The Great Bulgaria & Istanbul Adventure (2025)

Fly overnight to Sofia.

Welcome to Sofia, Bulgaria’s 7000-year-old capital and begin your adventure with a stroll down Vitosha Boulevard. A traditional welcome dinner will fill you and prepare you for a much earned night sleep in the most comfortable beds in the city.

Lodging: Stay a few steps away from Sofia’s premier outdoor walking street, Vitosha Boulevard, at the Thracia Best Western Hotel (30 Solunska Str., 1000 Sofia, Bulgaria)

Walk down the “Yellow Brick Road” as you pass through the historic section of Sofia and view sites from the time of Constantine the Great to post-communism and through to the modern day. Walk on a Roman road in the Ancient Complex of Serdica, see iconography of the Eastern Orthodox church at Alexander Nevsky Cathedral, and shop for unique souvenirs at the antique flea market. Break for lunch with a Bulgarian Vice Minister of government and learn more about the rich history and culture of Bulgaria.

Lodging: Thracia Best Western Hotel

See the countryside as you travel to Rila Monastery, a UNESCO World Heritage site, with colorful woodcarvings and frescos inside and out. Take a moment to appreciate the striking architecture against the beauty of the highest mountain range in Bulgaria. Travel along Bulgaria’s ancient Thracian wine road on the way to Plovdiv. Enjoy lunch, a behind-thescenes tour, and wine tasting at Villa Terres Winery.

Lodging: Stay on Plovdiv’s extensive pedestrian zone at the Ramada
Plovdiv Trimontium (2 Kapitan Raicho St., Plovdiv 4000, Bulgaria)

Wake to the ancient city of Plovdiv, one of the oldest cities in Europe. Boasting over 200 Thracian, Greek, and Roman archaeological sites, this city of seven hills lives up to its title of European Capital of Culture for 2019*. It was selected for this honor in a process as rigorous as choosing a host city for the Olympics. Sit in the ancient Roman amphitheater that is still used today and visit the TrakArt museum where you will find Roman mosaics and intricately beautiful 1700-year-old glass vases. Sample traditional Bulgarian, Turkish, and Armenian fare as you walk the cobblestone streets of Ancient Plovdiv, lined with restored houses from the Bulgarian Revival period.

Lodging: Ramada Plovdiv Trimontium

Travel through the Thracian Valley of the Kings with a visit to a Thracian tomb. Find out more about this unique culture and their magnificent golden hordes from expert Ivan Vasilev, founder of The Balkan Heritage Foundation. Continue on over the Balkan Mountains with a stop at the Shipka Church and Shipka Pass Monument celebrating liberation from 500 years of Ottoman rule. Arrive at Stone & Compass to enjoy 1500 acres in the heart of Bulgaria with spectacular views of the surrounding nature. A fully renovated three-story house of a freedom fighter for Bulgarian independence will be your home away from home for the next four days.

Lodging: Stay at the 2000-acre Stone & Compass Center in the foothills
of the Balkan Mountains in the village of Stolat, Bulgaria.

Step back in time as you enter the gates of Etara, a living museum featuring a traditional craft marketplace. Wind your way along the river while the waterwheels power machinery used for woodcarving, pottery, weaving, and silversmithing, among others. Try traditional apple pastry from the bakery or Turkish coffee brewed over hot sand while you watch the artisans at work and shop for unique handcrafted items. Return to The Center for a traditional dinner catered by a well-known Bulgarian chef. Celebrate with a Bulgarian performance group sharing music, song, and dance from a variety of different regions. Be prepared to join in and learn some of the steps along with local friends, including the mayor of Stolat himself.

Lodging: Stone & Compass Center

Explore Veliko Tarnovo, the capital of Second Bulgarian Empire. Climb the steps of the medieval fortress of Tsarevets for panoramic views of this city and the river that winds around it. Learn about local history on a private tour with the director of the Regional Museum of History – Veliko Tarnovo. Shop for gifts and souvenirs or enjoy a gelato in this city where old meets new. Overlooking Veliko Tarnovo, Arbanasi is a quaint village that rose to prominence as a trading center in the 17th century. Visit the 15th century Church of the Nativity of Christ where an experienced guide will explain the unique and unusual murals and icons not typically seen in other churches. Dine overlooking the river and the city aglow with light.

Lodging: Stone & Compass Center

Savor your last full day like a true Bulgarian in Tryavna a colorful mountain town with charming traditional architecture. Relax in the town square by the picturesque clock tower and meander over the bridge to the pedestrian walkway. Recharge yourself in one of the outdoor cafés that line the streets and browse the vibrant array of shops.

Lodging: Stone & Compass Center

On the last day of your main trip instead of heading home you will head off to Istanbul! This incredible city is home to many different cultures and is a crossroads for East meets West. Check into your hotel and head out into the city with a guide to spend the late afternoon walking through local bazaars, spice shops, craft markets, and more. Enjoy a traditional evening meal at a local café.

Today we do something truly extraordinary! After a hearty breakfast we will head off to visit the Basilica Cistern! This is the largest of several hundred cisterns that lie underneath Istanbul. This sunken underground palace holds wonders such as the Medusa Pillars and the Hen’s eye columns. Then it’s on to another incredible adventure as we take a sunset cruise on the Bosporus straight on a luxury yacht!

Today we get to see some of the wonders of the world as we visit the Blue Mosque and Hagia Sofia! In the late afternoon visit Topkapi Palace. This opulent 15th century palace was home to the sultans for 400 years and houses great Ottoman treasures.

Let’s go shopping! Today we visit the Grand Bazaar! This is one of the largest and oldest covered markets in the world. Get lost in the sights and smells of this cultural wonder.