Bulgaria and the Isle of Thassos

Hill Walks, Wine Tasting, Ancient Frescoed Monasteries, and the Delights of a Sun-Splashed Greek Isle

Trip Details at-a-Glance

Cost From: $4895  
Length: 14 days
Arrive: Sofia, Bulgaria
Depart: Sofia, Bulgaria
Lodging: 13 nights in hotels and lodges
Meals: All meals included
Activity: Archaeology, Cultural Adventures, Hiking / Trekking
Trip Level: 12 hiking days over rolling hills with some steep sections, 2-4.5 hours a day


  • Charming Koprivshtitsa, famed for its stone bridges and 19th century painted houses
  • Hiking, wine tasting, and home visits amid the traditional villages of the green Rhodope Mountains
  • Majestisc Bachkovo and Rila, two of the most resplendent Eastern Orthodox monasteries in Europe
  • Tranquil Thassos Island, with its wild, powder-white beaches and charming towns on the Aegean Sea

Bulgaria is an undiscovered gem. Fridendly and charming people, glorious countryside in spring, wonderful fresh food (terrific cheese), excellent wine, glorious hikes/trails. I hope more can experience this delightful country!Vivian L.—Alameda, CA

Choosing the Right Trip

We work hard to help you choose the right trip for you, paying attention to your individual interests, abilities, and needs. If you have questions about the level of comfort or any of the activities described in this itinerary, please contact us.


We are proud to have an exceptionally high rate of repeat travelers. For more information, we would be happy to put you in touch with a client who has traveled with us.

Join us for cultural discovery and delightful hikes as we weave our way through two ancient and fascinating countries. Our journey explores the mystique of beautiful Bulgaria, Europe’s best-kept secret, where the green Rhodope Mountains shelter  bucolic villages and the oldest Eastern Orthodox monasteries in Europe, dazzling with their frescoed interiors. Crossing the border into Greece, we savor hikes on tranquil Thassos, set on the blue Aegean Sea. Here our trails lead along sandy beaches, through olive groves, and into timeless cobble-street villages. Throughout our intriguing journey, we mingle with pilgrims in remote monasteries, hike woodsmen’s paths through ancient forests, enjoy lunches in village homes, and discover distinctive Old World cultures. We’ll also be sure to sample a delicious variety of local wines and cuisines, from spit-roasted kabobs and homemade feta cheeses to fresh-caught fish from the Aegean. Cultural highlights of the journey include Bulgaria's two most spectacular monasteries: majestic Rila, a World Heritage Site in a serene mountain setting, and Bachkovo, with its small chapels, holy springs, and pilgrims. This unique adventure brings us deep into an undiscovered European realm that is off the beaten path of most travelers and utterly captivating!

Itinerary at a Glance

For a more complete description, Download Full Detailed Itinerary

Days 1-2
Sofia / Koprivshtitsa / Valley of Roses

After a walking tour of Sofia, with its gold-domed Alexander Nevski Cathedral, we head up to peaceful Koprivshtitsa, an Ottoman-era village nestled in wooded hills and famous for its painted houses and stone bridges. From this lovely base, we hike in the Southern Djenden Nature Reserve and visit the Valley of Roses, one of the symbols of Bulgaria, with its rose farms and 16th century towns. Our hotel in Koprivshtitsa is a historic 19th century house.

Days 3-4
Rhodope Mountains / Bachkovo / Plovdiv

The pine-forested Rhodope Mountains form Bulgaria’s southern border with Greece. We visit the village of Starosel for wine tasting and a look at its enigmatic Thracian tombs dating to the 5th century BC, then make a pilgrimage walk through a UNESCO biosphere reserve to Bachkovo, one of the oldest Eastern Orthodox monasteries in Europe. We also visit graceful Plovdiv, the cultural center of Bulgaria, with its charming Old Town spread across three hills. Overnights are in the historic village of Kosovo.

Days 5-7
Rhodope Mountains / Smolyan / Trigrad Gorge

Circling through the green Rhodope Mountains, we enjoy hikes each day and visit historic mountain villages. In one village, we have lunch in a local home and hear the music of the kaba gaida (the traditional bagpipe of the Rhodope Mountains). We also explore the impressive 600-foot-deep Trigrad Gorge, one of the most spectacular settings in Bulgaria, with its sheer walls overhanging the foaming Trigradska River.

Days 8-13
Thassos Island, Greece

Crossing the border into Greece, we explore lovely Thassos Island, a beautiful setting of wild, powder-white beaches and charming old villages along the Aegean Sea. One hike brings us up to the mountain village of Kastro, and another brings us to the 5th century castle of Neposi. We also visit the village of Arnaia, set on the Halkidiki Peninsula, where people still live in traditional ways and occupations include agriculture, bee keeping, and carpet weaving.

Days 13-14
Rila Monastery / Sofia

Heading back to Bulgaria, we visit Rila, its most famous monastery, a serene World Heritage Site set on the slopes of 9,500-foot Mt. Rila. We enjoy our last hike, an easy pilgrimage walk to St. Ivan Rilksi’s hermitage caves in the deep forests of the Rila Monastery Nature Reserve. Return to Sofia and depart on Day 14.

