America's oldest city — cobblestone streets, Spanish forts, fresh seafood, and stories around every corner. Join the waitlist for first dibs on dates and pricing.
I went down to St. Augustine recently to scout this trip personally. I had been once before, years ago, but visiting again with fresh eyes — knowing I wanted to bring our group there — completely changed how I saw the city.
It is the oldest continuously-occupied European-settled city in the United States. That history is everywhere. Cobblestone streets you can actually walk on. A 17th-century Spanish fort that still stands at the entrance to the bay. Old Town buildings with stories that go back four centuries. Plus exceptional Spanish-influenced food, fresh Florida seafood, and a charm that feels like a smaller, more walkable Charleston.
I'm finalizing dates, pricing, and the exact itinerary now. Once it's locked in, the waitlist gets first notification with priority booking. No deposit required to join — just send me a quick email or use the button below.
Spanish Colonial Fort
A 17th-century coquina-stone fort overlooking the Matanzas Bay — the oldest masonry fort in the continental United States. Walking its battlements is a quiet, moving experience.
Historic District
Cobblestone streets, four centuries of architecture, and the Lightner Museum's stunning collection of decorative arts housed in a former Gilded Age hotel. The perfect way to slow down and take it all in.
I'm finalizing dates and pricing now — most likely spring or fall 2027. Waitlist members get first notification with priority booking before the trip opens publicly.
Yes — this one is just for our women members.
Email me using the button below. You go on the list with no deposit and no commitment. When the trip opens, you get a private email with dates, pricing, and a few days of priority booking before it goes public.
Significant — St. Augustine is best experienced on foot. Cobblestone streets, the fort, the historic district. Comfortable broken-in walking shoes essential.
None — joining the waitlist is completely free. A deposit will only be needed when you formally book once the dates are released.
Waitlist members get private email notification with priority booking before this trip goes public.
Browse our full lineup of trips, day adventures, and members-only gatherings.
See All Trips →