Day-by-Day Itinerary
Settle into Tallinn with a gentle introduction to the medieval
Old Town. Orient yourself with the main squares and soak in the atmosphere of this UNESCO World Heritage site.
Morning
After checking into your accommodation, take a self-guided walk through the cobblestone streets of
Old Town. Start at
Town Hall Square, admire the Gothic architecture, and wander through the atmospheric medieval lanes. Get your bearings and locate key landmarks you'll explore in detail over the coming days.
2-3 hours
$0
Lunch
Estonian comfort food
Budget
Afternoon
Visit Towers' Square and surrounding fortifications
Explore Towers' Square and the well-preserved medieval defensive walls. Walk along sections of the ancient fortifications and climb one of the accessible towers for your first elevated views of the red-roofed
Old Town. This gives excellent context for understanding Tallinn's strategic importance throughout history.
2 hours
$5-8
Evening
Casual dinner and early rest
Find a relaxed eatery in the
Old Town for traditional Estonian fare, then retire early to adjust to the time zone
Where to Stay Tonight
Old Town or nearby Vanalinn district (Mid-range hotel or guesthouse within walking distance of main sights)
Central location minimizes travel time and puts you in the heart of the medieval atmosphere from day one
Purchase a Tallinn Card if you plan to visit multiple museums - it includes public transport and entry to many attractions, potentially saving significant money over two weeks
Day 1 Budget: $80-100
Dedicate today to understanding Tallinn's medieval past through its best-preserved churches, museums, and historic guildhalls.
Morning
Visit St. Nicholas' Church & Museum
Explore this remarkable medieval church turned museum, housing an impressive collection of ecclesiastical art. The highlight is Bernt Notke's famous 'Danse Macabre' fragment. The church itself is a masterpiece of Gothic architecture, and the collection provides deep insight into medieval religious life in the Baltic region.
2 hours
$8-10
Lunch
A medieval-themed restaurant with vaulted ceilings in the
Old Town
Traditional Estonian with historical recipes
Mid-range
Afternoon
Explore Estonian History Museum - Great Guild Hall
Step into the Great Guild Hall, once the meeting place of Tallinn's most powerful medieval merchants. The museum's exhibitions trace Estonian history from ancient times through the medieval period. The building itself, with its impressive Gothic architecture, is as much an exhibit as the collections it houses.
2-3 hours
$8-10
Evening
Sunset at Danish King's Garden
Visit the Danish King's Garden for evening views and the legend of the Danish flag's origin, followed by dinner at a nearby restaurant with outdoor seating
Where to Stay Tonight
Old Town (Same accommodation as Day 1)
Staying put allows you to explore different parts of Old Town without repacking
Many
Old Town restaurants offer excellent lunch specials that are significantly cheaper than dinner prices - take advantage of these for your main meal
Day 2 Budget: $75-110
Discover Tallinn's seafaring heritage at the impressive maritime museum, then explore the trendy Kalamaja neighborhood with its colorful wooden houses.
Morning
Visit Estonian Maritime Museum 'Fat Margaret'
Housed in the imposing 'Fat Margaret' tower, part of Tallinn's medieval fortifications, this museum offers fascinating exhibits on
Estonia's naval and maritime history. Explore ship models, navigation instruments, and maritime artifacts across multiple floors. Climb to the top for panoramic views of the harbor and
Old Town.
2-3 hours
$10-12
Lunch
A casual waterfront cafe in Kalamaja serving fresh fish dishes
Seafood and Estonian coastal cuisine
Budget
Afternoon
Explore Kalamaja neighborhood and Balti Jaama Turg
Wander through Kalamaja's streets lined with colorful wooden houses, then head to Balti Jaama Turg, the renovated market hall near the railway station. This vibrant market combines traditional food stalls with modern eateries, local crafts, and antiques. It's perfect for picking up Estonian specialties, trying local snacks, and experiencing everyday Tallinn life.
