This 3.8-square-mile island sandwiched between Michigan's Upper and Lower Peninsulas has been a popular Midwestern tourist attraction since the 19th century for two major reasons: 1) Its ban on almost all motor vehicles (that's right, no cars allowed!), and 2) Its world-famous fudge. Stop by the Victorian-age Grand Hotel for afternoon tea, and pick up some of that legendary fudge from Ryba's Fudge Shop, a Mackinac favorite.
1. Equipment silk mini dress, $268, Net-a-Porter.
2. The Row tortoiseshell aviators, $220, SSENSE.
3. Fendi flap shoulder bag, $1,956, Farfetch.
4. Veronique Branquinho fisherman sandals, $241, SSENSE.
5. Stones of Character macramé bracelet, $425, Farfetch.
This sleepy Florida city is one of the country's favorite beach locales. With equal access to both the Atlantic Ocean and the Gulf of Mexico, there's hundreds of miles of pristine salt water beaches. Peep a play or cabaret at the historic Red Barn Theatre, then get an unbeatable view of the entire island atop the Key West Lighthouse.
1. Theory peplum top, $195, Net-a-Porter.
2. Mulberry banana key fob, $120, Net-a-Porter.
3. A.P.C. braided leather wedge sandals, $215, SSENSE.
4. Karen Walker sunglasses, $236, ShopStyle.
5. Zimmermann triangle bikini, $230, Net-a-Porter.
6. Michael Kors printed shorts, $455, Farfetch.