undefined Itinerary

Start your day with an adrenaline-filled adventure by booking a Gulf Keys Parasailing Adventure . Soar above the turquoise waters of the Gulf of Mexico and enjoy breathtaking views of Anna Maria Island from above. Afterward, grab a quick bite at Poppo's Taqueria for some tasty Mexican street food.

Explore the local culture by visiting the Anna Maria Island Historical Society Museum. Learn about the island's rich history through exhibits and artifacts. For a unique experience, take a guided dolphin watching eco-friendly cruise from Madeira Beach. Get up close to these majestic creatures in their natural habitat.

Head to Bridge Street in Bradenton Beach for dinner at The Bridge Tender Inn & Dockside Bar. This waterfront restaurant offers a diverse menu with fresh seafood and live music. After dinner, take a sunset cruise to see the Sunshine Skyway Bridge illuminated against the colorful sky.

Start your day with a kayak tour at Shell Key with Capt Yak . Paddle through mangrove tunnels and explore the pristine waters surrounding the island. Afterward, grab a quick snack at Two Scoops Ice Cream for some refreshing treats.

Spend the afternoon at Coquina Beach Park, where you can relax on the sandy shores or take a dip in the Gulf of Mexico. Enjoy a picnic lunch with sandwiches from The Donut Experiment. If you're feeling adventurous, rent a bike from Beach Bums and explore the scenic trails along the coastline.

For dinner, head to The Waterfront Restaurant for waterfront dining with stunning views of Sarasota Bay. Indulge in their delicious seafood dishes and craft cocktails. End your day with a peaceful walk along the beach as you watch the sunset over the horizon.

Start your day by renting a bike from Beach Bums and exploring Anna Maria Island's charming neighborhoods and hidden gems. Stop by Ginny & Jane E's Cafe for a quick breakfast or coffee to fuel your adventure.

Take a catamaran cruise to Egmont Key from St. Petersburg. Explore this uninhabited island known for its historic lighthouse, wildlife, and pristine beaches. Enjoy snorkeling, swimming, or simply relaxing under the sun.

As the day comes to an end, head back to Anna Maria Island and enjoy dinner at The Sandbar Restaurant once again. This time, savor their delicious dishes while watching the sunset over the Gulf of Mexico. End your evening with a beach bonfire and stargazing session on Bean Point Beach.

Start your last day in Anna Maria with breakfast at The Donut Experiment. Customize your own donuts with various toppings and flavors. Afterward, visit the Imagine Museum in St. Petersburg to admire contemporary glass art from around the world.

Spend your final afternoon on a private dolphin watching cruise from St. Petersburg. Enjoy a personalized experience as you search for dolphins and other marine life in the waters of Tampa Bay.

For a memorable farewell dinner, head to The Beach House Restaurant. This waterfront eatery offers stunning views of the Gulf of Mexico and serves delicious seafood dishes made with locally sourced ingredients. Raise a toast to an unforgettable trip as you watch the sun set over the horizon one last time.