2-3 hours
$15-25
Evening
Dinner in Kalamaja district
Enjoy the hip restaurant scene in Kalamaja, known for creative takes on Estonian cuisine and craft beer bars
Where to Stay Tonight
Old Town or Kalamaja (Same accommodation or consider moving to Kalamaja for a different neighborhood vibe)
Kalamaja offers a more local, residential feel while still being close to central attractions
Visit Balti Jaama Turg on Saturday morning for the best selection of local produce and the liveliest atmosphere with more vendors and shoppers
Day 3 Budget: $70-100
Immerse yourself in Tallinn's thriving creative scene at the Telliskivi Creative City complex and explore contemporary art spaces.
Morning
Explore Telliskivi Creative City
Spend the morning at this former industrial complex transformed into Tallinn's creative hub. Browse independent boutiques, vintage shops, and design studios. Admire the vibrant street art covering the buildings. The complex houses artist studios, creative startups, and unique shops selling everything from handmade jewelry to upcycled furniture. The atmosphere is relaxed and inspiring.
3 hours
$0-30 (depending on shopping)
Lunch
One of Telliskivi's trendy restaurants serving international fusion cuisine
Modern international with local ingredients
Mid-range
Afternoon
Visit PoCo Pop And Contemporary Art Museum | Popkunstimuuseum
Discover
Estonia's contemporary and pop art scene at this engaging museum. The exhibitions showcase both Estonian and international artists working in various media. The museum offers a refreshing contrast to the medieval focus of many Tallinn attractions, highlighting the country's vibrant modern creative culture.
2 hours
$8-10
Evening
Return to Telliskivi for evening entertainment
Telliskivi comes alive in the evening with bars, live music venues, and food trucks - perfect for a casual, creative atmosphere
Where to Stay Tonight
Kalamaja or Telliskivi area (Boutique guesthouse or modern apartment rental)
Staying near Telliskivi puts you in the heart of creative Tallinn and offers great evening options
Check Telliskivi's event calendar before visiting - they regularly host flea markets, concerts, and cultural events on weekends
Day 4 Budget: $65-95
Confront
Estonia's complex 20th-century history through powerful museums documenting Soviet occupation and the struggle for freedom.
Morning
Visit Vabamu Museum of Occupations and Freedom
This essential museum tells the story of
Estonia's occupations by Soviet and Nazi forces from 1940-1991. Through personal stories, artifacts, and interactive exhibits, you'll gain deep understanding of life under totalitarian regimes and
Estonia's path to independence. The museum is emotionally powerful and thoughtfully designed, making complex history accessible and moving.
2-3 hours
$12-15
Allow extra time - this museum deserves careful attention and reflection
Lunch
A quiet cafe nearby for reflection after the intense museum experience
Light European fare
Budget
Afternoon
Tour Hotel Viru & KGB Museum
Take a guided tour of the KGB Museum on the top floor of the historic Hotel Viru. This fascinating tour reveals the secret surveillance operations conducted from this hotel during Soviet times. See the actual equipment used to monitor foreign visitors and hear stories of espionage. The tour provides a chilling glimpse into Soviet-era surveillance culture.
1 hour
$15-18
Book in advance as tours run at specific times and group sizes are limited
Evening
Lighter evening after heavy historical content
Take a peaceful walk through the
Old Town or relax at your accommodation, processing the day's powerful historical insights
Where to Stay Tonight
Central Tallinn (Same accommodation)
Central location provides easy access to these museums and quiet evening retreat options
The KGB Prison Cells can be visited another day if you want more Soviet history - pace yourself as these topics are emotionally demanding
Day 5 Budget: $70-100
Dedicate today to visual arts, from contemporary photography to architectural exhibitions and traditional galleries.
Morning
Visit Fotografiska Tallinn
Explore this world-class photography museum housed in a beautifully renovated building. Fotografiska features rotating exhibitions from international and Estonian photographers covering documentary, art, and contemporary photography. The museum also has a excellent top-floor cafe with panoramic city views, perfect for a coffee break between exhibitions.
