Summer Traditions – Vacations in the North Carolina Mountains and Anna Maria Island

May 26, 2016 | Tampa Magazine | Culture

For generations, Tampa Bay’s most affluent families have summered in the azure blue beaches of nearby Anna Maria Island or . . . the cool Carolina Mountains near Highlands and Cashiers. Why? The stories follow.

Anna Maria Island

Parrots flew overhead just after midmorning, less than a block from the Anna Maria City Pier, the gentle Gulf breeze swaying the palm trees along Pine Avenue under a radiant sun. The bright green and feathered pandemonium danced above from one neighborhood jungle to the next, taking with them any reminder that this slender barrier island at the southwestern mouth of Tampa Bay was roughly an hour’s drive from reality.

Wedged in between Tampa Bay and the Gulf of Mexico, just south of Egmont Key, Anna Maria Island—the northernmost tip of the Bradenton-Sarasota archipelago that includes Longboat and Siesta Keys to the south—has always been a place for people to relax.

Spanish conquistador Hernando De Soto passed through on the way to arriving on the mainland, but, except for its brief role as a military outpost during the Battle of Tampa in the early years of the Civil War, Anna Maria remained an uninhabited scrubland until the arrival of George Emerson Bean.

“[He]was the first homesteader,” said Jonathan Crane of the Anna Maria Historical Society. “That was about 1895. In order to earn his homestead he had to develop [the land]. [That’s when] he ran into the other big name in Anna Maria’s history, Charles Roser. Roser invented the Fig Newton and sold it to the National Biscuit Company (NABISCO), so Bean had land and Roser had money. Their development company went bust when everyone else’s did in the late ‘20s, but they’re the ones who kind of got everything going.”

Roser left his mark on the island in numerous ways, none more visible than the great church named for his parents John and Caroline. The Roser Memorial Church (512 Pine Ave.) has not only survived the century but expanded to become the island’s primary house of worship.

During the 20th century the north end of the island was developed into three distinct communities, Anna Maria, Holmes Beach and Bradenton Beach, respectively, each with its own public works and personality.

“During the mid-‘50s, right after World War II, you had this explosive growth, all by the name of [Holmes Beach namesake] Jack Holmes,” said Dusty Crane, a member of Anna Maria Island Historical Society’s board of directors. “Holmes acquired what was once called School Key and started building affordable homes for returning GIs, and that became Holmes Beach. Many of those homes still exist and are being renovated by new residents.”

In the 1990s, growth on the island dramatically expanded thanks to the efforts of the Tourism Development Council, an elected panel of local business owners hired to redirect tax money into generating, supporting and enhancing tourism-creating activities.

The result was an increase in accommodation rentals, fine dining and pedestrian-friendly amenities. A three-story building height restriction has allowed Anna Maria to stay a quiet beach community full of ‘Old Florida’ charm. A free public trolley, one of the community’s initiatives to focus on green and renewable energy, runs the length of Anna Maria.

Whether it’s a stroll down Pine Avenue during lunchtime or a surfside seat to picture perfect sunsets, few places are as effortlessly charming as this island escape.

TAMPA Magazine spoke to Tampa resident Thom Stork and Anna Maria regulars Ray Arpke and Justin Moore about how to get the best experience the island has to offer.

Frequent Island Visitor: Thom Stork, President & CEO, Florida Aquarium

“We have been going to Anna Maria for more than 10 years now, usually on an annual basis for a week to 10 days, but then we will occasionally run down for dinner because there are restaurants down there that we enjoy going to,” says Thom Stork, president and CEO of the Florida Aquarium. “We’ve stayed a couple times down on Longboat Key, but we keep gravitating back to Anna Maria because we just like the neighborhoods there.”

Besides being only an hour drive from his front door in Lutz, Stork said Anna Maria’s peace and tranquility for the whole family is his main reason for returning year after year.

“I have a picture here on my desk of my grandson, who at the time of this picture was probably about 6,” Stork said. “He caught the biggest fish he ever caught, and it was down on the Anna Maria city pier. He caught a mackerel right off of that pier, and I’ve got a picture of it. That’s a proud memory.”


