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33 Years
experience
Your Trusted Insurance Partner in Annapolis, MD
Old Bay Insurance has been serving the Annapolis community for 30 years, providing personalized insurance solutions tailored to individual and business needs. Our team of licensed professionals prioritizes client relationships, offering expert guidance to protect assets ranging from auto and home policies to comprehensive business coverage. With a commitment to fair pricing and financial stability, we leverage our experience and partnerships with trusted carriers to deliver secure, customized protection.

Our dedication to local clients is reflected in over 85 five-star reviews, highlighting our responsive service and ability to meet unique insurance requirements. Neal Tatterson's leadership has established us as a reliable resource for Annapolis, Greater Anne Arundel County, and Queen Anne's County residents, ensuring peace of mind through attentive, professional service.
Services
Auto Insurance Home Insurance Business Insurance Watercraft Insurance General Liability Insurance Commercial Property Insurance Cyber Liability Insurance Landlord Insurance Life Insurance Umbrella Insurance
Details
  • Year established: 1993
Highlights and features
  • We offer 30 years of local insurance expertise in Annapolis
  • Our licensed professionals provide personalized policy guidance
  • We maintain strong partnerships with top-rated insurance carriers
  • Our team prioritizes transparent, fair pricing structures
  • We deliver responsive service with 85+ five-star reviews
What people say
Great for us Amazing representative Awesome service Personalized attention Responsive support
Services
Auto Insurance
Auto insurance protects drivers and vehicles against financial loss from accidents, theft, or damage. Our policies include liability coverage, collision protection, and comprehensive options tailored to individual driving needs. With personalized guidance, we help clients select appropriate coverage levels while maintaining affordability through available discounts.
Home Insurance
Home insurance safeguards residential properties against damage from covered perils like fire, storms, and theft. We offer customizable policies that include dwelling coverage, personal property protection, and liability insurance. Our agents help homeowners understand policy details and select appropriate coverage limits based on their specific property and risk profile.
Business Insurance
Business insurance protects companies from financial risks associated with operations. Our offerings include business owners policies, liability coverage, and industry-specific solutions. We help businesses in Annapolis and surrounding areas select appropriate protection for property damage, cyber threats, and liability claims while ensuring compliance with regulatory requirements.
Watercraft Insurance
Watercraft insurance provides protection for boats and personal watercraft against damage, theft, and liability claims. Our policies cover physical damage, towing assistance, and liability protection. We help boaters in Maryland understand coverage options for various watercraft types, including specialized protection for hurricane preparedness and pollution liability.
General Liability Insurance
General liability insurance protects businesses against third-party claims for property damage, bodily injury, and advertising injuries. We provide coverage solutions that help businesses manage risks associated with customer interactions and operations. Our agents assist in determining appropriate coverage limits based on industry-specific requirements and business size.
People
Neal Tatterson
Agency Owner
Neal Tatterson leads Old Bay Insurance with 30 years of local insurance expertise, building strong community relationships while maintaining a client-focused approach to coverage solutions.
Richard Bowers
Insurance Representative
Richard Bowers provides personalized insurance service to clients, offering responsive support and tailored coverage solutions based on individual and business needs in the Annapolis area.
Questions
What types of insurance do you offer?
We provide personal insurance (auto, home, watercraft, life), business insurance (BOP, liability, cyber), and industry-specific coverage for contractors, landlords, and landscapers.
Do you serve areas outside Annapolis?
We serve Annapolis, Greater Anne Arundel County, and Queen Anne's County, with insurance licenses in MD, VA, DC, PA, FL, and DE.
How can I file a claim?
Report claims through our Service Center online, by phone at 410-777-5390, or by visiting our Annapolis office during business hours.
What payment options are available?
Contact our office for payment details, as options are customized based on policy type and individual client requirements.
Why choose an independent agency?
As an independent agency, we offer multiple carrier options to find coverage that best matches your specific protection needs and budget.