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10 Days of Beach Bliss and Relaxation Itinerary

Last updated: 2024 Jun 14

Welcome to Treasure Island

Morning

Start your first day with a leisurely breakfast at The Floridian. This cozy spot offers a great selection of morning favorites to fuel up for the day. After breakfast, head over to the beach and soak in the sun while enjoying the pristine sands and clear waters of Treasure Island Beach. It's a perfect way to start your vacation by relaxing and getting into the island vibe.

Afternoon

In the afternoon, embark on an exciting adventure with Madeira Beach Pirate Adventure Cruise with Beer and Wine. This unique experience allows you to explore the waters around Treasure Island while enjoying some refreshing beverages. The pirate-themed cruise is both fun and informative, offering insights into local history and marine life.

Evening

As evening approaches, take a short drive to St. Petersburg for a delightful dinner at The Mill Restaurant. Known for its creative dishes and vibrant atmosphere, it's an excellent choice for ending your first day on a high note. After dinner, unwind with a stroll along St. Pete Beach or enjoy some live music at one of the local bars.

Bedtime

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4.81
Madeira Beach Pirate Adventure Cruise with Beer and Wine
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Treasure Island Thrills

Morning

Start your day with a delightful breakfast at Sweet Sage Cafe, known for its charming garden setting and delicious morning fare. After breakfast, head to the beach for some relaxation and sunbathing. Treasure Island Beach is perfect for unwinding and enjoying the beautiful Gulf Coast.

Afternoon

For lunch, visit Caddy's Treasure Island, a beachfront restaurant offering tasty dishes and refreshing drinks. In the afternoon, embark on an exciting activity from your wishlist: Clearwater Beach Dolphin and Island Sandbar Boat Tour. This tour provides an opportunity to see playful dolphins in their natural habitat and explore pristine sandbars.

Evening

As evening approaches, dine at Middle Grounds Grill, renowned for its seafood and steak dishes. After dinner, join another thrilling activity from your wishlist: Clearwater Sunset Celebration Cruise. Enjoy breathtaking views of the sunset over Clearwater Beach while sipping on a cocktail.

Bedtime

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4.75
Clearwater Beach Dolphin and Island Sandbar Boat Tour
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4.53
Clearwater Sunset Celebration Cruise
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Exploring Sarasota's Wonders

Morning

Begin your second day with breakfast at Station 400, a charming cafe known for its delicious brunch options. Afterward, visit Mote Marine Laboratory and Aquarium, where you can learn about marine life through interactive exhibits and see fascinating creatures up close.

Afternoon

For lunch, head over to Indigenous Restaurant, which offers farm-to-table cuisine in a beautiful setting. In the afternoon, enjoy an exciting activity from your wishlist: Anna Maria Island The Island Kayak Tour. Paddle through serene waters while taking in stunning views of Anna Maria Island's natural beauty.

Evening

In the evening, dine at Euphemia Haye Restaurant, renowned for its gourmet dishes and romantic ambiance. After dinner, consider joining Sarasota Evening Sip and Dine Tour to explore Sarasota's culinary scene further while enjoying some fine wines.

Bedtime

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5.00
Mote Marine Laboratory and Aquarium
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5.00
Anna Maria Island The Island Kayak Tour
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Exploring Sarasota's Hidden Gems

Morning

Begin your day with breakfast at Another Broken Egg Cafe, known for its creative breakfast dishes and cozy atmosphere. Afterward, visit Marie Selby Botanical Gardens, where you can explore beautiful gardens filled with exotic plants and flowers.

Afternoon

For lunch, head over to Owen's Fish Camp, offering Southern-style seafood in a charming setting. In the afternoon, enjoy an exciting activity from your wishlist: Robinson Preserve Mangrove Tour. Paddle through mangrove tunnels and observe diverse wildlife in this pristine natural preserve.

Evening

In the evening, dine at Michael's On East, an award-winning restaurant known for its sophisticated menu and elegant ambiance. After dinner, consider joining Sarasota Taste of Downtown Food Tour to explore more of Sarasota's culinary delights while learning about its history.

Bedtime

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4.88
Marie Selby Botanical Gardens
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5.00
Robinson Preserve Mangrove Tour
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Sarasota Cultural Delights

Morning

Begin your day with breakfast at First Watch, known for its healthy and delicious morning options. Afterward, visit The Ringling, where you can explore art galleries, beautiful gardens, and the historic Ca' d'Zan Mansion.

Afternoon

For lunch, head over to Duval's Fresh Local Seafood, offering fresh seafood dishes in a relaxed setting. In the afternoon, enjoy an exciting activity from your wishlist: Sarasota Ultimate Adventure. This adventure includes various thrilling activities such as zip-lining or paddleboarding.

Evening

In the evening, dine at The Capital Grille, an upscale restaurant known for its fine dining experience. After dinner, consider joining another popular activity: Sarasota Evening Sip and Dine Tour to explore Sarasota's culinary scene further while enjoying some fine wines.

