4 High-End Experiences Worth the Splurge After 50

A senior couple is sitting and traveling by a private jet while enjoying champagne and chatting with each other. — (Image credit: Getty Images)

For the couple who has seen it all, a splurge date is an opportunity to break the routine of the everyday spectacular. It’s about seeking out the hidden chef's tables and the sensory experiences that remind you why you worked so hard to get here in the first place. In a world where luxury can often feel mass-produced, the ultimate romantic investment remains the same: undivided attention in an incomparable setting.

Here are some luxury dates and getaways that will leave a lasting impression.

1. A multi-day luxury wellness "Staycation"

A wellness retreat is the ultimate gift of time and tranquility. It is an opportunity to step away from the digital world and reconnect through synchronized restorative treatments and quiet, shared presence. Whether you’re enjoying a private sound bath or a guided meditation, this experience is about leaving the noise behind to focus entirely on your physical and emotional well-being together.

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Instead of a single night, book a longer stay at an ultra-luxury wellness retreat. The destinations we've highlighted are ready to customize every aspect of your stay.

The vibe: Restorative and intimate.
The splurge: Focus on the in-room experiences. Many high-end resorts now offer "in-villa" spa treatments or private fire-pit dinners where a sommelier brings the tasting to your balcony. It’s the ultimate way to reconnect away from the noise of daily life.

Luxe recommendations:

The Ranch Hudson Valley, Sloatsburg, NY: The 26-room East Coast retreat is set in a historic former estate of J.P. Morgan on 200 acres of wooded lakefront. It’s perfect for couples over 50 who want a "hard reset" with guided hikes, organic plant-based meals, and daily massages in a quiet, forested setting. Depending on room size, the daily inclusive rate ranges from $2,195 for a deluxe room to $2,925 for a premier junior suite.

Take advantage of the The Ranch Private Program for a "bespoke wellness experience" tailored to your goals and/or pace. If you are on the left coast, the original ranch is in Malibu and offers 60-minute sound baths, with a massage village.

Golden Door, San Marcos, CA: Located on 600 acres in northern San Diego, Golden Door is frequently voted the best in the world. This Japanese-inspired retreat in San Marcos offers a high staff-to-guest ratio and a daily massage. It is the gold standard for privacy and restorative health. A room for a week-long retreat can cost anywhere from $12,950 to $13,450. For a villa, the cost goes up to $13,950 to $14,450.

Indulge in 'The Circle,' an "immersive symphony of sight and sound." It combines live music with custom art projections on a single, 12-foot-tall surrounding screen under the stars. The 'Golden Flight' package is a custom seven-night "transformational all-inclusive retreat" that starts with door-to-door transportation to the tarmac of your private plane to the spa.

Sensei Lana’i, A Four Seasons Resort, Lana’i, HI: This is a tech-forward wellness retreat where you can be assigned an integrated team of 'Sensei Guides' that includes nutritionists, exercise physiologists, and mindfulness coaches, with private "hales" (spa pavilions) featuring outdoor rain showers and hot tubs. If you are hungry for adventure, you can take a private helicopter tour for $6,600 or a private catamaran tour for $3,100.

The 'Discover Sensei Experience for Two' allows you to consult with your pre-arrival specialist to curate your itinerary. And, you retain access to the proprietary Sensei Portal to track and understand your personal data points during and after your stay. In addition to the amenities and services you'd expect at this level, this Hawaiian retreat also offers snorkeling and sunset sails. If you can't tear yourself away from this Polynesian paradise, there is a thirty-day 'Sensei Sabbatical Experience' on the menu. If you can't spare a week or more, a three-night guided wellness stay starts at $1,250 per person.

2. A private chef’s table at a Michelin-starred restaurant

Forget a standard reservation; book the Chef’s Table or a kitchen-side seating. This is a fun, unique experience, whether you are on vacation or want to do something extra special closer to home.

A chef’s table turns a meal into a private performance. Seated at the heart of the action, you’ll enjoy a front-row view of the artistry and technique that goes into every dish. It’s an intimate, immersive experience where the menu is personal and the service is entirely focused on you.

The Vibe: Immersive and theatrical.
The Splurge: This isn't just a meal; it’s a performance. You’ll get a customized multi-course menu (often $300–$500+ per person) and the chance to interact with the culinary team. Look for places that offer a "vertical wine pairing," where you taste different vintages of the same prestigious label

Luxe recommendations:

Oriole, Chicago, IL: Tucked away in an alleyway in the West Loop, the entrance is a hidden freight elevator. 'The Kitchen Table' experience has guests seated directly in the kitchen for a front-row view of the action. You may have heard the saying, "You don't have to go home, but you can't stay here." That's not the case at Oriole. You can spend that night upstairs at 'The Loft,' located above the restaurant. And, a booking at The Loft guarantees you a seat at Oriole’s Kitchen Table.

minibar by José Andrés, Washington, D.C.: This is one of the most coveted seats in the U.S. 'José’s Table' is a literal "culinary lab" where only six guests at a time sit at a counter. It is highly technical and perfect for foodies who want to be part of the creative process. The private dining room adjacent to the kitchen is where Chef Andrés presents his newest creations and ideas to the public. Tickets cost $550, excluding wine pairings.

