This sample 11-day (10 night) itinerary covers Tallinn, the island of Saaremaa, and its capital of Kuressaare, Parnu, Tartu, and Narva. This diverse tour takes you to the country's top sights, from medieval corners to 19th-century delights to places that will help you understand the effects of Estonia's Soviet occupation. Along the way, you'll have the opportunity to visit places and cultures that have changed little for centuries, while tasting delicious cuisine. All of our tours are custom, and this is just a sample meant to give an idea of what our trips are like, and the opportunities our destinations provide.
One of our team members in the region will be available to you leading up to and during your trip to answer any questions and arrange local services. You will receive access to your Guest Page, with its information on the best these destinations have to offer, including things to see and do, and other inside tips from restaurant recommendations to tipping advice. Upon arrival, we will provide you with a local cell phone that you can use to reach your local JayWay contact (who you will meet in person) throughout your trip. In all of our destinations, we offer a variety of memorable 3-5 star accommodation options, including boutique hotels, charming B&Bs, and spacious apartments. With our firsthand experience, we can ensure they are all clean, comfortable, and centrally located, with local ambience.
3 Nights in Tallinn
3 Nights in Tallinn


3 Nights in Tallinn
A visit to Tallinn, the oldest capital city in Northern Europe, is a trip back in time. The cobblestone streets, UNESCO-listed medieval walls, and stunning church spires give it an Old World charm you’ll love exploring. But there are all the modern amenities here too, and today Tallinn is a truly unique destination with the best of the old and the new. You’ll also see influences of both the east and west in the architecture and cuisine, as Estonia is a short ferry ride from Helsinki. The restaurants, quaint cafes and chic boutiques are places you’ll love to linger, while the long coastline is ideal for strolling. There are so many different ways to see the city, because Tallinn is so rich in history. See how beer influenced local history, or explore the reminders of life under the Soviet regime. Take a walking tour of the beautiful Old Town, or a driving tour to see more of the city. There are distinct neighborhoods here and each one feels distinct. Tallinn is very tech-savvy, so the business district is always modern and bustling. The bohemian Kalamaja neighborhood is a great place to have a drink or a bite to eat. The picturesque Lahemaa National Park is one of the best day trips from Tallinn, and you’ll have fun wandering through nature here before returning to the city to find more of its charms.
A visit to Tallinn, the oldest capital city in Northern Europe, is a trip back in time. The cobblestone streets, UNESCO-listed medieval walls, and stunning church spires give it an Old World charm you’ll love exploring. But there are all the modern amenities here too, and today Tallinn is a truly unique destination with the best of the old and the new. You’ll also see influences of both the east and west in the architecture and cuisine, as Estonia is a short ferry ride from Helsinki. The restaurants, quaint cafes and chic boutiques are places you’ll love to linger, while the long coastline is ideal for strolling. There are so many different ways to see the city, because Tallinn is so rich in history. See how beer influenced local history, or explore the reminders of life under the Soviet regime. Take a walking tour of the beautiful Old Town, or a driving tour to see more of the city. There are distinct neighborhoods here and each one feels distinct. Tallinn is very tech-savvy, so the business district is always modern and bustling. The bohemian Kalamaja neighborhood is a great place to have a drink or a bite to eat. The picturesque Lahemaa National Park is one of the best day trips from Tallinn, and you’ll have fun wandering through nature here before returning to the city to find more of its charms.
Day 1
Day 1 - Arrival in Tallinn
When you arrive, we'll have a driver waiting to greet you. You'll be taken to your accommodation in the photogenic medieval Old Town of Tallinn, the Estonian capital.
Go Bohemian in Kalamaja
Of all the neighborhoods in Tallinn, Kalamaja is one of the most exciting. This fast-growing area between Old Town and the scenic coast is known for its hip selection of cafes, shops, restaurants and bars. Once a closed-off Soviet border zone, it has seen a renaissance of development in recent years. Seaplane Harbour, the Estonian Maritime Museum, is very modern and quite interesting. It’s just one of the things worth seeing around here.
Day 2
Day 2 - Your First Full Day in Tallinn

