Cigar Aficionado

Five Classic Golf Destinations

Five Classic Golf Destinations
Photo/LC Lambrecht
Your view from paradise—looking back at the closing hole at Pebble Beach, the most famous golf resort on earth.
A quintet of unforgettable trips ideally suited for every golfer’s bucket list

More exclusive than the Super Bowl, older than the NBA, and steeped in time-honored traditions, sports fans worldwide turn their attention to the Masters every spring to witness the unofficial kickoff to golf season. But while Augusta National, the masterpiece where the tournament is held, is a great place to watch golf, it's a lousy place for a golf vacation. Not only is it nearly impossible to get a tee time to play the coursethere are few other notable courses nearby. Fortunately for golf-loving travelers, there are a number of traditional and historic choices that make up a classic golf vacation. These are immersion golf destinations that have long combined myriad world-class courses with everything else you could possibly want in a vacation, from luxury accommodations and fine dining to spas and other activities. In any field it is tough to become a true classic, and there are very good reasons why places like St Andrews, Pinehurst and Pebble Beach sit at the very top of every serious golfer's vacation dream list. Not only are these places unforgettable for what they have done in the past, many of them have undergone quiet but important changes for the better. As you sit back on the couch and watch the pros tackle the manicured fairways and slippery greens of a lovely golf course this weekend, begin thinking about crafting your own golf vacation, for there is very good reason to visit one of golf's great classics.

"There's no doubt that the current renaissance of golf course design has been a good thing, and these ‘build it and they will come' courses by hot designers like Tom Doak, Coore and Crenshaw, David Kidd and others have sparked an era of very high quality construction where only the best new projects make it from conception to fruition," says Michael Patrick Shiels, a veteran golf and travel journalist and author of Secrets of the Great Golf Course Architects. "But the bottom line remains, if you ask any avid golf fan where they would go if they had just one more trip, 99 out of 100 are going to say St Andrews or Pebble Beach, and they are not wrong."

These five remarkable trips are destination based and relatively turnkey, meaning that once you make your plans and get there, you do not have to do much more, except enjoy yourself. A week spent in a single resort is a very different kind of experience from a weeklong driving road trip, packing and unpacking every night and staying in different hotels. For that reason, the emphasis here is on specific destinations with a high concentration of excellent golf in a concise and easily navigated area.

Pinehurst, North Carolina

It simply does not get any more historic than Pinehurst. The very first golf resort in the United States, Pinehurst is also the largest, and the biggest in the world outside of China. While notable for the sheer bulk of its golf offerings, this is a case where quality is even more important than quantity, as Pinehurst doesn't just have a lot of golf, it has as a lot of exceptional golf, wrapped in a complete travel package combining upscale lodging and dining for a wonderful experience. Pinehurst has been in the news recently as the host of last year's unprecedented dual U.S. Open Championships, the first time the men's and women's versions were ever contested on the same course, one following immediately on the heels of the other, two weeks the likes of which the golf world has never seen. It was the third time the men's U.S. Open was held on the hallowed fairways of the resort's premier layout, Pinehurst No. 2, the only public course on earth that has hosted two different Majors and the Ryder Cup, along with a huge slate of other important amateur and professional events. No other 18 holes (with the possible exception of Scotland's Old Course) have seen so much drama. Every famed golfer of the past century has played here, and its welcoming ghosts still speak to every visiting player, a living museum of the game.

"No U.S. golf destination is more classic for me than Pinehurst. I never tire of going there," says Sam Baker, the founder and owner of Haversham & Baker, one of the world's top luxury golf travel specialists. Baker earns his living helping well-traveled golfers make their dreams come true, especially in Scotland and Ireland, and he is extremely well versed in all the world's hotbeds of great golf, yet has a soft spot for Pinehurst. "Not only does it include my favorite Donald Ross course, No. 2 , but also the good life that reflects the grand golf travel experience of decades past. I never miss an evening at the Pine Crest Inn, the small hotel Ross owned when he passed away in 1948. You begin by sipping a cocktail while you and your companions chip into the fireplace. For dinner, it's the famous chicken liver appetizer followed by the equally famous pork chops. When you conclude with after dinner drinks and a bit of singing around the piano, you hope for a late tee time in the morning."

