Southeast Vacation Itinerary

Sharing all the details on my Southeast vacation itinerary because I just got back and it was such an awesome trip with lots of awesome spots! My family lives far away so I don’t get to see them often, so I was super excited to do this trip with my mom.

I will break down my Southeast vacation itinerary day by day, so keep scrolling for all the details below!

I rounded up all my other travel posts here, if you want more travel ideas.

Sizing reference: I am 5’4″ and typically XS in tops and 25 in bottoms.

Day 1: St Augustine

We flew into Jacksonville early and rented a car (the car rental is right there at the airport and so quick) and drove about an hour to St Augustine, Florida. I love St Augustine because there is so much history and it’s very easy to walk around (check out my entire St Augustine blog post here). We ate lunch at Ice Plant, which is my absolute favorite restaurant in St Augustine! After lunch, we left the car at the restaurant and walked into town and explored.

This outfit was perfect for walking around on a hot summer day! My Train to Be tank is in the color Powder Blue (see my full review here) and my leggings are Maldives Green (see my full legging review here).

Outfit Details:

Tank, Leggings, Bracelets (c/o), Earrings, Necklace, Sunglasses, Sneakers, Bag

After a full day of exploring St Augustine, we drove to Jekyll Island and checked into the Club Resort. If you want more info on Jekyll Island, check out my blog post here. I highly recommend making your reservations at the Club or Cottages and not the Ocean side. You can easily take a shuttle or walk to the new ocean side of the resort, but I prefer the history and grounds on the Club side! A lot of the rooms have beautiful brick, wood floors and fireplaces. It’s truly exceptional to be able to stay in such a historical place! The food isn’t that great, but I would say the Pantry is the best.

We enjoyed the gorgeous sunset view at The Wharf, which is easy to walk to. I wore this cute Lilly Pulitzer outfit and both pieces are my normal size XS.

Outfit Details:

Tank, Skort, Bracelets (c/o), Earrings, Necklace, Sandals, Bag

Day 2: Jekyll Island

We walked over to Ocean Eighty for brunch. The food was just okay, but the views over there are great. After that, we rented bikes at the main resort and rode around on the path along the ocean. This outfit was perfect for bike riding around Jekyll Island! My Train to Be tank is in the color Tidal Teal (see my full review here) and my shorts are Sonic Pink (see my full legging review here). After that we visited the turtle hospital, which is a favorite activity of mine.

Outfit Details:

Tank, Shorts, Bracelets, Earrings, Necklace, Sunglasses, Sneakers, Bag

After a big afternoon, we laid by the pool and practically had the entire pool to ourselves! There is a bar there as well. My one piece swimsuit is so cute and is a size small!

Outfit Details:

Swimsuit (c/o), Earrings, Necklace, Sunglasses

For dinner, we grabbed food at the Pantry and sat outside and ate then went to the Wharf for some wine and sunset watching! This oversized tee is so comfy and great to wear around. I sized up to a medium. My shorts are full reviewed here.

Outfit Details:

Tee, Shorts, Bracelets, Earrings, Necklace, Bag

Day 3: Savannah

We wanted to spend the last leg of our trip in Hilton Head, so we stopped in Savannah for a full day on the way. Savannah is the perfect pit stop when traveling between Jekyll Island and Hilton Head (see my full Savannah blog post here)! We ate at Vic’s on the River (my favorite) then walked all around Savannah. We had the best salad and fried green tomatoes! It was the perfect day!

My tank and skort are perfect for a hot day and both size XS.

Outfit Details:

Top, Skort, Bracelets (c/o), Earrings, Necklace, Sneakers, Bag

Hilton Head is not too far from Savannah, so we made it in time for sunset and it was beyond gorgeous! We stayed at the Omni right on the beach, and I recommend staying on the beach so you can easily walk to and from.

I love Lilly’s athleisure pieces because they are the perfect vacation pieces on a hot day. Their pieces are perfect for everything from walks, biking to lunch and dinner. I love it more than traditional athleisure (like Lululemon) because it’s a little more dressy! My dress here got so many compliments and I wore it several times on the trip. The XS fits perfect.

Outfit Details:

Dress, Necklace, Sunglasses, Sandals

Day 4: Hilton Head

Day 4 and beyond, we spent relaxing at the pool and beach and just laying low. It was the perfect low key week! Our favorite spot to eat by far is Lulu’s Kitchen and we ate there daily. My Lilly dress was super easy to pack and wear and is a size XS.

Outfit Details:

Dress, Bracelets (c/o), Sunglasses, Earrings, Necklace

The pool at the resort is adult only (there is also a kids pool), which was really nice! It was the perfect spot to read and lay out. My swimsuit is super flattering and a size 6. If you have any other questions about my Southeast vacation itinerary feel free to leave a comment below!

Outfit Details:

Swimsuit (c/o), Bracelets (c/o), Earrings, Necklace, Sunglasses