re: USVI or Maui for 9 days?

I'd say Maui based on it being nearly prime hurricane season

It's true that Painkillers are sold everywhere down there but I wouldn't call it the official drink of the USVI particularly when the drink originated in the BVI. Every bar down there seems to have a drink that they call their own.

Speaking of drinks.

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A hurricane passes near the U.S. Virgin Islands, on average, every three years. A hurricane makes a direct hit on the islands, on average, every eight years.

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It's a risk but it wouldn't affect my choice.

I just got back from Maui. I had the same decision (USVI or Hawaii), but my wife was pregnant. So, we decided to avoid zika and went to Maui.

We stayed at the Hotel Wailea. LINK
It's adults only, and I would highly recommend it over the mega resorts.

We stayed for a week.
We took the trip to Hana.
Saw the sunrise on the top of Haleakala (2nd tallest mountain in the world from base to peak.... b/c it goes all the way to the bottom of the ocean).
We drove over to Lahaina and Kapalua for the day, shopped, and went to a Luau.
Went humpback whale sight seeing tour.
Snorkeled one day.

Cool thing about it is that you can see 12 of the 13 climates on earth on the island and tons of stuff to do.
I'm really glad that I went.

It's only an hour drive from kapalua to wailea. So, I wouldn't waste the time packing up and changing hotels. The beaches are about the same, and you'll be spending most of your time out doing things anyway.

Love both options but they're very different. Based on what you've said, I'd go Wailea the whole time. I've been to Maui about a dozen times, so it's one of my favorite escapes.

You can snorkel, hike, downhill bike ride, etc. the wailea area has great resorts all linked by a shoreline path. I've stayed at the Fairmont, Four Seasons and Grand Wailea as well as a couple of condos. Each are great for their own reasons.

You've got endless possibilities on Maui for activities, food, drunk, downtime, crowds/seclusion, etc.

Maui downsides are travel time, water temp (if you are sensitive to that) and perhaps price.

You can go half-way up the volcano and there are several towns with temperate conditions where they have a lavender farm, winery, etc.

You can head to Hana, hike ravines, waterfalls, stay overnight in lush surroundings, horseback ride and such.

St. John can be very chill, and as noted it's way off season due to hurricane season, so could be cheaper but may not have everything open.

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Assume you are using Marriott points. If not, take a look at the Grand Wailea.

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Correct! Saving HH points for a trip next year.

Thanks for the suggestions everyone. I'm going with Maui for now. But I can't wait to visit the USVI at some point down the road.

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Yes, Im leaning towards all 7 nights at the Wailea Marriot Resort myself.

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That's nice too, but I meant Hotel Wailea R&C on the other side of Wailea Alanui Drive. All private rooms. No kids.
It has a beach deal with the 4 Seasons to use their beach.

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Fairmont, Four Seasons and Grand Wailea

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We went eat one night at all of the big spots in Wailea. We also ate at the Andaz. So, I got to see pretty much what they all have to offer.

I didn't find one to be overwhelmingly better than the others. They all had their own feel.
Andaz was more for the younger crowd.

Four Seasons and Grand Wailea were Mega resorts for families, and there were kids all over the place.
Fairmont was really nice too, and probably was the best value.

You'll have a great time.

Not quite going to Oahu so no pearl harbor. I didn't want to waste time flying between islands. I feel like to really enjoy Hawaii you need to chill and stop and smell the roses. I don't mean the kind of chill where you hang out at the beach all week. But instead, hike, catch some sunsets/sunrises, cruise around, without being in a hurry.