Making Memories in Florida: Our Big Family Holiday to Anna Maria Island

As part of our early retirement journey, we decided to take the plunge and plan a special family holiday to Florida with the people that we love. The sun soaked gulf coast beaches of Anna Maria Island are our family happy place, providing an ideal location for two weeks of family fun. Our time together was adventure packed with laughter, fun, and unforgettable moments.
In this video, we share the highs and lows of traveling as a big family, how we balanced our time together, and the special memories we created with our loved ones. We’ll take you through our favorite spots, activities, and some travel tips for making the most out of your family holiday in the Sunshine State.
Being early retirees has given us the freedom to experience these precious moments with our family, and this trip was a reminder of just how rewarding that decision has been!
Whether you’re considering a family holiday or curious about early retirement adventures, we hope this inspires you to make the most of your time together.
We are Richard and Jackie and we live in the UK. We retired from teaching at the age of 51 in the summer of 2022. Our plans for early requirement include relocating to the Yorkshire Dales, developing our forever home and travelling the UK, Europe and eventually the world in our VW campervan Nelson.
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Many thanks,
Richard & Jackie

[@edandjane4050]

Loved seeing Anna Maria again. Thanks for the vid. We've also visited that beautiful island numerous times with our three childern. We were even trapped there in 2010 due to the Icelandic volcano! Shame! We liked to split the trips each time with a visit to the Keys for the snorkelling. We noticed accomodation has become more expensive on our most recent visit in 2022. We're also retired teachers and now spend time motorhoming around Europe so enjoying your travel vlogs.

[@motorroamingaround]

It looks like you’ve had a great holiday on Anna Maria Island. It’s one of our favourite places in Florida. Like you, we’ve been going to Florida for many years, but we’ve never been to Tropicana Field. We’ve been to the Amalie Arena to see Tampa Bay Lightning, we’ve been to Raymond James Stadium to see the Buccaneers and to the Amway to see Orlando Magic. We’ll need to get to Tropicana Field one day. We’re heading back for 8 weeks over Christmas & New Year so can’t wait for that. Keep safe. Irvine & Karen.

[@siuk65]

So funny watching this vlog as we have only just come back from Anna Maria island as well, we stayed near Bridge street pier and enjoyed happy hour at AMOB a few times, wink wink!! The place you stayed at looked amazing can you pass on the details please… we are only a few weeks into retirement so are glued to your vlogs when they come out, keep up the great work Simon and Keri ….

[@earlyretirementwanderlust]

How funny - not many people know where AMI is when you talk about it. We had a great meal and cocktails at the AMOB - it used to be "Rotten Ralphs' fish and chips restaurant with an all you can eat menu which we loved! The house we stayed at was on North Harbor drive just by the school which my sister booked - it was huge and I gather expensive!! We booked and payed for a house with our children but swapped our room for my sisters daughter so that all the 'kids' were together in their own party house 😂 I think we were the winners in that deal although the kids house was also fab. Sadly most of the island has been pretty devastated by the hurricane - there are loads of videos and photo's on the face book pages. There was upto 3 feet of sand on the roads and a lot of damage with the tarmac being lifted and lots of the life guard stations being destroyed. The Rod and Reel pier has gone just the restaurant standing - very sad - we can't believe we were there this time last week and now it is all in tatters! Hope you enjoy your retirement as much as we do and thanks for watching the channel 😊 x

[@MichaelBairstow-x2t]

Was it an Air bnb that you rented? Do you have a link? Looks incredible - we've currently got a hotel booked, but the thought of a full home is appealing... Thanks for sharing - lovely vlog as ever. I hope the island recovers quickly from the storm

[@earlyretirementwanderlust]

The house we stayed in my sister booked - Sadly the hurricane has severely damaged the infrastructure on the island which will take months if not years to fix - many of the shops and restaurants have suffered severe damage as well as the houses being under deep water from the storm surge and 3 feet of sand covering the roads which will need to be resurfaced. We booked the house the children stayed in on Airbnb and there is a huge amount of choice. Once they get back on their feet, the island is incredible - it was featured in Wanderlust magazine this month.

