Ultimate 21-Day Siesta Key Culinary Journey Itinerary

Wake up to the sound of waves and grab a hearty breakfast at Sarasota Surf and Racquet Club Beachfront Resort - Tiki Bar, where you can enjoy your meal with your toes in the sand. Post-breakfast, visit the Mote Marine Laboratory & Aquarium to learn about the local marine life and conservation efforts.

For lunch, head to Captain Curt's Crab & Oyster Bar, a Siesta Key institution, and indulge in their famous seafood platter. Afterward, spend a relaxing afternoon at Point of Rocks, a prime spot for snorkeling and beachcombing.

Dine at Clayton's Siesta Grille, known for its elegant atmosphere and diverse menu. After dinner, take a guided Turtle Beach kayak tour with Almost Heaven Kayak Adventures, where you may spot dolphins and other marine life in their natural habitat.

Start your day with a breakfast at Anna's Deli Siesta Key Village Market & Deli Inc., a local favorite for their fresh bagels and coffee. After breakfast, explore the charming Siesta Key Village, browsing the shops and art galleries.

Enjoy a casual lunch at Big Water Fish Market, where you can savor the catch of the day in a relaxed, waterfront setting. Post-lunch, take a guided Siesta Key Paddleboards tour through the mangrove tunnels and serene waterways of the island.

For dinner, experience the vibrant atmosphere and eclectic menu at The Hub Baja Grill, known for its innovative Baja cuisine. Afterward, join the Siesta Key Drum Circle at Siesta Beach, a local tradition where musicians and spectators gather to celebrate the sunset with live music and dancing.

Enjoy a leisurely breakfast at Sun Garden Cafe, a hidden gem with a lush garden setting. After breakfast, visit the Siesta Key Farmers Market to explore local produce, artisanal goods, and live music.

Have a relaxed lunch at Toasted Mango Cafe, known for its tropical-inspired dishes and refreshing drinks. Spend your afternoon at Siesta Key Rum, where you can take a tour of the distillery and sample their handcrafted spirits.

Dine at Cafe Gabbiano, an elegant Italian restaurant with a romantic ambiance. After dinner, enjoy a moonlit Siesta Key Ghost Tour with Sarasota Suncoast Tours, where you'll hear spooky stories and local legends as you explore the island after dark.

Start your day with a breakfast at The Old Salty Dog - Siesta Key, a laid-back spot with a menu featuring classic pub fare. After breakfast, visit the Sarasota Classic Car Museum to admire a collection of vintage automobiles.

For lunch, head to Blasé Cafe & Martini Bar, where you can enjoy a sophisticated meal paired with one of their signature martinis. Afterward, take a guided Siesta Key Bike and Kayak eco-tour to explore the island's natural beauty.

Dine at Miguel's Restaurant, a family-owned establishment known for its authentic Mexican cuisine and lively atmosphere. End the evening with a live performance at The Players Centre for Performing Arts, showcasing local talent in a variety of productions.

Enjoy a leisurely breakfast at Sniki Tiki at Captain Curt's Village, a tropical oasis with a menu of breakfast favorites. After breakfast, spend a relaxing morning at Siesta Key Public Beach Access 2, where you can sunbathe, swim, or simply unwind with a good book.

For lunch, visit Gilligan's Island Bar & Grill, a casual spot with a menu of island-inspired dishes. Post-lunch, pamper yourself with a spa treatment at The Met Day Spa & Salon, located in the heart of Siesta Key Village.

Dine at Turtles on Little Sarasota Bay, a waterfront restaurant offering a menu of fresh seafood and panoramic views. After dinner, take a moonlit Siesta Key Gondola cruise with Sarasota Tiki Tours, complete with music and sparkling lights.

Start your day with a breakfast at Subway Restaurants - Siesta Key Village, where you can customize your morning meal to your liking. After breakfast, take a guided Siesta Key Beach Yoga session with Siesta Key Beach Yoga, rejuvenating your mind and body with the sound of the waves.

Enjoy a casual lunch at Siesta Key Village Market & Deli Inc., a local deli offering a variety of sandwiches and snacks. Spend your afternoon at Siesta Key Marina, where you can rent a boat or join a fishing charter to explore the waters surrounding the island.

