Longboat Key, Anna Maria Island & Sarasota: My Favorite Part of Florida

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, Longboat Key, Lido Key, and Siesta 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. 

For YEARS when I was a kid my family made an annual early summer trip to Longboat Key so I’m pretty partial to this area. 

To get to this 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/Anna Maria Island area. 

Since I’ve spent so much time in this area over the years, here’s a little guide to my favorite spots and things to do on Longboat Key, Anna Maria Island and Sarasota: 

Things to Do on Longboat Key // Anna Maria Island // Sarasota


Make no mistake, bumming around the beach is what you do out here on the islands. The sand in this area is a great combination of being soft and white but still with a good mixture of shells. Between the upper stretch of islands all connected via bridge (Anna Maria, Bradenton, Longboat, and Lido), Anna Maria by far has the best public beach access. 

Coquina Beach has plenty of parking and good facilities if you’re packing it in and spending the day. 

But the beaches on Longboat Key are usually way less crowded. 


I’m a casual sheller, but I still LOVE to look for shells. This is a great area for it and it’s not unusual to find sand dollars. Sand dollars are definitely easier to find more towards the beginning of the year. 

***Want to save major $$$ on a fancy beach resort? My favorite travel hack is cashing in points to score free nights at some of the island’s most high end resorts. My go to hotel brand is Marriott so I use this Marriott Bonvoy Boundless card to rack up points for a lot of my trips to Florida. If you pay for your monthly expenses on the card and are responsible about paying it off every month, the points add up really fast. Plus, if you sign up through my link, you’ll get THREE bonus free nights to use. In Florida, use your points at some of my favorite Marriott properties like the Swan Reserve at Walt Disney World, the Vinoy in St. Pete, the EDITION Miami Beach, the JW Marriott Marco Island, and the soon to open St. Regis Longboat Key. 

Sunset at Beer Can 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. Beer Can 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. 

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. 

Side Note: If you’re looking for a rental car for your trip, I LOVE Discount USA Car Rental. They’re seriously the only company I ever use. I started using their sister company (Discount Hawaii Car Rental) on my Hawaii trips almost 10 years ago and now I use their main site for all of my other trips. They’ll give you the very best prices, you don’t have to reserve with a credit card or pay until you show up, you can cancel and re-book anytime if you find a better rate, and they usually have a special that adds additional drivers for no fee. It’s a no brainer. Click here to check rates for your trip.

The Ringling

Right on the bay in Sarasota, the Ringling is one of the truly don’t miss spots in the area. 

What started as the Ringling family home and winter home for their circus has grown into a world renowned art museum. 

Plus the Ringling is home to Ca’ d’Zan, the 1920s Venetian style mansion of John and Mabel Ringling. It’s one of the few (maybe only) gilded age estates on the gulf coast. 

Here’s what you’ll find at the Ringling: 

Circus Museum (Tibbals Learning Center)

There are two circus museums on the grounds (right next to each other), but the Tibbals Learning Center (the main museum) is my favorite. There are plenty of historic items on display, but they’ve really arranged everything in an interactive way (walk a tightrope, squeeze into a clown car, etc.) and it’s where you’ll do all the “learning” (reading, watching videos, etc.) about the Ringling Circus. 

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.

Circus Museum (Historic Galleries)

The Historic Galleries feels a bit like a sideshow. Haha. It’s a few rooms with cases of historic objects with tiny plaques to read that weren’t terribly exciting, but you’ll definitely want to walk through because in the back room (more like a warehouse) they have several original wagons and also one of the train cars. 

Ca’ d’Zan

Built during the roaring twenties in the Venetian style, this home of John and Mabel Ringling is really something to see. 

The Museum of Art

Opened in 1930 by John Ringling as a gift to the people of Florida, the State Art Museum of Florida features 21 galleries built in the Italian Renaissance style around a stunning courtyard. 

The art itself is impressive, but many of the galleries were built with the original panels from the Astor’s NYC gilded age mansion. 

Tips for Visiting the Ringling

The Ringling is open daily from 10AM-5PM. 

Admission for the Museum of Art, Circus Museums, and Bayfront Gardens (the grounds) costs $25/adult, $23/senior (65+), $5/child (6-17), 5 and under are free. It’s an extra $10/person for entry to Ca’ d’Zan where you can walk through the first floor of the home. There’s an online audio tour you can download as well. 

