Trip Overview
This comprehensive two-week journey through Estonia showcases the perfect blend of medieval history, cutting-edge digital culture, pristine nature, and Baltic island charm. Beginning in UNESCO-listed Tallinn, you'll explore cobblestone streets, Soviet-era remnants, and contemporary art before venturing into the country's stunning national parks, coastal landscapes, and the unique island cultures of Saaremaa and Hiiumaa. The itinerary balances urban exploration with nature immersion, offering encounters with bogs, forests, waterfalls, and wildlife. You'll experience traditional Estonian cuisine, sauna culture, and the warmth of one of Europe's most digitally advanced yet nature-connected societies. The pace allows for deep exploration without rushing, with strategic rest days built into the schedule.
Day-by-Day Itinerary
Arrival & Old Town Immersion
Where to Stay Tonight
Tallinn Old Town or nearby Rotermann Quarter (Boutique hotel or well-rated guesthouse)
Central location allows easy exploration on foot and sets the tone for your Estonian adventure
Walls, Towers & Soviet Echoes
Where to Stay Tonight
Tallinn Old Town or Rotermann Quarter (Same accommodation as Day 1)
Maintaining your base allows for efficient exploration without repacking
Parks, Palaces & Art
Where to Stay Tonight
Tallinn Old Town or Rotermann Quarter (Same accommodation)
Final night in your Tallinn base before heading out to explore wider Estonia
Coastal Forests & Manor Life
Where to Stay Tonight
Lahemaa National Park area (Country guesthouse or farm stay)
Immersive nature experience and convenient base for morning exploration before moving on
University Town & Soviet Legacy
Where to Stay Tonight
Tartu city center (Mid-range hotel or design hostel)
Central location for exploring Estonia's cultural capital on foot
Southern Charm & Lake District
Where to Stay Tonight
Otepää or lakeside area (Rural guesthouse with sauna facilities)
Authentic countryside experience in Estonia's most scenic region
Into the Wilderness
Where to Stay Tonight
Soomaa National Park vicinity (Eco-lodge or farm stay)
Remote location offers authentic wilderness experience and dark skies
Island Bound
Where to Stay Tonight
Kuressaare town center (Comfortable hotel or guesthouse)
Central base for exploring Saaremaa over the next two days
Saaremaa Coastal Circuit
Where to Stay Tonight
Kuressaare (Same accommodation as Day 8)
Convenient return to your established base after a full day of island exploration
Island Hopping to Hiiumaa
Where to Stay Tonight
Kärdla or countryside location (Guesthouse or small hotel)
Experience the remote island atmosphere and hospitality
Hiiumaa Nature & Return Journey
Where to Stay Tonight
Tallinn, Old Town or Kalamaja district (Hotel or guesthouse)
Back in the capital for the final days, convenient for last explorations and departure
Tallinn Neighborhoods & Hidden Gems
Museums & Maritime Heritage
Departure Day
Where to Stay Tonight
N/A (N/A)
Departure day
Practical Information
Getting Around
A rental car is essential for exploring beyond Tallinn, particularly for Lahemaa, Soomaa, and the islands. Book in advance for better rates. Within Tallinn, walking covers most sights, supplemented by efficient trams and buses using rechargeable smart cards. Inter-island and mainland ferries are reliable and scenic. Tallinn to Tartu can be done by bus (about 2.5 hours) if not renting a car. Estonia's roads are well-maintained, and driving is straightforward with good signage in English. GPS is recommended for rural areas.
Book Ahead
Book accommodation on Saaremaa and Hiiumaa in summer peak season. Reserve guided activities in Soomaa National Park (canoeing, bog-shoeing) at least a few days ahead. Car rental should be booked in advance for better rates and availability. Ferries to the islands don't require reservations for vehicles usually, but check schedules. The Tallinn Card can be purchased online if you plan intensive museum visits.
Packing Essentials
Layers for variable weather year-round; waterproof jacket and sturdy walking shoes essential. Insect repellent for summer nature areas. Swimsuit for saunas and summer swimming. Binoculars for nature observation. Power adapter (European plug). Reusable water bottle. Camera with extra batteries. Light backpack for day trips.
Total Budget
$1,200-1,650 for 14 days (excluding international flights)
Customize Your Trip
Budget Version
Stay in hostels or guesthouses throughout (Tallinn has excellent hostels in the Old Town). Use public buses instead of renting a car, joining group tours for Lahemaa and Soomaa. Skip the islands or visit only Saaremaa. Cook some meals in hostel kitchens. Focus on free attractions like parks, beaches, and walking tours. Visit free museums on certain days. Camp in national parks where permitted. Use the Tallinn Card for museum savings. Budget: $60-80 per day.
Luxury Upgrade
Stay in boutique hotels in Tallinn's Old Town and luxury manor hotels in the countryside. Hire private guides for national parks and cultural tours. Enjoy fine dining experiences featuring modern Estonian cuisine with wine pairings. Book spa treatments at Saaremaa's resort hotels. Take private boat tours around the islands. Arrange private sauna experiences with traditional smoke saunas. Stay in the best room at Kuressaare Castle Hotel. Enjoy helicopter tours over Tallinn. Budget: $250-400 per day.
Family-Friendly
Base yourselves in Tallinn for 4-5 days, taking day trips to Lahemaa and the Open Air Museum. The Estonian National Museum in Tartu is excellent for children with interactive exhibits. Spend more time on Saaremaa (skip Hiiumaa) with beach days and castle exploration. Book family rooms in guesthouses with outdoor space. Choose activities like easy nature walks, beach time, and hands-on museum experiences over long drives. The Tallinn TV Tower has activities for kids. Many restaurants are family-friendly with children's menus. Consider summer visits for warmest weather and longest days.
Book Activities for Your Trip
Tours, tickets, and experiences in Estonia