Saison, San Francisco, CA: For those who appreciate the art of fire, Saison offers two exclusive experiences: 'The Kitchen Table' (up to 9 guests) and 'The Salon' (up to 13 guests). Both meals offer a seasonal tasting menu with optional wine progression at a table exclusively yours all evening, with a direct view of the kitchen and hearth. However, the Salon experience begins with a canapé and Champagne reception. Saison is an open wood-fire restaurant, offering a sensory-heavy experience that feels more like a private loft than a bustling city eatery. Prices range from $398 to $598 per person, and wine pairings can be added for $198 and $298.

3. Chauffeur-driven vineyard "Grand Tour"

unrecognizable well dressed male chauffeur opening a car door

Skip the public tasting rooms. Hire a private chauffeur to take you to a select few "appointment-only" estates for a library tasting — sampling older, rarer vintages not available to the public.

The best way to experience wine country is with someone else behind the wheel. A professional chauffeur handles the logistics, allowing you to relax in a luxury vehicle and enjoy private tastings at your own pace. It is a seamless day of discovery where your only responsibility is to savor the scenery and the company. The cost of hiring a car and driver will vary depending on whether you start your trip in San Francisco and the duration of your tour. On average, you will pay anywhere from $100-$155 per hour for a luxury SUV, and $135 to $165 per hour for a limousine.

The Vibe: Relaxed, scenic, and luxurious.
The Splurge: The beauty here is the chauffeur. You can both fully indulge in the wine pairings without worrying about the drive, and the private setting allows for deep, uninterrupted conversation.

Luxe recommendations:

Jarvis Estate or Darioush, Napa Valley, CA: Hire a driver through a service like Napa Valley Tours & Transportation. Have them take you to Jarvis Estates — an entirely underground winery in a 45,000-square-foot man-made cave. Tours and tastings are available daily by appointment only and start at $150 per person.

At Darioush, you enjoy exceptional wines and taarof, the Persian art of gracious hospitality. The 'Sensory Sessions: A Caviar Experience' brings caviar from the Caspian Sea together with limited-release estate wines. The tasting lasts for 90 minutes as costs $300 per person. Darioush was founded in 1998 by Darioush Khaledi, an Iranian immigrant, after success in the grocery business.

Barboursville Vineyards, Charlottesville, VA: If you're on the East Coast, the Monticello Wine Trail is the splurge choice. Hire a private car to take you to the Octagon 1821 tasting at Barboursville, where you can walk through the historic ruins of Thomas Jefferson’s designed mansion with a private sommelier. If you are a fan of the bard, visit in August when you can see presentations of "Shakespeare at the Ruins," while enjoying a picnic with the appropriate wine parings.

4. Private skyline dining

There is nothing quite like dining against a backdrop of city lights. Private skyline dining takes you above the noise and crowds, offering a secluded table with an expansive, cinematic view. It is a sophisticated way to elevate your evening, combining high-end service with a perspective that feels entirely your own.

The Vibe: Iconic and undeniably romantic.
The Splurge: Look for "buyout" options at high-altitude venues. Whether it's a private pod on a giant observation wheel or a closed-deck dinner, the feeling of having the entire city "at your feet" is a powerful romantic gesture.

Luxe recommendations:

Peak with Priceless, New York, NY: Located at the top of 30 Hudson Yards (above the Edge), you can book the Sky Cellar, a private dining room that feels as if it is suspended over the city. It offers a 360-degree view that includes the Statue of Liberty. The room must be booked at least 30 days in advance. A basic meal lasts 2-1/2 hours. Lunch starts at $2,450, and dinner is higher at $3,150, plus tax and a service fee. The fee covers a three-course seasonal menu; beverages are extra.

Smith & Wollensky at South Pointe, Miami, FL: While it's a steakhouse, the restaurant's Overlook Deck or Vanderbilt Room each provides a private balcony with unobstructed views of the Miami skyline and the cruise ships gliding out to sea at sunset. The Overlook Deck, a second-story terrace that features sweeping views of South Pointe Park, Government Cut, Fisher Island, and Downtown Miami, would be my choice. If you want privacy, the Vanderbilt Room has a private entrance and can be combined with the Deck.

71Above, Los Angeles, CA: 71Above is the highest restaurant west of the Mississippi. Situated nearly 1,000 feet above downtown LA, 71Above offers one large and two small private dining rooms overlooking Dodger Stadium that can be booked for fully secluded dining. If you don't have time for a meal, you can have a bite or two at their "Golden Hour," a swanky happy hour that serves pork belly and yellowfin tuna.

Senior couple driving convertible car at sunrise on rural road

High-end dating is, at its core, a celebration of the finer things — and there is no finer thing than a night that feels entirely your own. While the world's most exclusive venues provide the backdrop, the real magic is between the setting and the company. As you plan your next grand outing, remember that the most successful splurges aren't measured by the invoice, but by the rarity of the moments created. The true splurge lies in the bespoke and the private.

Donna joined Kiplinger as a personal finance writer in 2023. She spent more than a decade as the contributing editor of J.K.Lasser's Your Income Tax Guide and edited state specific legal treatises at ALM Media. She has shared her expertise as a guest on Bloomberg, CNN, Fox, NPR, CNBC and many other media outlets around the nation. She is a graduate of Brooklyn Law School and the University at Buffalo.