Day 1 & 2: Tallinn – Explore Estonia’s Capital
Start your journey in Tallinn, Estonia’s capital and a true gem of the Baltics. Spend your first couple of days wandering through the Old Town, a UNESCO World Heritage Site. The mix of medieval walls, cobblestone streets, and colorful buildings will transport you back in time.
Make sure to visit the Town Hall Square, climb the towers at Toompea Hill for panoramic views, and stop by Alexander Nevsky Cathedral. This 19th-century Russian Orthodox church is hard to miss with its striking design. Don’t forget to explore the city’s hidden courtyards and alleyways, such as Katariina Käik, a vibrant place filled with artisan workshops.
For a different perspective of the city, head to Kalamaja. This trendy district is full of wooden houses, cozy cafes, and quirky street art. It’s where locals go to relax, so grab a coffee and soak in the vibe.
Where to Eat in Tallinn
For a traditional Estonian meal, head to Olde Hansa. It’s a medieval-themed restaurant where you can try dishes like elk stew or barley risotto. If you’d prefer something lighter, try the soup or fish at Kohvik Must Puudel, located in the heart of the Telliskivi area.
After these two busy days, relax by taking a walk along Pirita Beach, or unwind in Kadriorg Park just outside the city center.
Day 3 & 4: Lahemaa National Park – Nature and Manor Houses
Drive out to Lahemaa National Park, just an hour from Tallinn. This park is known for its diverse nature — from thick forests to bogs, rivers, and coastline. It’s a great place to stretch your legs after spending time in the city.

Start at the Viru Bog Trail, a wooden path that takes you through marshlands and offers beautiful views of the bog. There are observation towers along the way where you can snap some awesome photos.
On day 4, visit some of the park’s manor houses, such as Palmse and Sagadi Manor. They offer a glimpse into aristocratic life during the 18th and 19th centuries.
Where to Stay in Lahemaa
For an authentic stay, book a night at Vihula Manor. This historic estate is surrounded by nature and offers lovely rooms in a peaceful atmosphere. It’s the perfect spot to recharge.
Day 5: Rakvere – The Castle Town
On your way to your next destination, take a detour to Rakvere, a small town famous for its medieval castle. Spend the afternoon exploring Rakvere Castle where you can learn about medieval life, weaponry, and even enjoy some theatrical performances.
After exploring the castle, stroll through the town center to see the giant bull sculpture, Tarvas, a symbol of Rakvere. Grab a snack at one of the local cafes before heading to your hotel.
Day 6 & 7: Tartu – Estonia’s Student Hub
Welcome to Tartu, Estonia’s second-largest city. This university town is bursting with youth, culture, and history. Start by wandering through the old town, where you can visit Tartu University, the Estonian National Museum, and explore Toome Hill.
Make time to visit AHHAA Science Center, perfect if you enjoy interactive exhibits. It’s one of the largest in the Baltics and fun for both kids and adults. Take an evening walk along the Emajõgi River, relax in a riverside cafe, and treat yourself to Estonian craft beer at Püssirohukelder, an old gunpowder cellar turned tavern.

On day 7, visit the Tartu Covered Bridge and spend a few hours at the Botanical Gardens. Tartu is compact, so you can cover most spots by foot.

Day 8: Viljandi – Small Town with Big Charm
Spend a day in Viljandi, a charming town known for its medieval castle ruins and lively cultural festivals. Visit the Viljandi Castle Ruins and take a scenic walk on the suspension bridge nearby. If you’re here in summer, try to catch a traditional music festival or catch live performances at the town’s theater.
Check out the Kondas Center for Naïve Art, a small museum dedicated to outsider art. It’s got a quirky appeal that’s worth a visit. Spend your evening enjoying the laid-back atmosphere of a local cafe like Fellin.
Day 9 & 10: Pärnu – Estonia’s Summer Capital
Drive south to Pärnu, Estonia’s summer capital. This coastal resort town is a favorite with Estonians looking to enjoy sun and sand. Spend day 9 relaxing on Pärnu Beach, walk along the promenade, and enjoy the sea breeze.

Aside from the beach, Pärnu has a lot of cafes and spas to help you relax. Spend day 10 visiting one of the city’s many spas like Hedon Spa & Hotel, which offers a wide range of treatments. If you’re up for some adventure, rent a kayak and paddle through the nearby rivers.
For dinner, visit Villa Wesset or Supelsaksad, both known for their great food and lovely interiors. The pace in Pärnu is slow and chill—perfect for unwinding.
Day 11: Kihnu Island – A Cultural Gem
Kihnu Island is a great place to dive deeper into Estonian culture. This small island is home to vibrant traditions from songs and dances to traditional clothing that is still worn by local women.

Book a ferry from Pärnu and spend the day exploring traditional farmhouses, visiting the local museum, and chatting with locals while biking around the island. Much of the population here still lives in a similar way to how their ancestors did, so it feels like stepping back in time.
Day 12 & 13: Saaremaa – Estonia’s Largest Island
From Kihnu, head to Saaremaa, Estonia’s largest island. Begin in Kuressaare, the island’s capital, where you’ll find Kuressaare Castle – the only fully-preserved medieval stone castle in Estonia.
On day 13, rent a car and drive around the island to experience Saaremaa’s peaceful and countryside vibe. Don’t miss the Kaali Meteorite Crater, one of the most famous geological sights in the region. Stop by Angla Windmill Park to see traditional windmills and take a walk along the Sõrve Peninsula for a beautiful coastal experience.
Where to Stay in Saaremaa
Stay at Georg Ots Spa Hotel for a combination of comfort and wellness. After a busy day exploring, you can relax with a swim or indulge in a spa treatment.
Day 14: Return to Tallinn
Make your way back to Tallinn for your final day. Spend your time visiting any spots you might have missed earlier or simply relax with a good meal at Noa, one of Tallinn’s best seafront restaurants serving Estonian cuisine with a modern twist.
With a mix of cities, nature, beaches, and cultural experiences, this 14-day trip through Estonia offers a little bit of everything. Take your time, enjoy the slower moments, and savor the unique charm this country has to offer.
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