Despite such a rich history and long-earned stature, the resort has not rested on its laurels, and just made significant changes for the better. Most dramatically, the highly regarded design team of Bill Coore and Ben Crenshaw did a major and historically accurate restoration of No. 2 three years ago. Their goal was to return it to the state it was when Donald Ross, perhaps history's most famous designer, finally finished 30 years of tinkering (he lived alongside a fairway) and got his masterpiece into what he considered its best form, for its first Major, the 1936 PGA Championship. The restoration was universally acclaimed by critics, and the reality is that while it has been a popular destination for a century, virtually no living golfers have played No. 2 in better shape than it is right now. As a result, it immediately jumped from seventh to third in Golf Magazine's all-important Top 100 Courses in the U.S. list. If that wasn't enough, the resort added its first new course since Tom Fazio designed No. 8, aka "Centennial," to celebrate Pinehurst's 100th birthday in 1996. No. 9 opened last summer to rave reviews and brings the resort's total to a stunning 162 holes, adding Jack Nicklaus to a who's who of designers that also includes Ross, Fazio, Rees Jones and Coore and Crenshaw. This followed an impressive $4 million renovation of the main clubhouse, which serves courses 1 through 5.

The Pinehurst resort includes nine golf courses (No. 2, No. 6, No. 8 and No. 9 are the best), a world-class tennis center, an equally impressive croquet facility, 200-acre private lake with beach club and fishing, and three hotels. The main lodging option is the 230-room Carolina, the town's centerpiece grand hotel, with a large spa and the atmospheric Ryder Cup Lounge. The main resort has several bars and lounges with humidors and smoking areas, including the Tavern in the Holly Inn, the 91st Hole in the main clubhouse, and most notably the classic Ryder Cup Lounge in the grand Carolina Hotel, which boasts a smoker-friendly veranda, open late into the evenings. (The Village of Pinehurst also has a cigar and wine bar called Vine in the Ash, which opened in 2014, recently closed, and was scheduled to reopen in a new location as this story was going to press.)

The other two hotel choices are the 82-room Holly Inn, Pinehurst's first hotel, more intimate and home to the resort's best restaurant, the 1895 Grille, and the no-frills 42-room Manor Inn. Pinehurst also offers a broad range of condominiums and villas. "I always stay at the resort's original hotel, the small Holly Inn," says Baker. "It's in the heart of the village, the staff knows your name by the end of the first day and your life history by the end of the third. As for golf, Pinehurst has so many courses both within and near the resort, it's impossible to play them all during a normal length trip." While the resort anchors the area as a golf mecca, there is far more than "just" these nine courses. Other top choices include the Mid-Pines and Pine Needles resorts, across the street from one another and sharing facilities, including the Donald Ross-designed course at Mid-Pines, considered his second best here after No. 2,and similarly restored to near identical acclaim. There are dozens of other courses in the immediate region including definite must plays such as the semi-private Coore and Crenshaw-designed Dormie Club, the Ross-designed Southern Pines Country Club, breathtaking Tobacco Road and Pine Needles. As luxury travel agent and avid golfer Chad Clark of Chad Clark Travel, a longtime Cigar Aficionado travel panelist, puts it, "With over 50 courses in the area, it's what I call a golf buffet."

Scottsdale, Arizona

The golf smorgasbord doesn't get any bigger or better than the Valley of the Sun, the greater Scottsdale/Phoenix region. There are more than 50 courses just within Scottsdale city limits and more than 200 in the area, including many highly-ranked standouts, with seven of America's Top 100 public courses—more than any other U.S. metropolitan area. Complementing all this golf and great weather is a broad slate of top-tier luxury hotels such as the Phoenician, Arizona Biltmore, Boulders, Four Seasons Troon North, Fairmont Scottsdale Princess, and more, all with standout golf courses. Scottsdale is home to a fantastic and still-improving dining scene, some of the nation's top spas, several casino resorts with golf and so many great courses that while it is an easy destination to choose for a golf trip, picking where to actually play, stay and eat is the real challenge. Because of all this, coupled with easy air access from across the country, it is little wonder so many PGA Tour golfers live here, including five-time Major champion Phil Mickelson, two-time Masters champ Bubba Watson, U.S. Open champ Geoff Oglivy, British Open champ Tom Lehman, Kirk Triplett, Kevin Streelman and Aaron Baddeley. Mickelson, Lehman and Baddeley have all won the world's most attended golf tournament, the Waste Management Phoenix Open (formerly called the Phoenix Open and FBR Open), contested each February at TPC Scottsdale.