Discover Medieval Wonders
Baroque History: Kadriorg Palace and Park

Day 3
Day 3 - Your Second Full Day in Tallinn

Explore Nature and History Along the Coast
Today your guide will pick you up at your accommodations and take you to Lahemaa, an hour east of Tallinn. You’ll start by visiting the Bronze Age graves at Rebala, then continue on to the cute, fairy tale tower at Kiiu. One of the trip’s highlights is the boardwalk through Viru Bog, an otherworldly landscape marked by multitudinous berry bushes, stunted trees, and mirror-like pools of calm dark water, dotted with the occasional observation tower. The tour continues on to Palmse Manor, an 18th century Classicist manor home that's brightly painted, inside and out. Estonia has hundreds of manor homes, but Palmse is one of the best preserved, and its greenhouse is still filled with palm trees (a play on its German name, “Palms.”) You’ll then arrive at the “Land of Bay’s” rugged coast, making a stop at Kasmu, "The Captain's Village." Ironically, while its Sea Museum is located in a former Soviet border guard post, the museum has an exhibit on the village's long history of smuggling, in addition to fishing and the sea itself. The next stop is Altja, a more traditional fishing village where many buildings still have thatched roofs, including the tavern. On the way back home, you’ll make one last stop at the country’s highest waterfall, at Jagala.
Day 4
Day 4 - Traveling to Saaremaa by Private Transfer
Be prepared for an interesting day today as you say "hüvasti" to Tallinn, "tere" to Kuressaare, and enjoy a brief stop at Haapsalu in between. Based on your preferred departure time, a driver will pick you up at your accommodations in Tallinn and your journey to Kuressaare will begin. Please keep in mind this is a non-guided transfer. The journey, including stops and a 30 minute ferry ride, takes about 7-8 hours. The vehicle used for your transfer will be a standard sedan, station wagon or minivan, although we can arrange for an upgrade to a more luxurious class of vehicle for an extra fee.

2 Nights in Saaremaa
2 Nights in Saaremaa


2 Nights in Saaremaa
It’s hard to find a more medieval landscape than Saaremaa, Estonia’s largest island (its name translates to “Island Land”). With its windmills, 13th century churches, thatched roofs, and ancient stone walls, Saaremaa seems to have escaped the Soviet era intact. However, its preservation is due to Soviet border policy, which forbade entrance to this island by anyone not directly related to its inhabitants. This island’s rugged coast features bunkers and lighthouses, one of which is now surrounded by the sea, and leans far to its side. Much of Saaremaa's west coast is protected by Vilsandi National Park, which includes an island that can only be visited by an occasional ferry, or by taking a Soviet truck at low tide. Estonia has more meteorite craters per square mile than anywhere else, chief among them Saaremaa's Kaali crater, which hit the island during the Bronze Age with a force equal to the first atomic bomb. Viewed as holy since prehistory, this crater is thought to be the site where the sun falls to Earth in the Kalevala, the Finnish national epic. Saaremaa’s capital, Kuressaare, is a charming small town, with a tall, rectangular castle that sits within renaissance bastions. Kuressaare is best enjoyed with a quiet stroll along the coast and between the charming wooden villas near the castle. We also recommend visiting the Sorve Peninsula. Here, at the island's southern tip, the northern edge of Latvia is visible, especially from the top of the Baltics' tallest lighthouse. Thanks to a clerical error, the neighboring village of Torgu found itself legally independent in the 90s, and comically declared itself a kingdom.
It’s hard to find a more medieval landscape than Saaremaa, Estonia’s largest island (its name translates to “Island Land”). With its windmills, 13th century churches, thatched roofs, and ancient stone walls, Saaremaa seems to have escaped the Soviet era intact. However, its preservation is due to Soviet border policy, which forbade entrance to this island by anyone not directly related to its inhabitants. This island’s rugged coast features bunkers and lighthouses, one of which is now surrounded by the sea, and leans far to its side. Much of Saaremaa's west coast is protected by Vilsandi National Park, which includes an island that can only be visited by an occasional ferry, or by taking a Soviet truck at low tide. Estonia has more meteorite craters per square mile than anywhere else, chief among them Saaremaa's Kaali crater, which hit the island during the Bronze Age with a force equal to the first atomic bomb. Viewed as holy since prehistory, this crater is thought to be the site where the sun falls to Earth in the Kalevala, the Finnish national epic. Saaremaa’s capital, Kuressaare, is a charming small town, with a tall, rectangular castle that sits within renaissance bastions. Kuressaare is best enjoyed with a quiet stroll along the coast and between the charming wooden villas near the castle. We also recommend visiting the Sorve Peninsula. Here, at the island's southern tip, the northern edge of Latvia is visible, especially from the top of the Baltics' tallest lighthouse. Thanks to a clerical error, the neighboring village of Torgu found itself legally independent in the 90s, and comically declared itself a kingdom.
Day 4
Day 4 - Arrival in Saaremaa
Your driver will bring you directly to your accommodations in the center of Kuressaare.
Day 5
Day 5 - Your First Full Day in Saaremaa

