

Planning a holiday... whats the best option for my lil guy?
My pup is now 17 weeks and in 3 weeks, he will have his final vaccine. We are looking to go away for 5 days in 6 weeks for a beach holiday, and then over the summer, we have 3 weddings to attend, all 3-day events (flying overseas).
The thought of these trips worries me as we have never left him for more than a few hours. He LOVES people, and based on how he interacts with strangers, I get the feeling that as long as he is getting attention and love from someone, he is okay & it doesn't have to be from me. He sleeps in his crate next to our bed from about 11-6am and then I let him pee & he hops into bed with us. He is 65% (rough guess haha) housebroken. When we leave the house, he sleeps in his crate and seems fine but if I put him in his crate when I'm in the same room as him and awake i.e making dinner/ watching tv, he cries. I think a dog sitter would be best but I am open to advice from others as to what worked well for their cavs.
For some extra context: I really am contemplating if the beach trip for 5 days is necessary but we have dealt with two immediate family member deaths since Jan and would love a break if it is possible.
Thank you :)