Hamilton & Chase Tours
Estonia — Islands & Old Towns — 7 Days — Private Package 7-day Baltics tour: Tallinn's spires, Saaremaa's windmills, and bog walks at dawn.

7-Day Private Package Journey

Estonia — Islands & Old Towns — 7 Days

Tallinn's spires, Saaremaa's windmills, and bog walks at dawn.

Available as Private Semi-Private Self-Guided
From €3,490 per person 7 days / 6 nights
View Itinerary

Tour Overview

7 days across Baltics.

Estonia has more than Tallinn — though Tallinn alone could justify the journey. This seven-day route takes in the medieval capital, the coastal manors and raised bogs of Lahemaa National Park, the island of Saaremaa (Estonia's largest, with a medieval castle, windmills, and juniper fields that feel a century removed from the mainland), the seaside town of Haapsalu (known as the 'Venice of the Baltics'), and the university city of Tartu with its National Museum and 17th-century academic tradition. Estonia is a country where half the land is forest, where the coastline is wild and empty, and where the medieval and the modern exist side by side without apparent friction. This route is built for the traveller who wants to see all of it.

Detailed Itinerary

Your journey, day by day.

Every day is designed with breathing room. Sleep in, take a detour, linger at lunch — the itinerary flexes around you, not the other way around.

Day 1 — Arrival in Tallinn
Day 1
1

Day 1

Arrival in Tallinn

Inside the medieval walls.

Arrive at Tallinn Airport and transfer to your hotel inside the Old Town walls. Afternoon at leisure: the Gothic Town Hall, the Kohtuotsa viewpoint, the medieval lanes of the Lower Town, and the first coffee in a city that takes its café culture seriously. Welcome dinner at a restaurant that works with Estonian seasons — wild game, smoked fish, forest mushrooms, and the black bread that anchors every Estonian table.

  • Private airport transfer
  • Tallinn Old Town — first walk through the medieval quarter
  • Kohtuotsa viewpoint panorama
  • Welcome dinner with Estonian seasonal cuisine
Meals: Dinner Boutique hotel, Tallinn Old Town
Day 2 — Tallinn — Full Day
Day 2
2

Day 2

Tallinn — Full Day

Toompea, Kadriorg, and Telliskivi.

Full day with a private guide. Morning on Toompea Hill: the Estonian Parliament, the Alexander Nevsky Cathedral, the Dome Church, and the panoramic viewpoints. Descend through the medieval lanes — the Town Hall Pharmacy (operating since 1422), the merchant houses, the Dominican Monastery passage. Afternoon beyond the walls: Kadriorg Palace (Peter the Great's baroque gift to Catherine), the KUMU art museum, and Telliskivi Creative City — a former industrial quarter now home to studios, galleries, and the best weekend market in Tallinn.

  • Toompea Hill — Parliament, cathedrals, panoramas
  • Town Hall Pharmacy — continuous operation since 1422
  • Kadriorg Palace and KUMU art museum
  • Telliskivi Creative City
Meals: Breakfast Boutique hotel, Tallinn Old Town
Day 3 — Lahemaa National Park
Day 3
3

Day 3

Lahemaa National Park

Manors, bogs, and captain's villages.

Drive east to Lahemaa — Estonia's largest national park. Visit Palmse Manor, the finest restored Baltic German estate in the country. Walk the Viru Bog trail — a boardwalk through a landscape of moss, dark pools, and stunted pines that is one of Estonia's most distinctive natural environments. Continue to the coastal captain's villages of Käsmu and Altja, where wooden houses and stone fences preserve a way of life that disappeared elsewhere decades ago. Return to Tallinn or continue to Haapsalu in the evening.

  • Palmse Manor — Baltic German estate
  • Viru Bog boardwalk trail
  • Käsmu captain's village
  • Coastal Lahemaa landscapes
Meals: Breakfast Boutique hotel, Haapsalu
Day 4 — Haapsalu & Ferry to Saaremaa
Day 4
4

Day 4

Haapsalu & Ferry to Saaremaa

The Venice of the Baltics and a ferry crossing.

Morning in Haapsalu — a seaside town on Estonia's west coast, built on a narrow peninsula and known for its wooden promenade, its episcopal castle, and the light that earned it the 'Venice of the Baltics' nickname. Tchaikovsky composed here; the town's bandstand and shingle beaches preserve a 19th-century resort atmosphere. Walk the promenade and visit the castle before the ferry crossing to Saaremaa — Estonia's largest island, a place of medieval castle walls, working windmills, juniper fields, and a pace of life that feels entirely separate from the mainland. Dinner in Kuressaare.

  • Haapsalu promenade and episcopal castle
  • Tchaikovsky bench and the seaside bandstand
  • Ferry crossing to Saaremaa island
  • Kuressaare — Saaremaa's medieval capital
Meals: Breakfast, Dinner Island guesthouse, Kuressaare
Day 5 — Saaremaa Island
Day 5
5

Day 5

Saaremaa Island

Castles, windmills, and juniper fields.

