The first card we have is the King of Swords. The King of Swords represents authority, discipline and leadership. The King of Swords is a figure that indicates that you are ready to rely on someone to make important decisions. The upright position of the card indicates that you have great trust in Chiara to plan your holidays.
The second arcanum is The Fool. The Fool symbolizes spontaneity, unpredictability and freedom. His upright stance suggests that you should be aware that unforeseen things can happen when planning vacations and not rely on Chiara's planning alone.
The reversed Empress indicates that you need to keep control over the situation as there can be some problems with placing all the responsibility on Clare. There may be difficulties in managing the details and in the success of the planning.
The last card, the Seven of Swords, suggests that you should be flexible and not worry too much about the details. You should trust Chiara but also be ready to act quickly should something go wrong while planning your vacation.
Bottom line, the cards show that you should trust Chiara to plan your holiday but be aware that there are some risks to consider and you need to be flexible to handle any issues. Based on this information, it is likely that you can trust Chiara for planning your holidays: yes.