HOMER, ALASKA
Alaska's confusing. It's either always daytime or always nighttime, and it's usually way too cold. When's the best time to visit? Good guess! With 18 hours of daylight, fewer cruise ships on the water, and no threat of icicles forming on your nose, September is a great month to visit Alaska and its funkiest, artsiest town. This is the itinerary: You'll wake up in the Surf Shack, a two-story, one-bedroom cabin you've rented from local surfer Don "The Iceman" Macnamara (yes, "local surfer"). You'll be buzzing on the sparkling-blue view of Kachemak Bay, but go ahead and gulp down a coffee—and a pecan sticky bun—from the Two Sisters Bakery before slipping into a kayak to explore the velvety fjords and glaciers. Then hop on a fishing charter: It's your last chance to enter the $150,000-prize Halibut Derby, which ends September 30. (Check out that sockeye salmon in the picture—you can still catch them, too.) No sense in rushing the day along, though: Sunset's not for a few more hours, which leaves you plenty of time to go looking for brown bears or bald eagles, both plentiful in the nearby national parks.

Surf Shack
Tel: 907 235 7873
$145 per night, two-night minimum

Homer Halibut Derby
Tel: 907 235 7740