Things to Do on Longboat Key & Anna Maria Island, Florida

There’s not many things I love in life more than a good beach vacation and for YEARS my family made an annual early summer trip to Longboat Key in Florida. I recently headed back to Longboat Key for the first time in about 15 years. Since we used to vacation there, I have fond memories of the area and it’s a place I know pretty well. Honestly, not a ton had changed since I’d been there last (somewhat of a pleasant surprise) and it was pretty much exactly what I remembered. There’s something fun about revisiting places you vacationed as a child and seeing how the memories hold up. So I’m excited to share with you some of my family favorites!

In this post, I’ll give you a quick rundown of how I spent my five days on Longboat Key plus some ideas of other things to do in the Longboat Key and Anna Maria Island area, a few recommendations on where to stay in Longboat Key and Anna Maria, and some of my favorite restaurants. 

This post may contain some affiliate links, which means I’ll make a little money on anything you choose to purchase. But of course, I only recommend my absolute favorites to you. Thank you for supporting the brands that make Hulaland possible.

Just off the coast of Sarasota on the gulf coast of Florida (the west side) is a chain of barrier islands that, while they’re home to some of the best beaches in Florida, tend to fly a little under the radar. 20+ miles of white sand beaches stretch along (from north to south) Anna Maria Island, Bradenton, Longboat Key, and Lido Key. While the beaches and water are comparable to the St Pete and Clearwater areas just to the north (Tampa), the vibe in this area is totally different. If you like a laid back beach vacation (think more small beachtown vibes and less high rises) without gobbs of people around, this is the place for you. 

To get to the Longboat Key and Anna Maria Island area, you can either fly into Sarasota (SRQ) or Tampa (TPA). While the Sarasota airport is closer, there aren’t as many flight options (and flights are usually a little more expensive). It’s a little over an hour drive from TPA to the Longboat/Bradenton area. 

While the beach is obviously the big draw, there’s surprisingly a lot of things to do in the Longboat Key and Anna Maria Island area. That’s one of the things I love about Florida…every little area is totally different and there’s so much to do!

The details on this trip: I did this trip just before Memorial Day which seems to be shoulder season in this area. It’s not high winter season but peak summer travel hasn’t started either. We flew into Tampa International Airport (TPA), landing about 2 PM. We had a rental car reserved with Thrifty and honestly it was a real nightmare. We waited over an hour and a half in an enormous line at Thrifty/Dollar, but in the end they did have the car we reserved. After speaking with some airport employees, it sounds like super long lines aren’t uncommon but they’re not totally predictable either. Sometimes the Thrifty line is wrapped around the building and sometimes it’s the Budget line. No way to really know ahead of time. 

The rental car situation is one of the biggest challenges about traveling right now, but I will say that it’s absolutely necessary to have a car if you’re headed to the Longboat Key/Anna Maria Island area. 

We stayed at the Zota Beach Resort on Longboat Key (full review here) which is located right smack in the middle of the island. I liked the location because we were equally close to Anna Maria Island on the north and St Armands Circle and Sarasota to the south. 

After the rental car fiasco, we ended up getting to the resort pretty late so we spent the rest of the day at the beach and pool and scrounging around for something to eat at the resort. 

So here’s my biggest tip for staying in this area: stop by Publix (grocery store) early in your trip to stock up on supplies. There’s a Publix on the south end of Longboat Key and the north end of Anna Maria Island. Besides being just a grocery store, Publix is pretty famous for their prepared foods section. Made to order subs plus a huge selection of prepackaged sandwiches, salads, meals, snacks (literally anything you can think of) make it an ideal stop to stock up on beach food. There aren’t many full service resorts in this area, so pretty much anywhere you’re staying you’re going to have to go in search of food. While I like to have breakfast and dinner out, I don’t like leaving the beach when it’s time for lunch so having a lot of snacks on hand is perfect. 

Besides spending a ton of time at the beach and pool at our resort, we spent a day on Anna Maria Island having breakfast on the beach, walking through the shops in town, and checking out the pier. We also spent a day at the Ringling in Sarasota. There aren’t a ton of places to go for dinner on Longboat Key itself, so the big spot to go in the evenings is St Armands Circle just south of Longboat. It’s absolutely packed with shops and restaurants and we ended up there a few times. 

