Top 15 Old Money Vacation Spots In 4 Seasons
If you have a fascination with the old money elite, here are some travel destinations where they frequently gather. While you might be fortunate enough to cross paths with them, building relationships with this exclusive group is another matter. However, these encounters could lead to fruitful partnerships or lasting friendships if you share similar values or can offer mutual benefits. Beyond the potential for meaningful connections, these locations also offer beautiful settings for a personal getaway.
Spring destinations
Napa County, California
Napa County is renowned for its world-class vineyards and wineries, offering an elegant and sophisticated escape for the old money elite. Springtime brings the vibrant blooming of the vineyards, making it an ideal season for wine tastings and scenic tours.
Napa is home to luxurious resorts and spas that cater to an affluent clientele seeking relaxation and pampering in a serene environment. The high-end accommodations and exceptional service are a significant draw for those who appreciate refined comfort.
With numerous Michelin-starred restaurants and gourmet food options, Napa County appeals to the old money crowd who enjoy fine dining and exceptional culinary experiences. Springtime often brings special wine and food festivals, enhancing its appeal.
Jackson Hole, Wyoming
Jackson Hole offers breathtaking natural beauty, with the majestic Teton Range and lush valleys. Spring is a time when the snow begins to melt, revealing vibrant landscapes perfect for hiking, wildlife viewing, and enjoying the tranquility of nature.
Jackson Hole is known for its exclusive ranches and luxury lodges that offer privacy and seclusion. These high-end accommodations provide a rustic yet luxurious experience, attracting the wealthy who seek a peaceful retreat in a stunning setting.
The town of Jackson boasts a vibrant cultural scene with art galleries, museums, and the National Museum of Wildlife Art. The old money elite appreciate the blend of culture and nature, particularly during the quieter spring season.
French Riviera
The French Riviera, with its glamorous reputation, luxurious resorts, and stunning Mediterranean coastline, is a classic destination for the old money elite. Spring offers milder weather and fewer crowds, making it an ideal time to enjoy its beauty and sophistication.
The region is rich in history and culture, with charming towns like Nice, Cannes, and Monaco. These destinations offer historic architecture, world-class museums, and cultural festivals that appeal to affluent travelers with a taste for the finer things in life.
The French Riviera is a premier destination for yachting, and springtime provides perfect conditions for sailing and exploring the scenic coastline. The luxurious lifestyle and leisure activities attract the wealthy who enjoy both relaxation and recreation.
Newport, Rhode Island
Newport is famous for its historic mansions, which were once the summer homes of America’s wealthiest families. These grand estates and their beautifully landscaped gardens are particularly enchanting in spring, attracting those with an appreciation for history and elegance.
Newport has a rich maritime heritage and is known as a premier sailing destination. The old money crowd, who often have a passion for yachting, find spring to be a perfect time to enjoy the scenic waters and participate in regattas and other sailing events.
Spring in Newport features a variety of cultural festivals and events, including the Newport Music Festival and the Newport Flower Show. These sophisticated gatherings attract an elite audience who value high culture and social events in a picturesque setting.
Charleston, South Carolina, USA
Charleston exudes old-world charm and elegance with its well-preserved historic architecture, cobblestone streets, and antebellum mansions. The city’s rich history and Southern gentility attract the old money crowd who appreciate its timeless beauty.
In spring, Charleston comes alive with vibrant azalea and magnolia blossoms, making it an enchanting destination. The gardens of historic homes and plantations are in full bloom, offering breathtaking landscapes that appeal to those with a taste for classic beauty.
Charleston boasts a sophisticated cultural scene, with world-class dining, art galleries, and the annual Spoleto Festival USA, which features opera, theater, dance, and music performances. These events attract affluent visitors who value high culture and refined entertainment.
The Cotswolds, England
The Cotswolds is the epitome of the English countryside, with its rolling hills, picturesque villages, and historic manor houses. This idyllic setting is favored by the old money elite who appreciate its tranquility and traditional charm.
Spring is a particularly lovely time to visit the Cotswolds, as the historic estates and gardens burst into bloom. These meticulously maintained properties, often open to the public, offer a glimpse into the genteel life of the British aristocracy, attracting those with a penchant for history and horticulture.
The Cotswolds offers a range of exclusive and private retreats, from luxurious country hotels to secluded estates. These provide the perfect escape for the wealthy who seek privacy, luxury, and an opportunity to unwind in a serene and beautiful environment.
