A weekend getaway to Anna Maria Island is the ultimate escape for travelers seeking pristine white-sand beaches, turquoise waters, and the charm of Old Florida. Whether you're flying in for a quick trip or driving down for a long weekend, this barrier island offers the perfect blend of relaxation, adventure, and unforgettable coastal vibes.
From breathtaking sunsets at Bean Point to indulging in the freshest seafood with waterfront views, every moment feels like a postcard. At Best Beach Getaways, we provide premium Anna Maria Island vacation rentals to make your stay seamless and stress-free, placing you just steps from the best beaches, dining, and activities. Follow our curated 3-day Anna Maria Island itinerary to experience the island like a local, with insider tips and hidden gems to help you make the most of your Anna Maria Island adventure.
Getting to Anna Maria Island
Flying In? Here Are the Closest Airports:
- Sarasota-Bradenton International Airport (SRQ) – 30-minute drive from AMI.
- Tampa International Airport (TPA) – About 1 hour from AMI, with a wider selection of flights.
Transportation Tips:
- Car Rentals: Available at both SRQ and TPA for easy island access.
- Shuttle Services: Rideshare options like Uber and Lyft are available, or book a private car through AMI Transportation.
- Golf Cart & Bike Rentals: Once on the island, explore like a local with a rental from Beach Bums Rentals or Fun and More Rentals.
Here's an interactive map to show you all our suggested hotspots throughout the island located nearby our vacation rental properites.
Kicking Off Your Ideal Weekend on Anna Maria Island
Day 1: Arrival, Sunset & Seafood
Check-In & Explore Your Vacation Rental
Best Beach Getaways offers keyless entry, allowing you to head straight to your Anna Maria Island vacation rental without any hassle. Our local team is available to ensure you have everything you need for a stress-free stay, just steps from the shore.
Dinner at The Sandbar ($$, Beachfront, Kid-Friendly)
Enjoy fresh seafood right on the sand, with tables just steps from the waves and a front-row sunset view.
- Local Favorite: Try the Grouper Sandwich or Seafood Risotto paired with a tropical cocktail.
- Address: 100 Spring Ave, Anna Maria, FL 34216
- Local Tip: Arrive early for sunset seating—it's first-come, first-served!
Sunset at Bean Point Beach
Located on the north end of the Island, this secluded, picturesque beach offers stunning panoramic views of Tampa Bay and the Sunshine Skyway Bridge.
- Beach access points at Fern St & North Shore Dr and Gladiolus St & North Shore Dr.
- Parking at Bean Point Beach is limited—best to bike or walk.
Nightcap at The Doctor’s Office ($$, Craft Cocktails, Adults Only)
The Doctor's Office is one of the island’s best cocktail bars, offering elevated drinks in a cozy, intimate setting.
- Local Favorite: The "Painkiller" cocktail or the "Dr. Feelgood" Old Fashioned.
- Address: 5312 Holmes Blvd, Holmes Beach, FL 34217
- Local Tip: Reservations recommended—this place gets packed on weekends.
Day 2: Beach Day, Adventure & Local Flavors
Breakfast at Ginny & Jane E’s ($, Casual, Kid-Friendly)
Start your morning at Ginny & Jane E’s Cafe, a quirky café known for its giant cinnamon rolls and fresh-squeezed orange juice.
- Address: 9807 Gulf Dr, Anna Maria, FL 34216
- Local Tip: Arrive early—lines get long, especially on weekends!
Morning Beach Time at Manatee Public Beach
Spend a few hours soaking up the sun at Manatee Public Beach, one of the best family-friendly beaches with restrooms, picnic tables, and beachside concessions.
- Address: 4000 Gulf Dr, Holmes Beach, FL 34217
- Local Tip: Rent chairs & umbrellas from Beach Bums Rentals to stay cool all day.
Dolphin Tour & Snorkeling Excursion
Book a Dolphin Tour or Snorkeling Excursion to get up close with marine life in the Gulf of Mexico.
- Other Options: YOLO Adventures offers private tours & sunset cruises.
- Local Tip: Early morning tours have the calmest water and best dolphin activity.
Lunch at Rod & Reel Pier ($$, Overwater Dining, Kid-Friendly)
- Grab a bite at Rod & Reel Pier, a casual, Old Florida-style eatery sitting directly over the water. Try the fish tacos or fried shrimp basket.
Explore by Bike or Golf Cart
- Experience the island like a local by renting a bike or golf cart to cruise around Pine Avenue, stopping at local boutiques and art galleries.
Dinner at The Waterfront Restaurant ($$$, Fine Dining, Romantic Option)
- Dine at The Waterfront Restaurant, offering gourmet seafood dishes and waterfront views. The Crab-Stuffed Grouper is a standout.
Live Music & Drinks at Bridge Tender Inn ($$, Casual, Live Entertainment)
- End your night with live music at Bridge Tender Inn, a laid-back tiki bar on the bay.
Day 3: Brunch, Last-Minute Fun & Departure
Brunch at The Donut Experiment ($, Casual, Kid-Friendly)
- Create your own custom donuts at The Donut Experiment, where you pick the toppings for fresh-made donuts.
Last-Minute Shopping on Pine Avenue
- Visit Pine Avenue’s unique boutiques for souvenirs, from beachy home décor to handmade jewelry.
Quick Lunch at The Ugly Grouper ($$, Outdoor Dining, Family-Friendly)
- Before heading out, stop by The Ugly Grouper for fresh seafood, cold drinks, and a laid-back atmosphere.
Departure
- Complete a quick and easy list of check-out tasks including locking up the doors of your vacation rental, and ensuring you have not left any personal items behind!
- Head back to the airport (SRQ or TPA), or hit the road home with memories of an unforgettable Anna Maria Island getaway!
Make Your Weekend Getaway Unforgettable
At Best Beach Getaways, we offer the perfect vacation rentals on Anna Maria Island for a relaxing, stress-free escape. Whether you’re here for a quick weekend trip or an extended stay, we can help with beach rentals, grocery delivery, car rentals, and concierge services to make your trip seamless.
Ready to plan your trip? Browse our Anna Maria Island rentals now and book your dream beach retreat today!