2-3 hours
$12-15
Lunch
The museum's own restaurant with views over Tallinn
Modern Nordic-inspired cuisine
Mid-range
Afternoon
Explore Museum of Estonian Architecture and Tallinn Art Hall Gallery
Visit the Museum of Estonian Architecture to understand the country's architectural evolution from wooden vernacular to Soviet modernism to contemporary design. Then head to Tallinn Art Hall Gallery for contemporary Estonian art exhibitions. Together, these venues provide comprehensive insight into
Estonia's visual culture and design heritage.
3 hours
$10-15
Evening
Explore the cultural district
Dine at one of the restaurants in the cultural quarter, perhaps attending an evening performance if available
Where to Stay Tonight
Central Tallinn (Same accommodation)
Maintaining your base while exploring different districts keeps logistics simple
Many museums offer late opening on Thursday evenings - check schedules to maximize your visiting time
Day 6 Budget: $75-110
Discover Tallinn's quirky and lesser-known museums, from puppetry to health history, revealing unexpected facets of Estonian culture.
Morning
Visit Estonian Theatre for Young Audiences / Museum of Puppetry Arts
Explore this charming museum dedicated to puppet theater, a beloved Estonian tradition. The collection includes puppets from various eras and countries, stage designs, and exhibits on puppet-making techniques. Even if you don't speak Estonian, the visual artistry and craftsmanship of the puppets transcend language barriers.
1.5-2 hours
$6-8
Lunch
A neighborhood cafe in a residential area away from tourist crowds
Simple Estonian home cooking
Budget
Afternoon
Explore Estonian Health Museum and Tallinn City Museum
The Estonian Health Museum offers quirky and educational exhibits on medical history and human health - surprisingly engaging. Then visit Tallinn City Museum to understand the capital's development from medieval trading post to modern European city. These smaller museums provide intimate perspectives on Estonian life and culture.
3 hours
$10-12
Evening
Relaxed neighborhood dinner
Find a local restaurant in a residential area for authentic Estonian dining away from the tourist center
Where to Stay Tonight
Central Tallinn (Same accommodation)
Your established base makes it easy to venture out and return
These smaller museums are rarely crowded, offering peaceful, personal experiences - perfect for a relaxed midpoint in your two-week stay
Day 7 Budget: $60-85
Escape the city for
Estonia's stunning nature, exploring coastal landscapes, manor houses, and forests in the country's largest national park.
Morning
Travel to Lahemaa and explore coastal villages
Take a bus or join a tour to
Lahemaa National Park, about an hour from Tallinn. Visit the picturesque fishing village of Altja with its traditional wooden buildings and coastal trails. Walk along the boulder-strewn beaches and through pine forests. The park showcases
Estonia's natural beauty and traditional rural architecture.
4 hours including travel
$15-30 (transport and entrance)
Consider booking a guided tour for easier logistics and better nature interpretation
Lunch
Pack a picnic or eat at a simple cafe in one of the park villages
Simple local fare or packed lunch
Budget
Afternoon
Visit Palmse Manor and nature trails
Explore the beautifully restored Palmse Manor, a grand 18th-century estate with formal gardens. Walk some of the park's nature trails through forests and wetlands. Lahemaa offers a complete contrast to urban Tallinn, showcasing
Estonia's pristine nature and Baltic German heritage.
3-4 hours
$8-10
Evening
Return to Tallinn
Arrive back in Tallinn for a relaxed evening, perhaps with a simple dinner near your accommodation
Where to Stay Tonight
Central Tallinn (Same accommodation)
Day trip allows you to experience nature while maintaining your Tallinn base
Bring layers - coastal weather in Lahemaa can be significantly cooler and windier than in Tallinn, even in summer
Day 8 Budget: $70-100
Explore the historic upper town on Toompea Hill, home to government buildings, churches, and the best viewpoints over Tallinn.
