How to Spend a Week on Anna Maria Island

For many, there is no questions on how to spend a week on Anna Maria Island. However, first time visitors often wonder about what there is to do beyond the beach.

How to Spend a Week on Anna Maria Island

How to Spend a Week on Anna Maria Island

Here is a helpful daily itinerary on how to plan the perfect week and make the most of your visit to Anna Maria Island. A week may seem like a long vacation, but with so many local attractions seven days will fly by in a flash!

Saturday – Arrival

Typical check-in for Anna Maria Island vacation rentals will be 4:30. If you arrive on the island before check-in you’ll have to keep yourself occupied with easy local things to do. This is a great time to grab something to eat, or even begin exploring different beach accesses.

Hold off on the big grocery shopping trip because you won’t have anywhere to stash your groceries until you have access to your accommodations.

Get situated and don’t over plan for Saturday

Once you arrive at your vacation rental we recommend first getting situated. Divvying up bedrooms, finding where everything is and figuring out how things work. Half the fun of an Anna Maria Island vacation is enjoying a luxury home for a week.

Slip into relaxation mode then find the nearest beach access. Nearly all Anna Maria Island vacation rentals are within walking distance to the beach. Spend your first evening with a relaxing walk to the beach at sunset.

Don’t over plan your first night as you’ll likely be tired from traveling. However, Saturday arrival day is a perfect time to grab something to eat at one of Anna Maria Island’s outdoor dining restaurants. What better way to kick-off your vacation than with seafood and a view?

Sunday – Beach Day All Day

Sunday will be your first full day on Anna Maria Island. Your group will undoubtedly be excited to get the fun started.

Wake up at dawn and go for a morning beach walk. Totally worth the getting up early on vacay!

Plan to spend most of Sunday on the beach, but be careful not to get sunburned. Remember to apply a high SPF 20 minutes before you go out and reapply every 2 hours.

For those that sunburn easily, you may want to take a mid day break from the sun. This is an excellent time to put together a large grocery shopping list and plan out the meals you’ll be preparing at your rental. Stock up on food, beverages, and beach accessories.

Monday – Shopping and Trolley hopping

Now that your group has had a full day to enjoy what they came to the island for, the beach, Monday is a great time to explore island shopping!

This is the perfect time to use the free trolley too. Find the nearest trolley stop, hop on, and cruise up and down the entire island to find all the fun boutiques and souvenir shops. Some spots to stop include Historic Bridge Street in Bradenton Beach, The Island Shopping Center in Holmes Beach and Pine Avenue in the city of Anna Maria.

No shopping trip is complete without stopping for lunch! Stop just about anywhere for lunch really, all island restaurants are great!

Tuesday – Explore Beyond the island

While some folks prefer to spend their entire vacation on Anna Maria Island, some like to explore the many surrounding activities. Below we have suggestions on things to do off-island.

Cortez Fishing Village

  • Eat fresh off the boat seafood at Starfish Market.
  • Boat Tours of the Intracoastal.
  • Maritime Museum

Sarasota

Bradenton

  • South Florida Museum
  • Bradenton Riverwalk
  • Downtown nightlife on Old Main Street

St. Petersburg 

  • Downtown Central Ave. art districts – galleries, shops and restaurants
  • Salvador Dali Museum
  • Museum of Fine Art

Tampa

Wednesday – Early Breakfast, Eco-Tours and Wildlife Viewing

Anna Maria Island has really unique wildlife, and an eco-tour is a great way to get close. Get up early and go out for a big breakfast. This will give you plenty of fuel for a day of outdoors adventuring.

There are many local options for kayak and Stand up Paddle boarding tours. Explore beautiful Mangrove coastline. Hire a boat tour for a few hours, and your sure to see dolphins, Manatees and an array of aquatic life.

If eco-tours aren’t your forte, then head to one of the local preserves for a nature walk. Leffis Key is a fantastic spot! Located on the south end of the island, this preserve is just under a mile of walking trails. You’ll experience Mangrove tunnel board walks, salt marsh and shrubby uplands. See small mammals, an impressive variety of birds, and sea life along Sarasota Bay.

Thursday – Sightseeing

When  you visit Anna Maria Island there are certain things you must see!

Anna Maria City Jail and Historic Society

Having your picture taken at the old Anna Maria City Jail is the quintessential island sightseeing activity. For some it’s tradition! The Historic Society Museum is a great way to learn island history. Find out unique facts like why we call Anna Maria “The City that Fig Newtons Built”.

Piers

Find three public piers along the bay side of the island. Each is different, but all offer fishing, dining and gorgeous water views.

Friday – Beaches and a Big Night Out

Friday will be your last full day on Anna Maria Island. You’ll really want to just relax on the beach, swim in the pool at your rental, and soak up every last bit of the island life.

This is also the perfect time to splurge on a big night out! Make reservations at one of the fine dining restaurants like Beach Bistro in Holmes Beach, or Euphemia Haye on Longboat Key. After dinner head over to Bridge Street for cocktails and live music!

Saturday – Leaving is hard, but there is always next time!

Typical check-out is 10am, but this doesn’t mean you have to leave right away! Once you hand back in your keys, you can still enjoy the beach. The three big public beaches all have bathrooms and showers. (Manatee Public, Coquina and Bay Front Park) Squeeze in one last beach trip before you go, and we’ll see you next year!

Don’t forget to book your stay for the following year. Many visitors come back every year, so be sure to book your favorite rental before someone else does!