Katie Boswell

Sarasota has more to offer than most expect. From the vibrant art and dining scene downtown to the relaxed charm of nearby Siesta Key, Lido Key, and Longboat Key—each with its own unique personality—it’s a destination that perfectly blends coastal ease with cultural appeal. Whether you’re drawn to sugar-soft beaches, clear Gulf waters, or the rich local arts, Sarasota has something for everyone. Not sure where to stay? Sarasota boasts excellent hotels downtown, while the surrounding islands offer beautiful multi-generational vacation homes—ideal for families. I can help you find the perfect fit for your needs. This four-day itinerary offers a taste of it all, giving you a feel for each area so we can tailor a trip that works best for you. For those wanting to dive deeper, I’ve also created detailed destination guides on each location. Though Sarasota wasn’t always home for me, it quickly became it. After chasing snow out west, my husband and I planned a month-long stay on Lido Key seeking sunshine and a break from the cold. What we found was something better: a pace of life that felt just right. Now living near Anna Maria Island with our two young kids—who’ve fully embraced the beach life—we spend weekends anchoring at sandbars and enjoying boat-up lunches on Longboat Key. What makes Sarasota truly special is its seamless blend of family-friendly ease and cultural richness. Whether you’re building sandcastles, exploring art museums, or watching the sun set over the Gulf, there’s a magic here that stays with you. The Gulf Coast isn’t just a destination for us—it’s a way of life—and I love helping other families experience that same easy magic.

Anna Maria Island is a relaxed, family-friendly destination on Florida’s Gulf Coast that offers the best of laid-back beach living. With its white-sand beaches, clear Gulf waters and low-key atmosphere, it’s ideal for travelers looking to slow down and enjoy quality time together.

The island is known for its local charm — think independent shops, great seafood restaurants and coastal-inspired art galleries, all without the chain restaurants or high-rises. It’s especially well-suited for multi-generational trips or group getaways, thanks to its spacious beach homes and easygoing pace.

Just a short drive across the bridge from my home, Anna Maria Island is a place I’m very familiar with — and I take great joy in helping families fall in love with it.

Often the idea of a trip to Miami comes with thoughts of sultry beaches and legendary nightlife, but this guide will highlight that Miami’s combination of natural beauty, rich culture, outdoor adventure, top-notch dining and year-round sunny weather makes it an exceptional destination for all types of travelers, especially families.

Longboat Key is a picturesque barrier island located on the Gulf Coast of Florida, west of Sarasota. It stretches for over 10 miles and offers serene, white sand beaches, upscale living and rich natural landscapes. The area has a relaxed, yet sophisticated vibe, offering a more refined and upscale experience. It is just minutes away from a thriving boutique style airport making it an easy destination from anywhere!