Twenty-five years of making a relationship work is something to celebrate. Some couples may want to mark this silver anniversary with jewelry or a special gift, but if you would rather splurge on a memorable trip, I’ve brainstormed some 25th anniversary trip ideas that will make this occasion one you will never forget.
Whether you are an adventure couple, foodies, beach lovers, history buffs, oenophiles, or Scotch lovers, I have something to tickle your fancy. From Europe to the USA to the Caribbean and a few further afield, these anniversary trip ideas are not just about a beautiful hotel, they are about the unique experiences you can have and the memories you will make along the way. Which anniversary trip destination will you choose?
Sip Scotch on the Isle of Skye at Kinloch Lodge
Whisky lovers and foodies will fall in love with the magical Isle of Skye. Kinloch Lodge on the western coast of the Isle of Skye was originally built as a farmhouse and then used as the Clan’s shooting lodge. In 1972, it was opened to visitors by Godfrey, Lord Macdonald and High Chief of Clan Donald, and his wife, world-renowned cook Claire, in 1972.
It is now run by their daughter, Isabella Macdonald. From day one, Kinloch Lodge has pioneered using local ingredients from Skye’s natural larder and working with passionate artisan producers. This ethos and passion for seasonality and sustainability has been carried on by head chef Jordan Webb, who has created herb gardens and forages each day from the loch’s shore.
Kinloch Lodge has partnered with Torabhaig Distillery to introduce a new whisky-themed package, showcasing a true sense of place in the wild landscapes of Skye. This package includes a tour and tasting at the Distillery, foraging and cocktail making sessions, as well as the finest seasonal menus from Kinloch’s kitchen. Enjoy the views, spot the wild red deer on the hillside, experience the Northern Lights above, and return to cuddle up by a warm fire and whisky.
Sample Caviar in the Surf with Seabourn Cruise Lines
A Caribbean cruise may not be your first thought for your 25th wedding anniversary, but I’m not talking about a mega ship full of families and partiers. I’m talking about an ultra-luxury cruise on Seabourn for those that appreciate high-touch service, world-class dining, and over-the-top experiences.
Picture this…you are anchored off the gorgeous Carambola Beach on the idyllic Caribbean island of Saint Kitts, watching the crew wade into the ocean and serve you caviar and Champagne on a surfboard as part of its signature “Caviar in the Surf” event.
This memorable and unique experience is a perfect way to celebrate a special occasion. Seabourn’s tropical Caribbean voyages also include unlimited premium spirits and fine wines, world-class dining, a personal suite steward or stewardess, and unlimited WiFi so that you can share photos with your friends and family back at home.
Experience Tuscany Concierge Style
If you are the type of traveler that doesn’t enjoy planning but loves authentic experiences, book at stay at the Borgo San Vincenzo, Tuscany’s newest luxury boutique hotel in the gorgeous Val D’Orcio. The hotel’s Head Concierge and Experiences Director, Jonathan Vargas, was recently honored with the prestigious Les Clefs d’Or ‘Golden Keys’ distinction, which recognizes the world’s finest hotel concierges.
Vargas and his experiences team are on hand to assist guests in curating personalized experiences that invite them to enjoy the region’s vibrant culture, breathtaking views, historic wine scene, and culinary excellence.
These experiences can include local wine tastings, indulging in organic olive oil and pecorino cheese tastings at local farms, participating in cooking and cocktail-making classes, and embarking on tours of the region by foot, horse, e-bike, Vespa, or hot air balloon.
Tucked into Montepulciano’s most prestigious Vino Nobile vineyards, Borgo San Vincenzo celebrates Tuscany’s historic wine scene, culinary excellence, and vibrant culture, featuring twenty-one uniquely curated guest rooms and suites, a restaurant, two bars, a wine cellar, a library, and a pool with a sundeck.
Cuddle Up Under the Trees in a Montana Hideaway
The Resort at Paws Up in Western Montana is one of the most luxurious ranches in the country and now there is a whole new, adults-only offering that blends luxury accommodations and fine dining with a robust menu of outdoor activities from fly fishing to horseback riding.
The green o has a guest capacity of only 24 people in just 12 secluded Haus accommodations on 37,000 acres, which give you the ultimate in privacy while surrounding you in nature.
Located at the center of the resort, the Social Haus is just a short walk from each of the Haus accommodations. When you are done adventuring and exploring the forest, enjoy the inner circle bar, a dining area, and an open kitchen, home to Executive Chef Brandon Cunningham who was nominated as a James Beard Semifinalist Nominee.
