The Five On It • Charleston Guide

Five Charleston guide plans, already made.

Stop comparing options and building your own itinerary. We have already done it, every pick includes the full plan, insider tips, reservation advice, maps, backups, and the exact order to do it in.

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What's inside

Five guides, planned down to the minute

Every one runs start to finish, the spots, the timing, the order to do them in, plus reservations, maps, budgets, and a backup for each.

01
South of BroadThe genteel, historic tip of the peninsula.
02
The Historic DistrictCentral and walkable, everything at your door.
03
Upper KingHip and lively, the dining-and-nightlife end.
04
AnsonboroughLeafy and residential, quiet but still central.
05
The Beach IslandsSand and space, a short bridge from downtown.
The first of five · a first taste
Mansions and the Battery

The southern tip of the peninsula is the oldest, grandest, and quietest part of the city, columned mansions, hidden gardens, and the harbor promenade at the Battery.

Revealed inside

A stay in an actual 18th-century mansion once home to a signer of the Constitution, elegant, intimate, and rich with period detail, right among the grand houses.

Revealed inside

It's peaceful and residential, which means the restaurants and nightlife are a walk north rather than at your door. For most, that short stroll is a fair trade for the calm and beauty.

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Revealed inside

It's the difference between a relaxed, strolling trip and a frustrating one.

Planning a guide like this yourself can take 4–6 hours. Here, it's already done, yours to download in seconds.

5 complete guides, every one chosen and mapped, yours for $5.

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A note from us

From us to you

We've done every one of these guides ourselves.

Some are where we celebrate birthdays. Some are where we take friends visiting Charleston. Some have just become our favorite “we don't even need to think about it” go-tos.

These are the guides we recommend to the people we care about most.

Now go enjoy it,

The Five On It
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Five guides in Charleston, ready tonight.

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