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3 Countries - Bar Trip - need advice

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Hi,

First time posting!

My husband and I are planning a trip for after he takes the Bar Exam next summer, and I'm hoping to get some preliminary information/insights. For background, we live in NYC. I've been to England once (last year), and he travelled a lot throughout his teens, but hasn't been outside the US in over a decade.

What we're planning: 5 days in London, 5 days in Santorini, 5 days in Barcelona. My husband wanted London, I wanted Santorini, and we were open for the 3rd location. Based on direct flights (we are adamant about direct flights), it looks like Barcelona is the easiest third option, and we're both pretty stoked on that selection.

As I mentioned, we're not extraordinarily experienced international travelers, so I have a few questions (highlighted with stars below for the TL;DR out there):

1) A lot of travel websites recommend waiting until closer to the date to book flights unless it's a holiday weekend or you're traveling to a very sought after location. We're planning our trip for over labor day weekend, and Santorini seems to fall within the sought after component. **When is the most reasonable time to book flights?**

2) Generally speaking, what is a good price for a flight that goes from NYC-->London, and then Barcelona-->NYC? I'm seeing prices currently in the $800-1100 range, which seems reasonable to me. **Should I expect these prices to drop?** It's my understanding it's a more complicated scenario in which to get cheaper airfare given our multi-city itinerary. I travel back to CA 4-5 times a year, and so I know that generally any ticket price over $400 is on the expensive side, and anything under is on the reasonable side. Hoping to have that same perspective with these international tickets.

3) I'm hoping to do a hacker fare (is that the term?) through Delta in which we'd fly Virgin Atlantic premium economy TO London, and then we'd fly Delta regular economy back from Barcelona. I've read that Virgin Atlantic premium economy is one of the best for the price, and given that it's the only airline I've flown internationally, I don't have much to compare this to. **Has this been your experience? Do British Airways/American have better premium economy?**

Thanks for any advice!!

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