Multi-country trips
Itineraries we'd actually do
Each itinerary pairs two or three countries that work together — geographically, logistically, and tonally. Day-by-day routes, with the eSIM and VPN combo we'd take.
14 days · 2 countries
Iberian Loop
Madrid → Seville → Lisbon → Porto
Spain and Portugal share a peninsula but feel like different planets — and that's exactly the point. High-speed rail, a single short flight, and you've covered four world-class cities, two coastlines and arguably the best eating in Europe. A trip that flatters first-timers and rewards repeat visitors.
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21 days · 3 countries
Mediterranean Classics
Rome → Athens → Greek islands → Istanbul
The classic European cultural circuit, sequenced so the food and the history build instead of compete. Rome warms you up, Athens sharpens you, the islands soften you, and Istanbul finishes the meal. Three weeks is the minimum — four would be better.
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30 days · 3 countries
Southeast Asia Backpacker
Bangkok → Hanoi → Saigon → Bali
Cheap, hot, photogenic, life-changing. A month is enough to do each country justice without burning out, and the budget airline links between them are some of the cheapest international flights in the world.
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16 days · 2 countries
Golden Triangle Asia
Tokyo → Kyoto → Osaka → Seoul → Busan
Japan and Korea are easy to do badly — too many cities, too much shinkansen, no time to absorb. This pacing keeps you in each base long enough to break the surface. Plan around cherry blossoms (late March to mid-April) or autumn leaves (mid-November).
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21 days · 2 countries
Andean Adventure
Lima → Cusco → Machu Picchu → Bogotá → Cartagena
Two of South America's most rewarding countries, sequenced so you acclimatise to altitude before you need it and end on a Caribbean breeze. Lima alone justifies the flight; Machu Picchu and Cartagena seal it.
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18 days · 2 countries
East Africa Safari
Nairobi → Maasai Mara → Cape Town → Kruger
Time it for the Great Migration (July–October) and the Mara becomes one of the wildlife events of your life. Cape Town in the middle resets the trip with city food and wine; Kruger finishes you on the Big Five.
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28 days · 2 countries
ANZ Grand Tour
Sydney → Cairns → Uluru → Auckland → Queenstown
You'll fly a lot. You'll cover 10,000+ km on the ground. And you'll come home with the strongest camera roll of your life. Internal flights are essential — don't try to do this trip by car.
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24 days · 2 countries
Himalayan Pilgrimage
Delhi → Varanasi → Kathmandu → Annapurna
The trek is optional but transformative. Even without it, this is the most intense three weeks of cultural travel on the planet — Old Delhi food walks, dawn on the burning ghats, and Kathmandu's dust-and-incense backstreets.
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