Summer destinations
The Hamptons, New York
The Hamptons are renowned for their exclusive beachfront properties and luxurious summer homes. The old money elite flock to this area to enjoy private, upscale living with pristine beaches and stunning ocean views.
Summer in The Hamptons is marked by a vibrant social scene, including high-profile charity events, galas, and private parties. The affluent enjoy mingling with their peers in this glamorous setting, where social connections and networking opportunities abound.
The Hamptons boast a thriving arts scene with numerous galleries, art shows, and cultural festivals. The Parrish Art Museum and various local events attract those who appreciate fine art and culture, making it a sophisticated summer destination.
Ibiza
Ibiza is legendary for its world-class nightlife, drawing the international elite to its famous clubs and exclusive parties. The old money crowd enjoys the island’s glamorous and energetic atmosphere, where they can socialize and celebrate in style.
Ibiza offers some of the most beautiful beaches in the Mediterranean, along with luxurious villas and resorts. These high-end accommodations provide privacy and comfort, appealing to those who seek both relaxation and exclusivity.
Beyond its nightlife, Ibiza has a rich cultural heritage with historic sites, charming villages, and local festivals. The blend of cultural exploration and luxurious living makes it a multifaceted summer destination for the wealthy.
Nantucket, Massachusetts
Nantucket is known for its historic charm, with cobblestone streets, well-preserved colonial architecture, and quaint coastal ambiance. The old money crowd appreciates the island’s timeless beauty and serene environment.
Nantucket is a premier destination for yachting and sailing enthusiasts. The island’s sailing culture and prestigious yacht clubs attract affluent visitors who enjoy spending their summer days on the water.
Nantucket offers high-end shopping and dining experiences, with boutique shops, gourmet restaurants, and charming cafes. The island’s sophisticated yet relaxed atmosphere provides a perfect summer retreat for the wealthy.
Monaco
Monaco epitomizes glamour and luxury, with its upscale casinos, lavish hotels, and stunning Mediterranean views. The old money elite are drawn to this principality for its opulent lifestyle and exclusivity.
Summer in Monaco is marked by prestigious events such as the Monaco Grand Prix and the Monaco Yacht Show. These high-profile gatherings attract the international elite, providing opportunities for socializing and networking.
Monaco’s beautiful coastline and prime location make it a top destination for yachting. The affluent enjoy the opportunity to sail the Mediterranean waters and dock at the luxurious Port Hercule, mingling with other yacht owners in this glamorous setting.
St. Kitts
St. Kitts offers stunning natural beauty with its lush landscapes, pristine beaches, and clear blue waters. The island’s unspoiled environment provides a serene and picturesque setting that appeals to the old money crowd seeking a tranquil summer escape.
This is home to exclusive resorts and private villas that cater to affluent visitors. These luxurious accommodations offer privacy, comfort, and top-notch amenities, making it an ideal destination for those who value exclusivity and relaxation.
St. Kitts boasts a rich history and vibrant culture, with historic sites like Brimstone Hill Fortress and charming colonial towns, appealing to the old money elite. The island’s excellent yachting opportunities, with marinas and favorable sailing conditions, attract wealthy visitors who enjoy exploring nearby islands.
Additionally, world-class golf courses and leisure activities such as hiking and beachcombing offer a perfect blend of relaxation and recreation, making St. Kitts a desirable summer destination.
More places
Saint-Tropez, France
Known for its exclusive atmosphere and stunning Mediterranean landscapes, Saint-Tropez has been a favorite destination for old money families since the golden age of French cinema. Celebrities like Alain Delon and Jean-Paul Belmondo frequented its shores, while in the 90s, supermodels like Kate Moss and Naomi Campbell added to its allure with their presence in its renowned nightclubs.
Portofino, Italy
This picturesque fishing village on the Italian Riviera exudes charm with its pastel-colored houses, luxury boutiques, and azure blue sea. Portofino’s coastlines are graced by luxurious yachts, attracting old money families seeking a refined coastal retreat. Its seafood restaurants, set around the small cobbled square of Piazzetta, offer a taste of the Italian good life.
