Longboat Key and Anna Maria Island are two of the most popular vacation destinations in Coastal Florida – and for good reason! Both islands offer beautiful white sand beaches, clear blue waters, and plenty of activities to keep visitors entertained – so which island is right for you?
In this guide, we'll get into the details of what each island offers and discover the distinct qualities that make each island a fantastic destination.
From laid-back relaxation on Longboat Key to the bustling energy on Anna Maria Island, you are sure to find your perfect island escape with one of our vacation rental properties.
Sugar White Sand Beaches
The postcard worthy beaches on Longboat Key and Anna Maria Island have shown up on "Best Beaches" lists for the Sunshine State repeatedly over the years. Both barrier islands share a coastline with soft white sand and stunning turquoise waters, although they each have their own flavor and charm.
Longboat Key
Photo Credit: Andrew Kalat via Flickr CC2.0
Longboat Key has an 11-mile stretch of white, powder-soft sand. There are public beach access points along the length of the island, but due to sparse parking at these access points, the beach remains relatively uncrowded.
The water is crystal clear and tends to be calm, making it a great family-friendly choice. The beach on Longboat Key feels laid-back and private, with plenty of space to spread out and relax. And since Longboat Key is a narrow island, you are never far from the beach.
Anna Maria Island
Photo Credit: Manatee County Government via Flickr CC2.0
Anna Maria Island has beautiful beaches hugging the 7-mile island, with plenty of parking and beach access points. The sand is sugary white and slightly more coarse, with lots of seashells to be found.
Manatee Beach draws larger crowds in large part to amenities like volleyball courts, playgrounds, and other recreational facilities. If you like action, this is the beach for you!
There are quieter moments to be found at Coquina Beach on the south end and Bean Point Beach on the northern tip, where legendary sunsets can be enjoyed. Overall, the beaches on Anna Maria Island have a lively atmosphere, with distinct personalities from north to south.
Winner: Although you will certainly have a great beach day on either island, Longboat Key holds a slight edge with super soft sand and a relaxed, private vibe.
Outdoor Activities and Watersports
Longboat Key
Photo Credit: SURFit
Water sports like kayaking and paddleboarding are popular on Longboat Key, with a lot to explore on the island's Gulf and Bay sides.
On land, visitors love to bike the trails running along the island and stop at Joan Durante Park, where a peaceful trail winds through restored wetlands. The Ted Sperling Park Nature Trail offers a retreat into the mangroves, where you can have a quiet moment surrounded by the natural beauty of coastal Florida.
Above all, the beach is the star attraction on Longboat Key, with miles of powdery sand and picture-perfect water.
Anna Maria Island
Photo Credit: SR Productions
Anna Maria Island offers a similar variety of water sports, with sailing, parasailing, and jet ski tours launching from various points on the island. It is also close to several nature preserves which showcase the local marshland environment.
Perico Island Beach Preserve, Neal Preserve, and Robinson Preserve are accessible off Manatee Avenue between Bradenton and Anna Maria Island, and Leffis Key Preserve is located at the south end of the island.
These nature areas offer a variety of trails and boardwalks that provide a break from the beach crowds, along with a couple of observation towers where you can get a bird's eye view. Kayaking through miles of paddling trails in these reserves gets you an up close look at the coastal environment and abundant wildlife, including dolphins, turtles, and migratory birds.
Winner: The variety of outdoor activities and access to nature preserves on Anna Maria Island's doorstep put it on top.
Things to Do
Beyond the beach and nature preserves, what else can you get up to on these islands?
Longboat Key
Photo Credit: Mikael Damkier
Longboat Key offers a variety of activities to keep visitors entertained. The championship golf course at Longboat Key Club beckons you to tee off on lush, manicured greens surrounded by breathtaking views.
The Sarasota Bay Explorer takes visitors on a variety of eco-tours in Sarasota Bay to learn about the local ecosystem and encounter wildlife like bottlenose dolphins and manatees.
You can get even closer to marine wildlife at Mote Marine Laboratory & Aquarium, which features animals from seahorses to sharks. Longboat Key also offers excellent fishing opportunities, whether you prefer casting from the shore or joining a fishing charter for a deep-sea adventure.
