Where should I go??? Good use of all the miles and points.

I am planning a trip to boston and new hampshire this fall. Prob using starwood in boston, jetblue(amex pts) for the flights, club carlson in manchester, nh.

Then a trip to london and italy next spring/summer. using british airways(amex pts) and virgin first class. Not sure how im getting to italy. My wife has family in napoli.

Andrew's American Airlines Miles - 121087
Maria's American Airlines Miles - 64622
United Miles - 58610
US Airways Miles - 44240
Southwest Miles - 35859
frontier - 1000
Andrew's Virgin Atlantic miles - 48752
Maria's Virgin Atlantic miles - 48781
Chase UR points - 137287
Wells Fargo points - 2673
Citi TY points - 52
Amex points - 80585
Hyatt Points - 5400
Starwood points - 41019
Hilton points - 150885
Travelocity points - 9500
club carlson points - 97,576

Then...

Followed by..
So what do you need help with?

Just general ideas of the best way to use my points, I would like to visit Australia or maybe the Caribbean.

...is Virgin Atlantic 50k plus $450 worth a first class ticket to London one way non stop from Orlando?

Okay so your point of departure for all trips is Orlando, correct?
depending on time of year you plan to do the Virgin Atlantic trip in Summer as you said it sounds like a good deal. Winter not so much. Consider low cost like Ryan Air to France or Italy and the train to Milan or even train from London.

July is best for Alaska newbies.

St. Thomas is best for Caribbean newbies.

Meh to Australia - do New Zealand.

Echo this. Scenery is gorgeous and the exchange rate is more favorable.

+1. Especially the South Island. And return with a couple days in Sydney on AA miles if you want to squeeze in some Oz and a big city.

I don't know about that. After doing 3 weeks in Australia and 2.5 weeks in New Zealand we liked Australia more. New Zealand is great for outdoors things and if your ok with traveling long distances by car/bus but if you want to do a few cool things with driving or a few quick flights then its Australia. Yes prices are better in New Zealand but Australia has a lot of great things. The better thing would be to do both.

This is the kind of really good use of miles I am interested in. My home base is Orlando. I do not care where I go, I want to see things I have not seen. This is a free one way on american.

25,000 miles+$7.50 USD

10/1/13
BOS>MIA
MIA>MCO

3/12/14
MCO>ORD
ORD>NRT