Travel's more convenient these days, with Virgin leading the way

I came across an announcement about Virgin's new charter service on Techcrunch. I also learned this factoid:

"Twenty-five years ago, stuck in Puerto Rico after a canceled flight to the Virgin Islands, Branson found a charter plane and went around the airport with a blackboard that advertised a charter flight for $39 per person. He filled all 50 seats, and that is how he started Virgin Atlantic."

Pretty cool! Now there's a website that connects the consumer with charter flight operators, and importantly, allows leverage of this information by offering "Hot Deals". "Hot Deals" are basically flights that were chartered for one way trips and will be flying back empty to their home base, therefore any revenue generating passenger is better than none.

I was even more encouraged when I came across this operator. I would definitely consider flying from Dubai to NYC on a private charter aircraft, with all business class seats and fully flat beds, checking in 30 minutes before the flight at a private terminal with no serpentine security check lines for less than 4200 USD, round trip.

Now, I am looking for a company that will let me combine different modes of travel to optimize my travel by time or cost or convenience (child friendly would be great!). For instance, instead of flying San Francisco to London Heathrow and connecting at Heathrow to Rome like we did recently, a more sensible itinerary would've been to fly non-stop from San Francisco to London, and connect by train/chunnel to mainland Europe and onwards by Eurail to Italy. I even explored booking this itinerary but was put off by the complexity of figuring out flight/train/shuttle departures, connecting logistics across foreign geographies and the realization that I will be completely on my own trying to figure out Plan B in a foreign country with linguistic barriers, if my Plan A doesn't execute perfectly. Perhaps it's time to build another start-up....