6

Why does this sentence:

冬休みは家族でイタリアやイギリスへ行きました。

have there instead of ?

Wouldn't "with family" be 家族と?

7

家族で should be taken as "as a family" rather than "with family"

(Both と and で could be used, though IMHO, 家族で implies that all family members were present whereas 家族と implies you only went with some/maybe all family members.)

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8

Both 家族で and 家族と are correct.

で can sometimes mark an organization/group which makes some action, as if it were a subject.

It's the third definition on デジタル大辞泉.

動作・作用を行う主体となる組織・団体を表す。「政府側―検討中だ」「気象庁―光化学スモッグ警報を発令した」

東京外国語大学言語モジュール treats this as an extension of で as a location marker, as follows:

10 場所を表わす用法の拡張として、主語を場所風に表わすときに用いることがあります。

  • 警察事件を調べています。
  • クラス旅行に出かけました。
  • その仕事は自分やります。

This question is also related:

I think it's also possible to think of this as an extension of 1人で, みんなで, 全員で, etc.

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