Things to Do on Longboat Key & Anna Maria Island

THE BEACH: It’s why you go to Florida, right? The sand in this area is a great combination of being soft and white but still with a good mixture of shells. I will say that the beach in front of the Zota Beach Resort had my least favorite sand in this whole area. It was quite a bit coarser and darker than in pretty much every other area in this stretch. 

Overall, there seems to be a lot better public beach access on Anna Maria Island than on Longboat so if you’re not staying on the beach but you’re packing it in, Anna Maria Island is probably the better place to head for the day. 

Shelling: I’m a casual sheller, but I still LOVE to look for shells. This is a great area for it and although I didn’t find any sand dollars on this trip, I have in the past. Sand dollars are definitely easier to find more towards the beginning of the year. Much like the beach, it seemed like the shelling was better when I stayed on the south end of Longboat Key, but it’s also pretty good at the far north end. 

Sunset at Beercan Island: One of the best spots for shelling on Longboat, it’s also a great spot to watch the sunset. It’s not really an island, although it can seem like one at high tide. The best access is off N shore Road (the very last left turn as you’re driving north across the island). There’s not a ton of parking so you may have to be patient. There’s a pier right at the access point that’s great for watching sunset, but most people keep making their way north around to the end of the island. 

There was some construction going on when I was there this time so we weren’t able to go all the way around the end of the island (where you can see across to Anna Maria Island and the bridge), but normally you can. The end of the island (by the bridge) is a popular spot for boats to hang out. Beercan Island is a big local hangout so while it feels pretty secluded, there’s always plenty of people around. There are a lot of trees in the area and a ton of staubs (where pieces of the roots stick up through the sand) so either wear water shoes or be careful where you walk. 

Take a Boat Trip: The waters around this part of Florida are so beautiful that a boat trip is a must do. There are a lot of options from a quick sunset dolphin cruise, to a half day fishing excursion to a full day island exploring trip. My pick would be the Fun Run or Captain Casey’s Day Trip Special with Longboat Key Charters which includes a stop at Egmont Key, a couple of sandbars, snorkeling, and plenty of dolphin and manatee spotting. 

St Armands Circle: St Armands Circle (on St Armands Key just south of Longboat Key) is the place to be in the evenings. This bustling area is packed with shops and restaurants. It gets pretty congested (it’s also the route from Longboat Key to Sarasota) so have plenty of patience going around the traffic circle and finding a place to park. There’s a newly opened parking garage, a parking lot, and a lot of metered spaces (free and paid although all are free on Saturdays and Sundays). Prices range from $0.50/hour to $1.50/hour and most can be paid via credit card or the ParkMobile app (make sure you know your licence plate number!). 

Pine Avenue on Anna Maria Island: Pine Avenue on the north end of the island is the main walkable drag on Anna Maria Island. It’s loaded with cute shops and fun restaurants. There’s plenty of parking up and down the street (just don’t use it for beach parking). There’s also a public beach entrance at Pine Avenue. 

Anna Maria Island City Pier: At the east end of Pine Avenue is the city pier. You can fish off of it, but it’s also just fun to walk to the end. You can see the Sunshine Skyway Bridge in the distance. Also, super weird but…the bathrooms at the pier are seriously nice. Always good to know. 

Paint Sand Dollars at the Shiny Fish Emporium: One of the cutest shops on Anna Maria Island is the perfect place to spend a rainy afternoon creating a one of a kind souvenir. Drop in (if you have a large group you should call ahead) and paint your own design on a sand dollar. For $15, you’ll have all the supplies you need to paint a sand dollar including having it finished with a sealing spray and hung on a ribbon. 

Rent Bikes (or Golf Carts): A little known fact about me…my dream is to live somewhere where you get around by golf cart! While Anna Maria Island isn’t an exclusive golf cart island, there are quite a few places where you can rent one in town. It’s a fun way to get around, especially if you have a lot of stuff to cart back and forth to the beach. Bikes are also a popular way to get around and if you’re staying on the north part of the island, it’s a lot easier to bike than to get your car out and try to find parking. Beach Bums has bike and golf cart rentals as well as beach gear like paddleboards, kayaks, chairs, umbrellas, etc. 