Discover Kuressaare's Beauty
A walking tour around the charming small town of Kuressaare and its tall, rectangular castle and renaissance bastions is a trip back in time. Almost every building here is an architectural monument with a deep history. This town's restored 12th century castle is its main attraction, and naturally functions as a history museum. After an hour's walk in the town itself, you'll continue to the castle for another hour, after which you can remain at the castle, or have the guide return you to your accommodations.
Delve into Island Life

Saaremaa Highlights Private Tour
Discover Saaremaa, beloved for its folklore, picturesque villages, windmills and coastline, and of course, its famous meteorite crater. A visit to this island isn't complete without venturing beyond Kuressaare to take in the countryside's classics! Estonia has more meteor craters per square mile than anywhere else, chief among them Kaali crater, which hit the island during the Bronze Age with a force equal to the first atomic bomb. Viewed as holy since prehistory, this crater is thought to be the site where the sun falls to Earth in the Kalevala, the Finnish national epic. After seeing Kaali, you'll visit Angla, home to several restored windmills, a classic sight, before continuing on to the Panga cliff, part of a seaside escarpment that cuts from Sweden to Russia, passing through Tallinn and occasionally underwater.

Sõrve Peninsula Private Tour
The scenic peninsula forming Saaremaa's southern tip, Sõrve was the sight of pitched fighting during both World Wars, and even spent a brief period as a tongue-in-cheek sovereign kingdom following Estonia's return to independence in 1991. The tallest on the Baltic, Sõrve's beautiful lighthouse, recently opened to visitors, offers views of Latvia. You'll also see nearby natural sights, a coastal defense battery, and walk down to the peninsula's very tip.
Day 6
Day 6 - Traveling to Parnu by Private Transfer
The most relaxed way to get to Parnu is with a private transfer. Your driver will pick you up at your accommodations based on the time of your choosing, and drive you your accommodations at the other end. This is a direct non-guided transfer, but for an additional fee, you can make stops along the way.
1 Night in Parnu
1 Night in Parnu


1 Night in Parnu
Among beach lovers in Eastern Europe, Parnu has been legendary since the late 19th century. You’ll find a variety of different beaches here and places to enjoy the natural beauty of the landscape. But there aren’t only beaches here. Parnus is also a spa resort where you can enjoy a variety of world-class wellness treatments. There’s also a rich history here, as Parnu was the first place the Estonian Declaration of Independence was read publicly, in 1918. All of this makes it a unique destination combining relaxation, history and gorgeous nature. There’s plenty to do here, whether Parnu is your final destination or just a stop off in a longer tour of the region. The city has numerous museums dedicated to its vibrant history, as well as its modern culture. You’ll definitely want to visit a spa while you’re here, and of course the beaches are second-to-none. Most of the restaurants here offer lovely seafood that can’t be fresher, so enjoying the local gastronomy and wine is always a fun way to spend a day. Relaxation and nature come together here in perfect harmony. We can certainly provide a private walking tour, but if you're looking to see something special, we recommend a day trip to the island of Kihnu. Although home to only a few hundred people, Kihnu's cultural heritage is complete intact, from its dances to unique games and music, and people still wear folk costume in daily life.
Among beach lovers in Eastern Europe, Parnu has been legendary since the late 19th century. You’ll find a variety of different beaches here and places to enjoy the natural beauty of the landscape. But there aren’t only beaches here. Parnus is also a spa resort where you can enjoy a variety of world-class wellness treatments. There’s also a rich history here, as Parnu was the first place the Estonian Declaration of Independence was read publicly, in 1918. All of this makes it a unique destination combining relaxation, history and gorgeous nature. There’s plenty to do here, whether Parnu is your final destination or just a stop off in a longer tour of the region. The city has numerous museums dedicated to its vibrant history, as well as its modern culture. You’ll definitely want to visit a spa while you’re here, and of course the beaches are second-to-none. Most of the restaurants here offer lovely seafood that can’t be fresher, so enjoying the local gastronomy and wine is always a fun way to spend a day. Relaxation and nature come together here in perfect harmony. We can certainly provide a private walking tour, but if you're looking to see something special, we recommend a day trip to the island of Kihnu. Although home to only a few hundred people, Kihnu's cultural heritage is complete intact, from its dances to unique games and music, and people still wear folk costume in daily life.
Day 6
Day 6 - Arrival in Parnu
Your driver will bring you directly to your centrally located accommodations.