The center of all life on Anna Maria is, of course, the beach. With free parking at Anna Maria Beach, Bradenton Beach and Holmes Beach spread throughout the island, you’re never far away from relaxation.

Pine Avenue, the commercial and geographic heart of Anna Maria, feels less like a thoroughfare and more like a slice of small-town Old Florida, partially due to its Historic Green Village (HGV).

To spare its antique 20th-century beach homes like “The Rosedale Cottage” and “Thelma by the Sea” from being demolished for larger, multimillion-dollar properties, the Anna Maria City Council moved several of the oldest structures to Pine Avenue, successfully converting them into boutiques and restaurants, including AMI Outfitters (505 Pine Ave.) clothing store, Beach Bums (427 Pine Ave.) bike, golf cart and kayak rentals and confections specialists Hometown Desserts (507 Pine Ave.).

Earning its ‘Green’ designation through sustainable energy and resource technology, today the HGV on Pine Avenue is one of only 100 places worldwide to achieve the ranking of Platinum LEED, the highest possible green building standard.

A former ferry platform on the north side of the island, the Anna Maria City Pier (100 S. Bay) is the centerpiece of Pine Avenue and the perfect place to start or end your trip. It hasn’t unloaded any passengers since Anna Maria was first connected by the Cortez and Manatee bridges to mainland Bradenton, but after being restored and expanded, the Pier is now a thriving restaurant and prime fishing spot at all times of day.

The Key Royale Club (700 Key Royale Drive), Anna Maria’s only full-scale golf course, is a nine-hole, par-32 affair located on Holmes Beach with spectacular views of the water just beyond the next bunker.

Founded in 1949, The Island Players, Inc. (10009 Gulf Drive) is Manatee County’s oldest continual community theater. It is still performing strong in its 69th season. The season runs from October through the end of May, so summer visitors will need to make plans to attend on return visits to Anna Maria, during the performance season.


A short jaunt down Gulf Drive from Pine Avenue, the Mainsail Beach Inn (101 66th St., Bradenton Beach) is the height of interior luxury without the exterior flash that clamors for attention. Part of the Marriott Autograph Collection hotel series (the same collection as the Epicurean Hotel in Tampa), no expenses were spared on the details.

Only sliding glass doors and a private porch separate the beach from its elegant and spacious rooms, hardwood floors and large kitchen. Offering 12 individual two- and three-bedroom suites, many with rooms facing the western coast of Anna Maria, each suite offers views of picturesque sunsets from the living room.

“When the whole family goes down, we’ll rent two of those big three bedroom units, and it’s just very comfortable,” Stork says. “A three bedroom unit is as big as our home, and it’s just extremely comfortable. You can fix as big a meal as you want to in there. When we go fishing, we’ll come back, and if we had a good day, we’ll have a big fish fry.”

With a guest return rate of more than 70 percent, booking a room during the peak months of March through August can be difficult.

Sandy Zinck, general manager of the Mainsail Beach Inn, said plans are already in the works to develop a second waterfront property to the MainSail family, the Waterline Marina Resort & Beach Club (5325 Marina Drive, Holmes Beach), a 32-suite resort featuring a 50-slip marina and exclusive beach access, slated for opening in August 2017.

With exclusive pool access and a private beach entrance, guests and residents of the Tortuga Beach Resort (1325 N. Gulf Drive, Bradenton Beach) can enjoy all the luxury and exclusivity that Anna Maria has to offer. Divided between the BayFront Villa (studios and 2-bedrooms), Gulf View Studios (one-bedrooms), Palm Court South (studios to two-bedrooms) and Tortuga Gardens (one-bedrooms to deluxe apartments and penthouse), each room is available for daily or weekly rates.

Multiple pools, a fourteen-slip private boat dock on Sarasota Bay, pet-friendly accommodations and family-friendly amenities are available to guests of the Tortuga Beach Resort. On the rise as a wedding destination, especially with large groups, an event desk was recently created to help host nuptials or other events at all four resorts within the Anna Maria Island Resorts family.

