USVI-On-Line

I think you'll be very pleased that you are spending one night on STT. We did that our first trip and then we aren't doing it this trip. I totally kicked myself for not thinking to go down a day early and stay on STT for the night. We have no choice but to have a long travel day and it was so nice to just head for the hotel and start relaxing and then take our time getting over to the villa the next day after breakfast. We'll be rushing to make the ferry this time to get to the car rental before it closes.

The Ritz would be great!

Have you checked with your rental agent to see if your villa is available the night of the 14th? The exact same scenario happened to us 2 years ago, and we were able to stay at our villa, paying a pro-rated amount.

To me, it would depend on whay time my flight arrives on STT and how many connections I have.
If I were arriving later than 2PM or had any layovers of more than an hour, I would just take the crowd across the street to the Island Beachcomber or the Best Western, check in and hit the beach, or in the case of the BW, the pool. The accommodations are not high end but my guess is that you will not be up to much more than a drink, a meal and a bed. If I remember correctly, your trip is in November and it gets dark pretty early on STT-STJ at that time of the year, even though they are on the equivalent of DST. You can get a meal at the Island Beachcomber and eat at the be beachfront bar or you can catch a cab quickly downtown from either place. You could schedule your departure the next day to coincide with the downtown ferry and have only a short cab ride.
This is the plan my sister and I used, although it was 7 years ago, when we took her twin toddlers to STJ.Our flight got in about 2PM and we even had time to walk along the airport road with the stroller down to the gas station at the end to get milk. There is also a liitle playground between the hotels and the airport where we walked the next morning, as it wasnt a beach kind of day.
I was just reading a post on another board that the Westin will only have 100 guest rooms, all poolside, when their renovation is complete in November. Have you checked the Westin prices for you dates? I bet they will get top $$$ for those rooms if you dont have points. I think the Westin is the only other option I would consider if I were travling with your crowd. At least they will "cart" you to your room when you get there and you can pick up you villa car and make the luggage trip to/from the villa from the Westin before you put the people in. Its so easy there with young kids, you can wheel the stroller right up to the seating areas outside the bar if you want to have a drink.
I personally would not want to deal with the STT and STJ taxi drivers more than I have to in any 2 day period. And the time you would have to spend at the Ritz would be so minimal that I personally dont think it is worth staying there or in any of the large hotels on STT, especially Sugar Bay. PM me for the lowdown on staying at Sugar Bay with kids. By the time you got them down to the beach you would rather swim to STJ than walk back up and take the ferry.

Secret Harbour would be my choice too. Actually, we spent our first night there in May. It was lovely, we had a beachfront one bedroom, a nice balcony overlooking the beach and a short walk to the bar and restaurant.

Wasn't it your mother that visited St Thomas recently and drove herself around? If you changed your car rental to St Thomas, you could load up the bags just once, drive the scenic route to the hotel, shop if desired and then ferry over to St John. The ferry was easy for us.

Good luck!

I settled on a night at the Ritz on STT. Got a package deal that includes the night, breakfast for 2 (haven't decided who will go hungry yet), and a $100 resort credit I am hoping my hubby and I will use to enjoy dinner.

You will enjoy the Ritz. My husband and I stayed there a few years ago for several nights. The grounds and service are very nice. The only thing wrong with it, is its not on St. John!!