Soak in a Santorini Sunset
Santorini, Greece must be one of the most romantic places on earth. The white-washed stucco houses built into the cliffside and blue-domed churches dotting the landscape. There is no better spot for enjoying everything Santorini has to offer than the luxurious Canaves Oia Epitome hotel. Located just outside of the famous town of Oia and a short walk to Ammoudi Bay, it is well positioned to watch the famous Santorini sunsets.
While on Santorini, take a wine tour with Santorini Wine Trails to experience more of the island and learn their unique basket method of grape growing that preserves water, a scarce resource on the island. Enjoy a sunset on a catamaran sail from Ammoudi Bay and then sample fresh fish and octopus from one of the many fish restaurants that line the harbor.
For a quieter stay, you can also split your time between Santorini and other islands like Naxos or Paros. The Summer Senses Luxury Resort on Paros offers panoramic views of the azure Aegean Sea and 100 contemporary rooms, including luxurious suites with private pools, along with two swimming pools, a spa, and fine dining.
Escape to an Adults-Only Hideaway
The Bungalows Key Largo is one of my picks for the most romantic resorts in the U.S. With 135 private bungalows dotted across the property’s sprawling 12 acres, this adults-only luxury resort is the only all-inclusive in the destination. If you are looking for a relaxed and romantic getaway to celebrate your anniversary without dusting off your passport, this is it!
Enjoy the resort’s two pools and unlimited dining at five restaurants. If you would rather be active, there are kayaks, stand up paddle boards, snorkel gear, and even cruiser bikes that you can borrow, along with group yoga classes and a fitness tiki hut. For your special occasion, book a sail on a luxury catamaran and indulge in an evening of live acoustic music and an elegant culinary experience.
Taste Truffles in Piemonte
Visit Piemonte in Northern Italy during truffle season in the fall and you will have the foodie experience of a lifetime. We visited with another couple and the trip was a gastronomic delight! You can enjoy truffle hunting, attend the Alba Truffle Festival, sip Barolo and Barbaresco during the harvest season, visit hazelnut farms, and stroll through hilltop towns — eating and drinking to your heart’s content.
La Villa Hotel in the province of Mombaruzzo is the perfect place to stay to explore the countryside. This luxury boutique hotel has 15 rooms, each with its own character and simple style that blends vintage and modern in a beautiful farmhouse villa decor. With a spa, pool, restaurant, and bar, all attended with outstanding service, this gem of a property is perfect for an anniversary trip.
Stay on a California Wine Estate
California may have an abundance of wine regions, but one of my favorites is in Paso Robles. This quieter, cowboy town offers a less-pretentious environment than its northern competitors, but equally good wine, especially if you appreciate a good red.
In recent years, a growing number of excellent restaurants have also cropped up in Paso, creating a vibrant, yet uncrowded downtown. Nearby, you can enjoy horseback riding, a hot air balloon ride, natural hot springs, and fabulous wine tastings.
You can stay in the heart of wine country at the Allegretto Vineyard Resort, which is inspired by wine country and European hospitality, evoking an Italian estate on 20 acres of vineyards and fruit-bearing orchards. This Tuscan-style property offers 171 guest rooms and suites, a wine-tasting lounge, a full-service boutique spa, pool and cabanas, manicured gardens, and walking paths to explore.
Dining at Cello Ristorante & Bar features locally farmed and foraged cuisine from Executive Chef Jeremy Fike. Really make your stay special with the Aphrodisiac Package. Your stay will start with a bed strewn with flower petals and include a couples spa experience, vineyard tour and tasting at Allegretto Wines, a tour of three Paso Robles wineries with transportation provided, champagne, chocolate-covered strawberries, and a $500 food and beverage credit.
If you prefer to go further afield, try a stay at one of these wine hotels in Portugal instead.
Dive into Bahamian Luxury
Caerula Mar Club is perfect for couples looking for a mix of relaxation and adrenaline-pumping adventure. The resort, helmed by an HGTV couple, features five private villas and 18 gorgeous suites just steps from the shoreline, with restaurants ranging from an outdoor poolside bar to a fine dining restaurant, with ingredients sourced from an on-site organic farm.
Caerula Mar Club is located on 10 acres of gorgeous turquoise beach on South Andros Island in the Bahamas, where you can enjoy plenty of privacy. Relax by the pool or under the shade of palm trees, take a walk on the white sands, spend a few hours at the rejuvenating oceanfront spa, and enjoy the Bahamian breeze all from the comfort of this hideaway nestled between the mangroves. And, just minutes away lies four Blue Holes, just a fraction of the over 200 around South Andros. Couples can embark on the adventure of a lifetime as they discover the island’s folklore and dive below the surface of these mystical Blue Holes.