Ideal for the ‘get-up-and-go’ type of guests, Silver Surf Beachside Resort (1301 Gulf Drive N., Bradenton Beach) features 50 individual and adjoining rooms with king-size beds, pullout couches and small kitchens directly across Gulf Drive from a privately opened beach. Designed to look vintage with modern amenities, Silver Surf is a fan-favorite that prides itself on cleanliness and exceptional service.

Rodocker has owned the Silver Surf since 1984, eventually building its sister resort, the upscale BridgeWalk Resort (100 Bridge St., Bradenton Beach), above the Bridge Street shopping district, a short walk from Bradenton Beach. Offering everything from large single “Apartos” with mini kitchens and Murphy beds (up to six can be adjoined at once) to two-bedroom, 2.5 bath townhouses with private patios, full kitchens and living rooms with fireplaces.

Real Estate

If you’re looking to turn your weekend getaway into something more long-term, Anna Maria boasts abundant real estate options perfectly suited to every taste and need.

Island Real Estate (6101 Marina Drive, Holmes Beach) offers something for everyone in all three Anna Maria towns, from luxurious condos and private homes to quaint cottages and beachfront properties.

Sato Real Estate (519 Pine Ave, Anna Maria) is a company that pays attention to detail. Their “homes away from home” on Anna Maria range from cozy one-bedroom affairs to luxury condos and beach houses with six or more rooms.

Silver Resorts (Bradenton Beach) features two distinct resorts, the BridgeWalk (100 Bridge St.), offering roomy one-and-two bedroom condos and the Silver Surf Gulf Beach Resort (1301 Gulf Drive N.), an affordable and family-friendly resort with beach access across the street.

Anna Maria Island Resorts (6101 Marina Drive, Holmes Beach) represents two unique resorts that specialize in year-round, unlimited-use ownership, the Tortuga Beach Resort (1325 Gulf Drive N.) and the TradeWinds Beach Resort (1603 Gulf Drive, Bradenton Beach), an Old Florida-style neighborhood complex of one-bedroom cottages available for rental or purchase.

A hotbed of ocean activity, the mouth of Tampa Bay contains some of the most fertile and diverse waters in the Gulf of Mexico, a perfect place to look for manatees idling on the intercostal waterway or hook a giant tarpon.

If visitors are lucky, they might even spot Tampa Bay’s legendary hammerhead shark “Old Hitler,” described by many as longer than 20 feet with a head larger than a pickup truck, a shark that could eat other sharks in a single bite. Known along the coast from Boca Grande to Clearwater Beach, Old Hitler has reputedly been spotted between Anna Maria and Egmont Key, the uninhabited barrier island at the mouth of Tampa Bay only a short boat ride away.

Once the site of Fort Dade during the Spanish-American War and later World War II, today the Key is a National Wildlife Refuge and state park. Accessible only by private boat or ferry, Egmont Key State Park (4905 34th St. S. #5000, St. Petersburg) is partially a historical site with beaches, hiking trails and modern amenities while still preserving an important nesting area for ospreys, brown pelicans, American oystercatchers and more.

Fishing & Water Sports

Despite being the head of the Florida Aquarium and overseeing the largest decade of growth in its 21-year history, Stork still considers himself an avid fisherman.

“People ask that question all the time — do I eat fish when I go out to dinner — and the answer is yes,” he says. “Our message to people is to eat the right fish and not eat fish that are threatened or endangered. Fish is a sustainable product that we try to promote, so yeah, fishing is one of my favorite things.”

“I want to give a shout out though, to one of the best fishing guides in the state of Florida and a good friend. Justin Moore ( fishes out of Anna Maria, and a couple times a year I’m down fishing with him. He is a great, great guide. He is very good in terms of putting you on fish.”

Cannons Marina (6040 Gulf of Mexico Drive, Longboat Key) is a great way to see the water on a budget with 17-foot to 24-foot boats available for half-day, full-day, week- or month-long rental packages. Discounts are available for consecutive days or weeks, and accessories like water skis and inflatable tubes are rented out onsite.

If you want to skip the rental stage and get your own, Galati Yachts Sales (900 S. Bay Blvd., Anna Maria) sells luxury brands like Viking and Maritimo for purchase, as well as yacht charters and fishing charters. They also have a full-service store and a restaurant, Island Ocean Star (902 S. Bay Blvd., Anna Maria), which offers sushi, hibachi and Japanese cuisine overlooking Bimini Bay.