Parnu City Private Walking Tour
Feel the Sand
Parnu's beaches are known as the country's best, famed for its white sands, gentle nature, and various attractions. Whether you like to play mini-golf or try some windsurfing, there's always tons of thing to choose from. A curving path stretches along the sand, lined with fountains, park benches, and an excellent playground. Early-20th-century buildings are strung along Ranna puiestee, the avenue that runs parallel to the beach. Across the road, the formal gardens of Rannapark are ideal for a summertime picnic.
Day 7
Day 7 - Traveling to Tartu by Bus
Today you'll bid a fond farewell to the summer capital of Parnu, and head to the university town of Tartu. We'll arrange for a driver to take you to Parnu's bus station and from there you'll enjoy a comfortable ride on a luxury bus.
You can upgrade your transfer

Tartu by Private Transfer with a stop in Viljandi
Upgrade for an additional cost
2 Nights in Tartu
2 Nights in Tartu


2 Nights in Tartu
The “City of Good Thoughts,” Tartu is Estonia’s cultural and intellectual capital. This city is home to the University of Tartu, one of Europe’s oldest universities, and one of the most prestigious in Eastern Europe. The central role students play here is symbolized by the “Kissing Students” statue in front of the town hall. Tartu is centered around Toomemagi, a steep hill that hosted a pagan fort, followed by a Crusader castle. Toomemagi is Tartu’s gem, especially in September's foliage. Covered in forest and filled with paths, this hill contains a half-ruined cathedral, one of Europe’s oldest observatories, an anatomical theater, and Czarist bridges and fortifications, as well as statues, plaques, a cafe, and more. Toomemagi has excellent views of the city, especially from the cathedral towers, while beneath it lies a bar and restaurant built in a former gunpowder cellar, featuring a 40-foot ceiling.
The “City of Good Thoughts,” Tartu is Estonia’s cultural and intellectual capital. This city is home to the University of Tartu, one of Europe’s oldest universities, and one of the most prestigious in Eastern Europe. The central role students play here is symbolized by the “Kissing Students” statue in front of the town hall. Tartu is centered around Toomemagi, a steep hill that hosted a pagan fort, followed by a Crusader castle. Toomemagi is Tartu’s gem, especially in September's foliage. Covered in forest and filled with paths, this hill contains a half-ruined cathedral, one of Europe’s oldest observatories, an anatomical theater, and Czarist bridges and fortifications, as well as statues, plaques, a cafe, and more. Toomemagi has excellent views of the city, especially from the cathedral towers, while beneath it lies a bar and restaurant built in a former gunpowder cellar, featuring a 40-foot ceiling.
Day 7
Day 7 - Arrival in Tartu
A driver will meet you at Tartu's bus station and bring you to your accommodations in the city center.

Tartu for Foodies
Day 8
Day 8 - Your First Full Day in Tartu

Ponder the "City of Good Thoughts"
Explore Estonia's intellectual capital, as you stroll through its 18th century neoclassical Old Town, along the tranquil Emajõgi ("Mother River,"), and up Toomemagi ("Cathedral Hill"), getting to know the town's history through its historic buildings, some put to innovative uses, like the half-ruined cathedral, and the observatory, once home to cutting-edge research. Along the way, you'll take in charming views, whether from the riverbanks or the verdant hilltop park.