Bedtime

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4.81
The Ringling
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Sarasota Ultimate Adventure
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Siesta Key Serenity

Morning

Kick off your third day with breakfast at Sun Garden Cafe, known for its fresh ingredients and friendly atmosphere. Then head over to Siesta Key Beach, famous for its powdery white sand that feels like walking on sugar. Spend your morning lounging by the water or taking a refreshing swim.

Afternoon

For lunch, try out The Cottage, offering delicious seafood dishes in a relaxed setting. In the afternoon, embark on another thrilling activity from your wishlist: Bradenton Anna Maria Island Guided Kayaking Manatee Tour. This guided tour provides an opportunity to see manatees up close as you paddle through their natural habitat.

Evening

As evening falls, enjoy dinner at Captain Curt's Crab & Oyster Bar, where you can savor fresh seafood in a casual atmosphere. To end your day on a magical note, join the popular activity: Sarasota Sunset Charter, which offers breathtaking views of the sunset over Sarasota Bay.

Bedtime

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4.94
Bradenton Anna Maria Island Guided Kayaking Manatee Tour
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Sarasota Sunset Charter
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Siesta Key Relaxation

Morning

Kick off your day with breakfast at Toasted Mango Cafe, offering fresh and flavorful morning options. Then head over to Siesta Key Beach once again to relax by the water or take part in some beach activities like volleyball or paddleboarding.

Afternoon

For lunch, try out Snicky Snacky Shack, known for its tasty sandwiches and laid-back vibe. In the afternoon, embark on another thrilling activity from your wishlist: Osprey Guided Dolphin and Manatee SUP or Kayaking Tour. This guided tour provides an opportunity to see dolphins and manatees up close as you paddle through their natural habitat.

Evening

As evening falls, enjoy dinner at The Cottage once again but this time savor different dishes from their diverse menu. To end your day on a magical note, join another popular activity: Sarasota Sunset Charter, which offers breathtaking views of the sunset over Sarasota Bay.

Bedtime

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3.91
Osprey Guided Dolphin and Manatee SUP or Kayaking Tour
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Sarasota Sunset Charter
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Siesta Key Escapades

Morning

Kick off your day with breakfast at Breakfast House, offering hearty morning meals in a cozy setting. Then head over to Siesta Key Beach once again to relax by the water or take part in some beach activities like volleyball or paddleboarding.

Afternoon

For lunch, try out The Hub Baja Grill, known for its vibrant atmosphere and delicious Mexican cuisine. In the afternoon, embark on another thrilling activity from your wishlist: Bradenton Guided Pedal Kayak Tour. This guided tour provides an opportunity to see diverse wildlife as you pedal through scenic waterways.

Evening

As evening falls, enjoy dinner at Summer House Steak & Seafood, where you can savor gourmet dishes in an elegant setting. To end your day on a magical note, join another popular activity: Sarasota Sunset Charter, which offers breathtaking views of the sunset over Sarasota Bay.

Bedtime

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5.00
Bradenton Guided Pedal Kayak Tour
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Sarasota Sunset Charter
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Anna Maria Island Adventures

Morning

Start your day with a hearty breakfast at Ginny's & Jane E's Cafe, a local favorite known for its eclectic decor and delicious pastries. Afterward, head to the beach to enjoy the serene beauty of Anna Maria Island. Spend your morning soaking up the sun, swimming in the clear waters, or taking a leisurely walk along the shore.

Afternoon

For lunch, visit The Sandbar Restaurant, which offers beachfront dining with stunning views. In the afternoon, embark on an exciting activity from your wishlist: Anna Maria Island and Bradenton Beach Parasailing Tour. Experience the thrill of parasailing while enjoying panoramic views of the island and its surroundings.

Evening

As evening approaches, dine at Beach Bistro, renowned for its gourmet cuisine and romantic setting right on the beach. After dinner, unwind with a stroll along Pine Avenue or visit one of the local bars for a nightcap.

Bedtime

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5.00
Anna Maria Island and Bradenton Beach Parasailing Tour
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Farewell to Anna Maria Island

Morning

Start your final day with a delicious breakfast at The Donut Experiment, where you can customize your own donuts with a variety of toppings. Afterward, take a leisurely stroll along the beach and enjoy the serene beauty of Anna Maria Island one last time. The morning is perfect for reflecting on your trip and soaking in the peaceful atmosphere.

Afternoon

For lunch, visit Waterfront Restaurant, offering fresh seafood and stunning views of the bay. In the afternoon, embark on an exciting activity from your wishlist: Anna Maria Island and Bradenton Sunset Kayak Dolphin Tour. This tour provides an opportunity to see playful dolphins as you paddle through scenic waters, making it a memorable way to end your vacation.

Evening

As evening approaches, dine at Blue Marlin Seafood Restaurant, known for its fresh catch and charming ambiance. After dinner, take one last walk along Pine Avenue or relax at one of the local bars for a nightcap. It's the perfect way to say goodbye to Anna Maria Island and reflect on all the wonderful memories you've made during your trip.

Bedtime

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