Charter a Barge Cruise
If you enjoy celebrating your anniversary with friends, consider chartering a barge cruise in France. Each barge typically has three to six cabins and travels through the smaller canals, taking you through small villages and scenic waterways. Your trip is all-inclusive, with a high staff to guest ratio and includes private guided excursions each day. The best part is the amazing food and wine served at each meal!
There are many options and if you need help choosing, Barge Lady Cruises is a travel agency that specializes in barge cruising. I highly recommend the Hotel Barge Elisabeth, which cruises the canals of Burgundy. Another option is to book a single cabin on a barge cruise with European Waterways.
Be Blessed by a Shaman
Perched on the shore of Lake Atitlán in the Guatemalan highlands, Casa Palopó offers an exclusive getaway for couples looking to celebrate their silver anniversary with a rich dose of culture and wellness. This luxury hillside boutique hotel boasts incredible views of the magical lake with volcanoes that dot the shoreline.
Located in a destination built upon ancient Mayan culture and practices, Casa Palopo invites couples to participate in a personalized Mayan Shaman blessing. The ancient ritual is performed in front of a fire pit and is meant to offer well-wishes from spirits for a continuous happy relationship. In-room spa treatments, a cozy library, and top-notch personal service are among the hotel’s other offerings to ensure a peaceful and revitalizing escape.
Enjoy a Personalized Prelude for Music Lovers
Is your spouse a classical music lover? Surprise them with a luxurious stay at Grand Universe Lucca, a restored Italian palazzo in one of the most charming towns in Tuscany. Top it off with a curated experience in the Symphony Lounge, where the hotel’s classical composer will create your very own theme song based off of a brief questionnaire. While the composer prepares your Prelude, enjoy a selection of Italy’s best coffees, teas and pastries.
Your personalized “Prelude” will be written on music paper, tied with a silk ribbon, and tucked away inside a Tuscan leather box to cherish for years to come. Complete your trip with a romantic horse-drawn carriage ride through the city and a champagne to toast to a trip of a lifetime.
Bask in the Sun on a Private Island
If you’re seeking an enchanting, intimate escape for your anniversary, look no further than Baoase Luxury Resort, a five-star ultra-exclusive oasis in glittering Curaçao that sets the scene for a passionate retreat with your sweetheart. The resort features an infinity pool overlooking the Caribbean Sea, a coral reef on the outskirts of the private lagoon, and beach butlers who cater to guests’ every need.
If you are looking for an added dash of luxury, Baoase also offers exclusive bookings to their private island of Isla Kiniw, featuring a stunning villa, private beach, personal chef, and more. If you can draw yourselves away from the beach, there’s plenty to see and do on the colorful island of Curaçao from strolling the historic city of Willemstad, to taking a day trip to the secluded island of Klein Curaçao, to indulging in rich foods and live music in the romantic Pietermaai area.
Celebrate Under the Northern Lights
For those looking for scenic beauty, adventure, and a trip of a lifetime, cozy up in the Icelandic countryside at Hotel Rangá. Set in the secluded and spectacular countryside of Iceland’s South Coast, Hotel Rangá is a luxe and rustic oasis, which is ideal for adventurous lovebirds looking to celebrate in a big way. Choose from one of the resort’s seven themed suites, or mix it up with a few nights in each.
Couples can explore the land of ice and fire by daylight with a super jeep tour through rivers and valleys, share a kiss under a waterfall, hold hands on a stroll along a beautiful black sand beach, or hop on an Icelandic horse for a romantic ride.
After a day of adventure, enjoy a soak in one of the property’s geo-thermal heated outdoor hot tubs, or partake in a stellar star gazing session alongside a resident astronomer at the hotel’s own hi-tech, roll-off roof observatory. Visit from November through March for the best chance of seeing the Northern Lights (don’t worry, you can arrange a wake-up call if they make a late night appearance.)
Looking for more ideas?
- Most romantic resorts in the USA
- Romantic getaways on the West Coast
- Romantic getaways in California
- Romantic getaways in New England
Tamara is an over 50, award-winning travel writer, and recent empty nester based in Rhode Island. After years of writing about family travel on We3Travel and inspiring wanderlust as co-host of the Vacation Mavens family travel podcast, she started Your Time to Fly as a place to share ideas for girlfriend getaways, romantic escapes, and solo female travel for midlife women.