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The Ringling: Just across the bay in Sarasota, The Ringling is one of the truly don’t miss spots in this area. Originally established as the winter home of the Ringling Brothers Circus, the complex now includes a world renowned art museum, an interactive circus museum, and Ca’ d’Zan (the 1920s Venetian style mansion of John and Mabel Ringling). It’s easy to spend a whole day here and it costs $35/adult to get admission to all of the museums and the house ($25 without admission to the house). 

I especially loved the Howard’s Circus model. It’s an extremely intricate and detailed model based on the Ringling Brothers circus in the 20s and 30s. It’s so complex and large that it took probably 30-40 minutes to walk through and look at the entire model. The highlight of my last visit to the Ringling just happened to be the dolphins right outside of Ca’ d’Zan. There were a couple of dolphins that were feeding on some fish right at the seawall and I’ve never seen dolphins so close up and active before! 

My biggest tip for touring the Ringling is to pace yourself and have a good idea of what you want to see and how long you want to spend before you arrive. The art museum is absolutely enormous but we spent a lot of time in the circus museum at the beginning and then out watching the dolphins so we were running out of steam by the time we made it to the museum and ended up kind of strolling through. Find out more about the Ringling here

Jungle Gardens: This small scale zoo is a fun diversion if you have kids (we used to come here when I was younger). It’s heavy on birds and reptiles, but it’s a nice way to spend a few hours, especially if you’re needing a break from the beach. Find more information here

Golf: There are a few golf courses on Longboat Key and Anna Maria Island if you’re looking to spend some time on the links. The Longboat Key Golf Club is the premier place to golf in the area (one of the best in the country) and they have two courses (the Harbourside Course which has three different nines that you can combine and the Links of Longboat). There’s also the Key Royale Golf Club on Anna Maria Island. Besides these courses on the islands, there are LOADS of courses on the mainland at Bradenton and Sarasota. 

Tennis: If you like to work on your tennis game on vacation, check out the Longboat Key Public Tennis Center, or consider staying at the Resort at the Longboat Key Club where they have a pretty extensive tennis program. 

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My beloved Colony Beach and Tennis Resort (home to many childhood summers) is sadly no more.  After many years of sitting abandoned, the property has recently been cleared to make way for a St Regis resort. And I’m not exactly mad about it. Honestly, when the St Regis finally opens, I think it’s going to make Longboat Key a REAL destination. This whole area is severely lacking a super nice place to stay. And the St Regis is definitely going to fill that void. I think it will ultimately draw people to this area that hadn’t considered it before. But alas, that looks like it’s still probably a couple of years away. So for now…

Zota Beach Resort: This trip we stayed at the Zota Beach Resort. I must say, I had high hopes for this place (I’m always looking for the perfect beach resort in Florida) but it fell a little flat. Self advertised as Longboat Key’s newest “luxury resort,” the recently renovated property (previously the Longboat Key Hilton Beachfront Resort) makes a good first impression. The entry, lobby, and pool area all have a modern, polished vibe and visually pleasing aesthetic and that must be where they get the “luxury” tagline because there wasn’t anything else to suggest it. The room was ok but a little shabby and worn (this was actually the vibe in the lobby and common areas too…couches, furniture, anything upholstered, etc.) with a teeny tiny balcony. We stayed in the north tower which is the renovated tower, whereas the south tower is a new build. Maybe the rooms in the south tower were nicer? The balconies were considerably larger so just judging from the outside, you’re probably better off paying more to stay in the new south tower. 

All of that aside, the rest of my negative impressions may be due to COVID (or they may not since this was my only stay). Service everywhere was pretty lackluster and in general there were just waaaaaaayyyy too few people working there. There was no housekeeping and after 5 nights with three adults in a hotel room we found ourselves avoiding being in the room as much as possible. There was a provision where you could request to schedule a cleaning after the third night, but they were unable to get anyone to clean our room for the last two nights. Bummer. They were good about bringing fresh towels when we requested, but here’s the deal…changing out your towels, taking out the trash, making the beds, etc felt an awful lot like staying in a condo except we were in a small hotel room and it wasn’t exactly cheap. 

The food situation at the resort also wasn’t great. There’s one restaurant and a pool bar. We had a $50 credit daily to spend on food as part of our room rate and we struggled to be able to spend it! The first night we were there we just wanted a casual dinner (everyone had been in the pool) but the pool bar closed and they couldn’t seat us in the restaurant (it was crazy loud in there anyways) and no one would answer the phone to order room service. We ended up having to go back to the restaurant to see what was going on (turns out the hostess was also covering as a waitress and she was the one answering the phone for room service : ) In the end we were able to order take out from the restaurant and take it back to our room but it was just such an ordeal. We ended up just trying to use our credit on drinks from the bar in the afternoons (none of us ever had a drink that was halfway decent) so that credit ended up feeling pretty wasted. 

