Recommended Trip: Charming Southern Weekender

It’s become tradition to pack our weekenders for a quick trip every February. We need a break from the Northeastern winter and a chance to build motivation to power through the remainder of volatile weather conditions. This year, Yehua could not travel due to an injury, but I, Ev, visited several Southern destinations. Read on to learn about my itinerary, activities, and recommendations.

Basic Info

  • Flew into (and later, out of) Jacksonville International Airport in FL (from NYC) and rented a car.
  • Drove to St.Augustine, Florida -> Cumberland Island, Georgia -> Savannah, Georgia
  • Entire trip for three days cost about $500 per person


This was a great three-day weekend itinerary. The trip was relaxing, filled with good food, and all-in-all, a great break from the harsh NYC winter and city life in general.

What I would do differently

  • Spend half a day in St.Augustine (instead of the entire day)
  • Bring a bike to Cumberland Island (so you can see more of the Island, which is quite large)
  • Visit a plantation around Savannah

Read on for specific recommendations


Using some tips from Hitha On The Go, I packed light and for fair weather (high 60s- mid 40s), using pieces that could be worn multiple ways - and multiple times. I ONLY use carry-on, so if it doesn’t fit, it doesn’t go.

I wore my merino wool Pivotte tank the entire time (yes, the same one). Merino really is perfect for traveling - since it’s anti-odor and requires less frequent washing. I also wore my Good-To-Go cardi every day, also made of merino. I opted for jeans instead of my usual 24/7 pants, but regretted this. The jeans started sagging in the knees and butt a few hours into the trip.

St. Augustine

St. Augustine is the the oldest city in the U.S. It’s pretty and has historical significance. I think the best thing to do was just walk around. There are many tours, but I chose to read about the history at the visitor center, online, and through the many plaques placed around town.

Places to stop by/ walk through:

    • Castillo De San Marcos National Monument
    • Flagler college campus
    • Lightner Museum area
    • Historic District
    • Waterfront

Highly Recommended Meals:

    • Ice Plant: Flounder Sandwich with house potato chips
    • Caps Restaurant: Any of the fresh fishes

Cumberland Island, GA

Take a ferry to Cumberland Island for an enjoyable day of exploration and picnicking. This was my favorite part of the trip, as I found it relaxing to take in all the different terrain and views. You can see:  

  • Mansion ruins
  • Wild horses,
  • Beach
  • Beautiful Forests

Savannah, GA.


Again, I spent my time here just walking around.  Savannah is beautiful and relaxing.

Places to stop by/ walk through:

  • 24 squares - Each is slightly different - all are beautiful
  • Bonaventure Cemetery
  • Waterfront - both at night and during the day

Highly Recommended Meals:

  • Cottonwood - Crab Chowder and Seafood Tortellini were amazing
  • Treylor Park: Fried PB&J Chicken Wings