In the early years of the original Amazing Race, they didn't have those kinds of bunch-ups and sometimes teams ended up being a day or more behind the pack. In fact, in the very first Race, the final three was actually a final two because the third place team was stuck in Alaska while the top-two were racing to the finish in New York City.
Over the years, they've refined things to ensure the teams generally stay bunched-up together. It makes the production go a lot smoother because they don't have camera crews (and the host) scattered around different locations.
It's best to look at it as a bunch of single-leg races and the most-important thing is to not finish last on a leg.
There are some advantages to finishing higher on a leg even with the bunch-ups. For example, at the end of each leg, they do interviews with each team about that leg. Each interview can take up to a half an hour and they do them in the order the teams finished. So, by finishing first, you get your interview out of the way first and then you're free to eat or sleep at the Pit Stop while the other teams are waiting for their interviews.
On the US version, the teams tend to have more freedom with booking their travel arrangements. It's not uncommon for the teams to be spread across 2 or 3 different flights.
On the Canadian version, the flights available tend to be more restricted (Air Canada is a major sponsor, so they're not going to want to have teams flying WestJet). As a result, it's rare for them to have the teams taking different flights.
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