Hilton Head, Beaufort & Savannah: The Best Weekend Itinerary

The best weekend itinerary in Hilton Head, Beaufort & Savannah—maybe it’s the salty ocean air, the dreamy Spanish moss swaying in the breeze, or the perfect mix of history, charm, and adventure. We recently took a trip to Hilton Head, Beaufort, and Savannah, and let me tell you, this was one for the books!

Because of my cancer surgery and tons and tons of finger therapy and Dr. appointments back in November we could not celebrate our 40th anniversary in a fun way. So February we decided to go on a little trip to South Carolina and Hilton Head to celebrate. It has been a place on our bucket list for along time.

From biking on the beach to historic mansions and sunset cruises, we soaked up every ounce of Southern charm and beauty. Keep scrolling for all the highlights (and, of course, some fun photo ops along the way!).

Hilton Head Island: Biking, Beaches & Gator Sightings

Hilton Head is a little slice of paradise—gorgeous beaches, shady bike trails, and plenty of wildlife (sometimes a little too close for comfort!). We kicked off our adventure with a bike ride along the beach, feeling the ocean breeze as the waves crashed nearby. Is there anything better than biking on the sand with the sun sparkling on the water? I don’t think so!

We have done plenty of bike rides in Italy along the Adriatic coast but riding on the beach next to the waves was incredible!

Of course, it wouldn’t be Hilton Head without a little alligator sighting. We spotted one lounging near the water, and let’s just say, I was happy to keep my distance! It is funny because at first I thought it was fake because I didn’t expect his coloring to be so black.

A nearby sign reminded people NOT to feed the alligators—as if I needed any convincing.

Later, we climbed over some huge beach rocks, soaking in the salty air and taking in the breathtaking views. The best part?

Ending the day with a picture-perfect sunset over the lagoon. Talk about a moment straight out of a postcard!

Beaufort: Small-Town Charm with Big Personality

If you haven’t been to Beaufort, add it to your must-visit list ASAP! This town is dripping in Southern charm, with gorgeous historic homes, waterfront views, and the cutest little downtown.

We wandered the streets, snapped photos of stunning old churches, and even found a pair of giant, colorful boots—which, of course, I had to climb into! Because when you find oversized boots in the middle of town, you go full tourist mode.

We also took some time to just soak in the beauty of this little coastal gem. Between the waterfront parks, the charming cafes, shops, and the incredible history on every corner, Beaufort completely stole my heart.

Savannah: History, Architecture & All the Southern Charm

Savannah is one of those places that just oozes character—from the cobblestone streets to the grand mansions and dripping Spanish moss, it’s like stepping back in time.

One of my favorite stops was the Savannah Cotton Exchange, a stunning piece of history that tells the story of the city’s past.

We also strolled through some of Savannah’s famous squares, admiring the beautiful pink blooming trees and soaking in the old-world charm.

And can we talk about the food? Savannah is home to some of the best Southern cooking you’ll ever have. I had the best pecan pie bar I have ever had! Let’s just say we didn’t leave hungry!

Sunset on the Water: The Perfect Ending

To wrap up our trip, we hopped on a sunset cruise, and WOW—it was pure magic. We saw lots of dolphins frolicking in the water and different types of birds. As the sun dipped below the horizon in the most beautiful shades of orange and pink, and we just sat back, relaxed, and enjoyed the peacefulness of the open water.

It was quite chilly as traveling in February to Hilton Head is off season and can be somewhat cold as the sun goes down.

Sometimes, the best travel moments aren’t planned—they’re the ones where you just breathe, take it all in, and feel completely at peace.

You may remember when we took a sunset boat ride around Tremiti islands in Italy on a little wooden boat and we thought it was not going to be great but it turned out to be just incredible! We try to take in every moment.

Final Thoughts on The Best Weekend Itinerary

This Lowcountry adventure was everything I hoped for—beautiful scenery, rich history, amazing food, and plenty of laughs along the way. Whether you love beach biking, historic towns, or just a good sunset, Hilton Head, Beaufort, and Savannah have it all.

If you’ve been to any of these spots, tell me your favorite things to do! And if you haven’t yet—trust me, it’s time to start planning your trip!