Long story short, if you’re going to stay here, you’ve got to have a car and plan to either leave property for every meal or go to Publix and stock up so you’ll have stuff for breakfast and lunch if you don’t want to leave. 

The service from the valet (mandatory valet parking is included in your resort fee) and the beach concierge (arranging umbrellas and chairs) was top notch. Bonus tip: if you’re traveling with kids, they have a ton of beach toys at the beach concierge hut for you to use (mostly stuff that’s been left behind by other guests). 

So, overall: this place is in no way, shape, or form on a “luxury” level especially if your definition of luxury is comparable to Four Seasons, St Regis, Ritz Carlton, JW Marriott, etc. I would say it was more like a high end Courtyard Marriott. So if you go in with those expectations, you’ll probably be happy. But if you’re expecting a true luxury resort, just know that this isn’t it. I think price also plays a big factor in expectations. The price for this stay averaged out to be $340/night and that was AFTER they removed three nights of resort fees (an extra $40/night). If this place had been about $200/night (INCLUDING the resort fee) I would have been pretty happy. But $340-380/night is in the ballpark of what I paid the month before to stay at the Don Cesar Hotel on St Pete Beach and there is absolutely no comparison. 

I’m really not sure how much weight to give the “COVID effect” here.  I understand that staffing is hard right now and there are a lot of extra challenges in the tourism industry so I get why they’re struggling. But I’ve also stayed at other places where the guest experience was handled much better. Part of traveling right now is paying more and getting a lot less. In my experience (as a pretty frequent traveler) it’s not as extreme everywhere but this was definitely a case of paying more and getting less. 

That being said, there just aren’t a whole lot of options for true hotel/resort like accommodations on Longboat Key, so if you can find it at a decent price, it’s worth a look at. 

Click here to check pricing and availability during your stay.

The Resort at Longboat Key Club: This is where I would stay next time. It was a little more expensive than the Zota Beach Resort for this trip so I went the other way but this place seems to be a true resort. It’s been recently renovated and it’s a pretty large property with full amenities (plus amazing golf, tennis, spa, etc.). Pricing starts at $350/night. Click here to check pricing and availability during your stay.

Longboat Key Condos & Vacation Rentals

Longboat Key is a GREAT place to find condos and vacation rentals. There are so many options from small cottages to luxury homes to upscale condo complexes, etc. And at all different price points! I book all of my condos and vacation rentals with Vrbo. Click here to find the best condos and rentals on Longboat Key. You can filter for your wishlist (exact location, price, # of rooms, pet friendly, etc.). And if you’re on a tight budget, you’ll be pleased to find many options under $100/night. Search for Longboat Key condos and vacation rentals here

I’ve rounded up a few individual units plus overall complexes that I like the look of: 

Island West: This luxury tower is right on the beach and it’s definitely a place I would stay at if I was looking for condo type amenities. 

Luxury Condo at L’Ambiance: Anything at L’Ambiance is divine (it’s part of the Longboat Key Club), but this luxury unit looks particularly lovely. 

Chic Two-Bedroom with Resort Amenities: Perfect for longer stays (10-30 days), this condo is soooo chic plus the amenities at the complex are pretty swanky. 

Where to Stay in Anna Maria Island

There really aren’t a lot of resorts or hotels on the island (part of its charm). It’s mostly small inns and vacation rentals, but here are a few places to check out: 

Waterline Marina Resort & Beach Club: This is the only true resort in the area (bonus points because it’s a Marriott Bonvoy property) but unfortunately it’s on the bay side of the island and not the beach side. The Anna Maria Island Trolley does stop at the marina so it makes getting around the island easy. Pricing starts at $350/night.  Book a room directly with Marriott Bonvoy here and read hundreds of reviews here.

Bali Hai Beach Resort: Next time I’m on Anna Maria Island, this is probably where I’ll stay. It’s a small boutique hotel right on the beach and it looks so cute! The property is in the process of being completely renovated, and I think the key to having a perfect stay here is definitely booking one of the newly renovated rooms (I believe the beachfront rooms haven’t been renovated yet). Pricing starts at $230/night. Click here to check pricing and availability during your stay. 

