This episode is supported by Smart Travel a new podcast from Nerd Wallet. Travel smarter — and spend less — with help from NerdWallet. Follow Smart Travel wherever you get your podcasts.Smart Travel Podcast
Winging It On Location – Days 2-3-Tallinn: A Trendy …Check out the new Smart Travel Podcast
This episode is supported by Smart Travel a new podcast from Nerd Wallet. Travel smarter — and spend less — with help from NerdWallet. Follow Smart Travel wherever you get your podcasts.Smart Travel Podcast
Winging It On Location – Days 2-3-Tallinn: A Trendy Old Town, Estonian History and Monopoly Deal
In this second instalment of my Winging It On Location series from the Baltics, I spend two full days exploring Estonia’s capital beyond the first evening impressions. From avocado toast in one of Tallinn’s trendiest cafés to a deep dive into the country’s Soviet history, this episode blends food, culture, history and the small moments that make a trip memorable.
I wander through the cobbled streets of the Old Town in the sunshine, join a free walking tour to learn about Estonia’s path to independence, and take in panoramic views across the city. The next day I head out to the seaside district of Pirita, visit the Soviet memorials and cemetery, and reflect on how Estonia preserves difficult parts of its past.
There’s also excellent coffee, cardamom buns, goulash in a bread bowl, jazz at Philly Joe’s, and the beginning of a travel obsession that may last the rest of the trip: Monopoly Deal.
If you’re considering a European city break that feels safer, quieter and less crowded than many of the continent’s major capitals, Tallinn might be the perfect choice.
In this episode:
• Exploring Tallinn’s Old Town, cafés and bakeries
• Learning about Estonia’s history on a free walking tour
• Visiting Soviet memorials and Pirita Beach
• Jazz, wine and final thoughts on Tallinn as a city break
Support Winging It Travel Podcast
If you enjoyed this episode:
• ⭐ Leave a 5-star rating or review on your podcast app
• ☕ Support the show at buymeacoffee.com/wingingit
• 🌍 Explore more episodes at wingingittravelpodcast.com
• ✈️ Check out more great travel podcasts at https://voyascape.com
• 📺 Now also on YouTube - https://www.youtube.com/@wingingittravelpodcast
⏱️ Timestamps
00:00 Back in Tallinn and exploring the Old Town in daylight
02:30 Cafés, bakeries and the free walking tour
05:00 Evening food stops and first impressions of Tallinn
06:30 Morning coffee crawl and hidden gems around Rotermann
08:00 Pirita Beach, Soviet memorials and Estonia’s history
10:30 Monopoly Deal, seaside lunch and a slower afternoon
11:45 Jazz, wine and a trendy final night in Tallinn
12:30 Final thoughts: is Tallinn one of Europe’s best city breaks?
Check out all of our other travel podcasts from around
the world
This podcast is part of the Voyascape Network, a collection of some of the world’s best travel podcasts. Explore more at Voyascape Podcast Network . For advertising or sponsorship opportunities on this show and across the network, email [email protected] or you can find more information at Voyascape Ads.more
This episode is supported by Smart Travel a new podcast from Nerd Wallet. Travel smarter — and spend less — with help from NerdWallet. Follow Smart Travel wherever you get your podcasts.Smart Travel Podcast
Winging It On Location – Day 1: 5-Hour Layover in Am…Check out the new Smart Travel Podcast
This episode is supported by Smart Travel a new podcast from Nerd Wallet. Travel smarter — and spend less — with help from NerdWallet. Follow Smart Travel wherever you get your podcasts.Smart Travel Podcast
Winging It On Location – Day 1: 5-Hour Layover in Amsterdam & Arriving in Tallinn
The European tour is officially underway.
In this first on-the-road episode, I take you through my journey from Toronto to Tallinn via Amsterdam, including what you can realistically do with a 5-hour layover at Schiphol Airport. I share the exact train route into the city, why I chose the Jordaan district, and the coffee stop that made the short visit worthwhile.
After a quick wander through Amsterdam’s canals, bridges, and tree-lined streets, I head back to the airport for my flight to Estonia. Once in Tallinn, I give my first impressions of the city, explain the easiest tram connection from the airport, and meet up with friends for dinner in the heart of the Estonian capital.
If you’re planning an Amsterdam layover, a Tallinn city break, or simply enjoy hearing authentic travel stories from the road, this episode is for you.