[@allisonbennett641]

Lovely video, gorgeous place, sounds like hurricane made it's mark sadly. Glad you are all home safe. Did notice Jackie you had your fave jumper on way out there ! 😉😍

[@earlyretirementwanderlust]

Anna Maria island is definitely our little piece of paradise - hopefully they will be able to get back on their feet again soon - I think it will be very different next time we go - even the shape of the beaches and island has shifted with the sand and water surge! Always have my favourite jumper with me - glad I did it was freezing when we got back to the UK! 😂

[@louisesymonds9963]

Gosh it looks so beautiful. I wonder if the island has suffered in the hurricane? Really lovely to watch a sunny video while the nights are closing in and getting colder! X

[@earlyretirementwanderlust]

Sadly most of the island has been pretty devastated by the hurricane. There was upto 3 feet of sand on the roads and a lot of damage with the tarmac being lifted and lots of the life guard stations being destroyed. The Rod and Reel pier has gone just the restaurant standing - very sad - we can't believe we were there this time last week and now it is all in tatters! There is a lot of water damage 😢 Hopefully they will the support they need to get it up and running again soon x

[@dianeh1408]

A beautiful place - we love Florida but still stay in Orlando. Shame to hear about the damage the island has suffered - you were so lucky with your holiday dates.

[@janetbowen7854]

Your family holiday looked amazing, another viewer has asked the question that I was going to ask re the storm, ,how awful for the people of that beautiful island. I hope they restore it all as soon as they can, and that no one was injured, or worse. Take care. xxx

[@earlyretirementwanderlust]

We had such a lovely time thank you Janet - so nice to spend 2 weeks with all of our family. It is heartbreaking watching how much damage the island sustained, mainly from the water surge which moved a lot of sand into the roads and into peoples houses - it will take a lot of recovering from 😊 But luckily as far as I have seen no one was injured x

[@louisesymonds9963]

Devastating to hear about the damage during the hurricane. Thank goodness you’d left by then. Just ordered the snow peak coffee drip from your store, thank you! X

[@earlyretirementwanderlust]

Ah thank you for using the amazon link and I hope you like using the filter - it takes no 2 size filters that we buy from the supermarket and bulk buy when we are in France as they are so cheap there! Mum is booked to go out for 4 weeks in January on the island and is hoping that her 2nd floor apartment she has rented is still ok but I think it will be like a building site on the island for the next year or so as the water and sand damage was quite substantial x

[@louisesymonds9963]

Thank you for mentioning the filter, I’d forgotten about those! I’ll pick some up when I’m next at the supermarket. I should get the filter on Wednesday, can’t wait! No doubt your mum will be updating you on everything while she’s out there in January. I wonder how on earth you start to rebuild the damage to lives, businesses & buildings? All the best to you and your family. X

[@SuzannesSimpleLiving]

Lovely video, Can definitely see the difference between holiday & adventures 😊

[@earlyretirementwanderlust]

Thank you - it was such a lovely time with all our family ❤️

[@gailkoursari2599]

Looks amazing. We were in Madeira beach last September and I remember the heat and humidity was unbelievable. That said the Gulf Coast is still my favourite place 🤩😎

[@earlyretirementwanderlust]

The humidity was bit of a killer at times while we were out there 😂 But at least it has prepared us for what it will be like in Thailand - we are looking at accommodation on the Thai islands at the moment and are reconsidering that we may want air con!!! Anna Maria Island is such an amazing place - hopefully we won't leave it 8 years until we return again 🏝️🌅

[@gailkoursari2599]

@@earlyretirementwanderlust Thailand is stunning. Not as cheap as we expected unless you’re happy with street food. Forget alcohol altogether. Luckily we’re not big drinkers but we do like a glass with our meal on holiday. We stayed in the quiet side of Phuket but did day trips to the gorgeous temples and some markets too. We were there in October and the weather was perfect. Not sure if you’re animal lovers but it was a tough holiday for me seeing the elephants and monkeys tied up and working. Anyway defo worth a visit and definitely an experience- enjoy 😊

[@DanKeeley]

Anna Maria island looks amazing. We discovered sanibel a few years ago but sadly since been destroyed by one of the hurricanes

[@earlyretirementwanderlust]

Anna Maria is beautiful, sadly there has been a huge amount of water and sand damage from the tidal surge so it is going to need a lot of rebuilding and fixing. Not as bad as Sanibel as most buildings are still in one piece but a lot of issues drying the buildings out and repairing the damaged road system. We really want to visit Sanibel in the future as I hear it is quite similar to the island in many ways x

[@DanKeeley]

@@earlyretirementwanderlust I'd hold off on sanibel, even though it was a while ago the rebuild is very slow. Maybe in a few years!