Anna Maria Island
Anna Maria Island is heaven if you enjoy a more eclectic atmosphere. The vibrant energy around Pine Avenue and Bridge Street is contagious, with quirky boutiques, art galleries, and live music around every corner.
There are also several historical sites to visit, including the old city jail at Anna Maria Island Historical Park and the nearby De Soto National Memorial.
You have your pick of ways to explore the waters surrounding the island, with dolphin and snorkeling tours, tiki cruises, and fishing charters leaving from Anna Maria and Holmes Beach throughout the day. Local guides lead explorations of the island by bike and segway, and the two city piers offer a great place to cast a line or take in beautiful views.
Winner: Both islands offer enough activities and tours to keep you busy for days, but with a greater variety of things to do, Anna Maria Island comes out slightly ahead.
Restaurants
Longboat Key
The food scene on Longboat Key leans toward the upscale dining experience, yet it still offers a variety of restaurants to choose from.
Elegant dining options abound, from American fare at the quaint Harry's Continental Kitchen to the global cuisine served at the intimate Euphemia Haye, while upscale casual dining focused on local seafood can be found at Mar Vista and Lazy Lobster.
There are a range of options for a quick bite. You can hit up the outdoor patio with live entertainment at Whitney's or grab a slice at Solorzanos Pizzeria. There is also a Publix grocery store on the island and other supermarkets in nearby Sarasota, so you can easily stock up on food and drinks for your stay.
Anna Maria Island
The laid-back atmosphere of Anna Maria Island spills over to the local restaurants. There are a few fine dining options here, but you'll find more beachside restaurants where you can dine with your toes in the sand.
Find your beachfront bliss at Sandbar or Beach House, where Gulf breezes and ocean views are the perfect backdrop for delicious seafood dishes, or stop in for beachside cocktails and tiki vibes at Gulf Drive Café.
Along Bridge Street, you'll find cozy eateries like the rooftop Daiquiri Deck, while Pine Avenue offers cute cafés and ice cream shops to satisfy your sweet tooth. The island is also home to several farmers markets, where fresh produce, seafood, and local artwork or crafts are found.
Winner: Although Longboat Key offers excellent fine dining, Anna Maria Island wins this one with lots of dining options and beachside restaurants to choose from.
Shopping
Longboat Key
Photo Credit: Yendy Ponce
Longboat Key has a few shops scattered throughout the island, but the closest shopping center is St. Armands Circle Shopping District in nearby Lido Key.
This upscale outdoor shopping center is filled with a mix of high-end designer stores and charming local boutiques, as well as restaurants, day spas, and art galleries. The center plaza has a wonderful park-like ambiance and sidewalk cafés provide a place to stop and enjoy the atmosphere. For any other shopping needs, Sarasota is only a 15-minute drive away.
Anna Maria Island
Photo Credit: Mia Voss
Anna Maria Island has two shopping districts to explore, where you can find unique local art and souvenirs. Pine Avenue in Anna Maria is home to quirky shops and several art galleries showcasing local artists.
At the same time, Bridge Street in Bradenton Beach features gift shops among a row of restaurants. If you can't find what you're looking for on Anna Maria Island, a short drive over the causeway to Bradenton will bring you to retail chains and an outlet mall.
Winner: Anna Maria Island wins with a great balance between unique local shops and access to larger stores in nearby Bradenton.
Where to Stay in Longboat Key or Anna Maria Island
So, which island should you choose? It ultimately depends on what you're looking for. If you dream of a relaxing and luxurious vacation where your biggest worry is finding the perfect spot on the beach, Longboat Key is a great option.
If you're an explorer-style traveler who likes a variety of options, then Anna Maria Island offers plenty of things to discover.
Of course, since these islands are so close together, you can easily day trip between them! Both offer a free trolley, making it easy to experience the best of both worlds!
Whether you want to spend your time basking in the upscale, relaxed ambiance of Longboat Key or immerse yourself in the "Old Florida" vibes on Anna Maria Island, you are sure to have a memorable vacation on this magical slice of Florida Gulf Coast.
Book your stay on Longboat Key or Anna Maria Island today!
