holidays

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so my boyfriend has just come into some money and told me to book 2 holidays 1 for just me nad him and the other for me him and the 2 kids. he said he doesnt mind where either of the holidays are it is totally up to me where we go but i have no idea at all, i dont even know where to begin looking do i look online or do i use a travel agent???? and wheres the best places to go any ideas are welcome please help me