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Yes it is possible..
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Yep it is possible to go Singapore through roads.
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Delhi--Siliguri--Guwahati--Imphal--Monywa(Myanmar) via AH1 and Monywa-Kalaywa Highway. From Monywa to Thailand via Yangon-Mandalay expressway or Yangon-Naypyitaw-Mandalay expressway. The total distance is around 1,326 km. · Now head for Malaysia from Thailand via AH2 which carries the total distance of 1,701 km. · And the last rides remain that will make you reach your destination that is Singapore from Thailand via Lebuhraya Utara-Selatan expressway2.
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Yes road trip is possible https://traveltriangle.com/blog/bike-trip-from-singapore-to-india/ you can just take the reverse route of same article.
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Absolutely, to travel from India to Singapore by Road is possible. Starting from India the route will be from India-Myanmar-Thailand-Singapore via AH2.
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