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With World Class Food & Drink & Just 1.5 Hours Away, This City is the Best Weekend Trip from New York City


harleston Travel Guide

As soon as we touched down in Charleston we were blown away by how friendly everyone was. In fact in 2011, 2013 AND 2014 Charleston was voted “America’s Most Friendly City” by @travelandleisure.

What we loved about Charleston was how close it is to New York, just about 1.5 hours and yet felt so unique and removed from our day to day. The city dates back to 1670 and still has that old world feel. While in town we ate and drank our way through the city and discovered the best lobster roll we’ve ever tasted.

We’re going to cover everything you need to plan your own Charleston adventure including where to stay in Charleston, the best restaurants, and the best places to shop so you can pull off that Southern Gentlemen look.

If you’re not already following our adventures on IG, check out @Lifetailored for behind the scenes on our trips in our stories plus find out where we’re heading next, before it makes it to the blog.

Paula Rallis is a real estate developer, pilot and blogger that is most content sitting with her husband on their dock on Shem Creek.

Since this was our first time in Charleston, we sought the advice of our friend and insider @paularallis for her picks for can’t miss spots in Charleston. She’s got one amazing suggestion for a great place to eat, drink, shop and stay.

Make sure to give her a follow as well, she’s got amazing style.

Paula Rallis


here You Should Stay in Charleston

We were first introduced to the Belmond brand when we visited the Belmond Sorrento. We loved the level of service and attention to detail and that’s what convinced us to stay at the Belmond Charleston Place. It’s a large property with 8 floors and 400 rooms, and the best part was the Club Level. Club Level is a unique Belmond offering.

We had it in Sorrento and it was the same experience in Charleston. It’s a rotating all day buffet with eggs, frittata and bacon amongst the offerings in the morning and light bites and cheese around dinner time. Mixed drinks and wine are all complimentary plus for dessert they have petite fours and cookies. The Club Level experience is a refreshing change from some hotels who jack up the prices in the mini bar.

Paula’s pick is Zero George Street, “with welcoming gas lanterns and chic bikes for city exploration, boutique hotel @zerogeorgest will make guests feel like they’re staying in a private master suite, complete with palms outside your window and afternoon cocktails on the porch.”

Tip: At the Belmond, book the Club Level. You get access to free food and drink all day.


here to Eat in Charleston

We had some amazing meals in Charleston, but the one that stood out above the rest and I can’t wait to go back and try was @167_raw. It’s a tiny little spot with the best lobster rolls and tuna burgers I’ve ever had. They open at 11am, but they’re so popular you need to line up around 10:45 to ensure you get a table, otherwise you’ll be waiting at least an hour to eat.

The Dewberry Charleston was originally commissioned by Lyndon Johnson in 1965 as a Federal Building and transformed into the beautiful mid-century modern marvel it is today in 2016. Their bar cranks out a great selection of craft cocktails, as well as light bites. Spend some time strolling through the interiors and you’ll be transported back to the booming days of the 1960s.

Paula’s pick: “Down one of Charleston’s many unmarked alleyways is @cheznouscharleston – a quaint French restaurant worthy of an address in Provence.  Hand written menus describe the choice of two options for each course for the evening, and trust me when I say that you can never go wrong with either.  Round out the evening by visiting their sister location, @bin152winebar for wine and truffles.”

Charleston was voted the most friendly city in 2011, 2013 and 2014, and we noticed it immediately. People just seemed genuinely happy and excited to talk to you.


here to Shop in Charleston

To get the most out of your Charleston experience you’ll want to dress like a local, and that’s why you want to stop by M. Dumas & Sons. They’ve been selling clothes in Charleston since 1917 and have a great selection with everything from Barbour to Lardini to Common Projects. I had actually forgotten to pack a jacket and was able to score an entire new look from Dumas.

@ThreadTherapy had a ball shopping at Maris Dehart. They have a huge selection of on-trend pieces perfect for the streets of Charleston or to glam out on Sullivan Island. When you stop by Maris Dehart, make sure to say hi to Alden and tell them Life, Tailored sent you.

Paula’s pick: Recognized by publications, influencers and celebrities, the curated collection of Hampden Clothing is a love affair between the best of European and American brands, all sourced by owner Stacy Smallwood. You’ll have no problem finding what you never knew you needed.

Tip: The dress in modern Charleston today is pretty laid back. You’ll stand out and look great if you just pair a simple blazer with pants.


ow to Get to Charleston

Charleston is a lot closer than I realized. It took us just 1 hour and 20 minutes to be completely transported to a slower, more relaxed way of life. There are multiple flights daily out of New York. We flew down there via LGA and returned to EWR.

We booked the flight using AmexTravel.com and used on Amex Platinum card, which earned us 5X points on our bookings.

Once we landed at CHS, it’s just a quick 20-30 minute drive to lowcountry Charleston. On the drive into the city we passed all the major landmarks and got a quick mini-tour of the city and it gave us an idea about where we wanted to walk once we were unpacked.

We went down to Charleston in the summer, and it was hot. Probably too hot. I would recommend the best time to visit Charleston is September-November where you’ll get highs in the mid 70s and lows in the high 50s or 60s. Also, during this time period you can hit up Charleston Restaurant Week and Taste of Charleston.

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