There’s a handful of other admission options including $5 grounds admission, $15/adult and $5/child admission to the art museum on Thursdays after 5, and free admission to the grounds and art museum on Mondays. 

Obscure tip of the day: Don’t sleep on the dolphins! We happened to see several dolphins right along the seawall just south of Ca’ d’Zan. Now obviously, you can’t count on always seeing dolphins, but the dolphins were feeding on some sheepshead fish (which feed on barnacles on the wall) so there’s a pretty good chance to see them in the area. 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 more info about visiting the Ringling here

Where to Stay 

Sadly, my beloved Colony Beach and Tennis Resort (home to many childhood summers) is 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 (it’s slated for June 2024), 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. 

In the meantime, check out these places: 

Zota Beach Resort

On my last trip to Longboat Key, I 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) definitely makes a good first impression.

The entry, lobby, and pool area all have a modern, polished vibe and visually pleasing aesthetic and I think that’s where they get the “luxury” tagline. 

This place definitely isn’t “luxury” on the level of a 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 there’s still a lot to like here! You can’t beat the location!

There are two towers (the north tower is renovated and the south tower is a new build) and I’d definitely pay a little more to stay in the south tower. 

There’s an onsite restaurant and beach bar, but it’s definitely not the kind of resort where you feel like you never need to leave the property so you’ll definitely need a car and probably want to do a grocery run to the nearby Publix. 

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. And 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). 

Check rates for your stay here

The Resort at Longboat Key Club

If you want a beachfront resort experience in the area, this is a solid option. It’s been recently renovated and it’s a pretty large property with full amenities (plus amazing golf, tennis, spa, etc.). 

Check rates for your stay here

Other Places to Stay

Joie Inn is THE place to stay on Anna Maria Island if you’re looking to book a full week. 

Plus there are a ton of places to stay in Sarasota if you’re not looking to be right on the beach. The Ritz Carlton Sarasota has a FANTASTIC beach club on Lido Key plus a shuttle that runs back and forth and the Sarasota Modern looks pretty cool too. 

Condos & Vacation Rentals

This area 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! 

Check here to find the best condos and rentals on Longboat Key and Anna Maria Island. You can filter for your wish list (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.

On Another Note: If you’re looking for a condo or vacation rental for your trip, I always book with Vrbo. They’ve got the largest selection of rentals you’ll find anywhere and you can easily filter to find exactly what you’re looking for. Need a specific number of bedrooms and bathrooms? Narrowed it down to a certain location? Want flexible cancellation terms? Need to stay under a fixed budget? Click here to search for Florida vacation rentals for your trip.

Places to Eat

I’ve spent quite a bit of time in the Sarasota area (especially around Longboat Key and Anna Maria Island) over the years and snacked around a fair bit (nothing pairs better with the beach than eating, right?), so here’s a little roundup of some places I’ve been to and liked plus some places that are on my list to try: 

Dry Dock Waterfront Grill: The #1 best meal of my last 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. 

Shore: I’ve been to the location in St. Armands Circle and it was super yummy, but there’s also one on Longboat Key that maybe has more beachy ambience. The good was excellent so it’s definitely on my list to try the Longboat one in the future. But if you’re shopping on the Circle, this is a great spot for lunch or dinner. It’s got a great balcony too. 

Want to Read More Posts about Florida? I’ve got plenty!

Check out these destinations: Miami (Things to Do Besides Party & Where to Stay) // Key Biscayne // Sanibel & Captiva // Longboat Key & Anna Maria Island // Marco Island // 30a // St Augustine // Amelia Island // St Pete Beach // St Petersburg // Fort Myers // Dunedin // Crystal River & Weeki Wachee Springs // Honeymoon Island & Caladesi Island State Parks // Tarpon Springs // Matlacha & Pine Island // Apalachicola

Trying to narrow it down? Siesta Key vs Anna Maria Island // St Pete Beach vs Clearwater Beach // Sanibel vs Marco Island // Destin vs Panama City Beach // Destin vs 30a // Key Biscayne vs South Beach // Seaside vs Rosemary Beach 

Best Beaches in Florida with Seashells

Best Florida Tennis Resorts

P.S. If you want to follow along on my travel adventures in real time, you can follow me on Instagram (@caitylincoln). My post captions are full of travel tips and I have a ton of story highlights and videos with great info. And share my account with your travel loving friends! Your support really helps me keep this blog running!