Dine at The Cottage, a Siesta Key staple known for its fresh, seasonal menu and charming ambiance. After dinner, take a leisurely Siesta Key Sunset Cruise with Key Sailing, sipping on wine and enjoying the colors of the sky as the sun sets over the Gulf.

Begin your day with a delightful breakfast at The Cottage, where you can enjoy the morning breeze in their outdoor seating area. Post-breakfast, take a morning walk at Siesta Key Public Beach Access 3, a serene spot with beautiful views.

For lunch, head to Siesta Key Oyster Bar (SKOB) and try their famous fish tacos along with a refreshing drink. After lunch, spend your afternoon at Siesta Key Public Beach Access 4, known for its calm waters and family-friendly atmosphere.

Dine at Clayton's Siesta Grille, an upscale restaurant with a diverse menu and a great wine selection. After dinner, take a romantic Siesta Key Horseback Riding excursion with Siesta Key Horseback Riding, riding along the shoreline as the sun dips below the horizon.

Enjoy a sumptuous breakfast at Sun Garden Cafe, surrounded by lush greenery and the morning sun. After breakfast, take a peaceful morning walk at Siesta Key Public Beach Access 5, where you can collect shells and enjoy the gentle waves.

Head to Captain Curt's Crab & Oyster Bar for a classic seafood lunch, and then spend your afternoon at Siesta Key Public Beach Access 6, a less crowded spot where you can relax and soak in the island vibes.

Dine at Miguel's Restaurant, a lively eatery with a vibrant atmosphere and authentic Mexican cuisine. After dinner, take a guided Siesta Key Pub Crawl with Sarasota Suncoast Tours, exploring the local bar scene and enjoying a variety of drinks.

Start your day with a breakfast at The Old Salty Dog - Siesta Key, a casual spot with a menu of breakfast favorites. After breakfast, spend your morning at Siesta Key Public Beach Access 7, soaking in the sun and the vibrant beach atmosphere.

Enjoy a beachside lunch at Blasé Cafe & Martini Bar, where you can savor a delicious meal with a view of the ocean. Post-lunch, take a Siesta Key Parasailing adventure with Key Sailing, soaring above the crystal-clear waters and enjoying panoramic views of the coastline.

Dine at Gilligan's Island Bar & Grill, a laid-back restaurant with a menu of island-inspired dishes. After dinner, experience the lively Siesta Key Nightlife with a visit to the local bars and entertainment venues in Siesta Key Village.

Begin your day with a breakfast at Sniki Tiki at Captain Curt's Village, a tropical spot with a menu of morning delights. After breakfast, take a morning stroll at Siesta Key Public Beach Access 8, enjoying the soft sand and the sound of the waves.

Have a casual lunch at Big Water Fish Market, where you can enjoy the catch of the day in a relaxed setting. After lunch, visit Siesta Key Public Beach Access 9, a less crowded beach spot where you can unwind and bask in the sun.

Dine at Turtles on Little Sarasota Bay, a waterfront restaurant offering a menu of fresh seafood and local favorites. After dinner, enjoy a Siesta Key Live Music performance at one of the local venues, immersing yourself in the island's musical scene.

Start your day with a breakfast at Anna's Deli Siesta Key Village Market & Deli Inc., a local favorite for their morning offerings. After breakfast, head to Siesta Key Public Beach Access 10 for a morning of sun, sand, and relaxation.

For lunch, visit Toasted Mango Cafe, known for its tropical-inspired dishes and refreshing drinks. Post-lunch, embark on a Siesta Key Snorkeling excursion with Key Sailing, exploring the vibrant underwater world of the Gulf of Mexico.

Dine at Cafe Gabbiano, an elegant Italian restaurant with a romantic ambiance. After dinner, take a Siesta Key Sunset Kayaking tour with Almost Heaven Kayak Adventures, paddling along the calm waters as the sun sets on the horizon.

Enjoy a delightful breakfast at Subway Restaurants - Siesta Key Village, where you can customize your morning meal. After breakfast, visit the Sarasota Jungle Gardens to encounter exotic animals and lush tropical vegetation.