Karlova and Soup Town
Day 9
Day 9 - Traveling to Narva by Private Transfer
Be prepared for an interesting day as you head to Narva, with stops at the Pühtitsa Convent (a popular destinations for Orthodox pilgrims) and Alatskivi Castle (a showy 19th century chateau based on the royal Balmoral Castle in Scotland). Based on your preferred departure time, a driver will pick you up at your accommodations. The journey including stops takes about 5-6 hours. The vehicle used for your transfer will be a standard sedan, station wagon or minivan, although we can arrange for an upgrade to a more luxurious class of vehicle for an extra fee.

1 Night in Narva
1 Night in Narva


1 Night in Narva
Few cities are a better reminder of the divide between East and West than Narva. Here two castles face each other across the river dividing Russia from Estonia. We recommend Narva for those looking to get off the beaten path and explore Eastern Europe’s Soviet legacy. The Swedes developed the city, building a Baroque Old Town and extensive fortifications in addition to the castle. Largely destroyed during World War II, Narva was rebuilt and resettled by Soviet citizens. We recommend visiting the border, where one of Imperial Russia’s largest factories sits on an island between waterfalls. When the weather is warm, visit the beach near the two castles, one of Estonia’s most photographed spots. The seaside district of Narva-Joesuu, with its pine forest and fine sand, is the best place in town to stay, due to its calm surroundings and higher quality accommodations than available in the center of town. Next to Narva’s surviving Baroque town hall is an impressive new university building, with a roof that slopes outwards beyond the floor area of the building, and plenty of cozy places for travelers to rest. Photographers are fond of Narva’s Soviet architecture and Russian Orthodox and Lutheran churches, but the surrounding countryside has its own scenic and historic beauty.
Few cities are a better reminder of the divide between East and West than Narva. Here two castles face each other across the river dividing Russia from Estonia. We recommend Narva for those looking to get off the beaten path and explore Eastern Europe’s Soviet legacy. The Swedes developed the city, building a Baroque Old Town and extensive fortifications in addition to the castle. Largely destroyed during World War II, Narva was rebuilt and resettled by Soviet citizens. We recommend visiting the border, where one of Imperial Russia’s largest factories sits on an island between waterfalls. When the weather is warm, visit the beach near the two castles, one of Estonia’s most photographed spots. The seaside district of Narva-Joesuu, with its pine forest and fine sand, is the best place in town to stay, due to its calm surroundings and higher quality accommodations than available in the center of town. Next to Narva’s surviving Baroque town hall is an impressive new university building, with a roof that slopes outwards beyond the floor area of the building, and plenty of cozy places for travelers to rest. Photographers are fond of Narva’s Soviet architecture and Russian Orthodox and Lutheran churches, but the surrounding countryside has its own scenic and historic beauty.
Day 9
Day 9 - Arrival in Narva
Your driver will bring you directly to your accommodations in Narva-Joesuu.

Navigate Narva
Estonia’s easternmost town boasts the a restored castle keep overlooking the Russian border, and the castle built on the opposite site. Although once known for its baroque architecture, little survived World War II and the Estonian War of Independence, when the town became known as the "Estonian Verdun," although there are some vestiges of the town's former prosperity amid its classic Soviet architecture (including the ultra-modern University of Tartu building, whose exterior is an homage to the ruined building that preceded it. From Peter's Square, you'll visit the town hall and its neighboring university building, the city's bastions, the Dark Garden and river promenade, Alexander's Cathedral, and more.
Day 10
Day 10 - Traveling to Tallinn by Private Transfer
Today you're off to Tallinn! We'll arrange for a private car to pick you up at your accommodations. Along the way, you will revisit the Middle Ages at Rakvere Castle and enjoy a walk around Viru Bog. Please keep in mind this is a non-guided transfer, and tickets to the castle are not included. The journey, including stops, takes about 5-6 hours. The vehicle used for your transfer will be a standard sedan, station wagon or minivan, but we can arrange for an upgrade to a more luxurious class vehicle for an extra fee.