For a more complete description, Download Full Detailed Itinerary

What the Trip is Like

The trip is Level 3+, Moderate to Strenuous. We hike from 2 to 4.5 hours on hiking days, mostly over rolling hills, with some steep sections. Most of the hiking takes place at medium elevations, between 2,000 feet and 5,400 feet. The maximum elevation is 5,400 feet. The elevation change in a typical day is accumulated ascents and descents that vary from 1,200 feet to 2,400 feet (the uphill is equal to the downhill). Typically, we drive to the starting point of the trail and walk to the end of it, where we meet the vehicle once again. On Days 2, 4, and 6, we do loop walks as we explore eco-trails that start and end at same point. Some portions of these eco-trails are on wooden staircases. In general, we can expect terrain that includes about 50% dirt paths through broadleaf forests and about 50% on mountain trails.The trails are relatively smooth, with no long rocky sections or exposed tree roots. Distances are not long , but you should be in good shape and wear good hiking boots. Hiking poles are recommended. You need to carry only a daypack for your camera, water bottle, rain jacket, etc. A vehicle transfers our luggage between overnight accommodations. On some days, we enjoy picnic lunches prepared by the Trip Leaders with local produce, wine, breads, and cheeses. On “town” days, we have lunch at local cafes. Driving and hiking times are noted, but these can vary, sometimes dramatically, from the anticipated times. Road conditions and the group’s level of fitness also affect the travel and hiking times.

Please note that in Europe, the dinner hour is considerably later than what it is in the US. We do our best to secure early reservations for our groups, but most often the evening meal will be at 7:30 p.m. Although rooms are not always of uniform or international size, our leaders always try their best to assign rooms in a fair way so that all participants experience an equal advantage throughout the trip as a whole. Single rooms can be requested but are not always available, due to the limited space in the hotels. If you require a single room, please make the request as early as possible.

Explanation of Trip Levels


Departures & Leaders

Aug 30-Sep 12, 2015  Denitza Petrova

Trip Cost

Prices are for 2015
$4895 (11-15 members)
$5195 (6-10 members)
Single supplement: $420
Forced single supplement: $210
more on pricing

Trip Payment Schedule

At time of reservation: $500
120 days prior to departure: 20% of trip cost
60 days prior to departure: Balance

Cancellation and Transfer Fee Schedule

More than 90 days prior to departure: No charge!
90-46 days prior to departure: 25% of trip cost
45 days or less: 100% of trip cost

Trip Cost Includes:

  • Expert leadership of a Wilderness Travel Trip Leader and local guides
  • Accommodations as noted
  • All meals included
  • A glass of wine or beer with dinner
  • Entrance fees for museums and sites
  • All land transportation, transfers as noted

Trip Cost Does Not Include:

International airfare, transfers for independent arrival or departure, any meals not specified after each itinerary day, wine at dinner (except at welcome and farewell dinners), airport departure taxes, optional tipping or gratuities to leaders or staff, additional hotel nights that may be necessitated by airline schedule changes or other factors; pre-trip expenses of medical immunizations (if any), travel insurance, or passports and visas; and other expenses of a personal nature (alcoholic beverages, laundry, etc.).

Arrival & Departure Information

You are responsible for your own transportation arriving to and departing from Sofia, Bulgaria. For more detailed information, including transfers, please download the Detailed Itinerary.

Please do not purchase your tickets until you are confirmed on the trip and have reviewed your proposed air schedule with our office. Once your tickets have been purchased, please send us a copy of your airline schedule.

Meeting Place:
Sofia, Bulgaria
Date: Day 1

Suggested Arrival Airport:
Sofia, Bulgaria (airport code: SOF)
Suggested Flight Arrival Time: 8:00am or anytime one day prior


Sofia, Bulgaria
Date: Day 14

Suggested Airport for Departure:
Sofia, Bulgaria (airport code: SOF)
Suggested Departure Time: anytime

Denitza Petrova

Denitza Petrova  was born in Varna, a town on Bulgaria’s Black Sea coast. She graduated with a degree in sociology from Sofia University and spent her college summers in California. She later completed a two-year stint in outdoor education in the Santa Cruz Mountains (Camp Campbell Outdoor Science School), where she taught students about the beauty and uniqueness of the California redwoods. In her time in California, she became a passionate advocate for nature conservation, and on return to Bulgaria, she joined her country’s anti-nuclear and environmental movement. Today she works for as a Greenpeace representative in Bulgaria. She loves the mountains of her native country and is especially keen to share their beauty with travelers. “Bulgaria still has many hidden treasures waiting to be discovered, and it’s the perfect place for people who want to be in touch with wild nature and feel the true spirit of the Balkans.” Denitza also enjoys sharing Bulgaria’s folk music, both the dances and the songs. As a youth, she danced with one of the folk groups in Varna.

Upcoming Trips:

Bulgaria and the Isle of Thassos, August 30-September 12, 2015
Montenegro and the Adriatic Coast, September 18-28, 2016

Client Testimonials:

Denitza is absolutely delightful and handled the entire trip in a thoughtful, professional way. Richard R., Columbus, GA
Bulgaria and the Isle of Thassos