St. Augustine, FL

November 2025 - January 2026 and early spring.

The best times to visit St. Augustine, Florida, are late fall (November to early December) and early spring (March to early April). These periods offer mild weather (60s–70s°F), perfect for exploring the Historic District’s cobblestone streets, touring the Castillo de San Marcos, or relaxing on St. Augustine Beach. Late fall brings festive events like the Nights of Lights (mid-November through January), with millions of twinkling lights, and fewer crowds than peak winter. Early spring offers blooming azaleas and comfortable temps before the humidity rises. Summer (June–August) is hot and humid (80s–90s°F) with frequent rain and busier attractions. Winter (January–February) is mild (50s–60s°F) but can see occasional chilly spells, though it’s great for holiday events and senior-friendly trolley tours with fewer tourists.

TBD - based on participation, hotel selection, activities.

We’re excited to share this preliminary trip summary based on all of our meetings and input.  This is an actual group itinerary framework but it is in preview level only. This is being provided so we can see if we have enough committed interest to move forward with this trip.

Please keep in mind, the pricing is an estimated range but dependent on number of participants, single or double accommodations and time of booking and deposits. The dates are accurate and available but can be modified if needed.

** If you’re almost certain you would join this trip once final dates and pricing are confirmed, please click “I’m Interested.”

** If you are not interested, please do not click anything.

When a trip attracts enough committed interest, we’ll let you know and then finalize the details with our on-site travel partners, post the confirmed price and itinerary, and open for official registration.

Once confirmed, these will be fully hosted, small-group journeys — with every detail handled for you from start to finish. Each itinerary will be designed to include accommodations, in-country transportation, guided excursions, select meals, and expert local hosts. You’ll travel with the group throughout the program, so there’s no need to plan or arrange anything yourself.

Airfare: International airfare is not included, and you’re welcome to handle your flights however you prefer — including using frequent-flyer miles. For those who’d rather not manage flights personally, Sojourn Travel Advisors offers an optional Air Desk service (available for a small fee). Our air specialists not only book flights but also monitor for delays, cancellations, and schedule changes — often resolving issues before you even know about them. It’s a seamless, worry-free way to travel from door to door. We also will provide options for Travel Insurance to help you protect your investment.