3-Day Itinerary – Romantic Charleston for Foodies & Music Lovers

Afternoon: Check into somewhere stylish:
The Restoration – rooftop pool, sexy modern vibes.
The Ryder Hotel – hip, funky and close to nightlife.

Grab a light lunch and cocktails at Basic Kitchen (fresh, local, chic).

Evening: Dinner at The Ordinary – upscale seafood and raw bar in a converted bank. Oysters & bubbles = a love language.

After dinner: Head to Prohibition on King St. – swing dancing, craft cocktails and often a live jazz or swing band. Or try Republic Garden & Lounge for a sleek rooftop, DJ sets and a more modern club vibe.

Late-night idea: Hit up The Belmont for cozy leather booths and killer negronis or grab gourmet late-night bites at Little Jack’s Tavern.

Morning: Sleep in (you earned it) and do brunch at Callie’s Hot Little Biscuit – buttery, flaky heaven.
Grab coffee at Clerks Coffee Company and stroll through the Historic Market.

Afternoon: Start your downtown food crawl:
Share a few plates at 167 Raw (lobster rolls, crudo).
Pop into Goat.Sheep.Cow. for charcuterie and wine.
Grab a scoop from Off Track Ice Cream – vegan-friendly and seasonal flavors. Maybe sneak in a spa hour at The Dewberry to revive before round two.

Evening: Sunset dinner and rooftop drinks at The Watch at The Restoration – epic views and vibey lighting.
Then: your live music crawl begins.
Charleston Pour House – chill, funky and hosts everything from soul to reggae to jam bands.
The Commodore – retro jazz lounge with old-school energy and live soul or funk bands.
Finish the night at Burns Alley or Faculty Lounge – secret bars with DJ sets and vibey crowds.

Bonus: If it’s a Thursday-Saturday, check for live music events at Music Farm or Royal American.

Morning: Sleep in (again, yes), then go for a cozy brunch at The Darling Oyster Bar (try the Bloody Mary bar!)
Walk it off through Waterfront Park – sit by the Pineapple Fountain, people-watch, swing under the oaks.

Afternoon: Take a romantic harbor boat cruise with wine and live acoustic music (some local charters offer private sunset sails!). Grab a nap or chill by the pool back at your hotel.

Evening: Final dinner at Chez Nous – tucked-away candlelit French-Spanish magic.
Nightcap at Vintage Lounge – Charleston’s most romantic wine and champagne bar.

Optional surprise: Have champagne waiting in the room with a note or love letter. Or schedule a private musician to serenade during your cruise or dinner (very possible in Charleston!).