooms with a contemporary, beautiful, and relaxing atmosphere.




Located in the port, Port Square Hotel is a modern, chic, and stylish accommodation in the heart of Piraeus. From this vantage point you’ll witness cruise lines coming and going, the surrounding hillsides, and the hustle and bustle of the city.



Perfectly situated between the Cycladic hills and a protected bay in the Vathi of Sifnos, Elies Resorts is perfectly positioned amongst the Greek countryside and Aegean sea. Elies boasts traditional Mediterranean cuisine, a wellness center, boutique, tennis court, and luscious accommodations.



Perched on a hilltop just a hop, skip, and a jump from the center of Adamas, this 4-star hotel is a premier center for relaxation. Hosting olive and lemon trees outside, a pool and spa on the inside, this elegant accommodation is the perfect destination for your Cycladic vacation!



This 5 star hotel is located right in the heart of the action of Athens! Abounding night life is just around the corner in Syntagma square replete with art galleries, restaurants, shopping, and just a stone’s throw from the Acropolis and Ancient Agora. Here you’ll find chic urban accommodation offering a main restaurant, rooftop bar and pool, sauna, steam room, and gym.

* These exact accommodations are not guaranteed. In some instances alternative accommodations of similar quality and location may be used.

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