I needed a policy for my new $6,500 Santa Cruz. I was done with homeowners exclusions. I narrowed it down to the two heavyweights of 2026: Oyster and Sundays Insurance. I ran quotes, read the fine print, and tested their support. Here is the showdown.
Key Takeaways
- Oyster: Best for a slick, tech-forward experience. Fast quotes, easy interface. Strong on “Agreed Value.”
- Sundays: Best for the hardcore cyclist. Better coverage for racing, traveling, and rental reimbursement. Slightly more “traditional” feel but robust.
- Underwriting: Both are backed by major carriers (like Markel or others), so financial stability is equal.
- Price: Oyster was slightly cheaper for casual riders; Sundays was better value for racers.
The “Why” (Feature Wars)
Specialty insurance is competitive. They are fighting for your premium by adding perks.
The Investigation: Head-to-Head
1. Oyster
- Pros: Instant AI quoting. Very flexible on “composite” bikes (custom builds). Good bundling discounts.
- Cons: Lock requirements can be strict (Diamond rated often required for high value).
- Best For: The tech-savvy commuter or e-bike enthusiast who wants a “set and forget” policy.
2. Sundays Insurance
- Pros: deeply embedded in cycling culture. They understand “Gran Fondo” vs “Time Trial.” They offer better “Loss of Use” (taxi/rental) coverage.
- Cons: Application process asked more detailed questions about usage.
- Best For: The serious athlete or the car-free commuter who needs guaranteed mobility.
Comparison Table
| Feature | Oyster | Sundays | Velosurance (Markel) |
| Theft (Home) | Yes | Yes | Yes |
| Crash Damage | Yes | Yes | Yes |
| Racing Coverage | Optional | Strong | Optional |
| Medical Pay | Optional | Optional | Optional |
| Rental Reimbursement | Limited | Yes | No |
| Est. Monthly Cost | $45 | $48 | $50 |
Step-by-Step Action Plan
- Quote Both: Prices vary by zip code. Open two tabs.
- Check the Lock List: Before buying, email them: “Is my Kryptonite Evolution approved for this bike?” Get a yes in writing.
- Look for “Entrustment”: If you lend your bike to friends often, check which policy covers “permissive use” better. Sundays is often clearer on this.
FAQ
Are these better than Lemonade?
Yes. Lemonade is a generalist. These are specialists. They cover crash damage and racing; Lemonade generally does not.
Do they cover delivery riding?
Generally NO. Both exclude commercial use unless you buy a specific commercial policy.
[IMAGE: Split screen screenshot showing the dashboard of Oyster vs Sundays app]