Though only an hour’s drive from Tampa, guests with boats can coast down the bay in roughly 40 minutes. Docking is available at many resorts already, but Bradenton Beach Marina (402 Church Ave.) has plenty of space and easy access to the gulf and the bay through Longboat Pass.


Stellar seafood isn’t hard to find in Anna Maria, but finding the right combination of atmosphere, location and flavor is up to you.

For those seeking a hearty but no-frills meal, the Rod & Reel Pier (875 N. Shore Dr., Anna Maria) is the ideal pit-stop lunch spot. A former disembarkation spot for ferry riders from Tampa and St. Petersburg now converted into a bar, restaurant and lookout point, the pier still draws scores of fishermen and women from dawn to dusk for the daily specials and great catches.

Dusk on the island is an event you don’t want to miss, when radiant sunsets glimmer on the gulf and worries wash away with the tide. Gulf Drive Café (900 Gulf Drive N.) is one of the few places on the island that provides on-the-beach dining and outstanding waterfront views perfect for all ages. Open from breakfast to after-dinner dessert, wedding and event packages are also available through the restaurant’s website.

According to Thom Stork, “The Beach Bistro (6600 Gulf Drive, Holmes Beach) is right at the top of our list. We also enjoy The Waterfront (111 S. Bay Blvd.) on the north end of the island. Harry’s Continental Kitchen (525 St. Judes Drive) on Longboat Key is also a favorite. For ‘date night’ though, there’s no question, it’s Euphemia Haye.”

Known for world-class cuisine and incomparable atmosphere, Euphemia Haye (5540 Gulf of Mexico Drive) on Longboat Key is worth the 10-minute drive south from Anna Maria. Winner of 10 consecutive Golden Spoon awards from Florida Trend Magazine, the Haye features the eclectic culinary creations of head chef Ray Arpke, ranging from pasta and poultry to surf and turf.

The Haye Loft, an upstairs cocktail lounge added in 1991, offers live music, flatbreads and dessert for a dynamically different change of pace from the main dining room downstairs. Reservations can be difficult to secure at Euphemia Haye, but the experience is guaranteed to be unforgettable.

Vienna schnitzel, bratwurst and potato pancakes might seem a world away from typical island fare, but for 17 years the Old Hamburg Schnitzelhaus (3246 E. Bay Drive) in Holmes Beach has served up beloved German and Austrian cuisine for the community. Boasting a menu of authentic classic and contemporary German dishes and a bar stocked with imported beer and wine, Old Hamburg will have you saying, “Prost!” in no time.

An Anna Maria original just two blocks from the beach, Bortell’s Lounge (10002 Gulf Drive, Anna Maria) is everything you want out of a dive bar — low-key atmosphere, full bar, amiable regulars — with none of the grime or shadiness to discourage newcomers. Renovated by Tampa-Anna Maria residents Steve and Marcy Wilhelm, smoking has been moved outside, but much remains the same, keeping Bortell’s exactly the way the locals like it.

The sun had started its long, lackadaisical slink to the water, scattering amber hues across the water between the Gulf of Mexico and Tampa Bay. The Sunshine Skyway glittered in the distance, the cars it carried to St. Pete and Bradenton nothing more than a flowing line of dots. But slightly to the left, along the sugar-white sands where visitors risk sunburn just to linger a little while longer, the calming winds of paradise were still blowing.

Trying to reconcile the island life of Anna Maria with the bustle of the greater Tampa Bay area feels like straddling two very different, mutually exclusive worlds, until you realize the proximity between routine and extraordinary.

Your next getaway destination is only a weekend away.

Highlands/Cashiers, NC

Deep in the foothills of Appalachia, 40 minutes west of Asheville and two hours north of Atlanta, this region nestled between the Piedmont Plateau and the Blue Ridge Mountains has been called the Appalachian Temperate Rainforest for its cool climate and lush ecosystem. The summer air stays below 85 degrees year round, and verdant forests of oak and pine conceal a massive network of creeks, streams and rivers, ideal conditions for outdoor activities of all kinds.

