Anna Maria Island Trip Recap

Last week, I went on a trip to Anna Maria Island. Anna Maria Island (or AMI as the locals call it), is west of Sarasota, Florida, and is located in both Tampa Bay and the Gulf of Mexico.  I had never heard of AMI until about a year ago when my friend Laura mentioned that her parent’s best friends had purchased a vacation home there. (The house has been updated since the pics on this link were taken- new furniture, new flooring, and painted walls instead of pink wallpaper) We had been talking about taking a couple’s vacation somewhere warm, and quickly decided AMI was a great option. The house was only a block from the beach and had it’s own pool. I love renting houses on vacation instead of staying at the hotel. You can cook some of your own meals to save $$  and it always seems a little more relaxing than a hotel.  Plus, you get your own private pool.

House pool

We flew out of Minneapolis, MN on Christmas Day. Three couples flew on this flight and the other couple flew out of Des Moines, IA, since they lived there. Our flight took us to Tampa where we met our driver. Since it was Christmas Day, no grocery stores were open. We found a pretty sketchy 7-Eleven and loaded up on snacks and beer. (Classy, huh?) We got the house around 9:00 pm and even though it was only 60 degrees, we changed into our swimsuits and got in the pool! The last couple arrived at about 11:00 pm and we pretty much just hung out and had drinks after that.

The next morning, we woke up starving and since we weren’t smart enough to check the trolley schedule, we walked a mile and a half to the Beachside Cafe for breakfast. The Cafe is right on Holmes Beach. Their claim to fame is All-You-Can-Eat pancakes, but I had an omelet. Since I was starving, I declared it the best omelet I’d ever had. After that, one of the couples called and Uber and went to visit some relatives in Venice, FL. The remaining 6 of us split up and the girls went grocery shopping at Publix while the guys went and rented a 6 person golf cart. (Sidenote: Publix is to Florida what Hy-Vee is to Iowa. And they’re both fantastic.) After we were done shopping, we all cruised the island in the golf cart which was a blast. Unfortunately, we were only able to rent the cart for the day. If you go, I highly recommend renting the golf cart for your entire stay. It was awesome! That night we went out to a restaurant some locals recommended called The Ugly Grouper. The atmosphere at the Ugly Grouper is super casual and they had live music. I had fish tacos, calamari, and a pineapple mojito. I should have taken pics but I was too busy inhaling my food.


The next day (Day #3), the guys went golfing at Isla Del Sol Yacht & Country Club . One of the guys along on the trip managed to get them free golfing through someone he know. Needless to say, this was probably the best part of the trip for them. The ladies headed out to a vendor market at the beach where we bought the best guacamole we’d ever had. Seriously, I’m pretty sure it was made of angel tears or baby fairies. Then we headed to Bridge Street and to the Braedenton Beach Pier. Bridge Street had some great souvenir shops and bars. We ate lunch at the Bridge Tender. The theme of this bar was the Green Bay Packers and being a Packer fan, my friend Laura was in heaven. I had a balsamic chicken salad and the Shan’s Rum Runner. If you go there, you need to try this. It was heaven in a cup. And you can’t beat lunch with a view! After we went back to the house, we headed to the beach and met up with the guys to watch the sunset over the Gulf of Mexico. What is it about a sunset on the beach? It’s ten million times more amazing than any other sunset. And no picture can ever do it justice..but hey, I tried. That night we grilled steaks at the house and hung out.

On Day #4, we decided to make our own adventure and rented a boat and boated around in Tampa Bay. We were lucky enough to have dolphins swim right next to our boat.  How cool was that? Of course, they were too fast and I didn’t get a picture but hey, dolphins! We at lunch at the Bridge Tender since the guys missed out on it the day before. This time I had the Basa Bites (and another Shan’s Rum Rummer…hey, it’s vacation!) and they were delicious. Again, no pics, because I never think of it until later. That night we headed out to the Rod & Reel Pier.  As you can guess, it’s on a pier. You can fish while you wait or you can drink Bud Light. Guess which one I did? The atmosphere is super relaxed and they have white twinkly lights everywhere. I had the grouper meal with fries and grilled vegetables. Afterwards, we walked for awhile and then called the Monkey Bus to pick us up. The Monkey Bus is a party bus that runs off tips. I highly recommend it. When we were riding, a British Family got on and the driver was playing 80’s music. Everyone on the bus was dancing. How great is that? Apparently, 80’s music is a universal language. Ok..we all spoke English, but whatever….The Monkey Bus dropped us off at the Ugly Grouper and we had another drink and played bags.