For lunch, head to Siesta Key Village Market & Deli Inc., a local deli offering a variety of sandwiches and snacks. Afterward, take a guided Siesta Key Fishing Charter with Siesta Key Fishing Charters, trying your luck at catching some of the Gulf's finest fish.

Dine at The Cottage, a Siesta Key staple known for its fresh, seasonal menu and charming ambiance. After dinner, enjoy a Siesta Key Night Kayaking adventure with Almost Heaven Kayak Adventures, paddling through the mangroves under the starlit sky.

Start your day with a breakfast at The Cottage, where you can enjoy the morning breeze in their outdoor seating area. Post-breakfast, take a morning walk at Siesta Key Public Beach Access 11, a serene spot with beautiful views.

For lunch, head to Siesta Key Oyster Bar (SKOB) and try their famous fish tacos along with a refreshing drink. After lunch, spend your afternoon at Siesta Key Public Beach Access 12, known for its calm waters and family-friendly atmosphere.

Dine at Clayton's Siesta Grille, an upscale restaurant with a diverse menu and a great wine selection. After dinner, take a romantic Siesta Key Horseback Riding excursion with Siesta Key Horseback Riding, riding along the shoreline as the sun dips below the horizon.

Enjoy a sumptuous breakfast at Sun Garden Cafe, surrounded by lush greenery and the morning sun. After breakfast, take a peaceful morning walk at Siesta Key Public Beach Access 13, where you can collect shells and enjoy the gentle waves.

Head to Captain Curt's Crab & Oyster Bar for a classic seafood lunch, and then spend your afternoon at Siesta Key Public Beach Access 14, a less crowded spot where you can relax and soak in the island vibes.

Dine at Miguel's Restaurant, a lively eatery with a vibrant atmosphere and authentic Mexican cuisine. After dinner, take a guided Siesta Key Pub Crawl with Sarasota Suncoast Tours, exploring the local bar scene and enjoying a variety of drinks.

Begin your day with a breakfast at Sniki Tiki at Captain Curt's Village, a tropical spot with a menu of morning delights. After breakfast, take a morning stroll at Siesta Key Public Beach Access 15, enjoying the soft sand and the sound of the waves.

Have a casual lunch at Big Water Fish Market, where you can enjoy the catch of the day in a relaxed setting. After lunch, visit Siesta Key Public Beach Access 16, a less crowded beach spot where you can unwind and bask in the sun.

Dine at Turtles on Little Sarasota Bay, a waterfront restaurant offering a menu of fresh seafood and local favorites. After dinner, enjoy a Siesta Key Live Music performance at one of the local venues, immersing yourself in the island's musical scene.

Start your day with a breakfast at The Old Salty Dog - Siesta Key, a casual spot with a menu of breakfast favorites. After breakfast, spend your morning at Siesta Key Public Beach Access 17, soaking in the sun and the vibrant beach atmosphere.

Enjoy a beachside lunch at Blasé Cafe & Martini Bar, where you can savor a delicious meal with a view of the ocean. Post-lunch, take a Siesta Key Parasailing adventure with Key Sailing, soaring above the crystal-clear waters and enjoying panoramic views of the coastline.

Dine at Gilligan's Island Bar & Grill, a laid-back restaurant with a menu of island-inspired dishes. After dinner, experience the lively Siesta Key Nightlife with a visit to the local bars and entertainment venues in Siesta Key Village.

Enjoy a delightful breakfast at Subway Restaurants - Siesta Key Village, where you can customize your morning meal. After breakfast, visit the Sarasota Jungle Gardens to encounter exotic animals and lush tropical vegetation.

For lunch, head to Siesta Key Village Market & Deli Inc., a local deli offering a variety of sandwiches and snacks. Afterward, take a guided Siesta Key Fishing Charter with Siesta Key Fishing Charters, trying your luck at catching some of the Gulf's finest fish.

Dine at The Cottage, a Siesta Key staple known for its fresh, seasonal menu and charming ambiance. After dinner, enjoy a Siesta Key Night Kayaking adventure with Almost Heaven Kayak Adventures, paddling through the mangroves under the starlit sky.