Pull into the Madrones, a Mediterranean-looking complex in Philo, to sip at four tasting rooms (tasting fee $5 each). Just admiring the architecture of the complex, a 20-year labor of love for the owner, could take hours. Throw in a visit to the Sun & Cricket store, selling tools, books, and antiques harkening back to an earlier, more agricultural time, and you may be ready to spend the night. Luckily, you can–there are two separate guest quarters on the property.

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