"Although the exact history is shadowy, golf was played in Arizona as early as 1899," says Jeff Wallach, managing partner of Golf Media Network and executive editor of The Grain and golf travel website The A Position. "Several things make golf in Scottsdale spectacular: the warm, dry air that not only lets you hit the ball farther but also allows you to see where it's headed; the way green grass offsets red rock; and the sheer variety of courses, from classic target desert venues such as Troon North and The Boulders to the resorty, faux linksiness of Kierland to the Wild West feel of We-Ko-Pa to the pure carnage awaiting unsuspecting players at the TPC courses. Toss in the culinary delights of Scottsdale's Old Town, a visit to Frank Lloyd Wright's Taliesin West and hours relaxing at the pools and spas and you've got the perfect alignment of things that don't at first glance seem to belong together: golf and the desert. It's like peanut butter on a hamburger; it just sounds wrong until you take that first delicious bite."

There are more excellent courses here than you can play in one visit, but the handful of must-play standouts is anchored by the Stadium Course at TPC Scottsdale, where the Waste Management Phoenix Open, the "Greatest Show on Grass," is held. As the most popular tournament on the PGA Tour's annual roster—last year the event set yet another record with more than half a million spectators—it is instantly recognizable to golf fans and famous for its par-3 16th hole, the only one in golf within its own enclosed amphitheater, roughly the size of a minor-league baseball stadium. Golfers enter and leave through tunnels beneath the bleachers, and Tiger Woods famously wowed crowds here with his ace in 1997. The TPC just got a major renovation by original designer Tom Weiskopf and reopened in mid-November better than ever, with significant strategic improvements to every hole, all new bunkering, all new greens and more than 250 added trees. The on-site Fairmont Princess is one of the city's best resort hotels, and the TPC has a second high-quality layout, the Championship Course. In this respect Scottsdale excels, with several excellent 36-hole and hotel complexes that make it easier on the visiting golfer. Two have multiple top ranked courses on Golf Magazine's list, most notably We-Ko-Pa, with two very different but strategic and wonderful desert courses both among the Top 50 in the U.S. Likewise, Troon North has two Top 100 courses and an onsite Four Seasons hotel. Other top courses include North and South at the wonderful Boulders, now a Waldorf Astoria resort; Talon and Raptor at Grayhawk, Phil Mickelson's longtime home club; and both courses at the Talking Stick Casino Resort. On top of all this, Scottsdale is also an excellent vacation choice for game improvement, home to sixdifferent instructors honored by Golf Digest as "The Best Teachers in America," including Jim McLean (SunRidge Canyon), Stan Utley and Peter Kostis (Grayhawk), Pia Nilsson and Lynn Marriott (Talking Stick), and Mike LaBauve (Kierland).

Brandon Tucker, The Golf Channel Online's managing editor for courses and travel, had his bachelor party in Scottsdale, and explains why: "Tons of sunshine, slick resorts and a fantastic bar scene downtown, coupled with golf courses that are expertly designed and managed. I've played several dozen courses around the area and I don't think I've seen a clunker yet. The diversity is underrated, and the courses in North Scottsdale like Boulders and Troon North have surreal desert scenery."

Travel agent Chad Clark lives in Scottsdale, is a member of the area's oldest club, Phoenix Country Club and also a member of the Thunderbirds, the civic group that puts on the Waste Management Phoenix Open, whose proceeds all go to charity. As both an informed local and top travel consultant his picks for luxury lodging are The Four Seasons Troon North, The Boulders and the Fairmont Scottsdale Princess. For golf he recommends the TPC, We-Ko-Pa, Troon North and Grayhawk, and for dining he likes The Mission, Maestro's Steakhouse and Andreoli, plus the vibrant nightlife in Scottsdale's pedestrian friendly Old Town.

