With crowd-free beaches and clapboard buildings, it’s like Anna Maria Island, Florida, is timelessly rooted in a golden era of American travel. This barrier island off the state’s
Gulf Coast still holds on to that vintage Florida feel, making it the perfect romantic getaway for couples who favour an old-fashioned kind of love. Better yet, if you like laid-back nature walks, good seafood and spectacular sunsets, this one’s for you.
Ideal for combining with other destinations on a
Florida multi-centre holiday, here’s how you can experience all Anna Maria Island has to offer in 48 whirlwind hours…
DAY 1
Anna Maria Island might feel a world away, but it’s actually only 90 minutes’ drive from
Orlando and 45 minutes from
Tampa. So it’s easy to get to and from for a romantic weekend escape.
Stroll hand-in-hand down Pine Avenue
Spend your first morning getting to the heart of the island on Pine Avenue. This main street’s shoulder to shoulder with historic buildings. There’s not a high-rise in sight. You can walk past the former city jail, the General Store and the old bathhouse, which has now been transformed into the island’s famous Sandbar Restaurant. Don’t miss the Olive Oil Outpost, where you can fuel up for your day of sightseeing with some samples of lemon or jalapeno olive oil, pasta, cheese and olives. If you’d prefer to explore on two wheels, you can hire tandem bikes and peddle down Pine Avenue instead. The whole island is just 7 miles long and 1 mile wide, so sightseeing’s nice and sedate here – you can drive from one end to the other in under half an hour.
Hop from one picture-perfect beach to the next
Pine Avenue’s bookended by Anna Maria Beach on one side and the Anna Maria City Pier on the other. So, it’s always easy to fit in some time on the sands. Anna Maria’s the main stretch so there’s plenty going on. On Sunday mornings, you can sunbathe to the sounds of live jazz coming from The Gulf Drive Café. And, if you stroll away from the main drag, you might be able to catch glimpses of dolphins and stingrays in the crystal-clear shallows. Manatee Public Beach is another sandy stretch to check out. And the good thing about pretty much all the beaches on the island is that you never have to wander far for some alone time. Plus, you can really embrace the island vibes and order fresh coconut water to your towel, courtesy of local company, AM I COCONUTS?
See in the sunset… anywhere
Once you’re all beached out, it’s time to head to visit Anna Maria City Pier. This place is a popular fishing spot and it’s open 24 hours. Time your visit right and you might spot someone reeling in a big catch. And where there are fish, there are inevitably dolphins, herons and pelicans patrolling too. As the sun starts to set, it’s worth grabbing a spot at a waterfront bar or restaurant. The Sandbar’s a top-rated site, thanks to its back deck. Or, you can head to Bean Point, the island’s northernmost tip, for a more private sunset screening.
DAY 2
Rise and shine bright and early for another relaxing day on this idyllic isle. This time, wildlife encounters are on the agenda, before you sample some more of the island’s food and drink.
Get back in touch with nature
Since the island’s so untouched, it’s got wildlife around almost every bend. Spend your second day seeking out its marine visitors. Bottlenose dolphins splash around and feed in the shallows all year round, so you’re in with a good chance of spotting them on your rounds. Or, you can sign up for small group boat tours to watch them up close and personal. Loggerhead turtles lay their eggs on the island’s powdery sands from May to October. Bean Point’s a favourite spot, as it’s even more secluded than the rest. Plus, you can head out on mangrove tours, where you could end up kayaking alongside manatees. And, if you really want to up the romance factor, opt for a horseback ride along the beach. There are several tour companies that can organise this once-in-a-lifetime experience for you.
Feast on fresh seafood by the water
Farm to table and dock to table dining is all the rage on Anna Maria Island. In fact, the whole place is so committed to sustainability that it was the first in Florida to team up with the Leave No Trace organisation to protect their serene surroundings. And it’s no wonder with shorelines like these. Most of the restaurants are independently owned and family run so you can be sure of a warm welcome and many of them are along or near the waterfront. So, you can tuck into grouper tacos, oysters and homemade crab cakes to the sound of crashing waves. There’s a really relaxed vibe to dining here – the focus is on good food and company, not fancy décor. Toes in the sand dining is the order of the day.
Sip cocktails and dance to live music
You might think Anna Maria Island shuts down after sunset, yet you would be wrong. It might be unspoiled and charming, but the island still knows how to have some fun. It's not quite Miami, but there are plenty of bars to keep you busy after dark. You can order craft cocktails at The Doctor’s Office, alongside some tasty small plates. Or, head to The Ugly Grouper, where there’s live music every night of the week. The cocktail list is suitably tropical, including a rum punch served in a coconut. And, after you’ve slurped a cocktail or two, you can pose for photos by the giant grouper – made from old car and motorcycle parts – that gave the bar its name.
Fancy a romantic trip back in time? Check out our award-winning Anna Maria Island Holidays for 2024 & 2025.
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