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  • Writer's picturePoints By J

Charleston Weekend Itinerary

I did not expect to fall in love with Charleston, but that's exactly what happened. Here's the video highlight reel.

It is quaint, beautiful, and packed with fun things to do. In my opinion, it's a perfect weekend getaway destination.

See below for the full weekend itinerary (none of this is sponsored, just what I did!). Pro tip: don't forget to make meal reservations in advance.

Charleston Weekend Itinerary
Gorgeous Palmetto-lined streets

Charleston Weekend Itinerary


Dinner at S.N.O.B - 192 E Bay St

Delicious Southern dishes with a side of live music - the perfect way to kick-off a weekend.


Kayak on Shem Creek - 1 Shrimp Boat Ln

We went with Nature Adventures for a 2-hour kayak expedition. We saw dolphins (just feet away from our kayaks!) and so many pelicans. Added bonus: it was a fun workout.

Brunch at Saltwater Cowboy - 130 Mill St

After working up our appetites with kayaking, brunch at Saltwater Cowboy tasted extra delicious. Don't skip the fried green tomatoes!

Shopping on King St.

We enjoyed browsing the many boutiques clustered close together on King Street!

Afternoon Ice Cream at Republic - 431 King St

For an afternoon pick-me-up, grab a bowl of ice cream from Republic. I got a mix of coffee ice cream with cookies & cream. Delicious.

Sunset Drinks at Vendue - 19 Vendue Range

See below for the gorgeous sunset view. Need I say more?

Charleston weekend itinerary
View from Vendue at sunset

Dinner at Church & Union - 32B N Market St

This restaurant is inside a former church, creating a gorgeous dining atmosphere. They feature New American fare, which is definitely a crowd pleaser.


Breakfast at Big Bad Breakfast - 456 Meeting St

Adorable & affordable diner- can't go wrong!

Yoga at Salt Spa & Yoga - 483 King St

Enjoy a great morning yoga session at this woman-owned and operated business.

Lunch at Poogan's Porch - 72 Queen St

Indulge in a classic Southern lunch at Poogan's! You'll dine in a beautifully restored Victorian house.

Check out Rainbow Row & Wander

If you've only seen one photo of Charleston, it probably featured Rainbow Row. It's the famous series of pastel-colored historic homes located on East Bay Street. No Charleston weekend itinerary is complete without it!

Charleston Weekend Itinerary
Rainbow Row

Enjoy Sullivan's Island Beach

Charleston has many beautiful water-front views, but this one takes the cake. Perfect for an afternoon stroll.

Dinner at Obstinate Daughter - 2063 Middle St

I don't like to play favorites, but this was my favorite meal of the trip. I'm a sucker for oysters and Italian food- and they do both exceedingly well.


We stayed at the Hyatt Place because we were able to book by transferring Chase points to our Hyatt loyalty accounts. Plus, it was easy to get a room with a pull-out couch, which worked perfectly for our group of three. It was clean and comfortable, but nothing fancy.

If you're not trying to use points, there are many beautiful boutique hotel options in Charleston to choose from.

If you need a new travel credit card to book your trip with, check out my top recommendations here.


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