Explore the Islands...
We truly believe that a kayak adventure is the best way to experience the islands… but when you are forced to be off the water, try the activities we’ve listed below. We’ve been on the islands all our lives and have come to know and love many of the local hospitality businesses. Start exploring this unique place and discover the lodging, restaurants, and activities that have made us smile over the years! For a truly amazing authentic Florida experience, make sure to check out this Sustainable Island Travel Guide.
Introduction to the Islands
Anna Maria Island is known for its gorgeous beaches and clear waters, so if this is on your itinerary, kick off your flip-flops and get ready to fall in love with this salty little island! Explore things to do in Anna Maria Island...
Longboat Key is celebrated for its refined, yet "salty" lifestyle that savors a refined quality of life. This is one absolutely beautiful corner of the world and you don’t want to miss the best that this island has to offer. Explore things to do in Longboat Key...
While the islands often get most of the attention, some of the best places to explore around Sarasota Bay are actually just across the bridge! We have curated some adventures that will whisk you away to a nature-lover's paradise. Explore things to do in Sarasota & Bradenton...
Things to Do (off the water):
Anna Maria Island
Even though Anna Maria Island is only about 7 miles long, it’s actually comprised of three different cities: Anna Maria at the north end, Holmes Beach in the middle, and Bradenton Beach at the south end. Each of these cities has a unique character and are all well worth exploring. Read on for descriptions of each…
The north end of Anna Maria Island is beloved for its old & new island charm. At the heart of Anna Maria City is Pine Avenue, a recently revitalized thoroughfare lined with shops, eateries, bicycle rentals, and vacation rental homes. Pine Avenue is one of the most walkable streets on the island and has been hailed as a prime example of sustainable design, with newly constructed “green” buildings that are easy on energy and water consumption. At the northeast end of Pine Ave is the historic Anna Maria City Pier, completely rebuilt after being destroyed in 2017 by Hurricane Irma. What a great place for a view of Tampa Bay! Poppo’s Taqueria is a favorite local restaurant for Mexican-inspired deliciousness that uses only the freshest ingredients (often local and organic). Fair warning: their made-to-order chips are addictive! The Donut Experiment is also on Pine Avenue and shouldn’t need much of an introduction – order the donut of your wildest dreams with choices like key lime, sea salt, and bacon! At the southwest end of Pine Ave is the Gulf of Mexico, where the beach has that famous white sand that squeaks when you walk on it. Keep walking the beach to the northern tip of the island to Bean Point – perfect for a long walk on the sugar-white sand while you ponder just how awesome life (and that donut) is. Back to map
Holmes Beach has plenty of amazing beach-front bungalows, (one of our favorites is Cedar Cove Resort) and is also considered the island’s center of commerce, with the grocery store, gas station, as well as plenty of great restaurants. Check out West Coast Surf Shop, the oldest surf shop on Florida’s west coast, located right next to the main entrance to Manatee Beach, the main public beach on the island. Back to map
Bradenton Beach is a bustling part of the island and has a long history as the barefoot, beach-loving community. Its “city center” is the historic Bridge Street, with restaurants and shops squished into a very walkable space that is just across the street from the beautiful white sands of Cortez Beach. But before heading to the beach, make your way to the other end of Bridge Street and grab an amazing lunch on the pier at AMOB (Anna Maria Oyster Bar) – the reviews are correct – this place is awesome! And if you’re on Bridge Street in the morning, try the Island Creperie for a delicious French breakfast. Make your way to the beach and you’ll easily spot what locals call the “Three Piers“. Aptly named for the three piers that jut out into the Gulf of Mexico, this has been a surfer’s hotspot for decades (so enjoy the show if there are waves!) and is fun to walk out on any time. Leffis Key has a small but excellent boardwalk trail through the mangroves – so cool to explore the mangrove forest on one side of the island and then cross the street back to the white-sand beach! At the very south end of AMI is Coquina Beach, with its shaded walking trails, picnic tables, plenty of parking, and of course, award-winning white sand beach stretching all the way to the tip of the island. The south end of Anna Maria Island is the best area for enjoying the beautiful outdoors because there are plenty of beaches, sandbars, and mangrove islands to explore. And the marine life here at the south end is incredible, which is one of the reasons we launch many of our kayak tours here! Back to map
Heading to beautiful Longboat Key and wondering what fun you can have on your visit? Longboat Key has some of the most pristine mangrove islands along Florida’s West Coast. Based on our long history here, we’ve curated a list of some of the best things to do on Longboat Key. Whether you are looking to laze on the white sand beaches, tickle your taste buds, or spend time on the water, this guide will help you find that perfect experience.
At the north end of the island, the historic Longbeach Village (known locally just as “the Village”) is full of that old Florida charm we’ve grown up with… literally, this is where we grew up! Peacocks roam the streets, kayakers weave through the waterways, and hard-swept cottages peak out of patches of mangrove jungle. Back to map
Ok, when you’re ready to be back on the water, come out and paddle with us! We really do believe it is the BEST way to see this beautiful island! Longboat Key has some of the most pristine mangrove islands along Florida’s West Coast, so if you are seeking a laid back, family-friendly adventure, you will find it here. Happy Paddler’s guided kayak tours are consistently ranked the #1 adventure on AMI and LBK for a good reason… we pour our heart and soul into every tour, making each one absolutely unique and unforgettable. Back to map
At Longboat Key’s newly renovated Bayfront Park, you’ll find something to keep everyone in your group happy! A playground, tennis, pickleball, and basketball courts, walking trails, and a kayak rental pavilion could easily provide a whole day’s fun. Paddlers can traverse around the mangrove forests of the Town Islands, spot manatees and dolphins, and paddle around the Audubon Sanctuary Islands for a fantastic view of the birds. Or, you can bring your rod and reel and rent one of our premium fishing kayaks to try your luck in this locally famous fishing spot! Back to map
Waterfront restaurants are tucked in nooks across Longboat Key and aim to bring a relaxed + refined coastal vibe to your tummy. One of our favorites is Mar Vista. Located at the north end of the island in the Historic Longbeach Village, this is the best place to experience that perfect blend of authentic Florida charm with a modern (and delicious!) menu. Choose a seat under the shade trees with café lights strung up and watch the birds and boat life go by. Back to map
This “jewel of Sarasota” has been around since the early Sarasota days and continues to draw an eclectic mix of fine artists and gourmet restaurants. Shop St. Armands’ collection of more than luxury and boutique shops to find something unique for friends back home (and for yourself!). This place is perfect see and be seen. Enjoy people-watching while having lunch or dinner at one of the many historic cafe’s… but be sure to save room for a Settimi’s ice cream cone before heading to your next adventure! Back to map
Sarasota & Bradenton
While the islands often get most of the attention, some of the best places to explore around Sarasota Bay are actually just across the bridge! An excellent example is Bradenton’s Robinson Preserve, where you can paddle through the maze of mangrove trees and experience Florida’s unique “water forests” that are home to friendly manatees, the famous jumping mullet, an incredible diversity of birds, and so many more of our favorite wildlife friends! Back to map
Island Visitor's Guide
Check out our guide on things to do during your visit to Anna Maria Island and Longboat Key that will leave the people and places you visit even happier than you found them. However you choose to enjoy the islands of Sarasota Bay, remember to tread lightly so that all can enjoy these islands for generations to come.