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Henry & Caroline

Saturday, July 11, 2026 • Longboat Key, Florida

Henry & Caroline

Saturday, July 11, 2026 • Longboat Key, Florida

St. Armands Circle

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300 Madison Dr, Sarasota, FL 34236, USA

An iconic destination just minutes from Longboat Key, St. Armands Circle is known for its upscale boutiques, art galleries, and vibrant dining scene. With palm-lined streets, European-inspired charm, and lively energy day or night, it’s the perfect spot for shopping, dining, and enjoying the Sarasota coastal atmosphere


• Columbia Restaurant - A historic Florida favorite offering classic Spanish cuisine in a timeless setting


Blu Kouzina - A refined Mediterranean restaurant known for elevated Greek cuisine and an intimate atmosphere

Robinson Preserve

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1704 99th St NW, Bradenton, FL 34209, USA

A favorite spot for runners and outdoor enthusiasts, Robinson Preserve offers miles of well-maintained trails with beautiful coastal views. The scenic loop paths wind through mangroves and open wetlands, making it ideal for an easy run, long walk, or active morning surrounded by nature

Local Beaches

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Beer Can Island - A local beach known for its natural beauty, wide sandy shoreline, and unique driftwood


Longboat Key Beach - Quiet and pristine, perfect for relaxing walks along the Gulf


Coquina Beach - Wide white-sand beach with shaded picnic areas and amenities


Bean Point - Peaceful shoreline at the north end of Anna Maria Island, known for stunning sunsets

Anna Maria Island

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The Sandbar Restaurant - A classic beachfront favorite on Anna Maria Island, known for fresh seafood, open-air dining, and sunset views


Ginny & Jane E’s Cafe and Coastal Store - A beloved spot for breakfast and lunch with a charming boutique and relaxed, waterside feel


The Waterfront Restaurant - A bayside restaurant offering coastal cuisine in a relaxed yet refined setting with scenic water views


Pine Avenue - A charming, walkable street on Anna Maria Island lined with boutiques, cafés, and local shops


Bridge Street - Full of Old Florida charm, with local shops, casual dining, and ice cream near the water

Drinks & Nightlife

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Cha Cha Coconuts - A lively, tropical spot known for colorful cocktails and a fun, upbeat atmosphere


Daiquiri Deck - A casual favorite for frozen drinks and relaxed island energy


Tommy Bahama Restaurant & Bar - A polished setting for cocktails, live music, and a classic island vibe

Henry & Caroline's Favorites

Picture of Henry & Caroline's Favorites

• The Shore Longboat Key - Located on Longboat Key, a perfect spot for lunch or dinner with elevated coastal cuisine


Poppo’s Taqueria - A casual favorite located on Pine Avenue, known for fresh, simple tacos and bowls


North Shore Cafe - Located on Pine Avenue, a go-to spot for coffee, breakfast, and easy lunches


Green Zebra Cafe - An organic café in St. Armands Circle offering fresh, health-forward options