Nassau Trip Preview

Pinehurst, NC

The cradle of American golf. Nine courses at Pinehurst Resort including #2 — the most famous course in the country. Walking only with caddies. This is a pilgrimage, not just a trip.

Per person / day

$250–$650

Best months

Mar–Nov

Group size

4-8 players

Sample trip

3N · $2,200/pp

bucket listtraditionalgolf puristhistoricfather son

Top courses

Where you'll play

01

Pinehurst No. 2

Must stay at resort to play. Walking only with caddie ($50-100 + tip). Crowned turtle-back greens are the hardest in golf.

$295-495 (must stay at resort)
very hardDesign: Donald Ross (1907, restored Coore & Crenshaw 2011)Condition ●●●●◐Scenery ●●●●◐
bucket listwalking onlyhistoricchampionshiptop 10 us
02

Pinehurst No. 4

Redesigned by Gil Hanse 2018. Some say it's better than #2. Hosted 2019 US Amateur.

$200-395 (must stay at resort)
hardDesign: Gil Hanse (2018 redesign)Condition ●●●●◐Scenery ●●●●◐
bucket listwalking onlymodern classic
03

Pinehurst No. 8

Tom Fazio design — more forgiving than #2 or #4. Great for a 36-hole day complement.

$150-295 (must stay at resort)
moderate-hardDesign: Tom FazioCondition ●●●●◐
resortwalking only
04

Tobacco Road

Wildest course in America. Blind shots, crazy elevation, sand everywhere. Mike Strantz masterpiece. You'll either love it or hate it — but you'll never forget it.

$75-165
hard (but fun-hard)Design: Mike StrantzCondition ●●●●
uniquewildlove it or hate it

Sample itinerary

3 nights in Pinehurst, NC

4-8 players · ~$2,200 per person

1

Arrival & Warm-Up

11:00 AM Arrive RDU, drive to Pinehurst$30/pp
2:30 PM Pinehurst No. 8$200/pp
6:30 PM🎯 Thistle Dhu putting contest
7:30 PM🍽 The Carolina Dining Room$90/pp
2

The Main Event

8:00 AM Pinehurst No. 2 (with caddies)$450/pp
3:00 PM🎯 Spa / rest / range
7:00 PM🍽 The Deuce (casual recap)$40/pp
3

The Closer

8:00 AM Pinehurst No. 4 (with caddies)$350/pp
3:00 PM Tobacco Road (optional)$120/pp
7:30 PM🍽 Final dinner at resort$60/pp
4

Departure

9:00 AM Drive to RDU

From captains who've been

Insider tips

Tip 01

Stay at the resort — only way to play #2, #4, #8. Package deals are actually decent value

Tip 02

Play #4 before #2 — some groups like #4 better and it takes pressure off #2

Tip 03

Tip your caddie well ($50-75/bag min) — they'll read every putt and save you 5+ strokes

Tip 04

Thistle Dhu putting course is free and wildly fun. Do it the evening before your #2 round

Tip 05

Tobacco Road is 30 min away and worth the detour — completely different but unforgettable

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