So I asked Claude to plan my next 20 years of holidays.

I’m not bothered about visiting every country in the world – no offence to the Taliban or Kim Yong Un, but I can cope without visiting places with a fair chance of imprisonment/death.

But I’d like to get to at least 100 countries.

Plus I love my weekends away in Europe.

I enlisted Claude to create me a plan for the next 20 years. All reasonably safe countries, and all European Capitals of Culture. Not including places I’d already visited, and trying to not use more than 20 days annual leave a year.

This is what it came up with:
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📅 2026 [19 AL days]
✈️ Japan (Jun)
Japan
Tokyo, Kyoto, Osaka, Hiroshima
🗺️ Morocco & Southern Spain (Mar)
Morocco, Spain
Marrakech + Seville
🌍 Balkans cities (Sep)
Serbia, Bosnia & Herzegovina
Belgrade + Sarajevo
🌍 Baltic capitals (Oct)
Latvia, Lithuania
Riga + Vilnius + Kaunas
🏛 ECoC weekends: Glasgow 🏴󠁧󠁢󠁳󠁣󠁴󠁿 • Cork 🇮🇪 • Antwerp 🇧🇪

📅 2027 [19 AL days]
✈️ South America I (Oct–Nov)
Brazil, Argentina, Uruguay
Rio, Iguazu Falls, Buenos Aires, Montevideo
🗺️ Turkey (May)
Turkey
Istanbul, Cappadocia, Ephesus
🌍 Georgia (Sep)
Georgia
Tbilisi + Kazbegi
🏛 ECoC weekends: Liverpool 🏴󠁧󠁢󠁥󠁮󠁧󠁿 • Galway 🇮🇪 • Bruges 🇧🇪

📅 2028 [20 AL days]
✈️ Southeast Asia I (Jan–Feb)
Thailand, Vietnam, Cambodia
Bangkok, Chiang Mai, Hanoi, Ha Long Bay, Siem Reap
🗺️ Caucasus (May)
Armenia, Azerbaijan
Yerevan + Baku
🌍 Iceland (Jun)
Iceland
Reykjavik, Golden Circle, South Coast
🏛 ECoC weekends: Mons 🇧🇪 • Esch-sur-Alzette 🇱🇺 • Amsterdam 🇳🇱

📅 2029 [20 AL days]
✈️ East Africa Safari (Jul)
Kenya, Tanzania, Rwanda
Masai Mara, Serengeti, gorilla trekking
🗺️ Gulf States (Feb)
UAE, Qatar, Bahrain, Oman
Dubai, Doha, Manama, Muscat
🌍 Norway (Jul)
Norway
Bergen + Stavanger + Bodø
🏛 ECoC weekends: Rotterdam 🇳🇱 • Lille 🇫🇷 • Weimar 🇩🇪

📅 2030 [20 AL days]
✈️ India & Sri Lanka (Jan–Feb)
India, Sri Lanka, Maldives
Kerala, Colombo, Sigiriya, Maldives
🗺️ South Korea & Taiwan (Apr)
South Korea, Taiwan
Seoul + Taipei
🌍 Tunisia (Oct)
Tunisia
Tunis, Carthage, Sidi Bou Said
🏛 ECoC weekends: Leeuwarden 🇳🇱 • Avignon 🇫🇷 • Essen 🇩🇪

📅 2031 [20 AL days]
✈️ Central Asia Silk Road (Jun–Jul)
Uzbekistan, Kazakhstan, Kyrgyzstan
Samarkand, Bukhara, Almaty, Bishkek
🗺️ Jordan & Saudi Arabia (Nov)
Jordan, Saudi Arabia
Petra, Wadi Rum, AlUla
🌍 Bulgaria (Sep)
Bulgaria
Sofia + Plovdiv
🏛 ECoC weekends: Marseille 🇫🇷 • Chemnitz 🇩🇪 • Graz 🇦🇹