A full day on Saaremaa. Kuressaare Castle is the best-preserved medieval castle in the Baltics — a massive stone fortress surrounded by a moat and built by the Teutonic Knights in the 14th century. Beyond the town, the island unfolds: the Angla windmill hill (five historic windmills on a hilltop), the Kaali meteorite crater (formed 7,500 years ago and surrounded by legend), the juniper fields and limestone cliffs of the Sõrve Peninsula, and the fishing villages along the coast where the traditional wooden boats are still built by hand. Lunch at a farm restaurant serving island produce — the lamb, the smoked fish, and the Saaremaa craft beer.

  • Kuressaare Castle — best-preserved medieval fortress in the Baltics
  • Angla windmill hill — five historic windmills
  • Kaali meteorite crater — 7,500 years old
  • Saaremaa farm restaurant and island produce
Meals: Breakfast Island guesthouse, Kuressaare
Day 6 — Tartu
Day 6
6

Day 6

Tartu

Estonia's city of ideas.

Ferry back to the mainland and drive south to Tartu — approximately four hours through the Estonian lake district and forests. Tartu is built around the University of Tartu, founded by Gustavus Adolphus of Sweden in 1632. Walk the Town Hall Square, the university main building, and the Toomemägi hill with its cathedral ruins and observatory. The Estonian National Museum — a striking modern building on a former Soviet airfield — tells the story of the Estonian people from the Ice Age to digital independence. The Supilinn (Soup Town) neighbourhood, with wooden houses named after vegetables, is one of the most charming urban quarters in the Baltics. Farewell dinner.

  • University of Tartu — founded 1632
  • Estonian National Museum on a former Soviet airfield
  • Toomemägi cathedral ruins and observatory
  • Supilinn — Tartu's colourful Soup Town
Meals: Breakfast, Dinner Boutique hotel, Tartu
Day 7 — Departure
Day 7
7

Day 7

Departure

Through the forests, homeward.

Final morning in Tartu — a last coffee on Town Hall Square, a walk by the river, or a browse through the university bookshops. Private transfer to Tallinn Airport (2.5 hours) or south to Riga if continuing through the Baltics.

  • Final morning in Tartu
  • Private transfer to departure point
Meals: Breakfast

Where You'll Stay

Hand-picked hotels, every night.

We choose properties for character, location, and the kind of service that makes you feel looked after — not just checked in. Every hotel can be swapped for an alternative if you prefer.

Boutique hotel, Tallinn

Tallinn

2 nights

Boutique hotel

Old Town

Inside the medieval walls

Boutique hotel, Haapsalu

Haapsalu

1 night

Boutique hotel

Town centre

Near the promenade and castle

Island guesthouse, Kuressaare (Saaremaa)

Kuressaare (Saaremaa)

2 nights

Island guesthouse

Near the castle

Comfortable island accommodation with local character

Boutique hotel, Tartu

Tartu

1 night

Boutique hotel

Town centre

Walking distance to the university and National Museum

Hotels shown are indicative of the standard we book. Upon request, we will provide a detailed itinerary with specific hotel options tailored to your preferences and budget.

What's in the Price

Included

  • 6 nights in boutique hotels and an island guesthouse
  • All ground transfers including Saaremaa ferry crossing
  • Private guides throughout
  • Daily breakfast plus three regional dinners
  • All entrance fees, castle visits, and national park permits
  • 24/7 local support contact

Not Included

  • International flights
  • Travel insurance
  • Meals not specified in the itinerary
  • Optional add-ons and personal expenses
  • Gratuities for guides and drivers

Good to Know

  • Saaremaa ferry crossings should be booked in advance during July–August peak season.
  • The island's roads are a mix of paved and gravel — our vehicles handle both comfortably.
  • Haapsalu and Saaremaa are best visited May–September for the warmest weather and longest days.

Make It Yours

Optional add-ons & upgrades.

Every trip is different. These extras can be woven into your itinerary — just let your travel specialist know what catches your eye.

Estonian smoke sauna

Traditional smoke sauna on Saaremaa — a UNESCO-recognized Intangible Cultural Heritage practice.

€65 per person

Saaremaa cycling tour

Half-day bike ride along the island's coastal paths and through juniper fields.

€40 per person

Tallinn craft beer tasting

Guided tour of Tallinn's emerging craft beer scene with tastings at three breweries.

€55 per person

"Saaremaa was the highlight of our Baltic trip — the castle, the windmills, the emptiness of the coast. We felt like we had the island to ourselves."

James & Patricia C.

San Francisco, USA · Estonia — Islands & Old Towns — 7 Days

Common Questions

Questions about this trip.

How do you get to Saaremaa?

A ferry crossing from Virtsu on the mainland to Muhu island, then a causeway to Saaremaa. The crossing takes about 30 minutes and runs frequently.

Is Saaremaa remote?

Pleasantly so. Kuressaare has good restaurants and amenities, but the island's character is rural, unhurried, and beautifully empty.

Private Package Journey

Estonia — Islands & Old Towns — 7 Days

7 days / 6 nights

From €3,490

per person

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More Baltics Tours

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