The Highlands-Cashiers area in western North Carolina has been mesmerizing visitors since the land belonged to the Cherokee Nation. Judaculla Rock, a soapstone boulder in Cullowhee, North Carolina, is covered with strange markings and ancient petroglyphs of local wildlife, one of the best examples of indigenous culture east of the Mississippi.

Colonel John Zachary of Surry County, North Carolina, was one of the first to make his return to the area a permanent one, building a home for his wife and 14 children in 1833. The Zachary homestead included what today comprises downtown Cashiers and the High Hampton Country Club property.

In 1875, Kansas businessmen Samuel T. Kelsey and Charles Hutchinson drew two lines on a map: one from Chicago to Savannah, the other from New Orleans to Baltimore, reasoning that the intersection on the west side of Whiteside Mountain from Cashiers would someday become a future population hub.

The remoteness that hindered growth was actually a blessing in disguise; while the coastal Carolinas expanded and boomed, the natural splendor of the mountains stayed untouched. With the arrival of golf and the Highlands Country Club in 1928, the area took on a second life as a vacation destination for affluent travelers trying to escape the brutal summer heat.

TAMPA Magazine spoke with several Bay-area residents who have second homes in the mountains in and around Highlands and Cashiers, North Carolina. Their stories and insight on the area follow.

Long-time Cashiers, North Carolina Resident and Business Owner: Nancy Turner

Author, “The Summer Times: A Guide to Adventures Around Highlands, Cashiers and Toxaway” & Owner, High Covey Farm

“My parents bought a house in Cashiers in 1963 when hardly anybody was up there, and we’ve been going back for 54 years,” she says. “It was really hard because you couldn’t find anyone in that area to do work for you. We bought a house that had just four walls, so we had to pretty much build it out for ourselves. There also weren’t all that many places to go out to eat back then.

This may make me sound pretty old, but the construction of the Interstate Highway System made a big difference for the area. There used to be only back roads, and you could never make it from Tampa to Cashiers in one day. Now you can make it up there in about 10-and-a-half to 12 hours.

We were fortunate enough to have a house on the lake (Lake Glanville). We would swim in the summers and ski in the winters, and there was hardly anybody there but us. Just being in the cool air here is great.”

In 1978, Turner purchased High Covey Farm and began her Christmas tree farm. The business is called Turner Trees from High Covey Farm. Says Turner, “I grow Frasier firs. You have to be at least at 3,500 feet of elevation to grow them. The nice thing is that the farm gave me an entrée into the local community. Because it was hard to find workers, I had to do most of the work myself. The residents saw that someone from Tampa, Florida, was up here working as hard, or hopefully as hard, as they did. So I was accepted.”

Vacation Home Resident: Greg Ghodsi, Sylva, NC (About 30 Miles From Cashiers, NC)

Managing Director of Investments, Raymond James

“My wife and I were just talking about this subject the other day. Two of my friends from college both live in Tampa and have teenage kids like us. About three years ago, we were able to get all of our families up to the mountains for a few days. These are guys I grew up with in college, and now we’re all dads with kids in their teens. All of us were just hanging out together and relaxing because no one had to work. We were just there to relax.

When we’re back in Tampa we can never get everyone together at once, because our schedules are never in sync. But we’re able to work it out for most of the week in the mountains. Everyone is more relaxed there. The mountains just calm you down. Things are not as fast paced or crazy as they are down here.”

Outdoor Activities

Here, nature is more than just a backdrop; it’s a living, breathing sanctuary that offers as much time for reflection as it does for recreation.

One of North America’s most unique ecosystems, the Highlands-Cashiers area sits along the basins and plateaus of the foothills of the Appalachian Mountains, where heavy annual rainfall, moderate year-round temperatures and powerful rivers have created a temperate tropical rainforest home to more than 60 rare or endemic plant species.

Nearly 200 different types of wildflowers can be found in Jackson and Macon counties, growing along highways, rock outcroppings and hardwood forest coves. Beginning in March, spring bloomers like Solomon’s seal, mountain laurel, Indian paintbrush and giant chickweeds adorn hills and forest valleys.

