16 Romantic Ideas for Couples on Anna Maria Island, Florida

Anna Maria Island – A Romantic Florida Getaway

Nestled along Florida’s Gulf Coast lies the hidden gem of Anna Maria Island, a charming beach town with breathtaking sunsets, beautiful white sand beaches, and old Florida charm. We’ve spent countless winters on this island paradise and seen it change over decades, but it remains a magical, romantic destination we’re thrilled to call a second home.

From its quaint cafes to stunning seascapes, Anna Maria Island casts a spell that keeps you coming back. Join us as we share the top romantic things to do, favorite local spots only the locals know, and the island’s best beaches – you’ll soon be planning your own couples’ getaway!

We first stumbled upon this laidback island over 20 years ago and have watched it rebuild post-hurricanes without losing its character. Between lazy beach days, waterfront dining, and watching the crimson sun dip below the horizon wrapped in each other’s arms, it quickly became our happy place. Now we even spend our summers soaking up the seaside serenity.

Let us show you why Anna Maria Island needs to be at the top of your Florida travel bucket list! Whether it’s your inaugural visit or your fiftieth, there are always more breathtaking views to admire, hidden coves to uncover, and new adventures waiting around the corner.

Top 10 Romantic Things To Do

• Visit Bean Point Beach ~ Take long walks on this secluded shore, away from crowds. The peaceful atmosphere makes it perfect for romance.
• Make Donuts at The Donut Experiment ~ Getting creative in the kitchen together while crafting unique donut combinations at this beloved local spot.
• Sunset Dinner at The Rod & Reel Pier ~ Savor fresh gulf seafood alongside panoramic sunset views on the pier at this landmark restaurant.
• Shop Artisan Boutiques on Pine Avenue ~ Wander through the island-style shops showcasing locally made art, jewelry, gifts, and more.
• Paddle Board & Kayak ~ Paddle along the island coastline and keep your eyes peeled for dolphins, manatees, and other wildlife.
• Stroll Bridge Street & Play Mini Golf ~ Meander through this vibrant street lined with eateries, boutiques, and an old-school mini golf course.
• Book a Private Fishing Charter ~ Cast lines into the gulf waters during an intimate sunset cruise for two.
• Take the Anna Maria Trolley ~ Leisurely tour across the island and check out the sights via this free transportation.
• Drinks & Live Music at Beach Bars ~ Sip cocktails on the sand while listening to local bands perform as the sun goes down.
• Beach Picnic Sunset ~ Spread out a blanket on the beach, share a bottle of wine, and cuddle up to watch dusk’s vibrant display.

Finding Paradise on the Gulf Coast

Nestled along Florida’s Gulf Coast shores, Anna Maria Island feels blissfully disconnected from the daily grind. Yet this hidden gem is conveniently situated just 50 miles south of Tampa and 20 miles north of Sarasota for easy access. Orlando is also only a leisurely 2.5 hour road trip away – perfect for a romantic weekend getaway.

Upon crossing the bridge to Anna Maria Island, you can instantly feel everyday stresses fading away. Palm trees beckon you down the roads less traveled to discover seven miles of pristine beaches, old Florida architecture, and a simplified way of living. But you may find the biggest thrill is turning off your phone and truly disconnecting from the rest of the world with your special someone.

The island’s remote location lends itself perfectly to cozying up while watching a blazing sunset. When it seems like time stands still, you’ll have found paradise.

Your Tropical Escape Awaits

Two convenient airports provide easy access to Anna Maria Island. Tampa International Airport (60 miles away) offers lots of nonstop flights, while the smaller Sarasota-Bradenton International is under 20 miles away on the mainland. Flights to either, plus a quick and scenic drive or shuttle service, deliver you to island bliss in no time. You can also embark on a romantic weekend road trip from Orlando, just 2.5 hours inland.

