What you have planned is ambitious for 8 days and there will be a lot of close hauled sailing to get up to Bequia. Keep in mind that at this time of year, it can be brisk with a northeast fetch to the wind and you will likely do some tacking to get there. We leave tomorrow for a 10 day, one way charter starting from St. Vincent with a drop off in Grenada.

I can't speak to where to find the Super Bowl on Carriacou, but I'm sure that with diligence you will find a place. We once watched it on Mayreau. Not positive, but I think it was the only bar/restaurant with a functioning TV (19 inch). It was two of us, the owner/bartender and his friend. Carriacou is bigger with a larger population so you should have a few options.

You will need to check out of Grenada and in to St Vincent territory and vice versa.

Personally, unless you are driven and have to be there, with only 8 days, I'd forget about Bequia and Mustique. If you only do one, I prefer Bequia. If you have never been, I'd plan at least one extra day around the Tobago Cays with a night at Salt Whistle on Mayreau. We typically spend 2-3 days in this area. The hike to the church at the top of Mayreau is worth it for the incredible views.Dinner either with Dennis, or Righteous in the village is well worth it as well.You can get a taxi up and back for dinner, and frequently, the restaurant will pick you up and bring you back as well.

Other places worth a stop are Chatham Bay on Union (snorkeling and beach bbq) as well as PSV with a visit to Mopion. Unless you want to visit the new marina on Canouan, I wouldn't bother. It is ok, just nothing special.

Have a good trip.