Pineapple Insurance

Tampa, FL

(833) 528-3824
Car Home
Founded in 2021

Protecting your Assets, Family and Future.

At Pineapple Insurance, we believe insurance should feel personal, transparent, and built around real people - not policies alone. Based in Florida and proudly serving our local communities, we specialize in helping individuals, families, and business owners protect what matters most.


We are an independent insurance brokerage, which means we work for you, not a single carrier. Our licensed, experienced advisors take the time to understand your goals, explain your options clearly, and compare coverage across multiple top-rated insurance companies to find the right fit - whether that means staying with your current carrier or exploring new solutions.


From home, auto, flood, and umbrella insurance to specialty and hard-to-place risks, our approach is rooted in education, proactive planning, and long-term relationships. We're committed to helping clients avoid surprises, close on time, and feel confident in their coverage decisions.


Beyond insurance, Pineapple is about community. We're proud to support local businesses, real estate partners, and neighborhood initiatives throughout Florida. When you work with Pineapple Insurance, you're not just a policy number - you're part of the Pineapple family.

- Your Pineapple Insurance Team

Protecting your assets, family, and future.

States Served
Florida
Personal Insurance
ATV
Automobile
Boat
Builders Risk/Home Construction
Collectible Auto
Condo
Flood
Home
Landlord
Mobile Home
Motorcycle
Personal Watercraft
Pet
RV
Renters
Short-Term/Sharing
Trailer
Umbrella
Vacant Land
Valuable Items
Companies We Work With
Progressive Insurance
Slide Insurance
Florida Peninsula
Safe Point Insurance
Edison Insurance
Travelers
Bankers Insurance Group - FL
Citizens
GEICO
Cypress Insurance Group
Manatee Insurance Exchange
Security First Insurance Company
AmWINS Group
Tower Hill Preferred
Orange Insurance Exchange
Cabrillo Coastal
Safeco Insurance
Jewelers Mutual Insurance Company
Wright Flood
Olympus Insurance Company
American Integrity Insurance
Hagerty
Florida Family Insurance
CRC Group
National General Insurance (GMAC)
TypTap Insurance
Southern Oak Insurance
Mercury Insurance Group
National Flood Insurance Program (NFIP)
Neptune Flood
Pineapple Insurance Team
  • Jessica Rogers - Agent
    Jessica Rogers
    Agent
  • Chris Fitzgerald - Agent
    Chris Fitzgerald
    Agent
  • Tammy Sawyer - Director
    Tammy Sawyer
    Director
  • Gregory Tomlin - Principal
    Gregory Tomlin
    Principal
  • Marion Dowling - Agent
    Marion Dowling
    Agent
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