After Las Vegas, Scottsdale is arguably the most cigar-friendly golf town in the country. Every one of these marquee resort and daily fee courses has a pro shop humidor, many with surprisingly broad selections, plus outdoor bar areas welcoming your cigar. At the Talking Stick Casino Resort, the most upscale of its kind in the region, the Shadows Lounge is entirely devoted to cigars, Scotch and Martinis, with indoor and outdoor seating. It even hosts a Sinatra tribute band.

St Andrews, Scotland

The Holy Grail of golf travel destinations, St Andrews is more than just the birthplace of the sport, it is golf personified, an entire town that lives, breathes and tingles with the electricity of the beloved game. The medieval pub and castle-filled university and beach town is charming in many different ways, but what makes it so unique is how it is literally built around golf. Five courses, the Old, New, Eden, Jubilee and Strathtyrum comprise the city's green heart, and if you slice your tee shot on the Old, you are as likely to hit a car parked on a city street as you would be to go into the woods or desert on most other courses.

The Old Course is as much park as iconic links, and is closed to play every Sunday so residents of St Andrews can walk their dogs, play Frisbee or picnic on its vaunted fairways—imagine New York with Central Park as a golf course, the oldest golf course on earth. That is how inseparable golf and the town of St Andrews are, and it is amazing for first-time visitors to see how this historic, hallowed spot manages to simultaneously be steeped in rich tradition yet wonderfully laid back and informal. "The world's most famous course closes and turns into a public park every Sunday—how cool is that?" says Golf Channel managing editor Brandon Tucker. "It is the perfect sized golf town, all walkable, with fun restaurants and bars and incredible old sights, while the courses right in the heart of it permeate a rich golf vibe throughout. Everyone seems to always be in a good mood in St Andrews, and golfers depart with a new and lasting appreciation of the game."

As a whole, Scotland is the dream trip for almost all golf fans, but most just pass through St Andrews to check off the Old Course and then head to other fabled links like Turnberry, Dornoch and Muirfield. There is certainly no shortage of fantastic golf in Scotland, with the best collection of top courses on earth, but it is a mistake to cut a trip to St Andrews short, as it is easy to plan a hassle free weeklong stay you will never forget. While nothing can touch the magical, even mystical feel of the Old Course (it's truly a living museum, where you walk in the footsteps of everyone from Old Tom Morris to Ben Hogan to Nicklaus, Palmer, Woods and McIlroy) purely as a golf course, the adjacent New (1895), Eden and Jubilee are just as good, meaning they are all exceptional links. Many locals consider the Tom Morris-designed New the best of the bunch, while Jubilee, built just two years later, is the toughest.

All of that golf is right in front of visitors, a wedge from the famous Old Course Hotel or Russack's, and you could play, eat and drink happily for days without ever getting into a car. But there are several other notable choices in "greater" St Andrews, meaning a few minutes' drive or cab ride. The Links Trust, the nonprofit municipal group that operates the Old Course and its six siblings, built its latest effort, The Castle Course, in 2008 just outside town. Designed by David McLay Kidd of Bandon Dunes fame, it is by far the most dramatic of the Links Trust courses, a rough and tumble coastal maze of towering dunes, hazards, blind shots, ocean waves and wind, which seems especially rugged and intimidating when compared to the rather understated and subtle links courses in town. The Castle sits along a stretch of coast with three other nearby notable must-play courses, including the duo comprising the Fairmont St Andrews Bay resort, the Torrance and Kittocks. While just five minutes from the Old Course, these seem a world away, perched on the precipitous edge of a turbulent sea you can hardly see from the Old Course. Both are very good, fun, modern links efforts. But the one no visitor to St Andrews should leave without playing is Kingsbarns, widely considered the best modern golf course built in Scotland, though it hardly looks new. Both fun and playable, it features one jaw-dropping dramatic hole after another, making excellent use of its ample oceanfront exposure. A shocking number of American visitors to Kingsbarns, a purely public daily fee course, come back naming it their favorite, not just for the trip but in the world.

