Siesta Key to Anna Maria Island: Scenic Day Trip Guide (Local Tips)
Thinking about a day trip from Siesta Key to Anna Maria Island? You’re in for a scenic, easy 30 mile drive along Florida’s Suncoast, making your day out feel like a mini coastal adventure.
Living on Siesta Key, I’ve done this relaxing drive countless times. Sometimes it’s for a lazy lunch at The Sandbar on Anna Maria Beach – sometimes we simply enjoy stopping at the pockets of ‘Old Florida’, like historic Bridge Street in Cortez.
In this guide, I’ll walk you through what the journey from Siesta Key to Anna Maria Island is really like, how long it takes, where traffic can slow you down, and the best spots to pull over along the way. Get ready to buckle up!
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Quick Overview of Day Trip
If you’re short on time, or like summaries (like I do!), here’s what you need to know to plan your drive:
- Distance: 28–30 miles from Siesta Key Village to Anna Maria Island Waterfront via FL-789 N (Gulf Dr)
- Drive time: About 1 hour without stops
- Best start time: Mid-morning, so you can enjoy 2–3 stops along the way
- Tip: Plan for a full day to explore beaches, cafes, and charming towns.
Highlights Of the Drive
Here are some of the scenic and unique stops I recommend along the route:
- St. Armand’s Circle / Lido Key – Explore boutique shops, grab a coffee, and enjoy the resort atmosphere (I love grabbing a cappuccino here and walking to Lido Beach to catch a few rays of morning sun).
- Coquina Beach (Bradenton) – Perfect for a quick beach walk or a picnic with stunning Gulf views (the pine-shaded picnic area makes it extra relaxing for a short break).
- Cortez Village Shops – A historic fishing village with unique local art and seafood markets (I like walking to the pier end to watch pelicans diving, and a bite at Anna Maria Oyster Bar).
- Gulf Street Cafe – On the beach, ideal for a casual lunch with a view (my favorite is sitting outside to watch the waves while enjoying fresh fish tacos).
- Anna Maria Waterfront – Stroll along the shoreline, hit the beach, enjoy an ice cream (Two Scoops and Small Town Creamery get my vote).
- Longboat Key – Stop for dinner at the Shore on your return; time it for sunset for gorgeous water views (I love the tables right next to the water).
This isn’t a beach comparison — it’s a scenic road trip guide detailing best stops between Siesta Key and Anna Maria Island.
Starting Point: Siesta Key
Siesta Key isn’t directly connected to the chain of islands that lead to Anna Maria Island, so your adventure begins by crossing the north bridge back to the Sarasota mainland.
Drive past Marina Jacks, where yachts and fishing boats bob in the marina.
If you’re feeling adventurous, consider booking a morning or full-day fishing tour with Flying Fish Tours later during your stay. We’ve done this half day trip with visiting family and friends – we always catch fish!
Cross the Ringling Bridge to Lido Key
It’s about 2.5 miles from Sarasota’s Marina to St. Armands Circle and Lido Key beach.
The iconic Ringling Bridge was built in 2003. You will drive over this on your way from Siesta Key to Anna Maria Island. It is named in honor of the world-famous circus family who wintered in Sarasota.
Just as you get off this bridge, you will see a sign for Bird Key Park on your right. It’s a small strip really where locals enjoy walking their dogs, or popping their deckchair in the shallow waters.
We stop just to enjoy the views of Roberts Bay over to the waterfront buildings of Sarasota.
Rumor has it that some celebrities live nearby, though the island opposite the park is closed to non-residents, so we can’t confirm this 🙂
Stop In St Armand’s Circle / Lido Key (1 Hour)
A few minutes later, you’ll see St. Armands Circle and signs for Lido Beach. Although not far from Sarasota, this is a charming spot to stretch your legs.
Coffee Shops on the circle we recommend are Starbucks, Cafe on St. Armands, and Le Shop (new in 2026).
🎒Our Tip: Just out of town New Pass Grill (open from 7am) has outdoor waterfront seating if you prefer a more rustic stop.