Morning
Explore Toompea Castle area and viewpoints
Walk up to Toompea Hill, the historic seat of power in
Estonia. Visit the viewing platforms including Bishop's Garden Viewing Platform for spectacular panoramas over the red roofs of
Old Town and beyond. Explore the area around Toompea Castle, now housing the Estonian Parliament. The upper town has a distinctly different character from the merchant quarter below.
2-3 hours
$5
Lunch
A cafe with terrace views on Toompea Hill
International with Estonian touches
Mid-range
Afternoon
Visit Peter the Great House Museum
Explore this small palace built for Russian Tsar Peter the Great during his visits to Tallinn. The museum preserves the baroque interior and displays artifacts from the Russian Imperial period. It offers insight into the complex relationship between
Estonia and Russia throughout history, set in beautiful gardens.
1.5-2 hours
$6-8
Evening
Sunset viewing and dinner
Return to one of Toompea's viewpoints for sunset, then descend to the lower town for dinner at a traditional restaurant
Where to Stay Tonight
Old Town (Same accommodation)
Central location continues to serve all your exploration needs
Visit the viewpoints in different light - morning, afternoon, and evening each offer distinct atmospheres and photographic opportunities
Day 9 Budget: $70-95
Delve deeper into Soviet-era history by exploring the KGB Prison Cells and Soviet-era districts of Tallinn.
Morning
Visit KGB Prison Cells
Take a guided tour of the former KGB headquarters basement where political prisoners were interrogated and held during Soviet occupation. This sobering experience includes original cells, interrogation rooms, and exhibits on the methods of Soviet repression. The tour is emotionally powerful and historically essential for understanding
Estonia's recent past.
1.5-2 hours
$10-12
Book in advance; tours are guided only and spaces are limited
Lunch
A simple cafe in a Soviet-era residential district
Basic Estonian or Russian-influenced cuisine
Budget
Afternoon
Soviet architecture walking tour
Explore Tallinn's Soviet-era districts on foot or by tram, observing the distinctive apartment blocks, public buildings, and urban planning from the occupation period. Visit areas like Lasnamäe to see the contrast between medieval
Old Town and Soviet modernism. This self-guided exploration reveals how occupation shaped the city's physical landscape.
3 hours
$5-10 (transport)
Evening
Reflection and lighter entertainment
After heavy historical content, enjoy a casual evening with dinner and perhaps a movie or concert
Where to Stay Tonight
Central Tallinn (Same accommodation)
Familiar base provides comfort after emotionally challenging historical sites
Combine this with your earlier Soviet history day visits, but pace yourself - these sites are emotionally demanding and benefit from processing time
Day 10 Budget: $65-90
Spend a leisurely day in Tallinn's most beautiful park and palace complex, built by Peter the Great for Catherine I.
Morning
Explore Kadriorg Park and Palace
Wander through the extensive Kadriorg Park, Tallinn's most elegant green space with formal gardens, wooded paths, and ponds. While the main palace houses an art museum, simply exploring the baroque palace grounds and gardens is delightful. The park is popular with locals jogging, picnicking, and relaxing - a perfect spot to slow down.
2-3 hours
$10-15 (if entering palace museum)
Lunch
A park cafe or nearby neighborhood restaurant in Kadriorg
Light European cuisine
Mid-range
Afternoon
Visit nearby museums and presidential palace area
Explore the museum quarter around Kadriorg, which includes several art museums and cultural institutions. Walk past the Estonian President's residence (exterior viewing only). The entire Kadriorg district has an elegant, refined atmosphere distinct from both the medieval
Old Town and Soviet districts.
2-3 hours
$10-15
Evening
Seaside walk and dinner
Walk to the nearby Pirita beach area for sunset by the Baltic Sea, then dine at a seafood restaurant
Where to Stay Tonight
Central Tallinn or Kadriorg (Same accommodation or consider a guesthouse in Kadriorg for variety)
Kadriorg offers peaceful, elegant surroundings while remaining well-connected to the center
Visit Kadriorg on a weekend to see local families enjoying the park - it's a wonderful glimpse into everyday Tallinn life
Day 11 Budget: $75-105
Use today to revisit favorite spots, explore areas you've missed, shop for souvenirs, or simply relax and enjoy the city at your own pace.