"Asking why golfers should go to St Andrews is like asking why Jews should visit Jerusalem or Muslims make the pilgrimage to Mecca," says The A Position's Wallach. "It's the mother ship, ground zero, the most beautiful and ridiculous golf terrain on the planet stretched out across the most sublime links land and surrounded by the gorgeous, dark grey stone of the atmospheric town itself.  Any golfer who wants to truly understand the game we play, and finally ‘get' why it's so fun in the wind and why bunkers exist, has to play golf at St Andrews. It's not just the Old Course but the full deal—seven courses in town, salt breezes off the North Sea, sticky toffee pudding at the Dunvegan Pub, smoky Highland whisky, Old Tom Morris's golf shop, the ancient church ruins, fish and chips."

While a trip to St Andrews is convenient and hassle free in theory, in practice it all revolves around getting a coveted but tricky tee time on the Old Course, after which all the other rounds, meals and excursions fall neatly into place. There are many strategies, including the common and cost-effective one of simply showing up and hoping for the best, a plan used by those who enter the daily lottery for tee times. But the best way to do it is to book a package with a guaranteed advance slot through a high-end golf specialist like Perry Golf or Haversham & Baker. The best full-service lodging choice in town is the Old Course Hotel, close to everything, where you can hole up in a suite like Tiger Woods does when the Open Championship is played here. Owned by Kohler, the same folks who run Wisconsin's superlative American Club and Whistling Straits golf course, it has a fantastic spa, a great fine dining restaurant, the Road Hole Grill, with one of the world's best whisky lists, and the charming Jigger Inn, a thatched roof pub in the hotel's parking lot. Among the hotel's many amenities is the cigar terrace on the fourth floor, just outside the famous Road Hole Bar, with a list of cigars and more than 200 single malts, all overlooking the most famous golf course on earth. You can get even closer at the tables outside the atmospheric Jigger Inn, which are literally set against the out of bounds wall, one of the town's best spots for a smoke and a pint. You can also puff at the outdoor tables on the entry porch of the classic Dunvegan Pub.

For a second full-service hotel alternative there's the Fairmont, five minutes outside town (with free shuttle), with more of a resort feel and its own excellent spa. Because it stays light here until very late, especially in summertime, even if you play 36 holes a day you can fit in some sightseeing, and you should. Sam Baker of Haversham & Baker, one of the world's leading experts on Scottish golf travel, says, "For St Andrews golf pilgrims,I would encourage the discerning traveler to venture a bit off the beaten path. Take a privately guided tour of the castle, university, cathedral ruins and other parts of the Auld Grey Toon that was the ecclesiastical center of Scotland long before it was a golf mecca. Drive out to the Anstruther Fish Bar for what has been rated Great Britain's very best fish and chips. Organize a whisky tasting in the Road Hole Bar of the Old Course Hotel. Experience post-round drinks with your caddy at the Dunvegan or beers at the tables outside the Jigger Inn."

Pebble Beach, California

The most famous golf resort on earth, Pebble Beach is ironically a victim of its own success. Because it has been so well-known for so long, many would-be golf travelers overlook it in search of something newer or more exotic. This is a mistake: the quality of the golf is off the charts, with all three of its on-site courses ranked in the Top 50 in the United States by Golf Magazine. Most importantly, the namesake Pebble Beach Golf Links is the highest ranked public course in America (and second on the planet only to St Andrews Old Course) on the magazine's global Top 100. Similarly, Golf Digest has perennially picked it as America's single greatest public course for years, and also put it atop the magazine's newer "Most Fun Courses" list, describing it with the simple but quite accurate comment: "This is the course every fan wants to play."

That's true, and few courses with the exemption of Augusta have gotten the kind of television exposure Pebble Beach Golf Links has enjoyed, in part because it is so damn good looking, pure eye candy. Half its holes hug the cliffs of Carmel Bay, even the vistas toward downtown Monterey are inspiring, and the layout includes perhaps the most photographed golf hole on earth, the stunning too-good-to-be-true peninsula par-3 seventh, seemingly carved out of the waves of the Pacific. It is also steeped in history the way only a tiny handful of courses like Pinehurst No. 2 and the Old Course are: it has hosted five U.S. Opens and the PGA Championship, and is one of the few courses in the world that is an annual stop on both the PGA Tour and Champions Tour. Its AT&T National Pro-Am attracts the largest celebrity field in the world, and in addition to every legend of the game since the course opened in 1919, it has played host to every golfer in Hollywood, from stalwarts like Bill Murray, Samuel L. Jackson and Kevin Costner to more recent golf-mad entertainers like Justin Timberlake.