Once on Anna Maria Island, the daily grind fades away. Trade crowded highways for flip-flop-friendly trolleys that meander around this seven-mile stretch of sand. Here life moves at an unhurried pace in harmony with the lapping waves. Signs welcoming bare feet and ice cream cones epitomize the island ethos.

Anna Maria woos visitors with its white quartz beaches, bathtub-warm emerald waters, and Technicolor sunsets that steal your breath. Sprinkle in friendly locals, fresh-caught seafood, and peaceful open-air eateries, and you have an AAA-rated tropical vacation without a passport required.

Cross the Drawbridge to Paradise

Crossing the bridge onto Anna Maria Island instantly transports you to a more tranquil way of living. Gaze across the expanse of shimmering water flanking both sides before old Florida charm comes into view. Feel your breathing naturally slow and muscles unwind as your cares float away. You have arrived at your home away from home.

Things to do on Anna Maria Island, FL

Anna Maria Island may seem small, being only seven miles long. Yet, there is a lot of charm within those seven miles. You will not lack for things to do while visiting Anna Maria Island, Florida.

1. Find the Heart of the Island

You’ll want to go on a scavenger hunt along Anna Maria Island coasts and bridges to look for the heart of the island. As far as anyone knows, this heart formed naturally by way of water, eroding it over the years.

Most locals know its location, but if you ask anyone, they will politely tell you the thrill is in the hunt, and you are on your own. It’s not that difficult to find, but I do have to agree there is an excitement in getting to know the island while searching for its heart.

2. Anna Maria Island Historical Museum – Photo Op At The Old City Jail

The city jail was built in 1927 to “quarter the rowdies” who had drank too much at the local bar and dance hall. The jail was used until 1940 when it caught on fire. The wooden roof burnt away, but the exterior walls remained.

The city decided to use the jail as a photo op for visitors, so it was left standing and painted with the current slogan. The jail is the most photographed attraction on the island.

3. Go Beachcombing

Once you get to Anna Maria Island, one of the favorite things of young and old is to kick off your shoes and feel the sand between your toes. Wander the beach and do a little beachcombing. Sea Shells are a favorite souvenir for many. I know they are for us. Keep your eyes open. You never know what treasures may wash ashore.

When beachcombing for shells, make sure the shells are not alive if removing them from the water.

4. Go Fishing

If you enjoy fishing, you may want to pack your fishing gear to try your hand at the catch of the day. Anna Maria Island has various fishing spots that are enjoyed by locals and vacationers. You can also fish from the beach or the jetty or book an offshore charter through AMI Fishing Charter.

If you want to save space and not pack your fishing pole, you will find many rental places near the piers to rent poles and buy bait.

5. Be on the Lookout for Local Marine Life

The waters around Anna Maria Island are home to some fascinating marine life. When visiting the beaches or one of the local piers, look for dolphins, schools of rays, and manatees, all of which call this area home.

We have enjoyed catching sight of playful dolphins willing to put on a show for us. AMI City Pier is a spot where we have caught sight of hundreds of rays traveling under the pier. It was a sight to behold.

Keep in mind marine life should be enjoyed from a distance, and you should not interact with them in the wild.

6. Check out a Local Pier

Visit one of Anna Maria Islands Piers

• Anna Maria Island City Pier
• Bradenton Historic Bridge Street Pier
• Rod and Reel Pier

Anna Maria City Pier

In 1911, Anna Maria City Pier was built to make Anna Maria Island into Florida’s greatest resort city. At the time, the city pier was known as Anna Maria City Dock.

The dock was built 776 feet out into the water to allow steamboats to dock, bringing vacationers and potential buyers to Anna Maria Island. With the addition of the dock, visitors flocked to Anna Maria Island.

The city pier was one of the first places we set out to enjoy. The pier is located on the island’s north point.

In 2017 my daughter and I took a summer girl’s trip. One of our top places to hang out was the City Pier. At that time, there was an amazing restaurant on the pier that we loved visiting. The pier was a place where locals relaxed, fished, and shared friendly conversation.