📅 2032 [20 AL days]
✈️ Southern Africa (Jun–Jul)
South Africa, Namibia, Botswana, Lesotho, Eswatini
Cape Town, Etosha, Okavango
🗺️ SE Asia II (Mar)
Malaysia, Singapore, Brunei
KL, Singapore, Borneo
🌍 Moldova (Sep)
Moldova
Chisinau + wine region
🏛 ECoC weekends: Bourges 🇫🇷 • Linz 🇦🇹 • Florence 🇮🇹

📅 2033 [20 AL days]
✈️ SE Asia III (Apr–May)
Indonesia, Philippines
Bali, Lombok, Komodo, Palawan, Manila
🗺️ China I (Sep)
China
Beijing, Xi’an
🌍 Kosovo & Montenegro (May)
Kosovo, Montenegro
Pristina + Kotor
🏛 ECoC weekends: Salzkammergut 🇦🇹 • Bologna 🇮🇹 • Porto 🇵🇹

📅 2034 [19 AL days]
✈️ Australia & New Zealand (Mar)
Australia, New Zealand
Sydney, Melbourne, Auckland, Queenstown
🗺️ Laos & East Timor (Jan)
Laos, East Timor
Luang Prabang + Dili
🌍 Algeria (Oct)
Algeria
Algiers + Tipasa
🏛 ECoC weekends: Genoa 🇮🇹 • Guimarães 🇵🇹 • Santiago de Compostela 🇪🇸

📅 2035 [20 AL days]
✈️ West Africa (Nov)
Ghana, Senegal, Gambia, Ivory Coast, Togo, Benin
Accra, Dakar, Banjul, Abidjan, Lomé, Cotonou
🗺️ Caribbean I (Jan)
Cuba, Jamaica, Dominican Republic
Havana, Kingston, Santo Domingo
🌍 Kuwait (Feb)
Kuwait
Kuwait City
🏛 ECoC weekends: Matera 🇮🇹 • Évora 🇵🇹 • Salamanca 🇪🇸

📅 2036 [20 AL days]
✈️ Latin America II (May–Jun)
Peru, Bolivia, Chile
Machu Picchu, Salar de Uyuni, Atacama, Patagonia
🗺️ Cape Verde (Nov)
Cape Verde
Island hopping
🗺️ Caribbean II (Jan)
Barbados, Saint Lucia, Grenada, Trinidad and Tobago
Eastern Caribbean
🏛 ECoC weekends: San Sebastián 🇪🇸 • Aarhus 🇩🇰 • Turku 🇫🇮

📅 2037 [20 AL days]
✈️ Nepal & Bhutan (Oct)
Nepal, Bhutan
Kathmandu, Annapurna, Paro Taktsang
🗺️ Pacific Islands I (Jul–Aug)
Fiji, Samoa, Tonga
Island hopping from Fiji
🌍 Zimbabwe & Zambia (Aug)
Zimbabwe, Zambia
Victoria Falls
🏛 ECoC weekends: Oulu 🇫🇮 • Umeå 🇸🇪 • Athens 🇬🇷

📅 2038 [20 AL days]
✈️ Canada (Sep)
Canada
Vancouver, Banff, Toronto, Quebec City
🗺️ Seychelles & Mauritius (Oct)
Seychelles, Mauritius
Island hop
🗺️ Madagascar & Comoros (Apr)
Madagascar, Comoros
Antananarivo + Moroni
🏛 ECoC weekends: Kiruna 🇸🇪 • Thessaloniki 🇬🇷 • Rijeka 🇭🇷

📅 2039 [20 AL days]
✈️ Pacific Microstates I (Mar)
Palau, Micronesia, Marshall Islands
World-class diving
🗺️ Ecuador & Galapagos (Jun)
Ecuador
Quito + Galapagos
🌍 Bahamas (Mar)
Bahamas
Nassau
🏛 ECoC weekends: Patras 🇬🇷 • Novi Sad 🇷🇸 • Maribor 🇸🇮