1 Night in Tallinn
1 Night in Tallinn


1 Night in Tallinn
A visit to Tallinn, the oldest capital city in Northern Europe, is a trip back in time. The cobblestone streets, UNESCO-listed medieval walls, and stunning church spires give it an Old World charm you’ll love exploring. But there are all the modern amenities here too, and today Tallinn is a truly unique destination with the best of the old and the new. You’ll also see influences of both the east and west in the architecture and cuisine, as Estonia is a short ferry ride from Helsinki. The restaurants, quaint cafes and chic boutiques are places you’ll love to linger, while the long coastline is ideal for strolling. There are so many different ways to see the city, because Tallinn is so rich in history. See how beer influenced local history, or explore the reminders of life under the Soviet regime. Take a walking tour of the beautiful Old Town, or a driving tour to see more of the city. There are distinct neighborhoods here and each one feels distinct. Tallinn is very tech-savvy, so the business district is always modern and bustling. The bohemian Kalamaja neighborhood is a great place to have a drink or a bite to eat. The picturesque Lahemaa National Park is one of the best day trips from Tallinn, and you’ll have fun wandering through nature here before returning to the city to find more of its charms.
A visit to Tallinn, the oldest capital city in Northern Europe, is a trip back in time. The cobblestone streets, UNESCO-listed medieval walls, and stunning church spires give it an Old World charm you’ll love exploring. But there are all the modern amenities here too, and today Tallinn is a truly unique destination with the best of the old and the new. You’ll also see influences of both the east and west in the architecture and cuisine, as Estonia is a short ferry ride from Helsinki. The restaurants, quaint cafes and chic boutiques are places you’ll love to linger, while the long coastline is ideal for strolling. There are so many different ways to see the city, because Tallinn is so rich in history. See how beer influenced local history, or explore the reminders of life under the Soviet regime. Take a walking tour of the beautiful Old Town, or a driving tour to see more of the city. There are distinct neighborhoods here and each one feels distinct. Tallinn is very tech-savvy, so the business district is always modern and bustling. The bohemian Kalamaja neighborhood is a great place to have a drink or a bite to eat. The picturesque Lahemaa National Park is one of the best day trips from Tallinn, and you’ll have fun wandering through nature here before returning to the city to find more of its charms.
Day 10
Day 10 - Arrival in Tallinn
Your driver will bring you directly to your accommodations in the center of Tallinn for your last night in Estonia.
Day 11
Day 11 - Departure Day
Based on your departure time, we'll have a driver pick you up from your accommodations and take you to the airport.

Here are all the services provided as part of your complete vacation package. See what every JayWay trip includes.
Please let us know if you'd like to upgrade any transfers or add any additional tours or excursions to your itinerary.
Tallinn
Saaremaa
Parnu
Tartu
Narva
Tallinn
The package excludes:
- Flights to and from Europe.
- Tips for Tour Guides, Drivers and Local Reps.
- Meals (other than breakfast if included in room rate and meals listed as included in food tours and excursions, unless explicitly stated otherwise).
- Parking fees for your Rental Car (if you are booking one with us) unless otherwise indicated. Some hotels provide free parking facilities.
- Travel Insurance. See the insurance link on our website
A JayWay vacation is more than the sum of its parts. Our team work tirelessly to ensure your experience is memorable for all the right reasons. Your trip is personalized to maximize your enjoyment. You're taken care of every step of the way.
A Travel Advisor who speaks your language
We will make sure that all your requirements and interests are taken into account in preparing your itinerary.A totally tailored itinerary for your vacation
Your trip is customized for you by an experienced trip planner and an expert on the region.A choice of hand-picked hotels and excursions
We've personally inspected and tested all the hotels and local tour providers we work with to ensure quality.Detailed pre-trip preparation to make the most of every day
Your Europe-based Tour Manager will be in touch by email and phone a month before you arrive to finalize timings.On-trip Concierge Service to smooth out any bumps in the road
Our local staff are at your service throughout your journey via the local prepaid cellphone which we provide.Personalized Guest Page to make sure you're not missing out
Packed with detailed information and recommendations curated by locals on the best things to do, see and eat.Choose the month of travel, how many travelers and what star level accommodation you'd like to stay in, then get an instant price estimate.
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