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The Pine Ave/N Bay Blvd stop at Anna Maria City Pier is a central hub for the free island trolley, offering easy access to shops, restaurants, and the scenic pier. It's a convenient starting point for exploring the heart of Anna Maria Island.
Sarasota Bradenton International Airport offers convenient access to Florida’s Gulf Coast with a spacious terminal, two runways, and growing airline service, making travel smooth and efficient between Sarasota and Bradenton. It features modern amenities, international customs, and easy connections to popular beaches and attractions.
St. Pete-Clearwater International Airport (PIE) is a convenient, single-level airport serving 65 destinations with short walks from curbside to gates, comprehensive accessibility features including wheelchair assistance and visually impaired services, and amenities like free WiFi, therapy dogs, and pet relief areas.
Sarasota Bradenton International Airport offers a compact, easy-to-navigate terminal with modern amenities, direct flights from major U.S. carriers, and accessible services including wheelchair assistance and pet relief areas, making it a convenient gateway to Florida’s Gulf Coast. Ground transportation and rental cars are readily available.
Gulf Dr/42nd St (Manatee Public Beach) offers convenient access to Anna Maria Island’s most popular beach, with free parking, lifeguards, and nearby amenities, making it an ideal hub for beachgoers and visitors exploring Holmes Beach and the surrounding Gulf Coast.
Enjoy fresh seafood and American favorites with toes-in-the-sand dining or on a covered deck, all set against stunning Gulf views and unforgettable sunsets.
The Ugly Grouper is a lively outdoor restaurant in Holmes Beach offering fresh seafood, especially their famous crispy grouper tacos, paired with live music and a fun, casual island atmosphere perfect for families and friends.
Anna Maria Island Beach Cafe offers casual beachfront dining with a vibrant atmosphere, serving all-you-can-eat pancakes, fresh seafood, and tropical cocktails right by the Gulf. Enjoy live music and stunning views in a relaxed island setting.
Tide Tables Restaurant and Marina serves fresh, classic Florida seafood and American fare right on the water, where daily dockside fish cuts and frequent dolphin visits add to the laid-back, waterfront charm.
Wicked Cantina Bradenton Beach serves fresh Austin-style Tex Mex and American classics with a Gulf view, offering a lively, family-friendly vibe, daily live music, and award-winning margaritas on a spacious patio just steps from the beach.
The Waterfront Restaurant is a premier San Francisco dining destination housed in a converted longshoreman's bar on Pier 7, offering breathtaking views of the Bay and over 50 years of fine seafood cuisine that has attracted presidents, celebrities, and travelers alike.
Anna Maria Oyster Bar on the Pier is a casual waterfront seafood restaurant nestled on the Historic Bridge Street Pier, serving fresh Gulf oysters, fish, and coastal cuisine with stunning 180-degree views of the Intracoastal Waterway and a laid-back Florida atmosphere perfect for any occasion.
Ginny's & Jane E's Cafe and Gift Store offers a cozy, eclectic vibe with a menu of fresh, classic breakfast and lunch dishes alongside a bakery full of homemade treats, all paired with a unique collection of local art and gifts in a charming Old Florida setting.
Manatee Public Beach offers soft white sand, calm Gulf waters, and family-friendly amenities like playgrounds and volleyball courts, making it perfect for sun-seekers, swimmers, and anyone wanting a relaxed Florida beach day.
Anna Maria Island is a charming Old Florida beach destination offering pristine beaches, water sports like kayaking and paddleboarding, dolphin-watching tours, and a quaint historic village atmosphere perfect for families and nature lovers seeking relaxation and adventure.
Robinson Preserve is a stunning 600-acre coastal sanctuary in Bradenton featuring scenic hiking and biking trails, kayak paddling through mangrove tunnels, and an iconic observation tower with panoramic Tampa Bay views—perfect for nature lovers, families, and adventure seekers of all ages.
Anna Maria Island Beach offers soft, sugar-white sand and gentle waves, perfect for swimming, sunbathing, or simply unwinding in a laid-back tropical setting. Anyone seeking a classic Florida beach escape will love its natural beauty and relaxed vibe.
Holmes Beach offers a perfect blend of sun-soaked beaches, exciting water adventures like kayaking, jet skiing, and snorkeling, plus charming local shops and family-friendly activities, making it ideal for nature lovers, adventure seekers, and families looking for a relaxing island escape.
Bean Point Beach is a hidden gem at the northern tip of Anna Maria Island where the Gulf of Mexico meets Tampa Bay, offering a peaceful escape with stunning turquoise waters, pristine white sand, and spectacular sunset views—perfect for travelers seeking solitude and natural beauty away from crowded beaches.
Sink your toes into soft white sand and enjoy calm, clear waters perfect for swimming and sunbathing at Coquina Beach. Families and couples love its relaxed vibe, scenic bike paths, and chances to spot dolphins and sea turtles.
Palma Sola Botanical Park is a peaceful 10-acre oasis in Bradenton, Florida, where nature lovers can explore rare fruit trees, vibrant butterfly gardens, and native wildlife along scenic walking paths. It’s perfect for photographers, families, and anyone seeking a tranquil outdoor escape.
Experience the thrill of horseback riding on a pristine Florida beach, where you'll swim alongside gentle rescue horses and spot dolphins and manatees in their natural habitat. Perfect for adventure seekers and animal lovers alike, this unique activity combines relaxation with unforgettable aquatic excitement.
