5 Days Exploring Medieval Tallinn Itinerary

Begin your second day with a visit to the renowned Kumu Art Museum (Kumu Kunstimuuseum). This contemporary art museum showcases an extensive collection of Estonian art from the 18th century to modern times. It's an excellent place to immerse yourself in Estonia's artistic heritage. Enjoy breakfast at Kohvik Komeet, located within the museum complex, offering stunning views of Kadriorg Park.

After exploring Kumu Art Museum, take a leisurely walk through Kadriorg Park, one of Tallinn's most beautiful green spaces. The park is home to several museums, fountains, and picturesque walking paths. Make sure to visit the elegant Kadriorg Palace, which houses part of the Art Museum of Estonia's collection. For lunch, dine at NOP, a cozy café known for its organic and locally sourced menu.

In the evening, head back to Tallinn Old Town for an immersive experience with Tallinn Private Guided Walking Tour of the Medieval City. This tour will take you through hidden alleys and lesser-known spots while sharing intriguing stories about Tallinn's past. End your day with dinner at Olde Hansa, where you can enjoy medieval-themed dishes in an authentic setting.

Kick off your third day by visiting the majestic Toompea Castle (Toompea Loss). This historic castle now houses Estonia's Parliament and offers panoramic views of Tallinn from its viewing platforms. Afterward, explore the nearby Alexander Nevsky Cathedral, an impressive Orthodox cathedral known for its stunning architecture. Have breakfast at Pierre Chocolaterie, famous for its delightful pastries and hot chocolate.

Continue your exploration with a visit to the intriguing KGB Museum located in Hotel Viru. This museum provides insight into Soviet-era espionage activities in Estonia during Soviet occupation. For lunch, head to F-Hoone, located in Telliskivi Creative City—a trendy area filled with street art and creative spaces.

Wrap up your third day with an unforgettable dining experience at Tallinn TV Tower by booking a table for the unique activity:  Tallinn TV Tower evening dinner (3-course meal). Enjoy breathtaking views over Tallinn while savoring exquisite dishes prepared by top chefs.

Start your fourth day with a refreshing visit to Tallinn Botanic Gardens (Tallinna Botaanikaaed). These gardens are a peaceful retreat, offering a wide variety of plant species and beautifully landscaped areas. It's an ideal spot for a morning walk and some relaxation amidst nature. For breakfast, stop by Kadriorg Gourmet Cafe, which offers delightful pastries and coffee in a serene setting.

In the afternoon, delve into Estonia's rural history at the Estonian Open Air Museum. This expansive museum showcases traditional Estonian village life with its collection of historic buildings, including farmhouses, windmills, and chapels. It's an immersive experience that provides insight into the country's cultural heritage. For lunch, enjoy traditional Estonian dishes at Kolu Tavern, located within the museum grounds.

Conclude your day with an evening tour titled Behind the Iron Curtain of Tallinn - Secrets of the Soviets. This tour will take you through Tallinn's Soviet-era history, exploring hidden bunkers and secret locations that played crucial roles during the occupation. End your evening with dinner at Noa Chef's Hall, known for its innovative cuisine and stunning views over the Baltic Sea.

Begin your final day in Tallinn with a visit to Pirita, a coastal district known for its beautiful beaches and historical sites. Take a leisurely stroll along the shoreline or explore the ruins of St. Bridget's Convent. For breakfast, enjoy fresh pastries at Cafe Gustav, located near Pirita Beach.

In the afternoon, embark on an adventure with Tallinn Coastal Cliffs and Rummu Submerged Quarry Day Tour. This tour will take you to some of Estonia's most stunning natural landscapes, including dramatic coastal cliffs and the unique submerged quarry at Rummu. It's perfect for nature lovers and photography enthusiasts. For lunch, have a picnic-style meal prepared by your tour guide or visit a local café along the way.

Wrap up your trip with an unforgettable farewell dinner back in Tallinn Old Town at Restoran Tchaikovsky. This elegant restaurant offers Russian-inspired cuisine in a sophisticated setting, making it an ideal place to reflect on your journey through medieval Tallinn.