Don’t miss the Circus Hall of Fame, a small park celebrating circus legends such as May Wirth and Pinito del Oro. Weekend festivals and markets often take place in this same spot as varied as from seafood cookouts to local craft fairs.
Take a few minutes to read the performers’ stories etched on a circle of stones, before continuing your drive over Longboat Key toward Anna Maria Island.
🎒Our Tip: Parking can be tricky. Get here by 10am for metered roadside spaces, or use public city parking garages. St Armand’s Parking Website has garage directions, costs and payment methods..
Finally as you get ready to cross the next bridge onto Long Boat Key, look to your right just as you approach the beach. This used to be the turn off to the Mote Aquarium (now moved next to Benderson Park and UTC).
Once you are over the bridge you will arrive on Long Boat Key island.
Drive Through Long Boat Key
As you continue your drive from Siesta Key to Anna Maria Island, you’ll pass along Longboat Key. This 12 mile island is home to more than 30 golf courses, many with beautiful landscaping. You will also see grand resort entrances, providing glimpses of the island’s upscale reputation.
Long Boat Key has it’s share of the Florida Suncoast’s soft sandy beaches but many are restricted to resort guests. We suggest you keep going until your reach pretty Coquina (Bradenton) Beach.
The one exception is right at the north end of Long Boat Key: Whitney Beach. Although short at around 1/4 mile long, it’s a local hidden gem compared to other beaches.
Coquina (Bradenton) Beach – Picnic Spot (1-2 hours)
Cross the bridge from Longboat Key, and you’ll immediately arrive at Coquina Beach. This natural stretch of natural beach at the very southern tip of Anna Maria Island gets its name from the tiny shells that create it.
The waters that flow through the Pass here are gentle, making it perfect for SUP and kayaking. Weekends can be busy, but weekday late mornings are usually quieter. I love walking the beach, watching people fish, and seeing others enjoying watersports. There is also a small cafe for refreshments and snacks.
Local boats are often moored up in the shallow waters just below the bridge – it’s an ideal spot to jump in and splash around.
This is one of my favorite spots for a picnic lunch on your day trip from Siesta Key to Anna Maria Island. Oak Trees between the parking lot and shoreline provide good shade if you want to keep out of direct sun.
Parking is free, and the beach has bathroom and lifeguard facilities. Check the official Coquina Beach site for up to date service times.
🎒Our Tip: On windy days, the fine sand can get everywhere. So you might prefer to wait and eat in Cortez, or sit at tables just of the beach.
Cortez Beach and Bridge Street (1-2 hours)
Drive 1.4 miles from Coquina Beach, and you’ll start see some beach homes on stilts. Things start to feel a little more “old Florida” and less developed, giving you a glimpse into the island’s historic charm.
If you fancy a wander, park near Bridge Street and explore the shops until you reach Anna Maria Oyster Bar. Whenever we visit, we wait to get a seat outdoors on the deck – it’s fun watch pelicans dive for lunch.
Locals boats come and go, dolphins often play around here – the atmosphere is relaxed.
🎒Our Tip: Parking can test your patience — but if you find a spot, it’s worth taking an hour to explore, or a little longer if you eat lunch. An alternative is to stop here on your return drive to Siesta Key.
Gulf Drive Cafe, located right on the beach, offers a bright and welcoming casual bar and restaurant if you prefer this vibe! They outdoor patio area is great to sit at with an early bird cocktail.
This stop of the drive is a perfect combination of natural coastline, local flavours and relaxing island life – a highlight on any day trip from Siesta Key to Anna Maria Island.
Arriving in Anna Maria Main Village
Keep going north and within minutes you reach Anna Maria Island. Drive down to the main pier area. There is car parking here, but it can be busy, so try a side street nearby as a back up.
There are a number of small shops, cafes and restaurants beside the pier.
Things to Do On Anna Maria Island
Stroll Out to the End of The Pier
There’s been a pier here since 1911, though it has been re-built several times after hurricane damage. The iconic pier we all loved so much was totally decimated in 2024.
Luckily it is being re-built with a re-opening date in 2026. Concrete is replacing some wood structures making it more durable going forward.
Last time we walked here we were entertained by dolphins cavorting in the waters just off the pier.
