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It’s not uncommon to compare Longboat Key vs Siesta Key vs Anna Maria Island when considering a visit to the Sarasota area. All three have spectacular beaches, cozy vibes, and abundant Old Florida charm!
Sometimes just deciding where to go is more difficult than any other part of the trip planning process. That’s why I’ve broken down everything you need to know about these destinations on Sarasota’s barrier islands. I hope this article helps you make your decision.
🌴 Read Next: Siesta Key Village: Guide to Best Restaurants, Shops, & Fun!
Map Siesta Key vs Anna Maria Island
- Distance from Siesta Key to Anna Maria Island: 28 miles
- Distance from Siesta Key to Longboat Key: 18 miles
- Distance from Anna Maria Island to Longboat Key: 8 miles
Anna Maria Island is the northernmost of the three. It is actually not a whole island itself. Rather, it shares an island with Bradenton Beach.Â
Pine Avenue cuts Anna Maria Island in half. To the east, there’s the pier. To the west, you’ll find the public beach access. Getting around Anna Maria Island without a car is relatively easy, especially if you have a bike or golf cart.
Although it’s not too commercialized, Anna Maria Island has slowly but surely become built up over the years. While it’s not nearly as busy as St Petersburg or St Pete Beach, there is plenty to do for a weekend getaway.
To the South of Anna Maria Island, Longboat Key is just a short drive away. It is the most laidback and quiet of the three. In fact, there’s never any traffic.
Longboat Key Map
Longboat Key is primarily residential, but there is small share of resorts and vacation homes. There also aren’t many restaurants, stores, and such. Once you have a car, there’ll be no issue. Anna Maria Island is to the north and St. Armands Circle is to the south.
Siesta Key is south of Longboat Key but isn’t connected by a bridge. Instead, you get to it from Sarasota. There are two bridges from Sarasota to Siesta Key.
One bridge takes you to the northern end of the island. This is near Ocean Boulevard, where most of the activity in Siesta Key is concentrated. The other bridge takes you to the middle area — Midnight Pass. There’s not quite as much going on around here.
It would be a good idea to have a car while staying here. However, the free Siesta Key Breeze Trolley makes it easy to get around even without a car.
Longboat Key vs Siesta Key vs Anna Maria Island Summary
| Longboat Key | Siesta Key | Anna Maria Island |
| Quie and toned-down atmosphere | Lively but laidback island feel | Bustling little beach town vibe |
| Resorts, inns, condos, and vacation rentals | Condos, inns, and vacation rentals with a couple of resorts | Condos, inns, and vacation rentals with a couple of resorts |
| Tranquil, less crowded beaches | Famous, crowded beaches | Busy beaches and traffic around the island |
| Little nightlife or bars | Little nightlife — a few bars | Little nightlife — some bars |
| Not much good public beach access | Plenty of good public beach access | Good public beach access, though traffic can cause an issue |
| More affordable | Mid-range prices | Fairly expensive |
| Beaches are family-friendly and quiet | Beaches are family-friendly and Siesta Beach has lifeguards | Beaches are family-friendly and busy |
| Not many restaurants and shops | Quite a few restaurants and shops | Plenty of restaurants and shops |
| Golf, tennis, parks, and boat charters | Paddle boarding, farmer’s market, and ice cream shops | Parasailing, golf cart rentals, and a museum |
| 12-mile drive to Sarasota | 7-mile drive to Sarasota | 21-mile drive to Sarasota |
Longboat Key
All three locations have their differences, but Longboat Key is uniquely distinctive since it tends to be more tranquil and primarily residential. It is a popular retirement area with expensive homes and condos. Don’t be surprised to see many mega mansions lining the Gulf of Mexico. But most of the luxury homes you can’t see well (since they are behind gates).
It also doesn’t have much in the way of activities outside of golf and tennis. While Long Boat Key beaches are nice, they are on a much smaller scale than Anna Maria Island or Siesta Key. There are a few restaurants and shops but not many of those either. However, the tranquility is simply unmatched.
Anna Maria Island is a reasonably short drive north, and St. Armands Circle is just to the south. If you haven’t been to St. Armands Circle yet, you have to make a stop for delicious restaurants and high-end shopping.
🌴 Pro Tip: My personal favorite is the Columbia Restaurant at St. Armands Circle. I like getting an outdoor table on the circle and watching the cars and shoppers while eating a 1905 salad!
