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Winging It Travel Podcast · Wednesday, July 8, 2026

Hammond's Future Travel Itinerary: Toronto, Tallinn, Helsinki, and More

James Hammond shared details of his upcoming travel plans, starting with a long weekend in Toronto in three weeks to visit Aaron from The Curious Tourism podcast. He will then travel to Tallinn, Estonia, for a few nights before taking a ferry to Helsinki, Finland, for another long weekend. He also mentioned a potential six to eight-week trip before Christmas, with options including Cape Verde, Sao Tome, South Africa, and Kenya.

personAaronpersonEwan McGregorpersonCharlie Boorman

The tape

3 quotes
In three weeks. I'll be flying to Toronto where we have a long weekend. Being emigrants to Toronto. We're staying with Aaron from The Curious Tourism podcast. I'm going to check out Toronto for a long weekend. Can't wait for that. Should be great weather. We've got a few things planned. And then for me, I'll fly on to Tallinn in Estonia. Meet a couple of friends there. Got two or three nights in Tallinn. First time in Estonia, so new country for me, looking forward to checking out the city.
James Hammond
And then we're going to hop on the ferry across to Helsinki in Finland. Have a long weekend there. We're going to drive up to the Lãhdest from the East part of the country. About an hour and a half, two hours. We're going to get a train up there actually. Get a car out and drive around those iconic roads. If you don't know what they are, the guys who did the long way up series, your McGregor, Charlie Boorman. The latest one, they go through Europe, they go through Finland in that specific area and they camp on a little island and the peacefulness, the calm waters, the roads that traverse through those legs looks absolutely incredible. So we've booked a cabin and we've got a sauna there. All of this sort of stuff. So nice and relaxing. Get some views. I might have my drone ready up then, hopefully get some drone footage.
James Hammond
And then there will be another six to eight weeks before we go back to UK for Christmas. That's a pretty long trip. That's three and a half weeks as well. And I've got a week spare where I can't decide where to go. Maybe like eight days. Few options are Cape Verde, as I mentioned. Sao Tome. Uh, South Africa, Kenya. Looking something on the same time zone. Not cold. So I'm going south basically. Yeah, haven't committed to anything in there yet. We'll see what comes up.
James Hammond
Heard on Winging It Travel Podcast — “Why the World Cup Proves Travel Brings People Together | My Updated 2026 Travel Plans & Recovering From Kidney Stones, published Wednesday, July 8, 2026. Heardvine summarizes and quotes with attribution and timestamps, and links to the original everywhere.
Transcribed via Gemini audio transcription · $0.01