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Almost everyone you ask about shopping in St. Petersburg will say that you must go to Baywalk. There are several good restaurants like The Dish and Dan Marino's as well as a Muvico 20 movie theatre and several neat and trendy shops like Being, Birkenstock and Black & White. There is limited additional shopping across the street (to the east) at the Courtyard Shops. (There are only a few shops currently in the space but Vladimir's Collections,specializing in Russian curios and art, is worth checking out.) The atmosphere is family friendly and laid back during the day and early evening. Somewhere around ten o'clock Wet Willie's, an open air bar on the second level, turns up the hip-hop music and the crowds become mostly young adults. There are excellent and inexpensive parking garages just across the street on the east and south sides. Access to these garages on the weekends can be congested though so give yourself time to get in the garage if you are coming for a movie. This can be a problem especially on "First Friday" weekends when the city closes down Central Avenue between 2nd and 3rd streets to host the monthly "Get Downtown" street party.
By all means, any visitor must visit Baywalk to say that they have been to St. Petersburg but if you really want a unique shopping experience in downtown St. Petersburg take a walk over to Jannus Landing Courtyard two blocks to the south. Here you will find lots of independently owned specialty shops and art galleries surrounding the open air concert venue.
The Pier has some great boutique stores on its lowest level. This is a good place to get St. Petersburg logo shirts, sweaters and beachware and Just Hats has a great selection of hats, both novelty and practical. Be sure to stop by the Pier Winery for a free sample of their unusual wines (like chocolate wine or carrot wine).
Every Saturday from early October to late May, the city hosts the Saturday Morning Market in the street in front of Progress Energy on Central Avenue at 2nd from 9 am to 2 pm. Vendors from all over the country come to set up tents on each sidewalk and in the street. Vendors sell food, plants, clothes, art, crafts, herbs, and all types of specialty goods. Live entertainment and all the food smells make this a really fun activity for the whole family. Seating is very limited.
Tyrone Square Mall in western St. Petersburg is a typical American mall anchored by Macy's, Dillard's JC Penney's and Sears. In true mall fashion it is completely surrounded by all the prerequisite big chain stores like Best Buy, Circuit City, Ross, etc.
John's Pass Village and Boardwalk is a shopper's paradise close to St. Petersburg in Madiera Beach on the barrier island. It might be impossible to go into each shop there inside one day but it is definitely fun to try. In addition to all the different specialty and novelty stores it has two of the big beachwear stores and a boardwalk featuring several restaurants, boating/parasailing/jetski activities and MORE shops.
Westshore Plaza in Tampa is a popular mall that many St. Petersburg locals go to. It is just across the Howard Franklin Bridge as 275 enters Tampa. It is viewed as an upper end mall and is not surrounded by many other shops. It is anchored by Macy's, JC Penney, Saks and Sears and has a AMC 14 movie theatre.