Hiking the Greek Islands
Inn-Based Hiking Tours
9 Days, 8 Nights 33MI / 53KM
Trip Highlights
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!
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World Class Cuisine
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Island Hiking in the Cylcades: Sifnos, Kimolos, & Milos
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Aegean Sea Sailing
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Elegant Mediterranean Accommodations
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The Acropolis
Book This Trip
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Trip Details
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Trip Type
Inn-Based Hiking Tours -
Trip Length
9 Days, 8 Nights -
Daily Hiking Distance
Up to 7 miles -
Group Size
4-12 Guests
- day by day itinerary
- logistical and travel information
- gear and clothing lists and more
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Is This Trip Right For me?
This trip involves hiking with a light day pack (10-15 pounds) from 3-5 hours a day with elevation gain and loss averaging around 1200 ft. There is little to no height’s exposure. The terrain rated as moderate as the trails are quite rocky. This trip requires transport via ferry and one day on a sailboat. There is an option for swimming and snorkeling.
Difficulty Level
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Solitude Level
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Trip Itinerary
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.
Day 1
Drive: 45 minutes
Yassou and welcome to Greece! Upon your arrival into Athens, you will be picked up and transferred to our evening’s accommodation 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!
Trip Dates
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What's Included
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A detailed trip packet that takes the guesswork out of your travel, training, packing, and preparing for the trip
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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.
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Lodging for the duration of the tour
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Airport pick up and drop off
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Transportation via ferry, sailboat, taxi, and private transfer
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All meals from Dinner Day 1 to lunch on Day 9
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Admission and guide to the Acropolis
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Emergency equipment including a company-issued first-aid kit and communication device
What's Not Included
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Transportation to/from Athens, Greece -
All expenses due to unavoidable events e.g. flight cancellation, personal illness, strikes, etc. (we recommend trip insurance coverage for these variables)
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Hiking backpack (required) and trekking poles (recommended)
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Clothes, rain gear, and footwear
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Bar bills, drink bills, extra snacks, telephone bills, Wi-Fi bills and other personal expenses (shopping/laundry/spa or sauna)
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Sunscreen, toiletries and personal items
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Water bottles
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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.
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Trip insurance that includes medical coverage and at least $200,000 in evacuation and repatriation coverage
Accommodations
* These exact accommodations are not guaranteed. In some instances alternative accommodations of similar quality and location may be used.
MITSIS N'U PIRAEUS PORT
0-1 NIGHT
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.
PORT SQUARE
0-1 NIGHT
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.
ELIES RESORTS SIFNOS
3 NIGHTS
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.
SANTA MARIA RESORT & SPA
2 NIGHTS
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! Please note that the bathroom doors are glass and provide less privacy than some guests may desire.
NYX ESPERIA PALACE HOTEL ATHENS
1 NIGHT
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.
Trip Logistics & FAQs
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.
Guides
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.
Age Restrictions
Age restrictions on this trip are as follows:
- 7 and older to join scheduled and private tours
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.
Reviews
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Jane C
1 year agoWonderful Hiking
Wonderful hiking, spectacular scenery and off the beaten path. And the food!!! Our guides, Matthieu and Johannes, were excellent and accommodated our varying skill levels well. We loved having a sailing day to break up our hikes as well.
Kimberle B
1 year agoAbove and Beyond
The Greece trekking trip exceeded all of our expectations! Our guides, Matthieu and Johannes were both outstanding and made sure that all of us on the trip had a pleasant experience. They went above and beyond by adding special details including an outstanding sailing excursion, beautiful dining experiences and wonderful picnic lunches. They both were kind, personable, knowledgeable, and always looking out for our wellbeing. We enjoyed the beautiful resorts that we stayed at, which were perfect for relaxing after the daily hiking. We also loved the choice of the three Greek islands we hiked on, since they were not overcrowded with tourists. We highly recommend this trip!
Constance T
1 year ago“Wildland strikes again!”
This trip was such a unique, phenomenal way to see both incredible island hikes and cultural highlights! This was my fourth Wildland trip, but first international trip and it held up to Wildland’s high standards! Our guides, Matthieu and Johannes, were both incredible, very knowledgeable and handled every aspect of the trip so well. All of the day hikes offered something a little different so there was constant variety and plenty to see and learn of the Greek geography, geology, history and culture. I also enjoyed that the islands we visited were less tourist-popular, and truly felt like a more authentic, immersive cultural experience. The lodging and meals also exceeded expectations. With buffet breakfasts and family-style lunches and dinners, there were ample opportunities to sample the many varieties of local cuisines. The addition of the final day in Athens with a guided tour of the Parthenon was well worth it and very glad this was included with the tour. One of my other favorite aspects of participating in Wildland trips is that there is always a diverse group of guests that end up having much in common and also make the trip so enjoyable, and this trip was no exception. This trip is a great addition to Wildland’s offerings and another experience that will keep me coming back for more Wildland trips!
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