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How to Plan an Anna Maria Island to Orlando Twin-Centre Holiday

  • By Tammy van der Westhuizen
  • Published 09 September 2022
  • Revised 27 September 2022
How to Plan an Anna Maria Island to Orlando Twin-Centre Holiday
  • By Tammy van der Westhuizen
  • Published 09 September 2022
  • Revised 27 September 2022
How to Plan an Anna Maria Island to Orlando Twin-Centre Holiday
  • By Tammy van der Westhuizen
  • Published 09 September 2022
  • Revised 27 September 2022
A twin-centre holiday to Anna Maria Island and Orlando is the perfect way to combine a lazy beach break with an action-packed family holiday. Spend the first part of your trip relaxing on the stunning shores of Anna Maria Island before heading to Orlando for days filled with fun and laughter at Walt Disney World, Universal Orlando Resort, SeaWorld and beyond.

We can even give you the keys to Florida on a Fly Drive Holiday. This package provides competitively priced and comprehensively covered rental cars that turn your Anna Maria Island to Orlando journey into a road trip - only a left or right turn away from a new adventure every day. Now hold onto your hats, as we guide you on where to go, what to do, and give more reasons why this twin-centre trip has it all... 

Where Is Anna Maria Island?

Perched along Florida's Gulf Coast, south of Tampa and northwest Sarasota, is the Sunshine State's best-kept secret. Turquoise shores ring Anna Maria Island, a barrier land between the Gulf of Mexico and Manatee County's seaboard in Central Florida. The perfect spot to renew your spent energy, unwind on the breezy strip of 7-mile white sand beaches. 

Why Should I Visit Anna Maria Island?

Dreamy landscapes of sugar sandy bays, pure blue waters, and tropical palm trees create an idyllic setting. Slow island living enhances Anna Maria Island's tranquil atmosphere. With a speed limit of 35 mph, no one is rushing in this peaceful paradise. 

Likened to a 1950's beach town, strict regulations govern the island's ice-cream-coloured buildings, giving it a nostalgic charm. Even the wooden pier is 1911 original, well-preserved and maintained to extend the old-time feel of Anna Maria Island.

You'd be hard-pressed to find a more picturesque sunset than on this Gulf Coast isle. The island's pastel shades create a harmonious sight against dusk's soft glow. The evening's calm water reflects twilight's delicate skies on its still surface, a photo-worthy spectacle.

When Should I Visit Anna Maria Island?

Anytime is a good time to visit Anna Maria Island. With year-round sunshine on this cosy island retreat, any month of the year is a winner. But, if you want to enjoy the mildest weather of warm winter days and clear blue skies, plan your journey for January to March. This time also coincides with its quieter period. Although, December is a peak month where cold climate tourists escape winter's frostiness with a balmy island Christmas. 

Sun-worshippers cannot beat summer's sizzling rays on Anna Maria Island. With temperatures well into 30°C, the days are hot, and the sparkling beaches are the rage. Grab the surfboard, lather the sun lotion, and glide on summertime's large swells. Another summer highlight is a balmy evening beach stroll baring your bronzed sun-kissed limbs. The summer months are the rainiest, but who doesn't love swimming in the rain? You can avoid a quick rain shower with a treat from Anna Maria Island's heavenly bakeries or wander in the art gallery.

With a drop in temperature and, more importantly, price, autumn attracts fewer visitors. Enjoy 25°C+ days searching for the perfect beach spot along the secluded 7-mile sandy bay. While September carries summer rains, October and November are considerably dry, so you can ditch the umbrella.

Finally, spring's shoulder month is another pleasant time to visit. Like autumn, the prices are comparably lower, and the climate is tropical by day and cool by night. As spring progresses into summer, more visitors arrive, but Anna Maria Island's beaches are still uncrowded compared to Florida's other seaside hotspots.

What are Anna Maria Island's Best Attractions?

While this dreamy islet is small, there is surprisingly a lot to see. Its tiny size means that you can accomplish viewing the island's top attractions during your holiday. As an unspoken rule, starting in the island's north is generally recommended, then make your way south towards its more remote and serene escapes.

Anna Maria Village

The sleepy beach town of Anna Maria Village infuses a laid-back ambience. Its total population of 1,800 residents perfected slow-island living, which spills onto visitors needing a well-deserved break. 