Capri, Italy
An island in the Bay of Naples, Capri is renowned for its rugged beauty, exclusive hotels, and bustling commerce. Its natural wonders, like the famous Blue Grotto, have drawn the admiration of emperors since ancient Rome. Today, Capri remains a sought-after destination for old money families looking for luxury and natural splendor.
Mallorca, Spain
One of the Spanish islands in the Mediterranean, Mallorca captivates visitors with its beach resorts, secluded coves, and majestic limestone mountains. Old money families are drawn to its tranquil lifestyle and abundant sunshine, making it a favored retreat for relaxation and leisure.
Positano, Italy
Perched on the cliffs of the Amalfi Coast, Positano enchants with its narrow streets, charming alleys, and vibrant craft shops. Its picturesque beauty and romantic ambiance make it a dream destination for old money families seeking an escape from the ordinary. Positano’s allure lingers long after visitors depart, leaving them yearning to return to its idyllic shores.
Fall destinations
Aspen, Colorado
Aspen is renowned for its breathtaking fall foliage, with the aspen trees turning vibrant shades of yellow and gold. This natural beauty attracts the old money crowd who appreciate scenic landscapes and serene environments.
Aspen offers luxurious accommodations and a range of outdoor activities, including hiking and biking, that appeal to affluent visitors seeking a blend of adventure and comfort.
In the fall, Aspen hosts various cultural events, including film festivals and art shows, which draw the sophisticated and culturally inclined old money elite.
Cannes
Cannes in the fall features a mild Mediterranean climate and fewer tourists, providing a more relaxed and exclusive atmosphere for the old money crowd.
Known for its luxury hotels, upscale dining, and high-end shopping, Cannes continues to attract wealthy visitors who enjoy the glamorous lifestyle. The city hosts numerous cultural events and festivals in the fall, appealing to those who appreciate art, cinema, and refined entertainment.
Napa County, California
Fall is harvest season in Napa Valley, making it an ideal time for wine enthusiasts to visit vineyards and participate in grape harvesting and wine tastings.
The region’s rolling vineyards and picturesque landscapes are particularly beautiful in the fall, attracting those who appreciate natural beauty and tranquility.
Napa’s reputation for gourmet food and world-class wines draws the old money elite who enjoy fine dining and exceptional culinary experiences.
Newport, Rhode Island
Newport’s historic mansions and coastal scenery are especially enchanting in the fall, attracting those who appreciate history and elegance.
The fall season in Newport features a variety of cultural festivals and events, such as the Newport Mansions Wine & Food Festival, appealing to affluent visitors.
Newport remains a premier destination for sailing and yachting, with pleasant fall weather offering ideal conditions for maritime activities.
Swiss Alps, Switzerland
The Swiss Alps offer stunning mountain scenery and crisp autumn air, making it a favored destination for those who enjoy natural beauty and outdoor activities.
The region is home to exclusive resorts and luxurious chalets that provide privacy and top-notch amenities, catering to the affluent seeking a high-end experience.
Fall in the Swiss Alps is perfect for hiking, biking, and enjoying the serene alpine environment, attracting the old money crowd who value both adventure and relaxation.
Winter destinations
Aspen, Colorado
Aspen is renowned for its world-class skiing facilities, drawing affluent winter sports enthusiasts who seek the finest slopes and luxurious amenities.
The town boasts luxurious resorts and a vibrant après-ski scene, providing high-end accommodation and entertainment options for the old money crowd.
Maldives
The Maldives offers a tropical escape from winter’s chill, with its pristine beaches, crystal-clear waters, and exclusive overwater bungalows appealing to affluent travelers seeking luxury and relaxation.
The Maldives’ remote location and exclusive resorts provide privacy and seclusion, attracting the old money elite who value a tranquil retreat away from the crowds.
Jackson Hole, Wyoming
Jackson Hole is a paradise for skiing enthusiasts, offering some of the best slopes in the country and stunning winter scenery that appeals to affluent skiers seeking adventure and natural beauty.
The area boasts upscale accommodations and amenities, including luxurious lodges and fine dining options, catering to the discerning tastes of the old money crowd.
The Elser Hotel – Miami, Florida
Miami’s warm climate in winter provides a welcome escape from colder temperatures, attracting affluent travelers seeking sun, sand, and relaxation.
The city’s vibrant nightlife, beautiful beaches, and cultural attractions offer a diverse range of entertainment options for the old money elite looking for excitement and sophistication.