Morning
Return to a favorite museum or neighborhood
With nearly two weeks in Tallinn, you've likely discovered places you'd like to revisit. Perhaps return to Telliskivi Creative City for shopping, revisit a museum for a second look, or explore a neighborhood you only briefly visited. This flexible morning allows you to customize based on your interests and energy level.
2-3 hours
$10-30
Lunch
Return to your favorite restaurant discovered during the trip
Your choice based on trip experiences
Mid-range
Afternoon
Souvenir shopping and final explorations
Visit Balti Jaama Turg or
Old Town shops for Estonian handicrafts, woolen goods, local foods, and souvenirs. Take time to buy quality items rather than rushing. Alternatively, simply wander neighborhoods you've enjoyed, sit in cafes, or relax in a park - you've earned a slower pace after nearly two weeks of exploration.
3-4 hours
$30-80 (shopping)
Evening
Special farewell dinner
Choose a restaurant you've been wanting to try for a memorable final dinner in Tallinn
Where to Stay Tonight
Central Tallinn (Same accommodation)
Familiar base for your final nights in the city
Estonian handicrafts like hand-knitted woolens, juniper wood products, and locally designed textiles make excellent quality souvenirs
Day 12 Budget: $80-150
Take a final day trip to experience another Estonian city - either historic university town Tartu or seaside resort Pärnu.
Morning
Travel to Tartu or Pärnu
Take a bus to either Tartu (
Estonia's intellectual capital with its prestigious university and student atmosphere) or Pärnu (the summer capital with beaches and spa culture). Both are about 2-2.5 hours from Tallinn. Explore the town center, main sights, and soak in a different Estonian city's atmosphere.
4-5 hours including travel
$20-30 (transport)
Book bus tickets in advance for better prices and guaranteed seats
Lunch
A local restaurant in Tartu's
Old Town or Pärnu's beach district
Regional Estonian specialties
Mid-range
Afternoon
Continue exploring chosen city
In Tartu, visit the university area and museums; in Pärnu, enjoy the beach promenade and parks. Both cities offer charming contrasts to Tallinn - Tartu with its youthful energy and intellectual heritage, Pärnu with its resort atmosphere and coastal beauty. This day trip provides perspective on
Estonia beyond its capital.
3-4 hours
$10-20
Evening
Return to Tallinn
Arrive back in Tallinn for your final evening, perhaps with a quiet walk through
Old Town to say goodbye
Where to Stay Tonight
Central Tallinn (Same accommodation)
Final night in your established base before departure
If visiting in summer, Pärnu offers beautiful beaches; in other seasons, Tartu's museums and cafes are more appealing
Day 13 Budget: $75-110
Enjoy your final hours in Tallinn with a leisurely breakfast, last-minute activities, and departure preparations.
Morning
Depending on your departure time, enjoy a final breakfast at a favorite cafe and take one last walk through the
Old Town. Visit any spots you want to see one more time, or simply sit in a square and watch the city wake up. Soak in the atmosphere you've come to know over two weeks.
2-3 hours
$15-25
Lunch
Light meal near your accommodation or at the airport
Quick Estonian or international
Budget
Afternoon
Departure preparations and airport transfer
Check out of your accommodation, arrange transport to the airport (bus, tram, or taxi - all are efficient from central Tallinn). The airport is small and easy to navigate, so you don't need to arrive excessively early. Take time to reflect on your comprehensive Tallinn experience.
2-3 hours
$5-25 (transport to airport)
Evening
Departure
Depart Tallinn with deep knowledge of this fascinating city and memories of medieval streets, Soviet history, creative culture, and Estonian hospitality
Where to Stay Tonight
N/A (Departure day)
End of journey
The airport has a small but good selection of Estonian products if you need last-minute gifts or forgot souvenirs
Day 14 Budget: $50-80