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sample workation itinerary


Trip Overview

We have laid out a typical timetable for a Tallinn Workation in order to give you an idea what a month in the Estonian capital has to offer and the services we can provide.

Places to stay

Workation in Tallinn for a month

Contact Us

Opening Hours

Mon-Fri: 9am - 7pm EST

Your Workation Package Includes

Pre-Workation Coordination
Local Hero Support
Personalized Web Destination Guide
Local SIM with Monthly Data
Monthly Public Transport Pass
Orientation Walk with your Local Hero
One month Accommodation
Airport Arrival Transfer
Welcome Essentials
High-Speed Internet
Weekly Cleaning
Airport Departure Transfer

Pre-Workation Coordination

Preparation for your Workation starts long before you touch down in Estonia. You’ll be in touch with your Local Hero in Tallinn 1-2 months before departure, so we can get to know you and your preferences better. We want to make sure you get the most out of your time in Tallinn, so we’ll ask about your interests, what you want to see and do, eating choices, any equipment you’ll need, and what kind of work schedule you want to keep. We’ll provide you plenty ideas and suggestions for your free time.

Your Personalized Destination Guide Web App

After booking you will receive a personalized destination guide web app we’ve customized for your Workation. You’ll find a wealth of information in there about Tallinn, things to do, and the many services available to make your life easier. We also blog regularly about Tallinn, covering a wide variety of topics of interest to anyone workationing there. If there’s anything you need more help with, just ask your Local Hero!

Arriving in Tallinn

Welcome to Estonia! Upon your arrival at Tallinn Airport, a driver will meet you and drive you to your apartment. The drive takes about 20 minutes. Depending on your arrival time your Tallinn Local Hero will meet you after you check-in, or the following morning. At this time they will provide you with a local SIM complete with data as well as a public transport pass to cover you for the duration of your stay.

You’ll appreciate the dedicated workspace in your apartment, and the reliable high speed wifi. We can arrange for an external screen or other tech accessories to increase your productivity. We will also stock your apartment with all the necessities (e.g condiments, bathroom essentials, cleaning supplies) to start your stay off smoothly. You’ll be pleased to note that weekly cleanings are included in the price.

Route map

Tallinn Local Hero

Orientation Walk
with Your Local Hero

Upon arrival, your local hero will help you get settled and show you around your new neighborhood. She will inform you about what this part of the city has to offer. You will be introduced to the local shops, bars, and restaurants as well as other facilities such as gyms, parks, and other entertainment based on your specific needs. She’ll also help you get a feel for your location and the connections to other parts of the city using your public transportation pass. She’ll even help you install some useful local apps. You’ll get information about other useful services like dry cleaning and food/grocery delivery. We will make sure you are well prepared to make the most of your Workation ahead!

During your stay in Tallinn

We’ve got you covered with endless additional ideas and services to make the most of your stay. You can request any of the optional extra tours, excursions and getaways to be added to your Workation package now, or at any point after booking.

If you prefer the buzz of a workplace atmosphere, we can include a month’s co-working pass, with either a fixed desk assignment of flex-desk. Tallinn’s many co-working spaces mean we can help you pick one that suits you not just in terms of location but also the kind of people you’ll be sharing office space with. That makes it an ideal way to meet locals too.

We can include a month’s membership at a well equipped gym close to your apartment in your Workation package to help you keep up good habits from home.

If you’re already working with a personal trainer, you know how invaluable they can be to insure you maximize your workouts. We realize finding an English-speaking trainer who understands your needs isn’t always easy in Tallinn, so we’ve done our research. For an additional fee, we will arrange a private personal trainer for you to better keep in shape.

Please ask your Workation advisor for the cost to add these to your package

We are able to arrange a variety of experiences which will both immerse you in the local culture and provide unforgettable memories. Estonians are known for their love of the outdoors and sustainable living so we are happy to advise or arrange hiking, biking, climbing or other adventure sport options. Otherwise pick up a new language, discover your talent with dance or music lessons, indulge yourself in spa & wellness treatments or hire a business coach. The options are endless and we are happy to help you take full advantage of your time away.

