Destinations / South Carolina
Charleston
CHSThe grown-up version of this trip. Golf, boats and the best food per dollar in the country.
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The verdict
Charleston is the pick for a group in its thirties that still wants a big weekend but is done screaming over a DJ. You get real golf at Kiawah and Wild Dunes, inshore fishing twenty minutes from downtown, and a restaurant scene that beats cities four times its size. Everything downtown is walkable and last call is 2am, so the nights are big without being a wasteland.
It is wrong for a large loud group. Downtown Charleston is residential, the noise ordinance is enforced, and sixteen guys in matching shirts will be the villain of King Street by 10pm. It is also wrong if golf is the whole point and money is tight, because the Ocean Course is over $500 a man in season.
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Where to stay
A Cannonborough or Elliotborough carriage house
Walk to King Street, no car needed, and it costs less than three hotel rooms.
Book itThe Dewberry
Best hotel bar in the city on the ground floor. Worth the rate for one night of the trip.
Book itA Kiawah or Isle of Palms beach house
Trade downtown walkability for golf on property and a deck on the ocean. Right call for a pure golf trip.
Book itGet the Charleston blueprint
Worth timing the trip around
The things that come back every year and change the price of the weekend. Pick your dates around one of these on purpose.
Charleston RiverDogs baseball
Twelve dollars, walkable from downtown, beer in the grass. Runs most of the season, so it fits almost any weekend you pick.
Spoleto Festival USA
Seventeen days of performance across the city. Rates double and restaurants book out, which matters here more than in most places.
Cooper River Bridge Run
Forty thousand people and a closed downtown on Saturday morning. Either your group is running it or your group is trapped by it.
On the water
Prices checked September 2026
The Lowcountry is creeks and marsh, so the water day here is fishing or a boat to a sandbar, not offshore. Twenty minutes from downtown and a completely different world.
Inshore redfish charter out of Shem Creek
Half day, two boats for eight, and you are casting at tailing reds in eighteen inches of water.
Book itBoat to Capers Island or the Morris Island sandbar
Captained pontoon, cooler, and four hours nobody checks a phone.
about $800 a boat, up to 16 · 3 hours · book 2 to 3 weeks out
Book itOffshore wreck trip for cobia and mahi
Full day, forty miles out, and only for a group that will not get seasick and sulk.
about $1,400 a boat of 6 · 6 hours · 6 a boat, book 3 to 4 weeks out
Book itWhat else to do
Prices checked September 2026
The Ocean Course at Kiawah
One of the hardest courses in America and the reason half these trips get booked. Book five months out.
Book itWild Dunes Links Course
Thirty minutes out, ocean holes, and half the price of Kiawah.
about $130 and up a head · about 4.5 hours · Links and Harbor alternate days
Book itDinner at FIG or Chubby Fish
FIG takes eight at 9pm if you book a month out. Chubby Fish is walk-in only and worth the wait.
Book itOyster roast at Bowens Island
Cluster oysters on a shovel, cinderblock tables, beer in a cooler. The most Charleston hour of the trip.
Book itFirefly Distillery tasting in North Charleston
Twenty minutes out, sweet tea vodka, and a taproom big enough for a group.
$15 a head, $35 deluxe · about 1 hour · Tue to Sat, private tour needs 8
Book itKing Street bar run, starting at The Belmont
Six blocks, everything walkable, and Republic at the end if the group still has legs.
walk up, pay per drink · evening · walk up, no reservations
Book itRiverDogs game at The Joe
Twelve dollars, on the water, and a completely painless Friday evening for eight.
about $14 to $20 a head · about 3 hours · season runs Apr to Sep
Book itTours and activities in Charleston sell out for groups, so book the ones you care about before you fly.
Browse Charleston on ViatorGetting around
One SUV covers it. Downtown is walkable, but Kiawah is 50 minutes each way and Isle of Palms is 30, so you need a vehicle for golf and beach days. CHS to downtown is 20 minutes. Park downtown once and leave it there overnight.
The one thing people screw up
Groups book the Ocean Course for a Saturday morning without checking the tide and drive 50 minutes to play it into a 20 knot onshore wind, which turns an already brutal course into a five and a half hour march. Play Kiawah early in the morning, and if the forecast shows sustained wind over 15, move it to Wild Dunes and keep your money.
Cost per head, 3 nights, no flights
Per head, based on eight guys on a three night trip. It is a range because a trip is a range.
| Category | Per head |
|---|---|
| Lodging | $330 to $600 |
| Activities | $250 to $600 |
| Food and drink | $320 to $650 |
| Transport | $100 to $190 |
| Total | $1,545 to $2,559 |
Planning Charleston?
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