Siesta Key
Siesta Key offers the best of both worlds. It definitely offers more things to do than Longboat Key. When it comes to Anna Maria Island vs Siesta Key, though, the former takes the cake in terms of liveliness.
While it’s kind of a mix of the other two, there is one thing that makes Siesta Key really stand out. The beaches are phenomenal! Siesta Key’s beaches are made of quartz. There is also very good public beach access here. It’s definitely a winner in the Longboat Key or Anna Maria Island vs Siesta Key debate, in this regard.
Siesta Beach is the crown jewel, having ranked #2 on Tripadvisor’s list of the top 25 beaches in the U.S. Though there are plenty of parking spaces, it can sometimes be a struggle to get one during peak season.
Anna Maria Island
Last but not least, Anna Maria Island is where the (most) fun is! Though its beaches aren’t as famous as Siesta Key, Anna Maria Island is pretty well-known. It’s common for establishments in Bradenton Beach to use “Anna Maria Island” in their name.
In Anna Maria Island, most of the action is around Pine Avenue. You’ll find plenty of restaurants, shops, and things to do all around. There is a museum, as well as a pier with a grill and water sports. And, of course, the white sand beaches are as great as anywhere else in the area.
Activities in Longboat Key
Of the three, Longboat Key is the quietest area and has the least attractions and activities. It’s not a ghost town, though. You do have opportunities to get out of the house (or resort).
Best Longboat Key Activities
- Look for seashells along the 12 miles of beaches
- Golf at the Longboat Key Golf Club
- Play tennis at the public Tennis Center
- Go on a boat ride
- Hike through Joan M. Durante Park
- Take a stroll in Quick Point Nature Preserve
Another thing to do is to head over to St. Armands Circle. Located just south of Longboat Key it’s a small but busy shopping and dining hub.
Activities in Siesta Key
Siesta Key has a bit more going on than Longboat Island. Most of the action is on the northern end of the island, along Ocean Boulevard. This is the main street of Siesta Key Village, another shopping and dining hub with lots to do.
Best Siesta Key Activities
- Spend time in the charming Siesta Key Village
- Kayak and paddleboard Rentals
- Head down to Siesta Beach or Crescent Beach
- Visit the Siesta Key Farmers Market
- Watch sea turtles during nesting season (May to October)
- Go on an electric bike sunset tour
- Satisfy your sweet tooth at the local ice cream shops
Activities on Anna Maria Island
Anna Maria Island isn’t a big city, but it is pretty busy, especially around Pine Avenue. The bulk of the restaurants and shops are in this area.
Best Anna Maria Island Activities
- Go fishing at the Anna Maria Island City Pier
- Golf cart and bike rentals to explore more!
- Go on a parasailing adventure in Anna Maria Island
- Enjoy shopping on Pine Avenue
- Head over to Coquina Beach or Manatee Beach
- Learn at the Anna Maria Island Historical Society Museum
- Look for dolphins while on sunset cruises
Where to Stay in Longboat Key vs Siesta Key vs Anna Maria Island
Accommodation in Longboat Key
Though Longboat Key is the least commercialized of the three areas, it has the most accommodation variety. There are inns, vacation rentals, condos, and resorts.
Best places to stay in Longboat Key
The Resort at Longboat Key Club is the premier upscale destination in Longboat Key. It is also one of the few beachfront options that aren’t complexes.
Zota Beach Resort is another excellent option that is very highly rated. It is an Opal Collection property that offers onsite dining and an infinity pool.
Accommodation in Siesta Key
At Siesta Key, you’ll find several places referred to as resorts, but they’re often condos or apartment complexes. There are, however, a couple of actual hotel resorts worth checking out.
Best places to stay in Siesta Key
Turtle Beach Resort is location in an ideal location, just a short walk from Turtle Beach. Rooms offer kitchenettes, private hot tubs, and private patios. There is an outdoor pool and kayaks for guest to utilize.
Siesta Key Beach Resort & Suites is more on the affordable side. It’s also very close to Siesta Key Village. It’s a great option if you want to get out and explore.
Accommodation on Anna Maria Island
Anna Maria Island has upscale resort-style properties, as well as more quaint spots. Being the busiest of the three, accommodation is more expensive here, on average.
Best places to stay on Anna Maria Island
Anna Maria Beach Resort is a refined and modern location that is right on the beach. Each unit has either a kitchen or kitchenette, as well as a private balcony.
