Suggestions for first time visitors

Question

Hi! Visiting in mid-May with my 18-year-old son. We've booked a place near Crescent Beach on Siesta but would love to explore the area a bit. We enjoy nature, biking, and charming downtowns with mini golf or other fun activities. Any recommendations for things to do or must-visit spots nearby?

Considering a visit to Anna Maria Island and/or St Pete area, jungle garden(?)

Answer

Mid-May is a beautiful time to visit Sarasota and Siesta Key—warm, lively, and full of outdoor activities without peak-season crowds. Since you’re staying near Crescent Beach, you’ll be in one of the prettiest (and quieter) parts of Siesta Key, which also makes it easy to explore nature, charming downtowns, and other coastal towns nearby.

Below are detailed suggestions tailored for nature lovers, biking fans, and those who enjoy fun, casual activities like mini golf or small downtown strolls.

To start, Siesta Key itself offers enough to fill several days, but since you're interested in exploring beyond the beach, the surrounding Sarasota area, Anna Maria Island, and even St. Pete make great day trips.

Legacy Trail – A fantastic, well-paved biking/walking trail stretching from Sarasota down to Venice. Perfect for a long ride or a scenic, relaxing cruise.
Myakka River State Park – One of Florida’s oldest and best state parks. You can bike, kayak, walk the canopy trail, spot wildlife, and enjoy huge open landscapes. Great for an active day.
Oscar Scherer State Park – Located between Sarasota and Venice, calmer than Myakka and excellent for biking, hiking, or looking for scrub jays.
Point of Rocks (near Crescent Beach) – A top snorkeling and tidepooling spot on Siesta Key, especially good during clear-water days.

If you love charming downtowns and easy strolling, Sarasota and nearby towns offer several walkable areas with shops, cafés, and casual attractions. These spots are great for evenings or a break from the beach.

Downtown Sarasota / Main Street – Super walkable, fun restaurants, gelato shops, and occasional street events. Great energy for you and an 18-year-old.
St. Armands Circle – A circular shopping/dining district near Lido Beach. Very charming for browsing, grabbing food, and people-watching.
Downtown Venice – Beautiful, old-Florida charm with boutiques, palm-lined streets, and easy parking. Pairs well with a bike ride on the Legacy Trail.
Siesta Key Village – Laid-back beach shops, live music, ice cream, and plenty of casual restaurants. Fun for an evening.

If you're looking for fun activities you can do together—mini golf, wildlife encounters, or light adventure—Sarasota and the barrier islands have several great options.

Smugglers Cove Mini Golf – A classic Florida-style mini golf course with a pirate theme and live alligators (safe, enclosed viewing).
Sarasota Jungle Gardens – A quirky, old-school Florida attraction where you can see flamingos, parrots, and small shows. Nice for a short half-day visit.
Mote Marine Laboratory & Aquarium – Great hands-on exhibits and marine life education, especially if you enjoy wildlife and nature.
Kayaking in the Lido Mangrove Tunnels – One of the most popular outdoor activities in the area; peaceful, shaded, and full of marine life.

Anna Maria Island and St. Pete both make excellent day trips, each offering something very different from Siesta Key.

Anna Maria Island (AMI) – Known for its charming small-town feel, gorgeous beaches, and relaxed vibe. Don’t miss Pine Avenue for shops and a stroll to Rod & Reel Pier.
Bean Point (AMI) – A stunning, peaceful beach area perfect for walking and photography.
St. Pete Pier – Large waterfront area with restaurants, art, green spaces, and playful outdoor activities.
Downtown St. Petersburg – Walkable, artsy, filled with murals, cafés, museums, and waterfront parks.
Fort De Soto Park – Incredible nature, kayaking, biking, and a great beach—all in one location.

Since your interests are nature-focused and casual exploration, here’s a suggested activity flow that fits a mid-May trip:

A perfect itinerary might look like this: one day doing nature/biking (Legacy Trail or Myakka), one day exploring Sarasota downtown + a fun activity like mini golf, one day for Siesta Key Village + Crescent Beach sunset, and one dedicated day trip to either Anna Maria Island or St. Pete depending on whether you want charming or artsy.

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