We used to haul our snorkieling/diving gear - at least mask, fins and dive knives - over to Paradise - but haven't done so since the baggage fees zoomed.

Also - the Snorkel Bob's of this world rent pretty good gear now - and by the week prices are reasonable - and you can take it with you from island to island. http://www.snorkelbob.com/

As for winter snorkeling - you take your chances - and hope you get some calm days amongst the bigger surf days.

The old lesson still applies - go early for the calmest conditions, best vis.

Oceans are calmer south in winter. I'd skip Kapalua and Napili on Maui then. Hana may have rain.

The beaches around Wailea and Makena have been lovely for snoekeling when we've been there in February the last several years. We stay in Makena and can walk to Malauka Beach where there is often great snorkeling and turtles. We bring our own gear.

I'd bring your snorkel set, as even Snorkel Bob wants $30/wk for a good set. They do have a cheapie one for around $10, and an intermediate one for under $20

Unlike Chisue, I wouldnt avoid Kapalua, Napili and Honolua in the winter. In all my years, I might have had one or two days that swells made snorkeling poor. However in the South, a good wind chop can do that too

The calmest conditions are in the mornings. I tale my mask and snorkel and rent the fins.

I pack my mask and snorkel--should have previewed.

On 2nd thought - I usually do take my mask but not the fins as they weigh too much/take up too much space. It's all a tradeoff - considering the new baggage fees.