13. John Chestnut Park

The beautiful boardwalk path at John Chestnut Park in Palm Harbor, Florda

John Chestnut stands out as a quiet, shady Pinellas County Park with the beautiful boardwalks, great views of Lake Tarpon, and pre-historic looking cypress swamps. It’s the best park in the area for exercise. Take a morning or evening stroll and you are bound to come across dozens of deer and the occasional armadillo. Even on hot afternoons, you can find a shady escape at John Chestnut. The main loop around the park is great for walks, bike rides, and runs. In addition, you will also find picnic shelters, a sand volleyball court, softball fields, and a large dog park.

Address: 2200 E Lake Rd, Palm Harbor, FL 34685

14. Bayshore Blvd.

Tampa's Bayshore Blvd. path

Tampa’s wonderful 4.5 mile long pedestrian path, the longest continuous side walk in the world, is the best place in the city to go for a relaxing weekend morning stroll, jog, or bike ride. Gorgeous views of the skyline and river make exercise a breeze. An occasional dolphin or manatee sighting makes a visit even more memorable. Beautiful homes, palm trees, and clear skies make this one attractive urban ride. Plan your visit around sunset for even more spectacular views.

Address: 312 Bayshore Blvd Tampa, FL 33606

15. Clearwater Beach

Palm trees on Clearwater Beach

A visit to Florida’s Gulf Coast just isn’t complete until you have step foot upon the crystal smooth white sand of Clearwater Beach. The wide, sandy beach offers plenty of room to enjoy a summer’s day of swimming in the warm waters of the Gulf (be sure to avoid noisy, crowded -impossible to find parking- weekend visits). In addition, Pier 60 offers a lively year-round celebration of arts, entertainment, and live music.

Address: 1 Causeway Blvd, Clearwater, FL 33767

16. Silver Moon Drive In

Silver Moon Drive In - Lakeland, Florida

Located between Tampa and Orlando lies Lakeland, a city known for its’ abundance of lakes (38 named lakes plus several smaller ones). In this town, you will find one of the remaining drive in theaters in the area. This clean, affordable (only $5 for a double feature!), family friendly drive in is the perfect weekend date or family activity. Plus, it is easily accessible for  locals and tourists, both in Tampa and the Orlando area.

Address: 4100 New Tampa Hwy, Lakeland, FL 33815

17. John’s Pass Village and Boardwalk

Pirate ship on John's Pass Boardwalk

Conveniently located right next to the beach, you will find John’s Pass Village and Boardwalk, a fantastic dining, shopping, and entertainment destination featuring over 100 local businesses. You will be treated to beautiful views of Boca Ciega Bay as you stroll along the 1100 foot long wooden boardwalk.

Aside from scenic waterfront dining choices and unique local shops, you have plenty of interesting activities to choose amongst including a pirate themed sunset cruise and a narrated dolphin cruise at Hubbard’s Marina. When you tire of a long day of dining and shopping, you can walk right over to Madeira Beach for a little R&R.

Address: 12901 Gulf Blvd, Madeira Beach, FL 33708

18. Hyde Park Village

Hyde Park Village in Tampa, Florida

This quaint, open air shopping & dining destination in Tampa’s Hyde Park neighborhood is a relaxing alternative to a stuffy, crowded indoor mall. Nice landscaping, an excellent collection of upscale shops, great local restaurants, and Cinebistro (a luxury dinner/movie theater) will give you plenty of options for an all day weekend excursion. Be sure to check out the Calendar of Events, which is loaded with both weekly (Irish 31 running club) and annual events (Holiday Tree lighting ceremony, Fall Festival and Pumpkin Patch).

Address: 1602 W Snow Cir, Tampa, FL 33606