The Gasparilla Inn isn’t just another luxury hotel, it’s a family-run gem that’s been around since 1913, and it still holds onto that classic “Old Florida” vibe everyone loves. Readers raved about its pastel decor, the afternoon tea, and all the traditions that make the place feel like a step back in time, but with all the comfort and service you want in a modern getaway.

You’ll find The Gasparilla Inn tucked away on Boca Grande, a barrier island on Florida’s southwest coast. It’s a perfect spot for families, couples, or an unforgettable wedding weekend. 

The resort stretches across 180 acres and really pulls out all the stops: 163 rooms ranging from cozy guest rooms to sprawling villas and cottages, an 18-hole oceanside golf course, a full-service marina, a beach club, and even an award-winning spa. The whole vibe is pure nostalgia, a breath of fresh air if you’re tired of sleek, cookie-cutter hotels.

Travel + Leisure’s readers put The Gasparilla Inn at the top of their list this year, outshining big names like the Ritz-Carlton and Hyatt Regency Coconut Point Resort & Spa, which also made the Top 15. There’s something about Gasparilla that just stands out. Family-owned for generations, it hasn’t lost an ounce of its charm. If you’re looking for a place that feels both timeless and welcoming, this is it.

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Virgin’s signature twist doesn’t stop there. Passengers, or “Sailors,” as they call them, can also hop on luxury buses bound for Manasota Key. Think quiet beaches, fossilized shark teeth hidden in the sand, kayaking through wild coastal waterways, and seafood that actually comes from the Gulf. 

These aren’t your standard shore excursions. They’re curated with a sense of place, made for people who want to immerse themselves in Florida culture, not just snap a picture of it.

Tom McAlpin, Virgin Voyages’ CEO, put it plainly: “Our Sailors want something real. Boca Grande has a soul. It’s not another crowded port where you’re elbow-to-elbow with tourists. It’s authentic, it’s local, and it feels discovered.” 

He’s not wrong. There’s a deliberate strategy here, fewer crowds, richer experiences, and an actual connection to the places you visit. For Manasota Key, that means guided shelling walks, shark tooth hunts with local experts, eco-tours, and the kind of seafood that reminds you why you came to Florida in the first place.

Industry insiders see this as Virgin’s next big move, shifting away from the usual hurried, packed ports and toward something slower, more intentional. When asked about it, McAlpin didn’t mince words. “We’re not just checking off ports on a map. We’re giving Sailors stories to bring home. We want them to feel like they’ve been somewhere, not just passed through.”

For travelers, this means less time in crowds and more time soaking up what makes Florida special. For Boca Grande and Manasota Key, it’s a form of tourism that respects the pace and character of these towns, something leaders in the area have already said they appreciate.

Virgin Voyages’ Boca Grande debut marks a real shift. The cruise world is changing. Hidden gems matter more than ever, and the future belongs to the lines willing to look beyond the obvious. 

Virgin Voyages’ Boca Grande and Manasota Key sailings kick off January 2026, with The Scarlet Lady departing from Miami. For exact dates and details, check CruiseWise or Virgin’s website. 

This isn’t just a new route; it’s a new way to cruise. Virgin isn’t following the old map—they’re drawing their own.

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