It sounds like he's back from his travels. Do you know if he had a good time?
I heard he's back from his trip. I wonder if he had a nice time in 〇〇.
この場合、次のように言えますよ。
ーIt sounds like he's back from his travels. Do you know if he had a good time?
「彼は旅行から帰ってきたみたいだけど、彼が楽しんだか知ってる？」
to be back from one's travels で「旅行から戻る」
to have a good time で「楽しい時間を過ごす」
ーI heard he's back from his trip. I wonder if he had a nice time in 〇〇.
「彼が旅行から帰ってきたって聞いたけど、〇〇で楽しんだかなあ」
to be back from one's trip でも「旅行から戻る」
to have a nice time in 〇〇 で「〇〇で楽しい時を過ごす」
ご参考まで！
I heard that he came back from a trip overseas, but did he seem to have fun?
I heard he's back from his overseas trip, but did he seem like he was enjoying himself on the trip?
ご質問ありがとうございます。
① "I heard that he came back from a trip overseas,"＝「海外旅行から帰って来たと聞いた」
"but did he seem to have fun?"＝「楽しんでいるようだった？」
② "I heard he's back from his overseas trip, "＝「海外旅行から帰って来たと聞いた」
"but did he seem like he was enjoying himself on the trip?"＝「彼は旅行を楽しんでいるようだった？」
ご参考までに。
カナダ 
アメリカ合衆国 