In this episode:
• How to do Amsterdam on a short layover
• Using contactless payment on Dutch trains
• The best area to wander for 2–3 hours in Amsterdam
• Coffee recommendation in the Jordaan district
• Arriving in Tallinn and getting into the city for €2
• Hotel information
• Dinner, drinks, and the start of the Baltic adventure
Support Winging It Travel Podcast
If you enjoyed this episode:
• ⭐ Leave a 5-star rating or review on your podcast app
• ☕ Support the show at buymeacoffee.com/wingingit
• 🌍 Explore more episodes at wingingittravelpodcast.com
• ✈️ Check out more great travel podcasts at https://voyascape.com
• 📺 Now also on YouTube - https://www.youtube.com/@wingingittravelpodcast
⏱️ Timestamps
00:00 Intro & recording live from Tallinn
01:38 Toronto to Amsterdam: the journey begins
02:20 Getting through Schiphol and heading into the city
03:15 The fastest train from Amsterdam Airport to Central Station
04:05 Why I chose the Jordaan district for a short layover
05:30 Canals, bridges, sunshine, and wandering without a plan
06:40 Coffee stop recommendation: KOF Café
07:30 The unexpected challenge of finding a public toilet
08:10 Where to see the famous houses sitting on the water
09:05 Is a 5-hour Amsterdam layover actually worth it?
09:45 Flying to Tallinn and first impressions of Estonia
10:20 Tallinn hotel, tram tips, and city-centre arrival
10:55 Dinner with friends and Estonian food prices
Check out all of our other travel podcasts from around
the world
This podcast is part of the Voyascape Network, a collection of some of the world’s best travel podcasts. Explore more at Voyascape Podcast Network . For advertising or sponsorship opportunities on this show and across the network, email [email protected] or you can find more information at Voyascape Ads.more
Estonia's medieval charm, beautifully preserved naturescapes, and Baltic culture are cultivating a burgeoning tourism scene. Bradt guidebook author and Estonian authority Neil Taylor lets us in on the abundant appeal of the former Soviet republic. And a certified Cicerone — that's "craft beer expert…Estonia's medieval charm, beautifully preserved naturescapes, and Baltic culture are cultivating a burgeoning tourism scene. Bradt guidebook author and Estonian authority Neil Taylor lets us in on the abundant appeal of the former Soviet republic. And a certified Cicerone — that's "craft beer expert" — takes us on a tour of European suds and helps us tap into the best pints across the continent.more
We’re toasting 2026 with whiskeys and liqueurs around the world. There’s a new favorite Irish whiskey, a liqueur that causes you to make a sour face, a drink made from cacti, and the signature drink of Estonia. [Ep 370]
Show Notes:
Destination Eat Drink foodie travel guides
Destination Eat Drink …We’re toasting 2026 with whiskeys and liqueurs around the world. There’s a new favorite Irish whiskey, a liqueur that causes you to make a sour face, a drink made from cacti, and the signature drink of Estonia. [Ep 370]
Show Notes:
Destination Eat Drink foodie travel guides
Destination Eat Drink blog
Rick’s publishing company Eckhartz Press
David Hammond and Monica Eng’s book Made in Chicago
Simon Bajada’s website
Simon’s book Malta: Mediterranean Recipes from the Islands
Some of our favorite travel moments are the ones you’d never in a million years expect. These are where the best travel stories are born. And this week, Afar’s executive editor, Billie Cohen, has a very delicious, very serendipitous story for us.
As you’ll hear in the episode, Billie was in Estonia…Some of our favorite travel moments are the ones you’d never in a million years expect. These are where the best travel stories are born. And this week, Afar’s executive editor, Billie Cohen, has a very delicious, very serendipitous story for us.
As you’ll hear in the episode, Billie was in Estonia (one of Afar’s picks for where to travel in 2024) for work. It was 9 p.m. and she was due to fly home the next day. But then her guide, Hanno, mentioned something about the country’s “open café days,” where Estonians across the south open their homes, cook food, and serve anyone who wanders in. Smart traveler that she is, Billie changed her flight home and joined Hanno in a very unique foodie road trip through the south.
In our companion video for the episode, Billie shares some of the discoveries that didn’t fit into her story—including an encounter with an Estonian wedding hazing involving Santa Claus—and her travel superpower, talking to everyone. She also shares some of the favorite foods she ate, from freshly made onion rolls to a red currant cake baked by the grandmother of one of her new friends. So really our only tip for you this week is: Don’t listen to this one hungry.
Resources
Read the transcript of the episode.
Listen to the episode on YouTube.
Read about Billie's bog hike in Estonia.
Explore the Onion Route Buffet Day
Learn more about Tartu's European Capital of Culture 2024 (events).
Find more food festivals in Estonia.
Be sure to subscribe to the show and to sign up for our podcast newsletter, Behind the Mic, where we share upcoming news and behind-the-scenes details of each episode. And explore our second podcast, Unpacked, which unpacks one tricky topic in travel each week.
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