[@annajeram9251]

Looks like a wonderful place 🇺🇸

[@earlyretirementwanderlust]

It is a pretty fantastic place ❤️ - sadly it has been severely damaged by the hurricane, fingers crossed they can get it up and running again soon 😢

[@seeanda1]

We're just coming out of the theme park age with the kids thank god, there's only so much Universal you can take over 3 weeks, we've managed to get over to Casperson Beach a cpl of times and had a few days at Clearwater. Anna Maria is definitely one we will explore in the not so distant now we have a bit more freedom.

[@earlyretirementwanderlust]

I don't think I would have the energy for 3 weeks at the parks now!! Last time we went to universal we stayed overnight at the Hardrock cafe which gives you early access to the parks (We headed straight to Harry Potter) and the room key was a fast pass card too (not sure if they still do that?) we did 2 days at the parks then headed to the coast and that was enough!! Sadly the hurricane has severely damaged the infrastructure on the island which will take months if not years to fix - many of the shops and restaurants have suffered severe damage as well as the houses being under deep water from the storm surge and 3 feet of sand covering the roads which will need to be resurfaced.

[@seeanda1]

@@earlyretirementwanderlust definitely hard work around the parks now, we try to get to Volcano bay as many times as possible now so we can lay around while the young ones go mad on the slides, such a shame with the hurricane damage, we go through August normally just beating the start of hurricane season. They do rebuild fast and often thanks to the timber framed buildings.

[@earlyretirementwanderlust]

mum is keeping a careful eye on the progress as she has booked a small apartment for January

[@joannesaunderson4506]

Those sunsets 🌇 wow looks fab

[@earlyretirementwanderlust]

We do love a sunset! ❤️

[@rostaylor7723]

Looks like you had an amazing time, and what a great idea to rent somewhere for the summer! Would be interested to know which sites you used to book?

[@earlyretirementwanderlust]

We used to really enjoy the slow pace of life staying for the summer when the kids were younger. It is probably 10 years since we last did that and we used to use the flip flop company who would do special deals as the summer was actually the low season due to the heat on the island! This has sadly all changed since covid and the prices have sky rocketed! Mum regularly stays in the winter months and books through either airbnb or Vrbo which is how we booked this summers house. Sadly the hurricane has severely damaged the infrastructure on the island which will take months if not years to fix - many of the shops and restaurants have suffered severe damage swell as the houses being under deep water from the storm surge and 3 feet of sand covering the roads which will need to be resurfaced.

[@rostaylor7723]

@@earlyretirementwanderlust that’s terrible news about the hurricane damage. I hope they get the support they need from the government to make the repairs.

[@jillchew-tetlaw3388]

Now I ‘get’ the holiday/adventure thing!

[@earlyretirementwanderlust]

I saw a video clip that Governor De Santas who is the Florida governor was on the island with promises of money to help with redeveloping the infrastructure so fingers crossed x

[@Lilrom2003]

Did the island survive Hurricane Helene ?

[@earlyretirementwanderlust]

Sadly not 😢 The whole island was evacuated fortunately, the storm surge has destroyed much of the island with upto 3 feet of sand covering the road - the images and videos we have seen are heartbreaking, places we visited only a week ago are wrecked. The Rod and Reel Pier is severely damaged and most houses water and sand damaged.

[@Lilrom2003]

@@earlyretirementwanderlust how sad and surreal, at least America in particular Florida is good at rebuilding, so the tradition can continue!

[@earlyretirementwanderlust]

Fingers crossed x