Question: I'm planning a trip to western Florida this spring. I have a long itinerary, but I'm considering shortening it down because it might be too much. My plans are to visit Caladesi Island, Anna Maria Island, Gasparilla Island and Sanibel/Captiva Islands. Are they all worth a visit or should I pick a few of them? Which ones?
I'm after white and secluded beaches, not lots of fun and activities. I also plan to visit Clearwater Beach, St Pete Beach, Sarasota, Fort Myers and Naples. Same question here, should I remove any of them if they are more or less the same?
This is a tough question since I don't know how much time is available. I'll assume your vacation will be at least 2 weeks.
Caladesi Island and Clearwater Beach are quite close to each other. The water, sand and weather will be the same in both places. St. Pete Beach is about 30 minutes south of Clearwater Beach. If you want to visit this area, I recommend that you consider picking a place to stay, then make day trips to Caladesi Island and to either Egmont Key or Shell Key. You could stay in St. Pete Beach or on Clearwater Beach. All of the beaches in the area are white quartz sand. Caladesi, Egmont, and Shell Key are all preserves and offer "secluded" beaches. Egmont and Shell Key do not have water or bathrooms, but the boats that take you over usually do.
Anna Maria Island Beaches and Sarasota beaches are fairly close together. Neither island really offers "secluded" beaches without walking a good distance. However, they are both worth a visit because Anna Maria Island and Siesta Key offer the best sand and water on the peninsular Gulf Coast. You could stay on Anna Maria and make a day trip to Siesta Key beach. If you are going to a public beach, go on a weekday and arrive before 10 a.m. in order to find parking.
Gasparilla island (Boca Grande) is worth a visit. It is a small, lush and fairly scenic island with a rich history. Be sure to go down to the Lighthouse Park for a great view of Boca Grande Pass and Cayo Costa Island State Park. This island is rather out-of-the-way.
Sanibel, Captiva and Fort Myers are close to each other (relatively speaking). You have to drive past the road that leads to Ft. Myers Beach in order to get to Sanibel/Captiva. I highly recommend going to Sanibel and Captiva. Spend 3 or 4 days if you can. The beaches are not crowded (though the public accesses can get crowded on nice spring weekends). They are totally unique islands. Magical, almost. Since you are looking for secluded beaches, I recommend that you not bother with Fort Myers Beach. It is heavily congested. However, if you have time, you might enjoy Lover's Key State Park, just south of Fort Myers Beach.
Naples is a good hour south of the Fort Myers area. Naples beaches have lots of coconut palms but they are not "secluded." Lots of traffic too. I'd recommend that you drop Naples off your itinerary if you're running short on time. Do Naples and Marco Island next time.