Kailua-Kona in $320s-$390s RT

Kailua-Kona is kinda like the Hawaii of Hawaii, you know?

The beaches are beachier, the snorkeling is snorklier, and there's enough great coffee to keep you going all day long. It's no wonder this spot used to be a favorite retreat for the Hawaiian kings of old!

As an added bonus, you're getting dates during the fall shoulder season, so the weather is nice and warm and the crowds are thinner.

And if you find yourself getting bored, you've still got the whole Big Island to explore :-)

P.S. Hawaii is a beautiful place to visit, but overtourism can be a burden on the people who live there. Check out the Sustainable Tourism Association of Hawai'i site for some tips on minimizing your footprint.