Your first weekend: Getting to Know Tallinn

If you’ve been working hard all week, now is the time to appreciate your surroundings and mingle with the locals a little. Your local hero will already have pointed out some of the city’s popular spots for locals and foreigners. It being your first weekend, it’s time to do the touristy thing and we’ve got some suggestions for how to spend the whole day in and around Tallinn’s medieval center, After a walking tour that’ll give you some historical and cultural background, we suggest ticking off a few more must-dos by heading to trendy Telliskivi Creative City, the hub of Tallinn’s creative scene, and the nearby unique Seaplane Harbor Musuem. The following day you can get to know Tallinn, and Estonian culture even better, by taking a Czech beer and small plates tour in a non-touristy neighborhood.

Tallinn’s seemingly endless UNESCO-listed Old Town welcomes you with its captivating medieval charm. Everywhere you go you’ll find narrow cobblestone streets, lovingly preserved buildings, merchant’s homes, and thick city walls dating back centuries. Have a nice cup of coffee and cake in one of the cafes set in quiet small courtyards or passageways. Admire wonderful views from the Upper Town to the red-tiled roofs, church towers, and Baltic Sea below.

Please ask your Workation advisor for the cost to add this to your package

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.

Discover the Estonian food and history of Kalamaja, the bohemian district of Tallinn. Get out of the old town and venture off the beaten path to the oldest suburb of Tallinn! You’ll explore the history of this part of the city through its food; from the humble fish dishes and freshly baked pies to Estonian farm produce and modern cuisine. Estonian food is an interesting mixture of local produce and foreign influences, of changing tastes and old traditions. The tour covers the most important sights in Kalamaja and brings together food and history of this diverse area in Tallinn.

Please ask your Workation advisor for the cost to add this to your package

Ideas for the rest of your Tallinn Workation

Tallinn’s reputation as a startup hub has brought entrepreneurs from all over the world to the Estonian capital. This continual enrichment of the city’s diversity makes it an inspiring place to spend time. When you consider also that the advantageous location on the Baltic coast means your weekends will be as fun as your workdays are productive.

Optional Day Trips – Explore Estonia

Coastal Cliffs and Soviet Paldiski

Discover the hidden wonders amidst the wilderness along the coast west of Tallinn, including the Soviet Union’s main naval training base. This tur includes Estonia’s most romantic waterfall, coastal limestone cliffs, Paldiski military town, the lunar landscape of the Rummu prison quarry and many more. You will also have a chance to sit in the cockpit of an old Soviet plane. Our young and entertaining guides show you the places you would never stumble across on your own and share personal stories about Estonia from the perspective of the local youth.

Bog-Shoe Hiking

For something a bit more unusual, walk across one of Estonia’s largest bogs with special bog-shoes (otherwise, you would sink right in!) Bogs are very dear to all Estonians and have been part of its culture for centuries, so a visit to Estonia is incomplete without a bog walk. Visiting an Estonian bog is a strangely unworldly experience, with their calm pools of black (but drinkable!) water, stunted trees, and endless berry bushes. This tour will take you beyond the boardwalks and observation towers to normally inaccessible areas, home to more wildlife.

Make the Most of Your Time, Before and After Work

Get Sporty

Feel the wind in your sails, with kitesurfing and windsuring both popular sports on the open waters of the Baltic sea. Or work on your golf handicap on on of the courses outside the city. If you’re traveling with a partner you might even want to try the off-the-wall sport of wife carrying. Although invented in Finland, the Estonians are frequent world champions.

Drink in the Views

Tallinn’s gorgeous from any angle, but from a rooftop terrace you can admire the sweeping panorama over the medieval old city and beyond to the deep blue of the Baltic Sea. The helpful info we provide for your Workation includes our tips for the very best places to eat, drink, and admire the city from above as well.

Optional Weekend Getaways

See more of Estonia by heading to either seaside spa town Parnu, or university town Tartu. If you’d like to see other countries, then two easy weekend breaks are available. Hop o a two-hour ferry to the design-obsessed Finnish capital, Helsinki, or take a luxury bus to Riga, capital city of Latvia, a captivating mix of Art Nouveau and a reconstructed old town that shares a Hanseatic heritage with Tallinn.


Departure Day

With such an action-packed time, your month in Tallinn will fly by and sadly it’s time to leave. But where to? Back home? Or another Workation destination? And if you fell in love with the Estonian way of life lifestyle, we can hook you up with an immigration assistance agency, and even a realtor. Plenty to think about on the short ride to the airport, as our driver whisks you off for your departing flight.