De Soto National Memorial offers a unique blend of rich history and outdoor adventure, perfect for history buffs and nature lovers alike. Explore immersive exhibits, scenic trails, ranger-led kayak tours, and living history camps in a peaceful waterfront setting.
| Date | Price (USD, excl. fees and taxes) | Availability |
|---|---|---|
| Nov 24, 2025 | $4566 | Not Available |
| Nov 25, 2025 | $3400 | Not Available |
| Nov 26, 2025 | $4830 | Not Available |
| Nov 27, 2025 | N/A | Not Available |
| Nov 28, 2025 | $3534 | Not Available |
| Nov 29, 2025 | $2182 | Not Available |
| Nov 30, 2025 | $2125 | Not Available |
| Dec 1, 2025 | $2210 | Not Available |
| Dec 2, 2025 | $2238 | Not Available |
| Dec 3, 2025 | $2322 | Not Available |
| Dec 4, 2025 | $2463 | Not Available |
| Dec 5, 2025 | $2463 | Not Available |
| Dec 6, 2025 | $2407 | Available |
| Dec 7, 2025 | $2322 | Available |
| Dec 8, 2025 | $2351 | Available |
| Dec 9, 2025 | $2407 | Available |
| Dec 10, 2025 | $2379 | Available |
| Dec 11, 2025 | $2294 | Available |
| Dec 12, 2025 | $2238 | Available |
| Dec 13, 2025 | $2238 | Available |
| Dec 14, 2025 | $2238 | Available |
| Dec 15, 2025 | $2266 | Available |
| Dec 16, 2025 | $2294 | Available |
| Dec 17, 2025 | $2294 | Available |
| Dec 18, 2025 | $2266 | Available |
| Dec 19, 2025 | $3904 | Available |
| Dec 20, 2025 | $5571 | Available |
| Dec 21, 2025 | $5571 | Available |
| Dec 22, 2025 | $5640 | Available |
| Dec 23, 2025 | $4995 | Available |
| Dec 24, 2025 | $5709 | Available |
| Dec 25, 2025 | N/A | Not Available |
| Dec 26, 2025 | N/A | Not Available |
| Dec 27, 2025 | $9159 | Not Available |
| Dec 28, 2025 | $9251 | Not Available |
| Dec 29, 2025 | $9251 | Not Available |
| Dec 30, 2025 | $9343 | Not Available |
| Dec 31, 2025 | N/A | Not Available |
| Jan 1, 2026 | N/A | Not Available |
| Jan 2, 2026 | N/A | Not Available |
| Jan 3, 2026 | $3310 | Not Available |
| Jan 4, 2026 | $3261 | Not Available |
| Jan 5, 2026 | $3296 | Not Available |
| Jan 6, 2026 | $3227 | Not Available |
| Jan 7, 2026 | $3123 | Not Available |
| Jan 8, 2026 | $3123 | Available |
| Jan 9, 2026 | $3227 | Available |
| Jan 10, 2026 | $3330 | Available |
| Jan 11, 2026 | $3330 | Available |
| Jan 12, 2026 | $3192 | Available |
| Jan 13, 2026 | $3123 | Available |
| Jan 14, 2026 | $3123 | Not Available |
| Jan 15, 2026 | $3020 | Not Available |
| Jan 16, 2026 | $3107 | Not Available |
| Jan 17, 2026 | $3229 | Not Available |
| Jan 18, 2026 | $3192 | Not Available |
| Jan 19, 2026 | $3192 | Available |
| Jan 20, 2026 | $3229 | Available |
| Jan 21, 2026 | $3229 | Available |
| Jan 22, 2026 | $3229 | Available |
| Jan 23, 2026 | $3229 | Available |
| Jan 24, 2026 | $3229 | Available |
| Jan 25, 2026 | $3266 | Available |
| Jan 26, 2026 | $3340 | Available |
| Jan 27, 2026 | $3376 | Available |
| Jan 28, 2026 | $3376 | Available |
| Jan 29, 2026 | $3376 | Available |
| Jan 30, 2026 | $3756 | Available |
| Jan 31, 2026 | $4184 | Available |
| Feb 1, 2026 | $4233 | Available |
| Feb 2, 2026 | N/A | Not Available |
| Feb 3, 2026 | N/A | Not Available |
| Feb 4, 2026 | N/A | Not Available |
| Feb 5, 2026 | N/A | Not Available |
| Feb 6, 2026 | N/A | Not Available |
| Feb 7, 2026 | $4595 | Available |
| Feb 8, 2026 | $4595 | Available |
| Feb 9, 2026 | $4639 | Available |
| Feb 10, 2026 | $4683 | Available |
| Feb 11, 2026 | $4774 | Available |
| Feb 12, 2026 | N/A | Not Available |
| Feb 13, 2026 | N/A | Not Available |
| Feb 14, 2026 | $6262 | Not Available |
| Feb 15, 2026 | $6200 | Not Available |
| Feb 16, 2026 | N/A | Not Available |
| Feb 17, 2026 | $6081 | Available |
| Feb 18, 2026 | $6081 | Available |
| Feb 19, 2026 | $6081 | Available |
| Feb 20, 2026 | $3766 | Available |
| Feb 21, 2026 | $3386 | Available |
| Feb 22, 2026 | $3473 | Available |