📅 2040 [20 AL days]
✈️ Pacific Microstates II (Apr)
Nauru, Tuvalu, Kiribati, Solomon Islands
The hardest countries to visit
🗺️ Central America (Feb)
Costa Rica, Panama, Belize
Rainforest, canal, ruins
🗺️ European Microstates (Jun)
Monaco, San Marino, Vatican City, Andorra
All 4 microstates
🏛 ECoC weekends: Eleusis 🇬🇷 • Nova Gorica 🇸🇮 • Plzeň 🇨🇿

📅 2041 [20 AL days]
✈️ Uganda & Horn of Africa (Jul)
Uganda, Burundi, Djibouti
Gorillas, Bujumbura, whale sharks
🗺️ Caribbean III (Jan)
Saint Kitts & Nevis, Antigua & Barbuda, Saint Vincent & the Grenadines, Dominica
Eastern Caribbean
🗺️ Turkmenistan (Apr)
Turkmenistan
Ashgabat + Darvaza crater
🏛 ECoC weekends: České Budějovice 🇨🇿 • Košice 🇸🇰 • Pécs 🇭🇺

📅 2042 [20 AL days]
✈️ China & Mongolia (Apr)
China, Mongolia
Yunnan, Sichuan + Beijing→Ulaanbaatar by train
🗺️ Central Africa (Jun)
Gabon, Republic of Congo, São Tomé and Príncipe
Libreville, Brazzaville, Sao Tome
🌍 Nicaragua (Feb)
Nicaragua
Granada
🏛 ECoC weekends: Trenčín 🇸🇰 • Veszprém 🇭🇺 • Sibiu 🇷🇴

📅 2043 [20 AL days]
✈️ Latin America III (Feb)
Colombia, Paraguay, Guyana, Suriname
Cartagena, Medellin, Asuncion, Georgetown, Paramaribo
🗺️ Vanuatu (Apr)
Vanuatu
Port Vila + islands
🌍 Guinea & Sierra Leone (Jan)
Guinea, Sierra Leone
Conakry + Freetown
🏛 ECoC weekends: Timișoara 🇷🇴 • Lublin 🇵🇱 • Liepāja 🇱🇻

📅 2044 [19 AL days]
✈️ SE Asia Finale (Feb)
Vietnam, Laos
Ho Chi Minh City, Mekong Delta, Vientiane
🗺️ Equatorial Guinea & Cameroon (Nov)
Equatorial Guinea, Cameroon
Malabo + Yaoundé
🌍 Malawi (Aug)
Malawi
Lake Malawi
🏛 ECoC weekends: Paphos 🇨🇾 • Leuven 🇧🇪 • Victoria, Gozo 🇲🇹

📅 2045 [18 AL days]
✈️ 100th Country — My Choice (TBD)
TBD
The dream destination. To be revealed.
🗺️ Flex (TBD)
TBD
Mop-up or revisit
🌍 Celebration (TBD)
TBD
🏛 ECoC weekends: Larnaka 🇨🇾

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📊 THE NUMBERS
✈️ 61 trips over 20 years
📆 376/400 annual leave days used
🌐 ~126 countries visited
🏛 58 European Capitals of Culture (mostly free weekends)
💷 ~£136,000 estimated total (£6,800/yr avg)
🚫 No FCDO red or amber countries

travel #100countries #bucketlist #travelblogger #travelplanning #worldtravel #digitalnomad #traveller

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Claude’s hashtags – not mine. I’m not a fucking #digitalnomad.

More or less the logistics add up…I’m not sure I’m going to do 6 African countries in 10 days in 2035, that feels a tad ambitious, likewise it reckons I can do Laos & East Timor in a week, or Malaysia, Singapore and Brunei in a week (the above text doesn’t list the annual leave required, but the spreadsheet Claude created does).

Will I follow it? Probably not but it’s something to aim for!