In the summer they’re joined by fire pink, enchanter’s nightshade, and grass-of-Parnassus that flower well into September and October, transforming the region into a multicolored wonderland. Learning the names and likely flowering spots of the region’s many unique plants is a pastime that can enhance your appreciation for the area.

Known collectively as the Jocassee Gorges, the Chattooga, Nantahala, Cullasaja and Tuckaseigee rivers flow through Macon and Jackson counties eastward, playing host to several spectacular waterfalls accessible by hike or highway.

“We have guests that come up, and one of the things we really like doing is going to the waterfalls,” says Ghodsi. “We have a waterfall tour that we take people on. The ride between Franklin and Highlands on Highway 64 runs along the Cullasaja River, and there’s several beautiful falls that are easily accessible, [like] Dry Falls where you can walk and go under the falls. Highway 64 runs past Bridal Veil Falls, so close that you can drive your car within a few yards of the bottom of the falls.”

“Some falls, like Glen Falls, are more horizontal than vertical. To get to them, you have to hike down trails to get to the river. The bad part is that you’ve got to hike back up again.”

The rivers run through Gorges State Park (976 Grassy Ridge Rd, Sapphire) in Transylvania County. The recently created national park is home to hundreds of rare or endangered animal and plant species but still offers year-round recreation and camping.


The best way to see the rivers and forests is to take advantage of the many whitewater rapids and rafting expeditions available throughout the region. Though some rivers are tame enough to ride an inner tube down, others like the Nantahala and Chattooga rivers can veer from Class II rapids all the way to Class III or IV in a matter of miles, a challenging trip for enthusiasts of all stripes.

A short drive from several active rivers, Ghodsi says some rivers are tame enough for a 4-year-old to enjoy.

“Over the years we took our kids on the more basic ones, and now that they’re teenagers, they want to go to the ones where we’re staring off a cliff every time,” he says.

If you’re looking for a whitewater rafting adventure, either in North Carolina or abroad, the Nantahala Outdoor Center (13077 Highway 19 W., Bryson City) is your premier destination. Named one of the best outfitters on Earth by National Geographic ADVENTURE for its “Boaters without Borders” program to Bolivia in 2009, the Nantahala Outdoor Center offers 80 different rafting or land-based itineraries and a resort with four restaurants and rustic but sumptuous accommodations.

If you’d rather be high and dry during your outdoor adventures, Highlands Aerial Park (9625 Dillard Road) takes the fun to the tops of the trees. The “World Class Canopy Zip Line Tour,” for more active participants, spans the mountains between North Carolina and Georgia, while the “Giant Mountain Swing” offers a seated view during an 80-foot arc through the trees.

The first commercial rafting company to operate in the Southeast, Wildwater (10345 Highway 19 S.) offers all types of rafting packages on four different rivers, including an overnight trip called “Chattooga River Under the Stars” that takes riders through some of the region’s most difficult rapids. Wildwater also offers multiple zipline canopy tours and individual or group packages that combine rafting with ziplines and lodging.


When golf prodigy Bobby Jones came to Highlands in 1928 to christen the newly built Highlands Country Club (961 Dillard Road), it began a long and celebrated tradition still thriving today. One of the premier social and recreational clubs in the country, members enjoy croquet, a state-of-the-art fitness center and a bridge club in addition to the famous golf course carved by Donald Ross out of the surrounding mountain landscape.

Though shorter than most modern courses, the Highlands course’s demand for precision supposedly sharpened Jones for his 1930 Grand Slam.

According to Greg Ghodsi, “It’s a short course, only about 6,200 yards. I thought it would be ‘an old man’s course’ when I played it with a client and that it would be too easy, but it was one of the hardest courses I’ve played. [It has] very challenging short holes with greens well below or well above your approach shots. Some shots looked 200 yards away and were actually only 100. The changes in elevation mess with you.”

Another set of links touched by PGA royalty is Balsam Mountain Preserve’s (81 Preserve Road, Sylva) Arnold Palmer Signature Golf Course, an 18-hole experience at an elevation of 3,700 feet. It was designed by Palmer to capitalize on the beauty of the area while still staying player-ready for all skill sets.

