If this is the year you’ve officially stepped into empty nester or retiree territory, it’s the perfect time to celebrate with a well-earned vacation. Whether you’re excited about your new freedom or still figuring it all out, travel is hands-down one of the best ways to kick off this next chapter.
Think of this as your chance to check out places you might’ve overlooked before, or to finally dive deeper into the hobbies and interests that already excite you. To help you get going, here are five trending vacation spots for empty nesters and retired couples worth putting on your radar.
1. Walla Walla, Washington
Walla Walla produces some of the Pacific Northwest’s best wines. Compared to Napa, whose first grapes were planted more than a hundred years earlier, Walla Walla is still considered a young wine region, so you’ll find fewer crowds and more of a laidback vibe, with plenty of things to do. And with more than 120 wineries, you’ll have your pick of wines to sample.
One of my favorites is Long Shadows, which is on the west side. Their tasting room is consistently voted as one of the best in the U.S. The breathtaking chandelier was designed by renowned glass artist Dale Chihuly and marks the focal point of this elegant space. Sit back and sip exquisite wine pairings as you enjoy spectacular views of the Blue Mountains. Next, head downtown for a tasting at Seven Hills, a vineyard-designated winery, with their facilities right in town. Established in 1988, they’re best known for their Merlot and Cabernet Sauvignon-varietals, which offer distinct flavors of the region’s rich AVA.
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Book a room at The Inn at Abeja, a historic farmstead featuring seven luxury accommodations and five-star dining. Set across 38 acres, each of the cottages once performed a function on the farm; now they’ve been lovingly restored with modern amenities and comforts. Wake up to a freshly prepared hot breakfast that changes with the seasons. I also suggest a romantic evening at the Marc Restaurant, which is inside the historic Marc Whitman Hotel. A majority of their menu focuses on partnerships with local farmers and purveyors. Start with their house-made focaccia bread and beef tartare. Entrees like the roasted lamb loin and lemon ricotta agnolotti bring flavor to every bite.
2. Scottsdale and the Greater Phoenix area
Scottsdale and the Greater Phoenix area are ideal for empty nesters seeking sun, scenery, and incredible food. Because it’s the desert, many people are surprised to learn that Arizona has a thriving agriculture scene. In fact, Arizona’s vibrant agriculture fuels a restaurant scene that rivals top cities—without the steep prices.
Downtown Scottsdale boasts standout dining. FnB, helmed by James Beard Award winner Charleen Badman, celebrates desert-grown vegetables and local proteins. Citizen Public House offers hearty farm-to-table fare and a lively social hour. For a splurge, book a table at Kai, Arizona’s only AAA Five Diamond, Forbes Five-Star restaurant, known for its innovative Indigenous cuisine.
Stay close to the action at Sanctuary Camelback Mountain, A Gurney’s Resort & Spa. Nestled into Camelback Mountain, it offers luxe mountain-view suites and a serene spa with massages, Pilates, and tennis or pickleball courts. For something more remote, The Four Seasons Resort at Troon North is tucked into the desert near Pinnacle Peak, perfect for hiking and relaxation, with gourmet dining and a luxe adults-only pool.
3. San Luis Obispo
For a relaxing getaway, San Luis Obispo delivers charm, history, and outdoor fun. Situated on California’s Central Coast, SLO is home to Cal Poly and the iconic Hearst Castle. The historic downtown offers shopping, dining, and walkable streets perfect for strolling. Just 15 minutes away, Pismo Beach offers butterfly watching at the Monarch Grove and hiking at Dinosaur Caves Park.
Shop local boutiques like Ambiance or Apropos, then grab Neapolitan pizza on the patio at Flour House or Afghan-inspired dishes at Kor Kitchen. For dinner, Novo serves global fare in a romantic creekside setting—don’t miss the coconut chocolate pie. Nate’s on Marsh is great for upscale comfort food, while Alex Madonna’s Gold Rush Steak House delivers classic steaks with quirky, unforgettable flair. For lodging, enjoy European flair at Petit Soleil B&B with luxury linens, robes, and house-made breakfasts. Prefer modern? The more contemporary Hotel SLO features sleek rooms with balconies and SoCal style.
4. Williamsburg, Virginia
No matter when you choose to visit Williamsburg, Virginia, you’ll find pleasant weather along with historical attractions and plenty of tee-time opportunities for golfers. Founded in 1699 as the Virginia Colony, the town is home to Colonial Williamsburg, which houses numerous museums and historical sites. The American Revolution Museum at Yorktown and The Jamestown Settlement are significant spots for history buffs to explore exhibits and follow the stories of soldiers and citizens of that era. Hop on the Stanley Steamer Wagon for a short tour of Yorktown; it offers a scenic view of the battlefield.
Williamsburg has more than 18 golf courses, including some of the top-ranked courses in the U.S., including the River Course at Kingsmill Resort, the Williamsburg National Golf Club, and Ford’s Colony Country Club. In fact, the course at Kingsmill Resort has hosted some of the most well-known golfers on the LPGA and PGA Tours, including David Duval and David Toms.
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For convenience, stay at the Kingsmill Resort, which spans 2,900 acres along the James River. Featuring luxuriously-appointed accommodations, the property also has four dining options, indoor and outdoor pools, along with a full-service spa. Although the Williamsburg Lodge doesn’t have a golf course, it’s a historic property that offers modern comforts and amenities. Located in the heart of downtown, you’ll be within walking distance to shops and restaurants.
5. Providenciales, Turks and Caicos
Further afield, empty nesters can get a taste of the good life in the Turks and Caicos. On Providenciales, stay at Blue Haven, an all-inclusive resort offering 45 studios, suites, and penthouses. The spectacular waterfront property caters to couples with a vast assortment of activities including snorkeling, SUP, sailing, and bike rentals. Guests have access to six dining options, as well as restaurant offerings at its sister property, the Alexandra Resort.
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Plan a day of rest and relaxation with a couples treatment, or head to Grace Bay Beach for sun and sand. Consistently recognized as one of the world’s most beautiful beaches, Grace Bay is just an eight-minute drive from the resort and boasts cerulean waters where you can spot turtles and eagle rays when snorkeling. Book a romantic horseback ride along the beach through Provo Ponies. Your professional tour guide will take you along Long Bay on the south side of the island, which offers magnificent views.
