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Originally Posted by AMB444
We've been all over FLA and have seen many gorgeous wonderful places but I've never seen St Augustine yet!
If you've been to that area (plus beaches) can you recommend the "must see" places and things to do? I know there is a trolley/tour bus that you can jump on/off... any experiences with this?
Would you do it as a day trip? Places to stay overnight? I like quaint B&B's and smaller lodgings.
I research fairly well on Yelp and Tripadvisor, etc. But I think the best itinerary for travel and tips is always word of mouth and TV peeps know a lot... so... TIA!! 
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I don’t see mention of the San Sebastián winery for their free tour, you can opt for an additional couple of glasses for I think $5 more. Also the distillery has the ice plant bar on the roof which is always crowded when we’re there. Both distillery and winery are free, there is also a chocolate tour that I think is $10, but worth for one time. we’ve done the winery, distillery and chocolate shop all at the same time as they are all a few blocks apart.
One addition, go in Dec thru Jan to see the historic section done up in lights… big crowds but worth seeing. Probably during the week will be less crowds than weekends. We’ve done day trips but we’ve been there many times. About 2 hours from TV. Just take a designated driver. We did spend a weekend once as there is a great Kentucky Derby party (if you like bourbon) that supports hospice and palliative care.
Derby Run – Community Hospice Foundation