Open from the beginning of May until the end of October, the Highland Falls Country Club (1 Club Drive, Highlands) features an 18-hole, par 70 course designed by “Gentleman Joe” Lee. Known for creating courses that are fair but also friendly and fun, Lee incorporated the park’s natural splendor, like stunning views of Big Bear Pen Mountain, water hazards made of the Cullasaja River and the famous Highland Falls waterfall at the 15th hole, when he redesigned the course in 1979.

The Sapphire Valley National Golf Club (50 Slicers Ave, Sapphire) is the only public course available for play in the area, meaning you don’t need to buy a membership in order to hit the links.

Real Estate

With properties ranging from just under half a million to nearly eight-figures, Landmark Realty Group (828-743-0510) offers a change in lifestyle as well as a change in scenery. Office locations in Highlands, Cashiers and Sapphire deal with locations all over the area.

A wide array of properties in some of Cashiers best neighborhoods at 3,500 feet are available through Cashiers Real Estate (828-743-4207), from budget-friendly townhomes to indulgent multi-room manses near Lake Toxaway.

If you’ve always dreamed of owning a 19th century mansion estate in the woods around Cashiers, Silver Creek Real Estate (828-743-1999) has you covered. Opulent custom homes and and refurnished historic halls each have their own breathtaking views. Prices may be steep, but more affordable townhomes and residences are available around Sapphire as well.

Says Greg Ghodsi, “A lot of the locals joke that the Floridians only want to buy homes at the highest point in the mountains and the furthest from town. Those homes are great on a beautiful day, but when you get bad weather, the steep roads can be challenging. That’s something to keep in mind.”

“We’re about a mile from the town of Sylva, but at 2,500 feet, we still have a beautiful view. We can walk to downtown, and the hospital is close by. You have this little town right there if you need groceries or want to go out to eat. It’s not a 25-minute ride down a steep mountain at nighttime.”

Art & Entertainment

Voted one of the “Top 12 Small Town Art Places” in 2013 by online magazine AdobeAirstream, Highlands and Cashiers are brimming with independent and community art spaces, galleries and events.

The Bascom Center for the Visual Arts (323 Franklin Road) has been providing the public and community with gallery space for regional artists and educational programs for youth and adults through instructional classes in different mediums. During the summer of 2016, the Bascom featured “Beyond the Sock: Knitted Art by Charles Gandy” (3/12-6/12) and “Of Land and Spirit: Cherokee Art Today” (6/12-9/18) in addition to artist residencies and open art contests for members.

In the heart of Cashiers is The Village Green Commons, an open-air, multi-purpose event space home to art shows, weddings, lectures and concerts throughout the year. According to Nancy Turner, “The community in Cashiers started this thing on Friday nights called Groovin’ on the Green. They bring in a band, and everybody who comes sets up picnics with food and drinks. If there is a good band, everybody jumps up and dances. It’s like this great outdoor party. You can’t always count on good weather, but this year the ‘Tampa Tribe’ is paying for the band, so there will definitely be great music – and dancing.”

The Village Green hosted the 2016 Cashiers Plein Air Art Festival from July 12-16, where artists from around the country gathered to interpret the area’s natural landscapes in multiple mediums.

North Carolina’s oldest active theater, the Highlands Playhouse (362 Oak St.) has been rolling out performances almost every year since 1938. Known for delivering adaptations of everything from Broadway standards to eclectic, lesser-known works, especially during the summer season, the Playhouse still has tickets available for its summer season.


The good news about dining in Highlands and Cashiers is that, with so much hiking around, you’ll be burning calories off in no time. This bodes especially well for foodies looking for savory mountain cuisine and sapid drinks against awe-inspiring scenery.

Located just outside of Cashiers in the community of Lonesome Valley, Canyon Kitchen (150 Lonesome Valley Road) is known throughout the Southeast for its inventive takes on local traditions like Columbia River Wild King Salmon, rabbit roulade and peach profiterole.

Founded by award-winning celebrity chef John Fleer in 2009 after a 14-year-stint as executive chef at Blackberry Farm in Walland, Tenn., the Kitchen’s focus on fresh and seasonal dishes soon earned them their stellar reputation. Fleer would eventually leave Canyon Kitchen to focus full-time on his family and Asheville restaurant Rhubarb (7 S. Pack Square). Taking his place was Chef Adam Hayes, a North Carolina native and former executive chef at the Barnsley Resort in Atlanta and the Grand Bohemian Hotel in Asheville.