I wanted so much to share the experience of The City Pier with Gary, but when we got there, it was gone. I was so disappointed to discover that Hurricane Irma had destroyed The Anna Maria City Pier.

Slight damage has been done to Anna Maria Island Pier by minor storms and smaller hurricanes throughout the years, but nothing as extensive as Hurricane Irma. Each time, the pier has been repaired and reopened. This time, the only choice is to rebuild and then reopen.

Fast forward to 2024; on our recent visit, the Pier has been rebuilt. The City Pier Grill and Bait restaurant is open and ready to serve you dockside while you enjoy a day fishing from the pier.

Locals are back to fishing, just like the good old days. Fun and conversation flow freely among the locals and visitors. It was beautiful to see Anna Maria Island getting back to its former glory.

Historic Bridge Street Pier

Explore the island’s clock tower and the Historic Bridge Pier, complete with a fishing pier that offers stunning views of the harbor and bayside.

The Historic Bridge Street Pier boasts an array of attractions, including Floridian-style restaurants, beachside boutiques, and town events. Whether you’re looking to enjoy happy hour or have dinner, there are numerous fantastic restaurant options to choose from.

One of our favorite restaurants, The Anna Maria Oyster Bar, is located on the pier. We have enjoyed some of the best fish and chips at the Oyster Bar.

With the nostalgic charm of Old Florida in the air, this is an ideal location to wrap up a delightful day at the beach. The best part is that you can hop on the trolley for a convenient trip to and from Bridge Street!

Rod and Reel Pier

This is one of our favorite areas on Anna Maria Island, you can enjoy The Rod and Reel is the perfect place to experience the taste of Old Florida. The water by the pier is so clear that you can see the marine life that calls the area home. Manatees have been known to like to hang around the area, as well as dolphins and rays.

This is also where you can hang with the locals who like to sit a spell and cast a line.

7. Enjoy Time on the Water

Water activities are plentiful on Anna Maria Island; you can rent a kayak or paddleboard for extra fun. How fun would it be to paddleboard alongside a dolphin or manatee? (Remember, no interacting with them; enjoy them in their habitat)

Happy Paddler has a variety of Kayak and Paddleboard tours available. Explore the waters around Anna Maria Island with a certified instructor through the mangroves, along the coast, or even during sunset.

Parasailing is another fun way to enjoy the waters, or should I say fly above the water. This is more than just a quick ride being pulled by a boat. This is your opportunity to see the entire coastline from above while you feel the breeze against your skin and taste the salt from the gulf.

If you love the water and are not afraid of heights, this activity should be on your bucket list.

8. Relax on Anna Maria Island Beaches

The beaches on Anna Maria Island are breathtaking. The island is home to several beaches with two things in common: white sand and emerald-blue water. Yet each of the beaches has its own characteristics and is very different depending on where they are located on this small island.

The following beaches are some of our favorites and ones that we love visiting repeatedly. Who am I trying to kid? They are all my favorites.

Cortez Beach has a southern beach feel. You cross small wooden footbridges to get from the parking to the beach. The breathtaking Cortez Beach is hidden by tall grass. Keep your eyes open. This is an excellent beach for finding shells.

Coquina Beach is the ideal beach for strolling. You’ll enjoy discovering local shells, including the tiger’s paw and tiny coquinas, which look like little butterflies on the beach. Keep your eyes peeled. You may even find a shark’s tooth, sandstone, or a starfish.

Bradenton Beach is the center of all the action. After crossing the bridge, you enter Bradenton Beach. You will find plenty of unique shopping opportunities, bars, and restaurants within this general area.

Holmes Beach has clean sand and tons of shells. The water is always gorgeous here. Holmes Beach is highly accessible, quiet, low-key, and peaceful. This beach has an outside shower to get the sand off your feet before getting back on the trolley.