"You wonder how anyone could pay that much money for a round of golf [around $500] until you get there and experience the combination of competitive and celebrity history, the oceanside scenery and the very comfortable luxury. Pebble Beach is not America's first course but it is America's home course," says golf journalist and author Michael Patrick Shiels. If there was nothing more than the Pebble Beach Golf Links, traveling golfers would still flock here, but there is much, much more, and it is one of the biggest self-contained golf resorts in the world, where it is easy to spend a week. All three on-site courses are excellent, with Spyglass Hill and the Links at Spanish Bay ranked 11th and 44th in the U.S. respectively, an amazing showing. There is also a nine-hole par-3 course next to the famed Pebble Beach Golf Links, and a fourth 18-hole course owned and operated by the resort, just outside its borders, the inland Del Monte—the oldest course West of the Mississippi, in continuous operation since 1897. If there has been one criticism of the golf facilities it was the lack of a good practice area, but that changed last year with the opening of a brand new facility with a double-ended natural grass driving range, a 40,000-square-foot short game complex and the new state of the art indoor/outdoor Pebble Beach Golf Academy, featuring a revolutionary robotic swing trainer, 3-D motion capture system, HD video analysis, computerized putting stroke evaluation and indoor golf simulator. Laird Small, the resort's director of instruction, is annually ranked a Golf Digest Best 50 Teacher and now hosts regular immersion golf schools with visiting VIP guest instructors in the new space.

In addition to the 81 holes, there are also three luxury hotels, the larger Inn at Spanish Bay and Lodge at Pebble Beach, both full-service properties, plus the snazzier boutique Casa Palmero with just 24 lavish suites. There are 14 restaurants and bars, 18 retail stores of every description, a huge spa that was awarded five stars by the Forbes Travel Guide, two tennis clubs, a beach club and countless swimming pools. The resort spans a whopping 5,300 acres and is bounded by the impossibly scenic 17-Mile Drive, widely considered one of the world's greatest stretches of roadway. In short, this is one-stop shopping for world-class golf—and everything else you could want in a vacation. And if you have the right connections to wrangle an invite, the resort is flanked by three of the finest private golf courses in the world, the 36 holes of the Monterey Peninsula Club and one of the few layouts even more desirable than Augusta National, Cypress Point.

Cigars have become such a traditional part of the annual AT&T Celebrity Pro-Am that they are virtually synonymous with Pebble Beach. Club XIX, which had an extensive cigar program to go with its rare whiskies and brandies, has closed, but America's most famous resort still has lots of choices for the cigar lover, especially the well-stocked humidor in the Tap Room, its most famous watering hole. There are cigars, including many in tubes for convenience, at all three pro shops as well as on the beverage carts.

"I think it's the finest all-around golf resort experience we have in the U.S., an experience worth paying dearly for," says luxury travel agent Chad Clark. "Nobody loses on this trip—the Monterey Peninsula has some of the most amazing golf courses on the planet while also being one of the most romantic places on earth. Don't miss the sunset bagpiper at the Inn at Spanish Bay or the artichoke soup and prime rib chili in the Tap Room—with a killer wine list too."

Hawaii

The 50th state is a classic golf destination for the same

reason it is a classic honeymoon and vacation choice for almost every personality—it has an incredible array of activities set amongst stunning natural beauty with near-perfect weather and an unparalleled infrastructure of luxury hotels, spas and dining. It is hard to imagine someone who doesn't love Hawaii.

"Playing golf in Hawaii is as close to the City of Oz as most of us will ever get, from emerald-green grasses to indigo blue skies to licorice-black lava fields, surrounded on all sides by the Pacific Ocean. Everything here shimmers in Technicolor hues. If your idea of heaven has more greens and fairways than milk and honey, Hawaii comes pretty close," says Mike Hiller, a journalist, AvidGolfer Magazine travel editor and Cigar Aficionado travel panelist who has played more than 1,000 courses.

