Illustrated group golf trip scene at Pinehurst
September 24-27, 2026

Pinehurst Guys Trip

Two condos, three rounds, breakfast included, and a long weekend at the home of American golf.

See the planView cost
2Three-bedroom condos
3Rounds included
8No. 2 spots held

The short version.

Amish has two condos held, and the weekend is shaped around Pinehurst No. 1, The Cradle, and a Sunday No. 2 slot for eight players.

Stay

Two condos for the crew.

Thursday to Sunday, two 3-bedroom condos, each sleeps 5.

Details
Package

Breakfast plus 3 rounds.

The structure is simple: arrive Thursday, play Friday through Sunday, and keep the group together.

Details
No. 2

The signature round.

Eight Sunday morning spots are held for the championship course.

Details

Why Pinehurst matters.

Pinehurst is not just another resort stop. It is one of the centers of American golf, and No. 2 is the reason this trip feels different from a normal buddies weekend.

No. 2
No. 2
1907

Donald Ross designed Pinehurst No. 2. Pinehurst calls it the resort's pounding heart, known for turtleback greens, native wiregrass, and championship pressure.

Open
Championships
2024

No. 2 hosted the 2024 U.S. Open and is an anchor site for future U.S. Opens in 2029, 2035, 2041, and 2047.

No. 1
No. 1
1898

Pinehurst No. 1 is where the golf course story starts: a classic, approachable opener later touched by Donald Ross.

789
The Cradle
789

The Cradle is Pinehurst's nine-hole short course: 789 yards, par 27, built for a looser Saturday round.

Pinehurst No. 2U.S. Open historyPinehurst No. 1The Cradle
Resort scale

More than the three rounds.

Pinehurst lists ten 18-hole courses, The Cradle short course, and Thistle Dhu putting. The trip only touches a slice of the resort, but the extra course depth is why the place works for a full golf weekend.

No. 1No. 2No. 3No. 4No. 5No. 6No. 7No. 8No. 9No. 10No. 11The Cradle
Food & drinks

Easy post-round targets.

The useful move is casual and close after golf, with one nicer option if the group wants it.

The DeuceClubhouse bar/restaurant by No. 2. Best fit after the signature round.Official page
Pinehurst Brewing Co.Casual brewery option for a bigger group dinner or beers.Official page
Carolina Dining RoomClassic resort dining room; relevant because breakfast is part of the package.Official page
1895 GrilleMore upscale dinner option at The Holly Inn if the group wants one nicer meal.Official page

Weekend flow.

Arrive Thursday, play No. 1 Friday, use The Cradle for a looser Saturday round, and close Sunday with the No. 2 slot currently held.

Thu Sep 24

Check in.

Arrival and condo setup.

Check-in
Fri Sep 25

Pinehurst No. 1.

The historic opener and easiest fit for day one.

Round 1
Sat Sep 26

The Cradle afternoon.

Short-course round with Thistle Dhu as the extra option.

Round 2
Sun Sep 27

Pinehurst No. 2.

Bucket-list round, extra cost, eight Sunday morning spots held.

Round 3

Cost reality.

The current No. 2 package is materially more expensive than the alternate-course version. The table keeps the numbers plain.

Current hold$2,944
No. 2 premium+$640
LineStatusPer personNotes
Package with No. 2Current holdHeld$2,944Breakfast and 3 rounds included; only 8 Sunday morning No. 2 spots currently available.
Alternate-course packageComparison onlyAvailable to switch$2,304Breakfast and 3 rounds included, with another Pinehurst course substituted for No. 2.
No. 2 premiumBefore caddie effectEstimate+$640No. 2 is cart-path-limited and caddies are encouraged, so the real premium may feel higher.

Footnote: Amish put down a refundable $300/person deposit to hold the package.

The crew.

VA/MD core, Amish from Raleigh, Tarak and Rishi from Atlanta, Boner from California.

VA / MD core
NishilTapanBhavinMaseAlpeshMananKrupal
Raleigh
Amish
Atlanta
TarakRishi
California
Boner