Anna Maria Beach is great. The water is calm and clear—an excellent beach for watching the sunset. Not many shells, but the sand is beautiful, and there is plenty of potential for a sandcastle.

Bean Point was named after the original settler, George Bean. It is where Tampa Bay meets the Gulf of Mexico. It’s one of the most beautiful beaches you will ever step foot on. The sand is super soft white, and the emerald blue water is filled with schools of fish and manatees almost within touching distance. It is advised that you NOT SWIM here because of the riptide.

It does not matter what time of year it is; don’t hesitate to dip your feet in the Gulf of Mexico. Warm or cool, the water is always welcoming.

9. Sea-renity Beach Spa & Bou-tiki

Try the islands only spa with the option of massage on the beach in a private tiki hut. This one-of-a-kind experience is anything but ordinary and takes place in a very serene environment. Best of all is that couples massages are available.

Sea-renity Beach Spa is conveniently located on Bridge Street in Bradenton Beach, with the beach on one end of the street and the bay on the other.

For ease, you can take the island trolly right to Bridge Street

10. Go Sightseeing

There are times when we love to drive around and go sightseeing. Whether it’s by car, bike, or golf cart, there are so many things to see on the island, and driving around is the best way to see what you may be missing.

We love to stop anywhere that looks fun. And have been known to find some exciting selfie spots.

11. Go Bike Riding

Can you think of anything more romantic than riding around an island on bicycles? Renting a bike is a fun way to get a different view of the island. We love to make it a day of adventure; we grab our sunscreen, sunglasses, and water bottle and set off for a day of exploring.

If you are staying on Anna Maria Island, bicycles are a great way to get around without having to worry about finding a parking spot. There are several places to find rentals.

• Beach Bums rents bicycles, golf carts, and beach supplies.
• Fun and More Rentals rents bicycles, kayaks, paddle boards, fishing gear and beach supplies
• Anna Maria Island Beach Fun Rentals rents bicycles, golf carts, kayaks, scooters, and beach supplies.

12. Do Some Shopping at Bradenton Beach

If you need a little break from the beach activities, there is a charming main street with restaurants and small shops. You will find everything from t-shirts, swimwear, one-of-a-kind jewelry, souvenirs, and quaint beachy home decor.

This charming area is alive from morning to evening. You will find the best shopping on the island and a good cup of coffee or an evening nightcap at one of the local bars.

13. Take a Tour

Make the most of your vacation with a relaxing local tour or excursion in hopes of spotting dolphins and manatees.

Several local tours from Anna Maria Island will take you out on the water.

Island Boat Tours and Adventures offers snorkeling tours, private boat tours and sunset boat tours Anna Maria Island Dolphin Tours offers sunset cruises and dolphin cruises.

14. Enjoy Some of the Island’s Non-water Activities

If you want to get away from the water, try golfing at Timber Creek, mini golfing at The Fishing Hole, visiting a local orange orchard or the local bird sanctuary.

Let’s not forget the Coquina Baywalk, which winds through inviting wildlife areas. The Baywalk is located directly across from Coquina Beach. Grab your camera; this is an ideal way to get up close to Florida’s wildlife and native plants. The boardwalk trail offers breathtaking views of the bay.

Pay a visit to Motes Marine Aquarium. This is a great way to meet some of the area’s wildlife. You’ll meet sea turtles, manatees, sharks, jellyfish, and other marine wildlife. You’ll also get to explore hands-on activities and displays at Motes.

15. Enjoy an Island Sunset

Last but not least, the highlight of any day spent on Anna Maria Island has to be the sunset. Each sunset is more breathtaking than the next, and each sunset is unique. Picture sitting on the beach, holding hands as the sun slowly sets. Little by little, it is as if the sun slowly falls into the ocean.

Many evenings, while we have been watching the sunset, playful dolphins are enjoying the sunset off in the distance.

Ask any of the locals; the best way to end every day is to pull up the beach and watch as the day comes to an end.