Tortuga Inn Beach Resort is closer to the Bradenton Beach side of the island but the affordable rates and proximity to the beach make up for it.
Compass by Margaritaville Anna Maria Sound is right off the island, but an excellent choice if you plan to split your time between Bradenton and Anna Maria Island. It’s a beautiful hotel overlooking the marina with a restaurant and bar on the property.
Best Time to Visit Anna Maria Island vs Siesta Key vs Longboat Key
Being so close in proximity, the weather is similar across Longboat Key, Siesta Key, and Anna Maria Island. Like the rest of the Sunshine State, there aren’t huge differences in temperature throughout the year. It’s hot during the summer and mild during the winter.
Note that Florida’s rainy season stretches from around late May to early September. This also roughly coincides with hurricane season (June to November) and a heightened chance of storms in general. The rain tapers off as you get to the winter months. Late winter through spring, the area sees the least rainfall of the year.
Common Frequently Asked Questions
Which Beach Is Better?
All three have white sand beaches, but without a doubt, the best beaches in Siesta Key vs Anna Maria Island vs Longboat Key is Siesta Key.
The sand there is actually quartz, making it as soft and pure white as sugar. The beaches of Anna Maria Island and Longboat Key are amazing, too, but they can’t really compare to the number of amenities at Siesta Beach in Siesta Key.
My favorite amenities at Siesta Beach are the beautiful playgrounds with picnic areas and barbecue grills. Or if you don’t like to cook, Siesta Beach Eats provides food from the Sand Pavilion and the Sun Deck. It also has the usual public restrooms, outdoor shower stations, and volleyball courts. Everything looks new and well-kept, and it feels very safe with multiple lifeguards and staff available.
Siesta Beach is also very accessible, with beach wheelchair rentals available and a massive and spacious parking lot.
Which Beach Is Most Affordable?
In terms of affordable beaches, though, Siesta Key takes the prize. Siesta Key has great public beach access. It’s easy to get to the beach and there are plenty of amenities, too.
Anna Maria Island has public beach access but the traffic can be a hindrance. Longboat Key has excellent beaches but more limited public beach access with fewer amenities.
Which Is Better for Vacation?
This one depends on what you want out of a vacation. If you want nothing more than peace and quiet, Longboat Key will be like heaven. If you’d like to get out and have a full day every day, head to Anna Maria Island. Somewhere in between? Go for Siesta Key since it has the best beach and a charming village.
Which Is Better for Shopping?
Hands down, Anna Maria Island is the place to be for shopping. There are plenty of stores and shops, especially along Pine Avenue. Siesta Key comes in second place, while Longboat Key only has a couple of stores.
Which Is Better for Shelling?
If you’d like to collect some shells, visit Longboat Key. It definitely has the best shelling opportunities. This is perhaps because the beaches here don’t see as many visitors.
Anna Maria Island is good for shelling, too, but not as good as Longboat Key. Siesta Key has the best beaches in general but it’s actually the worst for shelling!Â
Final Thoughts | Siesta Key vs Anna Maria Island vs Long Boat Key
Despite their differences, these three locations each make a great vacation spot, even for just a day trip. The Longboat Key vs Siesta Key vs Anna Maria Island debate doesn’t have to be too heated, anyways. Their close proximity means you can see them all on the same trip!
You have many accommodation choices, from cozy short-term rentals to luxurious resorts. While in the area, you can enjoy water sports, learn some history, and lounge on the beach all day.
If you’re looking for white sandy beaches, quaint beach town vibes, any of the three would satisfy you. So pack your bags, leave your worries at home, and head over to Sarasota’s barrier islands!
Frequently Asked Questions
Is Siesta Beach water clear?
Siesta Beach has beautiful clear blue water with white quartz sugar sand.
Is parking free at Siesta Beach?
Siesta Beach has a massive parking lot with approximately 850+ parking spaces. It has free parking for everyone to enjoy. However, despite there being lots of parking spots, you’ll definitely want to come early during holidays and peak season.
How early to get to Siesta Key Beach?
The best time to go to Siesta Beach is early morning, late afternoon, or after to avoid large crowds. However, this truly depends on the time of year and day of the week. Holidays as well as weekends during peak season are the most challenging with crowds.
Does Longboat Key have white sand beaches?
Longboat Key, like nearby beaches, has beautiful white sandy beaches with gorgeous clear water.