To witness the island's relaxed charm, head to Pine Avenue, the heart of this mellow village. Time moves slowly on this lush scenic road, as urgency is unheard of in this snail-paced utopia. The pastel wooden structures add to the village's charm, preserved to retain the island's nostalgic aesthetic.

Wander towards the iconic wooden Anna Maria City Pier for sweeping views of the island's beachy coastline and the Sunshine Skyway Bridge extending over Tampa Bay. Grab an ice-cream treat on the historic pier, a prominent place to admire the amber sunset mirrored against the calm bay. 

While near the sea, visit Bean Point, the northernmost beach, for a treasure hunt of exotic shells. Remember to shuffle your feet to ward away stingrays so close you can spot them in the clear crystal waters.

Holmes Beach

Sandwiched in the middle of Anna Maria Village and Bradenton Beach is Holmes Beach, the first point of entry on the island. The flour-white sandy Manatee Beach with ombre shades of blue water is pure bliss. Kick off your sandals, feel the soft fine sand beneath your feet, and dip in the warm Gulf Coast sea. 

After a refreshing swim, dry off at the all-time favourite Anna Maria Island Beach Cafe, decked with umbrella-shaded tables on the sandy bay. Tuck into fresh seafood still marinated in saltwater with one of the restaurant's speciality ocean platters. A tiki bar is onsite, mixing tropical cocktails that pair perfectly with the seaside setting.

Once you've satisfied your hunger, why not catch your next meal? Board a fishing charter for a fun day out. The family-friendly boat trips entertain kids allowing them to catch their own small fish. The boats then dock along a sand bar for a run-around and teach children to net fish. Educational for adults and children, the fishing charter packs another highlight of the pristine views of Tampa Bay and the Gulf of Mexico.

Bradenton Beach

Make your way south of the island to the idyllic community of Bradenton Beach. Visit the southernmost Coquina Beach for dolphin sightings along the Gulf of Mexico. Community spirit comes alive at the beachside market on Wednesdays and Fridays. Local vendors sell their crafts and greet each passerby with warm Florida charm.

For a slight change of scenery, find the Coquina Baywalk in Leffis Key Preserve. Wander the wooden trails along the lush environment with thriving, dense mangrove forests. After admiring the path's leafy flora and stunning views of Sarasota Bay, spare some time for a fun activity. Hit a hole-in-one at the beautifully landscaped Fish Hole Miniature Golf, featuring pockets of koi ponds. Kids will love feeding the turtles onsite.

Finally, what better way to relax on Anna Maria Island than a trip to the spa? Book a seaside chamber at Sea-renity Beach Spa & Bou-tiki for a massage of your dreams. Melt into tranquillity to the sound of the crashing waves and the smell of salty sea air as you feel the tension slip away with every knead.

How Would I Drive to Orlando?

After picking up your Fly Drive Holiday rental car from a convenient location in Anna Maria Island, you would head towards the US-41, from there you'll turn on the I-75 motorway, taking you to the playground of Orlando. Spanning a mileage of 126 miles, the road trip is doable in just 2 hours.

It's also important to note that with Ocean Florida's Fly Drive Holiday package, you get more than just vehicle hire. The plan also includes:

- 24-hour roadside assistance
- Sat Navs on request for a small fee
- Free one-way drop-offs within Florida
- Comprehensive insurance - including a full petrol tank, GPS, underage driver's fee, three extra drivers, and child seats
- Online check-ins for your ease
- A Florida team available 24/7

How Could I Fly to Orlando?

We offer a range of both UK and US airlines, including partnerships with United Airlines and Delta that are ideal for internal flights. These planes can fly direct to Orlando or even next door to Tampa. Though whichever airline or airport you choose, you'll fly in style with onboard entertainment, seat-back TVs, in-flight meals and baggage areas all included as standard. Plus, don't miss out on our Airline Sale this September 2022 for up to 40% off holiday packages flying with British Airways, Virgin Atlantic and Aer Lingus. 

Why Should I Visit Orlando?

We could tell you many magical reasons why you should visit the Theme Park Capital of the World. But, we'll let our official Theme Park Tester, Alexandria, take over. Fresh from plunging down roaring riptides, soaring through clouds aboard musical coasters - and hitting more high notes than the Bee Gees throughout – Alexandria’s here to reveal the hits and misses of Florida attractions in 2022. Click here to read her review of each Florida theme park. 

Ready to plan your Anna Maria Island and Orlando holiday? Get in touch with our Travel Specialists for a personalised package.

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