Tortuga Inn Beach Resort: Located more towards the southern end of the island in Bradenton Beach, this place is cute, right across from the beach, and it has a pool. Pricing starts at $150/night. Click here to check pricing and availability during your stay. 

Bungalow Beach Resort: Another little idyllic beachside bungalow inn with a pool. Click here to check pricing and availability during your stay. 

Silver Surf Gulf Beach Resort: A quaint little inn right across the street from the beach. Rooms are updated and most have little kitchenettes. Pricing starts at $140/night. Click here to check pricing and availability during your stay. 

Anna Maria Island Condos & Vacation Rentals

Like I said before, the vast majority of accommodations on Anna Maria Island and Bradenton Beach are vacation rentals and condos. I book all of my condos and vacation rentals with Vrbo. Click here to find the best condos in Anna Maria Island and Bradenton Beach. You can filter for your wishlist (exact location, price, # of rooms, pet friendly, etc.). And if you’re on a tight budget, you’ll be pleased to find many options under $100/night. Search for Anna Maria Island and Bradenton condos and vacation rentals here

Here are a few rentals that look pretty dreamy: 

Home with Private Pool: Right in town (shops and restaurants close by!), super close to the beach and with its own pool! Perfect for a big family vacation.  

Beachfront Paradise: Right on the beach on Anna Maria Island!

Sea Shack: Super, super cute colorful bungalow style cottage with private pool. 

Favorite Restaurants around Longboat Key and Anna Maria Island

Dry Dock Waterfront Grill: The #1 best meal of the trip by far. There aren’t too many restaurants on Longboat Key and there are fewer truly good ones, but I will come back here every time now. We lucked out with an amazing table so it felt like a private dining experience but overall this place is hopping! Definitely make reservations. I had the seafood pasta but absolutely everything everyone had looked amazing. 

Gulf Drive Cafe: We’ve been coming to this place for breakfast since it was a tiny little indoor restaurant and it has since expanded into a huge footprint which includes quite a few feet in the sand tables and a fun tiki bar area. They do breakfast, lunch, and dinner now but my childhood memories will forever include the most extravagant strawberry belgian waffles WITH ICE CREAM. 

Crab and Fin: I wanted to try a new place on St Armands Circle and this place didn’t disappoint. We had a large party so we were seated inside (if you’re a party of two definitely go for the sidewalk), but the food here was amazing. I’m not exaggerating…best crab cakes of my life.

Hometown Desserts: So many restaurants on Anna Maria Island serve desserts from this place, but I wanted to visit the shop myself. I opted for key lime pie (naturally) but my actual favorite was the key lime coconut CAKE. This place is right on Pine Avenue so if you’re out shopping, stop in for a slice or take one to go for later. 

Salty Dog Cafe: Another childhood favorite, we always liked the City Island location because it’s right next to the marina and there’s always a lot going on. Nothing fancy, but good food. 

First Watch: Yes, it’s since become a chain, but the original was in Sarasota and the food here is totally different. Healthy but hearty breakfast…a great stop if you’re heading into Sarasota for the day (to visit the Ringling maybe?).

Blue Dolphin Cafe: A great breakfast dive on St Armands Circle. It’s not a very big restaurant so go early or be prepared to wait. 

Beach House: The location and setting of this place is perrrrfect (so many of the tables are literally in the sand) but the food was just ok. They don’t take reservations and the wait gets pretty long. 

Chart House: I said earlier that there aren’t many great restaurants on Longboat Key, well…this is one. High end seafood with a view. Make reservations in advance. 

Columbia Restaurant:It’s become a local chain in Florida (the original was in Ybor City) but it started as one of Florida’s oldest restaurants and it’s Cuban food is pretty legendary. All locations are still owned and operated by 4th and 5th generation members of the founding family. 

Restaurants on My List to Try

Anna Maria Island: Anna Maria Beach Cafe (breakfast and lunch, patio), Beach Bistro (romantic dinner), The Donut Experiment, Duffy’s Tavern (burgers), Ginny’s & Jane E’s (cinnamon rolls), Sandbar (feet in the sand dinner)

Longboat Key: Shore 

St Armands Circle: Cafe L’Europe

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