Why You'll Love It: Though it's on Lake Michigan, this town has been nicknamed the "Malibu of the Midwest." Master surfers catch waves at Deland Park and kite boarders get aerial at King Park. You can learn stand-up paddle boarding basics at demos during June's SUP 'n' Surf Championships, and watch the largest gathering of freshwater surfers in the world at the Dairyland Classic on Labor Day weekend. Sailing is big here too: Sheboygan Youth Sailing Club has affordable lessons for kids as young as 8.
Where to Stay: The Blue Harbor Resort & Spa is lakefront on a calmer section of the beach, perfect for swimming or windsurfing lessons. Enjoy fish fries and beach bonfires, before settling into your family suite or multi-bedroom villa. What if the weather turns stormy? No worries! The onsite indoor Breaker Bay water park will keep kids entertained for hours.