Mid November or early December should be least expensive.
Many charters take a break early December because the
demand pre holidays is so low. Of the times you mentioned,
Xmas would be the most $$$ by far and early January 2nd
in expense routinely but a good time to travel. Mid Nov can still
find hurricanes(we experience a hurricane on a vacation
Nov 5-15th a few years ago), not fun! Also-all these times
except Xmas will be low on children travelling.
Good golf in the Carib is unheard of. Jamaica has
the most courses AND the most resorts. Sandals resorts
are nice but won't be inexpensive in the winter. Often they
run a sale starting after labor day but the savings is usually
only $500 per couple. I like Grand Lido Negril but no golf there.
Also, Jamaica leaves much to be desired regarding snorkeling.
And -no gambling in Jamaica. Negril's beach is the best and
the prettiest on Jamaica. Grand Lido has a wonderful spa.
My personal favorite island is St. John. No golf there either
because there's not a bit of flat land but that's why it's so
beautiful. Great hiking trails, wonderful snorkeling, ferry
to St. Thomas for a 1/2 day of shopping, I COULD spend
two weeks on the beach and snorkeling and often do so
this island might be a bit low key for you. There are speed
raft trips to the British virgin islands from the dock in
Cruz Bay(bring your passport) and the most beautiful sunsets
anywhere. The Westin is nice, Caneel Bay is exclusively
low key deluxe and house rental is a good option too. You
might get a good deal on a house there early January or December. Shop the internet heavily if you're renting a house,
there are lots of rental agencies out there.
Consider Cayman, the Hyatt has a golf course, snorkeling at
Stingray City is a gas as is other snorkeling. The island is
very small so a quick trip to "hell" and the turtle farm rounds
out the possible activities but the snorkeling should keep
you busy for a long time.
St. Lucia is worth a look, great hiking and some fabulously
unique resorts. Anse Chastanet should be considered as
well as the Sandals resort there. I don't think there's any
golf.
Puerto rico has much to offer and some easy flights and maybe
great deals from NYC. Good golf there, casinos, rain forests and
limited snorkeling. Be careful which resort you choose-saving
money in PR often results in remorse. IF you can find good
prices at the better resorts-go for it.
You should also consider the Riviera Maya south of Cancun.
I love the Oasis Akumal. It's low key, good food and snorkeling
there is wonderful. Again-no golf. Good prices though. Food
at some of the other larger all inclusives has been described
as uninventive in this area.
I was a
travel agent for 29 years and could go on. Take a look
at the charters from your area. This should save you money.
