Flying groups of people.... need advice

As I mentioned in another thread I have a place on Virgin Gorda for a month next January It accommodates four couples at a time (including us). So I will be organizing groups coming and going. For the initial group, I'd like everyone to fly out of Boston together just to make life easy. I was going to just put the one way flights on my credit card and let them pay me back. (I like the miles) My question is- is there a reason TO book all 7 (I'm going a two days early to prepare) on one "ticket" as a group traveling together? Or does it make more sense to break them up ? My fear is I will get couple 3 on the plane and go to book the 4th couple and it won't accommodate. From a travel agent's perspective, is there a reason to keep the group together ? Or a more compelling reason to just book them separately should someone have an emergency and not be able to go....... I will be going thru this in weeks two and three as well but they're coming from separate parts of the country so a no-brainer.

Thank you in advance for any advice

Many airlines have a group booking desk. Here is a link for JetBlue. It’s says 8 or more but I would give them a try.


https://www.jetblue.com/help/group-bookings

Too many times I've paid the bill (usually at a restaurant) after everyone has contributed what they figure was their fair share of the bill only to get screwed when somebody "underestimates" their bill or someone doesn't come through with payment after they "forgot" about that evening.

I would be reluctant to pay for all of those flights up front, but that is just me.

If you are set on paying the entire bill, go with a travel agent or the airline group booking desk. I did exactly what you are contemplating and got burned do to dynamic pricing. The ticket prices jumped by more than $200 pp after I purchased the first six tickets. Because family members 7, 8, 9 and 10 made their decision to go based on the original price, I paid the difference.

Let them make their own arrangements, it will be less stressful for everyone. If they can't or are unwilling to do so, VG might not be a place they want to be for a vacation.

I think booking all together is better as the computer algorithms may bump rates up after 1st couple books. Also some advantages with "groups" in regards to connections and cancellations.

I would have immediate payment required from all parties (Venmo, etc) once you book. Likely include travel insurance in this amount as well. A group text can confirm all are in agreement to pricing after on airline website even before buying. Don't get caught being their banker!

I book it all so it gest done right...you may want to look at charter flight on 2nd leg with 8 people. We use Island Birds