According to Tampa area resident Ben Hill, litigator and co-founder of Hill, Ward & Henderson, “Nancy Turner helps host a dinner at Canyon Kitchen, usually sometime in July. They invite everyone they know from the Tampa area. There’s sometimes more than 100 people that go to that dinner, and that’s just a fraction of the people from Tampa that are up there at that time of year.”

The sign for Winslow’s Hideaway (48 Village Walk Way) advertises “steak, seafood and spirits,” which is all you need to know about this cozy, 34-seat restaurant. Family owned and operated, Winslow’s eclectic menu includes everything from trout and French onion soup to conch fritters, steaks and escargot. A favorite for locals and visitors alike, Winslow’s is one of Cashiers’ best-kept secrets.

One of the more unexpected culinary surprises in Highlands, Wild Thyme Gourmet’s (343-D Main St.) Asian-influenced American cuisine is a delicious contrast to more regional menus and a sign of Highlands’ increasingly diverse palate. Nepalese chef and owner Dindu Lama has spiced up traditional and exotic dishes like wasabi pea-encrusted wild salmon and bacon-wrapped quail for more than 20 years. The newly redesigned restaurant features a full service bar and an extended wine list.

According to Greg Ghodsi, “In the center of downtown Sylva, there’s a restaurant called Lulu’s (612 W. Main St.) that’s been there for about 25 years and is probably the most famous restaurant in the area. The produce is all locally grown—they’ve been “farm-to-table” for a long time.

The place my wife and I go to is Innovation Brewery (414 W. Main St.). It’s a craft brew pub – a small place – but they make everything right there in the facility. If we need to get away from the kids for a bit, that’s where we go.”


Many of the “Tampa Tribe” own summer homes in the Highlands-Cashiers area, but if you’re looking for a less permanent stay, there are plenty of historical and modern accommodations suited to all types of lifestyles.

“The Old Edwards Inn (445 Main St.) is the type of place that a husband and wife can go to hang out at a high-end spa for several days,”says Ghodsi. “There are a lot of beautiful restaurants right there at the Inn and within walking distance.” Ranked as Condé Nast Traveler’s Top Hotel Spa in North America, The Old Edwards Inn is Highlands’ earliest boarding house. The Inn has steadily grown into one of the most indulgent and unrestrained stays available. Offering rejuvenating activities through its world-class spa, fitness center, solarium and refined accommodations, The Old Edwards offers an experience unlike anything else in Highlands.

For over 100 years, Colonial Pines Inn-Bed & Breakfast (541 Hickory St.) has treated guests to seclusion and comfort while remaining just a short walk from Main Street Highlands. Seven bedrooms are spread across the Inn’s compound, from the Main House (one bedrooms) to The Guest House Apartments (two bedrooms) and Miss Rebecca’s Cottage (three bedrooms, great room and full kitchen), each with spectacular views of Satulah Mountain and the surrounding area. All rooms are available for short or long-term rentals.

Built by Confederate cavalry leader Wade Hampton III before the Civil War, the Hampton Hunting Lodge passed through many owners and incarnations during its long history to become the High Hampton Inn & Country Club (1525 NC-107), a rustic but spacious mountain resort on more than 1,400 acres in Cashiers. Featuring a 116-room Main Lodge and a collection of cottages crafted to embrace the pastoral settings, High Hampton is rustic modern luxury. The legend goes that General Hampton was sitting on the porch of the old inn when he learned he had been made governor of South Carolina.

Standing out in the valleys or on mountain peaks, feeling the cool air rush through the trees or the refreshing splash of a mountain stream, it isn’t hard to dream of living outdoors here and loving it, as people have done for hundreds of years. The sky remains a perfect shade of “Carolina Blue” until the sun sinks westward beyond the Appalachians, bringing incredible panoramas of starry nights and flickering constellations almost close enough to touch. In the morning, the day will rise over the eastern hills, and another beautiful summer day will reveal itself, waiting to be explored.

Do you want to see more of this or similar features?