(Our whole group at the Rod & Reel and a random pelican)

On Friday (Day #5), it was a little chilly so we headed out for souvenirs. We stopped at Alvin’s Island, where we got some shirts for the kids and stuff for ourselves. And then, we went parasailing. Well, 4 of us did. That was definitely the biggest adventure of the trip and of course, no pics! Captain CJ picked us up on the pier in an airboat. Tiny boat, big waves, what could go wrong? He took us to the other side of the island and we saw more dolphins on the way. Then we went to the middle of the ocean, lined up with the other boat, and jumped from one to another.  Again, what could go wrong? The parasailing guys were 24 year old beach bums. Ok, I don’t know their actual ages, but it’s a good guess. Also, I’m pretty sure they were hungover. But one of them guessed my age at 27, so I don’t mind the hangover. We were all young once.  So if you haven’t been parasailing, you get hooked into a harness, hooked up to a parachute thing, and then you fly over the boat. The view is incredible. I flew  with my husband we were lucky enough to see a shark. Toward the end of the flight, they pull you down and dip your toes into the freezing cold water. I will definitely be doing that again! If you are scared of heights or don’t like water, I don’t recommend it. Or if you get motion sickness or you’re queasy already…..We made burgers for lunch at the house, took naps by the pool, and then watched the sunset one last time before heading out for supper at the Sandbar. The Sandbar was the nicest restaurant we went to. I had the Sweet Corn Salad with grouper and It was amazing. Fresh greens, sweet corn, grouper, and a lemon vinaigrette. My husband had stone crab which was his sole purpose of the trip. I tried it and it was amazing as well. I also had another Rum Runner (Are you sensing a theme here?) that had 5 kinds of alcohol in it. I loved it but everyone else thought it tasted like turpentine. Some people have no sense of adventure.

Saturday (our last day…boo), one couple had a 6:00 am flight back to Iowa so they were gone before we were up. Since we didn’t have food in the house, the remaining six of us went to the Beachside Cafe for breakfast. We took the trolley this time instead of being dumbasses and walking a mile and a half. I ordered the All-You-Can-Eat Pancakes this time. They were good and I’m not even a huge fan of pancakes. Of course some dumb pigeon wandered in and was around my legs. I kicked it. There, I said it. I kicked a bird. However, I didn’t mean to. It brushed up against my legs and startled me. That’s my story and I’m sticking to it. We spent the afternoon packing up the house and watching Iowa State beat Memphis in the Liberty Bowl. That’s what you get for turning our helmet upside down, Memphis! Boom! Laura, Cheri, and I went on one last souvenir run where I got gifts for my kids’s significant others. I’ve reached that stage in my life. My kids have significant others who I buy presents for. So that might make me old…or generous. Let’s go with generous. At 5:00 the driver came to pick us up and drove us to the airport in Tampa. We had a quick supper at the Hard Rock Cafe and then flew home to the bitter cold of Minneapolis. Talk about a rude welcome!

All in all, this was one of the best vacations I’ve ever been on. Would I go back to Anna Maria Island? ABSOLUTELY! In fact, we are hoping to go again with the same group. The house was awesome and being a block from the beach made for some great photo ops. (Not that I remembered to take any!) Everyone on the island was super friendly, it was easy to get around (You don’t even need to rent a car!), and best of all, it was affordable. Actually, scratch that, best of all, I made some awesome memories with some great friends. The one thing I would recommend is to rent a golf cart in advance so you can have it the whole week. Also, schedule your activities in advance. We were lucky to get a boat and get parasailing but I’ve heard that’s not always the case.  If I’m lucky enough to go again, I’d like to go on one of the dolphin watching tours. But seriously, if you want a relaxing vacation with awesome restaurants, beautiful beach sunsets, and cool adventures, Anna Maria Island is the place to go!



Where We Stayed:

Where We Ate:

Other Stuff:






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