The Perfect 4-Day Summer Getaway Trip to Anna Maria Island

Published on March 20, 2019 by Lyn Puskas
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The cool aquamarine waters of the Gulf of Mexico splash onto the white sandy beaches. Happy vacationers float and play in the waters off Anna Maria Island. 

Are you planning a family reunion for this summer? Do you want to get together with all your college pals?  Plan a couple’s getaway or bring the whole family. 

Anna Maria Island is just the place for that summer escape. Full of opportunities to play in the water and relish the charm of “Old Florida.” There is a plethora of fun things to do in Anna Maria Island. 

Book your vacation rental and get ready for a taste of paradise on Anna Maria Island. 

Anna Maria Island, Paradise Found

Anna Maria Island is perfect for your family or friend getaway. It has two airports nearby. The Sarasota airport is only 25 minutes away, while Tampa’s airport is only 75 minutes away. Take advantage of those inexpensive summer flights. 

While offering the warmth of summer, this island doesn’t get any warmer than your other summer destination options. Temperatures range from the mid-70s in the evening to high 80s during the day. 

There are plenty of things to do. Whether you want a getaway full of activities or days of relaxation and good food, Anna Maria Island has it. 

Day One: Let the Fun Begin

Once you arrive at Anna Maria Island get settled in your rental getaway, big enough for the whole group.  It’s time for some exploring. 

Start by hopping on the free trolley that runs the length of the island. Ride the length of Gulf Drive to start to plan out your weekend of fun. Stops are every two to four blocks and you can hop on and off to shop, eat, and check out the sites.

Along the way, you might decide to partake in a true Florida lunch. The Ugly Grouper offers food, live music, and even games for the kids. On the Historic Bridge Street Pier, you might check out the Anna Maria Oyster Bar. It’s a great choice that offers scenic views with a menu that has more than oysters. 

Lunch and Toes in the Sand

After getting the lay of the island and lunch, it might be time for some beach fun.

You might try the Manatee Public Beach, where there is more than sitting in the sand to do. No need to haul chairs and umbrellas, rentals are available right at the beach. There are facilities for changing, shopping and more restaurants nearby.

After some water fun, you might be ready for a later afternoon cocktail and to get ready for dinner on the island. 

Dinner and Sunsets

With plenty of dining options, from casual beach fare to more fine dining Anna Maria Island will meet all your foodie needs. The Freckled Fin offers live music and outdoor seating. This beachy location has a wide menu of options for everyone in the group, including seafood and pizza. 

After all that activity, you’ll be ready to take your family and friends back to your weekend rental.  You don’t want to miss the epic sunsets that are a part of summer living on Anna Maria Island.

Sit out on your private beach or deck. Finish the day with all the colors and sounds of summer, while enjoying the sun going down. 

Day Two: A Day Full of Fun

Want to be the most popular person in your rental? Get up early and head to Ginny and Jane E’s in the northern historic part of Anna Maria Island.

The cafe/bakery/gift shop is housed in an old grocery story. It’s a year-round island favorite. Bring back their giant cinnamon rolls to get everyone in your party ready for a full day of fun on Anna Maria Island. 

Walk off the cinnamon rolls with a morning beach walk. You can hunt for shells and let your feet wander the water’s edge. Take a morning swim and watch for dolphins playing in the gulf. 

Middle of the Day: Sports or Culture

With a full day, there are many things to do on Anna Maria Island. An array of options awaits you.

Check out one of the many summer festivals planned on the island. 

Gulf of Mexico Adventure

Charter a fishing boat. You can go offshore, nearshore or inshore fishing on a variety of boat options. Hop aboard one of the many chartered boats leaving the marina for a day out on the gulf. Reel in those grouper, snapper and kingfish while out on your boating adventure.

A Cultural Experience More Your Thing

Visit one of the many art galleries scattered throughout. Many featuring local artists. 

Need a good read for the beach? Stop for a visit at The Paradise Found Book Store. It is filled with not just books, but original art and plants too. 

Museum lover in the group? Escape inside for a visit to the Anna Maria Island Historical Society Museum. It houses plenty of island history including the island’s first jail. 

You’ve Earned a Great Dinner

You will not be disappointed in the many island options. 

Try Beach Bistro, an award-winning choice on the island’s white sand beaches. It received a rare 4.9 review from Zagat making it a must try.

Two menu favorites include the One Helluva of a Soup, a tomato blue cheese wonder.  For the seafood lover, try the Bistro Bouillabaisse.

You might also try Vinny’s Italian Kitchen for authentic Italian. You could even take it to go and enjoy it with view of the gulf from your vacation rental. 

Day Three:

Enjoy an early morning beach walk. Collect some shells and read a chapter of your book with your toes in the sand. 

Ready for some food? French cuisine comes to Old Florida at My AMI. Take the whole group for an al fresco lunch before your afternoon activities. 

Finish with lunch and take a stroll through the quaint island streets. Or hop back on the trolley or Monkey bus.  Head towards Pine Avenue for shopping treasures and vacation memorabilia. Stop into AMI Outfitters Coastal Gear & Apparel for an Anna Maria Island t-shirt of hat for the afternoon sun. 

The kids will enjoy a stop at Shiny Fish Emporium or the Flip Flop Shop for some treats of their own. 

Water Fun on Anna Maria

After lunch and shopping, it’s time to cool off with some water fun

Take a guided tour with kayaks. Among your choices, you can choose either a coastal tour or a river safari tour. 

Try your hand at paddleboarding with a day rental. Jet skis, sailboats, and parasailing are also options. Want to really make a splash, try out wakeboarding, tubing, or parasailing. A number of locations on the island offer water sport rentals of many different kinds. 

Dinner the Island Way

After this fun-filled summer day, you’ll be ready for another great island dinner. Try The Waterfront Restaurant. Enjoy outdoor seating right by the beach, fresh seafood, and handcrafted cocktails from this island legend. 

Have a sushi lover in your group? Try Island Ocean Star in the Galati Marina for fresh sushi or hibachi. Outdoor seating is also available. 

Day Four: Make the Most of the Last Day

No one in your group will want the escape to be over.

Make the most of it by starting the summer day with a trip to The Donut Experiment. Here everyone in your group will get a cake donut. Then it becomes theirs to customize just to their liking with an array of icings and toppings. 

Time to ride off those donuts. Rent bikes for a ride around the island. You can  rent your bikes ahead from many locations on the island. They will drop off and pick up right from your weekend rental. 

Summer is for bike riding after all. In the northern part of the island ride through the historic streets on designated bike paths. Ride along the beach and watch the dolphins playing in the gulf. You can even stop at some of the piers dotting the water’s edge while on your ride. 

One Last Hooray

Enjoy one last lunch before leaving your summer weekend getaway. Try The Sandbar’s specialty, a grouper Reuben. Or enjoy one last meal at Eat Here Anna Maria. One thing is for sure, you won’t leave Anna Maria Island hungry. 

Fun Things to Do in Anna Maria Island in Summer

Anna Maria Island offers the perfect balance of sun, surf and fun for a summer getaway. 

Spend your time laying on the beach. Or take advantage of one of the many water sports available on this Gulf of Mexico paradise. Shop the galleries, beach shops, and boutiques through this old Florida gem. There are fun things to do in Anna Maria Island for everyone during your stay. 

The things to do on Anna Maria Island will make your weekend fly by. You’ll be dreaming of your next visit to the island paradise before you even leave. 

Are you ready to head to Florida? Have you been convinced this is your summer destination? Check out these vacation rentals. Make sure you to spend your weekend in luxury digs overlooking one of the many beach vistas.