Winging It On Location – Days 2-3 - Tallinn: A Trendy Old Town, Estonian History and Monopoly Deal
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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?
--------------------------------------------------------------
Produced by Winging It Productions - https://www.wingingitproductions.com
Voyascape: Travel Podcast Network - https://voyascape.com/
Winging It Travel Podcast - Website
--------------------------------------------------------------
Winging It Travel Podcast Credits
Host/Producer/Creator/Composer/Editor - James Hammond
Contact me - [email protected] or [email protected]
Social Media - follow me on:
Instagram
TikTok
Facebook
--------------------------------------------------------------
Affiliate Links
If you click one of the below to book something, I get a tiny commission, which helps the podcast.
Book Flights with Skyscanner - Here
Use Revolut Travel Card - Here
Book Hostels With Hostelworld - Here
Booking.com - Here
Book Experiences With Viator - Here
Discovery Car Hire - Here
Book Buses With Busbud - Here
Book Trains With Trainline - Here
Travel Insurance with SafetyWing - Here
Book Flights With Expedia Canada - Here
--------------------------------------------------------------
Thanks for supporting me and the podcast!
Cheers James.
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.
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?
--------------------------------------------------------------
Produced by Winging It Productions - https://www.wingingitproductions.com
Voyascape: Travel Podcast Network - https://voyascape.com/
Winging It Travel Podcast - Website
--------------------------------------------------------------
Winging It Travel Podcast Credits
Host/Producer/Creator/Composer/Editor - James Hammond
Contact me - [email protected] or [email protected]
Social Media - follow me on:
TikTok
--------------------------------------------------------------
Affiliate Links
If you click one of the below to book something, I get a tiny commission, which helps the podcast.
Book Flights with Skyscanner - Here
Use Revolut Travel Card - Here
Book Hostels With Hostelworld - Here
Booking.com - Here
Book Experiences With Viator - Here
Discovery Car Hire - Here
Book Buses With Busbud - Here
Book Trains With Trainline - Here
Travel Insurance with SafetyWing - Here
Book Flights With Expedia Canada - Here
--------------------------------------------------------------
Thanks for supporting me and the podcast!
Cheers James.
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.