If you want to be more sure of seeing dolphins or even swim with them, why not head to Crystal River during your trip here. We have a Swimming with Dolphins with all you need to book this once in a lifetime experience.
Anna Maria Pier is also a popular spot for fishing. If it has re-opened when you visit, don’t forget your rod, bait, sunscreen essentials and your patience!
The new facility on the pier looks good, with bathrooms too. We haven’t eaten here yet but for a snack and drink, it looks to fit the bill.
Be Entertained by Pelicans
Spotting pelicans and ospreys are another highlight of this drive along the Florida Coast. Pelicans dive with incredible precision and often show up in larger numbers.
Florida has two types of pelicans – brown and white. The white are nicknamed ‘Snow birds’ as they only show up here in the winter months. Up close, they are large birds but so graceful to watch in the sky. Get your camera or phone ready.
As you drive up from Siesta Key to Anna Maria Island, it’s easy to lose track of how far north you have travelled.
From the shoreline, you can spot the Skyline Bridge that connects St Petersburg and Manatee County in the distance (ie. I-75). A quick reminder that Tampa is just across the water.
Where to Eat In Anna Maria Island
I know we mention food a lot in this day trip but that’s to help you decide where and when to eat. If you are early birds and arrive on Anna Maria Island in the late morning, you’ll have plenty of options for brunch before exploring further.
We like to stop at Ginny’s & Jane E’s Café and Coastal Store — part café, part eclectic store, full of art work, gift ideas, and things you didn’t know you needed.
Their fruit smoothies and coffees are excellent, and everything is made to order — so don’t rush. It’s the kind of place to linger over your order and end up browsing longer than you planned. They have on-site parking as well as spaces right on the road outside the entrance.
Just steps from the historic pier area is The Waterfront Restaurant, one of the island’s most popular dining spots. We’ve eaten here many times, and it’s one of our go-to spots for a celebration meal.
The menu is consistently excellent, and the wine list is surprisingly strong for a small island restaurant.
(If you’re heading back south later, Ophelia’s on Siesta Key is another favourite of ours for a special occasions.) Pre-book for water-facing tables at both restaurants.
If your idea of the perfect Gulf Coast late lunch or early evening dinner, involves toes in the sand, head to The Sandbar Restaurant. For me, it’s one of the best sunset spots on the island, and we’ve always found the food and service reliably good.
Shore Restaurant on Long Boat Key is definitely worth considering if you want to wait and eat nearer Siesta Key on your return trip.
Finally, if you prefer, return to Sarasota via I-75 Highway. Just cross the bay from Holmes Beach, or Bridge Street, but make sure you avoid rush hour.
FAQs
Yes, Anna Maria Island is easily accessible by car. From Tampa International Airport, take I-275 south across the Sunshine Skyway Bridge (toll). The drive is approximately 55 miles and typically takes around one hour, depending on traffic.
That’s a tough question. Both islands have amazing beaches and casual dining. As locals, we feel Siesta Beach is better for families, with excellent facilities and so much beach space. Anna Maria has better waterfront dining options and is perhaps better suited for couples looking for a quieter place.
Yes, Anna Maria Island is considered a very safe destination for visitors, and has a relaxed, family-friendly atmosphere. During hurricane season (June to November), it’s important to monitor weather forecasts and local advisories before traveling.
Anna Maria Island is 28 miles from Siesta Key, taking around 1 hour to drive if not stopping. It is best done by car as public transport is limited on this coastal route.
Is the Drive from Siesta Key to Anna Maria Worth It?
Absolutely. What we love most about the drive from Siesta Key to Anna Maria Island is that it is so much more than an A-B journey – it always feels like a full day out.
You can sample world class beaches, mingle with locals in charming restaurants and cafes, soak in coastal views, and slow down away from busy highways and city centers.
If you’re on a multi-generational trip to the area, check our guide to Kid-Friendly Things to Do in Siesta Key, written after planning adventures for my own grandkids.
For more Sarasota experiences, see our guides on:
We hope you can take this leisurely drive soon. As locals, this is still one of our favorite day drives — and that says a lot!