"The only problem with Hawaii as a golf destination is that guys simply can't get away with going there without bringing their spouses," says Golf Channel's Tucker. "It is certainly a ‘couples' destination but if you could put the top courses anywhere else they'd be as good as any destination in the U.S. In any case, even honeymooning golfers always try to sneak in a couple rounds, and rightly so."

Each island has its own personality and attracts a slightly different traveler, but all have excellent golf courses. The Big Island is focused more on getaway single-course luxury resorts like the Four Seasons Hualalai with its Nicklaus Signature course carved out of stark black coastal lava fields for an unforgettable contrast of black, blue and green, all strikingly vivid. The island is also home to Hawaii's most famous luxury golf resort, now totally revamped and better than ever, Mauna Kea, with its legendary tee shot across a wave-crashed inlet. Kauai, with its incredible lushness, rain forest and waterfalls, all used as backdrops for Jurassic Park, has always appealed more to the adventurer, and the same holds true for golf. It is home to what is typically the highest ranked—and most challenging—resort course in the state, the Prince at Princeville, fresh off renovations that have elevated its stature. Rated number one in Hawaii by Golf Digest, the Robert Trent Jones Jr. layout is carved through thick jungle and about as beautiful a place to lose balls as you could imagine. (You will lose balls.) At the opposite end of the spectrum is Kauai's wide-open and player-friendly Poipu Bay. Beautiful in its oceanfront groomed splendor and immaculate flowerbeds, it's reminiscent of a tropical Augusta National, and for many years was home to the season-ending Grand Slam of Golf.

You can have a great golf vacation on any of these islands, but in keeping with the concept of a user-friendly destination golf trip with few moving parts, the ultimate turnkey Hawaiian golf trip combines course- rich Maui and its satellite island Lanai, technically part of Maui County and just a ferry ride or very short commuter flight away. Maui has several multi-course large resort communities anchored by one or more luxury hotels, all close to one another. Kapalua is home to the fabled Plantation Course, which has long been the season opener for the PGA Tour. The Coore and Crenshaw design is a stunner with rolling elevation changes and drop-dead vistas of ocean or mountains at every turn, benign except when the wind howls, which is most of the time. The resort also has a second layout, the Arnold Palmer-designed Bay Course, and an excellent Ritz-Carlton hotel. Just down the road is Wailea, a vast resort with three standout courses, Blue, Gold and Emerald, plus a broad assortment of shops, restaurants and top hotels, including the Four Seasons and Grand Wailea. Also nearby is the Kaanapali Resort with two windswept, palm tree-lined courses and several hotels including a Westin and Hyatt. The A Position's Wallach calls Maui "the Fantasy Island or Disneyland of golf, a ridiculous collection of pleasures all gathered in one locale of golf perfection," and describes the gusty Plantation Course, Maui's finest golf experience, "like getting pummeled by a beautiful woman."

For escapist exclusivity it is impossible to beat the Pineapple Island, Lanai. Almost the entire island is owned by billionaire Oracle founder Larry Ellison, and his holdings includes two sibling Four Seasons resorts—Lanai's only resorts—which effectively function as one private island property, with shared facilities and free shuttles. The hotels have two stunning and very different golf courses, one of which, the Jack Nicklaus designed Manele, has the most ocean exposure of any course in the state, with cliff-top holes that seem ready to tumble into the surf and beg comparison to Pebble Beach, with long-range views all the way to Maui. The Ted Robinson and Greg Norman-designed Experience at Koele is inland, carved from thick jungle, and features some of the most dramatic elevation changes of any golf course, accented by waterfalls and a lost-world primordial feel. Between these two stunners, which Four Seasons guests have to themselves, the two luxury hotels, private marine preserve, world-class sporting clays facility, and four-wheel drive tours of ancient ruins and desolate, unspoiled beaches, Lanai is an exceptional off-the-grid golf vacation choice. It has always been stellar, but it is getting better, thanks to the millions new owner Ellison is investing in upgrades. He recently opened a Nobu restaurant here, Hawaii's first, and as this story went to press announced plans to renovate both hotels and the Koele course.

The Aloha State has some stiff smoking laws, but you can puff on the golf course, and the pro shops at Wailea, Kaanapali and Lanai's Manele all sell cigars, including the locally grown lineup from the Kauai Cigar Co.

Larry Olmsted is a Cigar Aficionado contributing editor.