Extended Stay in Florida & the Carolinas – Itinerary Help & Ideas - Remote Workers🌴🌅🏡

Hey everyone! My boyfriend and I are both remote workers, and we’re planning to spend January and early February 2026 doing a long working road trip through Florida and the Carolinas. We’re thinking about 6–8 weeks total.

We’d love help building a rough itinerary, especially places to stay a couple weeks at a time (Airbnbs or similar), and can move around a bit in between. Open to a mix of beach towns, nature spots, walkable cities, and maybe some small towns with charm.

Here’s what we know so far: ✔️We’d like to focus more heavily on Florida, with at least 4–5 weeks there. ✔️We definitely want to check out St. Pete (have heard great things), and Charlotte NC (friend that lives there) ✔️We’re not super interested in Miami, but not opposed to day trips or a short stay near Key West. ✔️We’re flexible on the order/direction of travel and open to suggestions from people who know these areas well!

Places we’re curious about (but don’t know how to fit it all): ⭐️ Coconut Grove - heard good things? ⭐️Key West – maybe a few days or a week? ⭐️Sarasota / Naples – worth it for a longer stay? ⭐️Savannah or Charleston – maybe on the way down or back? ⭐️Raleigh or any other NC/SC reccs?

We’re into: • walkable towns/cities • warm-ish weather • good food scenes • beach walks / water views • occasional hiking or nature excursions • good remote work environments (quiet cafés, Airbnbs with solid Wi-Fi)

Would love to hear: • Where would you spend a few weeks vs. just a night or two? • Underrated spots we might not know about? • Good routes/direction for driving? • Any winter weather considerations for NC/SC that we should think about?

Thanks so much! Would love to hear from people who have done something similar or just know the Southeast well 😊