Three Perfect Days on Longboat Key

Despite close proximity to nearby beach vacation hotspots like Siesta Key and Anna Maria Island, Longboat Key has a distinct island vibe of its own. The pace is a bit slower, the people linger longer, and the food is spectacular on this 11-mile slice of paradise.

STAY

Longboat Key is wildly popular with long-term vacationers (especially in the winter months), but nightly rentals are yours to discover with a bit of online sleuthing. The northern and middle portions of the island are your best bet, with a handful of beachfront resorts and inviting rentals.

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Opt for the contemporary Zota Beach Resort for beachfront amenities and stylish accommodations. The property boasts a central location, restaurant and wine bar, infinity pool, pool bar, beach access and more.

The Diplomat Beach Resort—planted firmly in the middle of the island—combines the comforts of home with beachfront amenities. Full kitchens, tiki huts, a swimming pool, and ocean views are all part of the package. It doesn’t get much better than opening your door and walking right out onto the beach. Rentals begin at $169/night, and most units have a 2-night stay minimum.

For longer stays, check out the available VRBO options.

PLAY

The white sand beaches, clear gulf waters, and seashells galore are mesmerizing enough to keep your bum in your beach chair all day. Part of the allure of Longboat Key is that it’s mainly residential, lending to secluded beaches. Still, look closely and you’ll find 12 public beach access points along Gulf of Mexico Dr. Whatever you do, make time to soak up at least one sunset – they’re notoriously beautiful here!

Speaking of the beach, Beer Can Island is worth a visit for an afternoon, and getting there is part of the adventure. Walk along the beach, weave your way through the narrow mangrove path, and emerge to your almost private hideaway. Admire the driftwood dotting the shore, lay claim to a private enclave and pack a picnic lunch to enjoy. Hurricane Irma altered the landscape, but this spot still retains its off the beaten path charm and remains popular with adventurous beachgoers and boaters.

Take a break from the sun with a visit to Mote Aquarium, a marine research facility and aquarium on Lido Key. Mote works to rescue and rehabilitate, while also caring for the sea turtles, seahorses, fish, sharks, manatees, otters, and more that call the aquarium home.

St Armand’s Circle, also on Lido Key, is a hub for shopping, dining, and drinking complete with boutiques, shops, and modern eateries. Across the bridge, Marie Selby Botanical Gardens offers a tranquil respite from the hustle and bustle of St. Armand’s. Wander the immaculately kept botanical garden, formerly the humble home of William and Marie Selby, which Marie donated to the community after her death.

Outdoor activities are also a must on Longboat Key. The island is incredibly bike-friendly, so bring your own or rent wheels to explore. Or, hit the water with a kayak rental from Happy Paddler. From here, you can paddle to Jewfish Key near Longboat Pass, check out Beer Can Island and cruise out into the Gulf.

DINE

Many of the restaurants on Longboat Key are hidden in residential areas, so you’ll feel like a local in the know no matter where you dine.

Dinner ambiance reaches new heights at Mar Vista, where twinkling lights strung between trees set the mood for a romantic dining experience by the water. It’s worth waiting a bit longer for a table under the trees, facing the calm bay waters. The menu features a variety of surf & turf fare, but the poke bowl and Caribbean grouper (a dish I’ve tried unsuccessfully to make at home many times since) are personal favorites.

Dry Dock Waterfront Grill is a Longboat Key hidden gem in the truest sense, tucked alongside a small marina. After navigating the parking lot and riding an elevator to the hostess and bar area (appointed with nautical décor), you’ll be rewarded with fantastic food and an outdoor dockside-dining atmosphere. Any menu choice is a good choice, but the lobster rolls are in a league of their own. Two crispy, buttery rolls stuffed with lobster and served with a side of fries? This is the stuff of foodie dreams.

Every vacation needs at least one fancy night out, and the newly opened Shore definitely fits the bill. This hip eatery features fresh dishes and craft cocktails in luxurious waterfront digs. I can personally vouch for the shrimp ceviche, beet salad, miso marinated black grouper and Ruby Red cocktail. After dinner, head outside to stroll along the pier and breathe in the salty air.

More fun options:

• Grab brunch or dinner from Whitney’s
• Enjoy a waterfront burger and fries at New Pass Grill
• Hit up the popular happy hour at Chart House (daily from 4-6:30pm–go early!)
• Treat yourself to Italian and seafood dishes at Speaks Clam Bar (St. Armands)

KNOW BEFORE YOU GO

From Tampa, plan for a 1 hour 15 minute drive.

High season is January-March, meaning traffic headaches and higher rental prices. You’re better off visiting April-May or September-October when prices are lower and the weather is beautiful.

The public beach areas on Longboat Key don’t have restrooms or facilities, so keep that in mind. You can find more information on public beach access at longboat-key.net.

To get to Beer Can Island: park in the public parking area at the end of N. Shore Rd. Enter the beach through the public access point, turn right, walk past the pier, and walk into the mangrove path. Keep walking until the path clears and you’re able to see the bridge to Anna Maria Island.

If you visit St. Armand’s, park on Arthur Dr. or another side street a short walk away instead of hassling with parking in the actual circle, which can be challenging.

This article originally appeared on our sister site, Orlando Date Night Guide.

All images by Stephanie Patterson unless otherwise noted