Reaching two decades of love and commitment deserves an equally monumental celebration! This special anniversary is the perfect excuse to take the trip of a lifetime. For you and your partner, that could be a weeks-long adventure across the globe. Or, your dream trip could be a romantic retreat over a long weekend in an idyllic part of the U.S. You get to decide how you spend this special day with your true love. Here are hand-selected 20th-anniversary trip ideas to help you choose the perfect destination.
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20th Anniversary Trip Ideas for a Special Milestone
1. New Zealand
This country is the perfect place for active, adventurous couples looking for romantic anniversary trip ideas. It offers breathtaking mountainous landscapes, hiking trails, and lakeside cabins. Plus, the colder months in the United States are warmer months in New Zealand. It’s ideal for a winter escape!
Rent an RV for an epic road trip. Start in Queenstown and ride the Skyline Queenstown gondola up Ben Lomond. Cruise through Milford Sound’s majestic fjords. Take the ferry to the North Island and continue your adventure in Rotorua, where you can relax in the hot springs. Lord of the Rings Fans can’t miss Hobbiton, anniversary trip or not! Wine lovers should head to Hawke’s Bay, where you can officially toast your milestone.
Where to stay: Even intrepid RVing couples need proper pampering during their 20th-anniversary trip. Treetops Lodge & Estate in Rotorua is one of the best five-star luxury hotels in the area. Stay in one of their secluded villas with a whirlpool bath and indulge in traditional Maori spa treatments.
2. French Riviera
This Hollywood hotspot is one of the best romantic getaway destinations. The French Riviera effortlessly blends old-world opulence with relaxation. Visit for a long weekend city break or hop along the Mediterranean coastline for an epic anniversary trip – your choice!
Throw dice in your best outfits in Monaco or sunbathe on the beaches of Cannes. Hire a private luxury catamaran and sail around the waters off St. Tropez. Don’t miss the small town of Èze or the charming Menton on the Italian border.
Book ahead for the several Michelin-starred restaurants along the coast. La Palme d’Or in Cannes, La Vague d’Or in Saint-Tropez, and La Chèvre d’Or in Èze are perfect for a milestone romantic dinner.
Where to stay: The iconic Hotel Carlton in Cannes has welcomed Hollywood royalty for generations. Everyone from Alfred Hitchcock to Julia Roberts has slept in their guest rooms! Take advantage of their private beach club and Belle Époque-inspired bar.
3. Florida Keys
The Florida Keys are a popular destination for couples booking romantic anniversary trips. Visiting these tropical islands is an ideal way to experience paradise closer to home. It suits active couples who love water sports as well as couples planning a relaxing, romantic stay.
Rent a car and drive the entire length of the Overseas Highway. It’s the perfect excuse to be spontaneous and stop whenever you see a beautiful view!
Catch the sunset at the market for the Southernmost Point of the Continental USA in Key West. This island is a great place for couples who like historical buildings. Visit the Hemingway House, Little White House, and the beautiful pastel-colored conch houses on Caroline St.
Take a glass-bottom boat tour through John Pennekamp Coral Reef State Park. These colorful coral reefs are just off the coast of Key Largo. They are incredible to witness in person with your love.
Where to stay: Stay at Ocean Key Resort, a boutique hotel with private balconies and a full-service spa. Enjoy the modern convenience of an on-site restaurant. You’re just a short walk from the bustling Duval Street.
4. St. Lucia
When curating 20th-anniversary trip ideas, St. Lucia can’t be left out. This idyllic Caribbean island’s luxurious resorts and diverse landscapes make it a great spot to celebrate an important occasion.
View the stunning Pitons, two volcanic mountain spires, from a boat tour. Active couples can book a guided hike through the lush tropical forest. Check out Sulphur Springs, the world’s only drive-in volcano, and soak in the rejuvenating natural hot springs.
Watch the sunset from one of the island’s white sand beaches, like Anse Chastanet Beach. Many beaches are next to the natural habitats of colorful angelfish and parrotfish. Snorkeling is a better way to see these beauties up close!
Where to stay: There are many luxury resorts in St. Lucia, but Jade Mountain Resort is one of the best. It’s set in a lush forest with many rooms boasting a hot tub, an infinity pool, or a whirlpool tub. Book a couples massage in their open-air spa with panoramic views of the Pitons.
5. Newfoundland, Canada
Imagine telling your friends and family that you’re going to Newfoundland for your 20th anniversary. They won’t be able to conceal their confusion, but you’ll know exactly why you picked this spectacular Canadian province. The remote, rugged landscapes provide the perfect setting to disconnect from everything else and reconnect with each other.
Fogo Island, in particular, is a dream for nature lovers. Puffins nest there from April to November, and you can get up close and personal with icebergs on a Fogo Island boat tour.
Hike to Brimstone Head, one of the four corners of the earth. Buy a souvenir from the art galleries in Joe Batt’s Arm to commemorate your unforgettable experience.
Where to stay: Staying anywhere besides Fogo Island Inn would be a mistake. This ultra-contemporary five-star hotel is perched on stilts on top of rocky terrain. Custom-made furniture, underfloor heating, and ceiling-to-floor North Atlantic views make the inn’s suites the best places to relax with your spouse.
6. Mississippi Cruise
Does Mississippi seem like a weird place to spend your 20th-anniversary trip? Well, it was the 20th state admitted to the Union in 1817. If you’ve loved gifting your spouse year-appropriate gifts for the last two decades, this would be a memorable way to celebrate this milestone! Plus, you’ll both have the best time cruising along the Mississippi River.
Viking’s Heart of the Delta 12-day cruise is the perfect choice. Sail north from New Orleans to Memphis, stopping at historic towns like St. Francisville and listening to the blues in Greenville. Dine on Creole and Cajun cuisine and sleep in a stunning cabin on a luxury riverboat. Spring is a good time to sail to see cherry blossoms along the riverbank; September’s fall colors are unbeatable.
Where to stay: Arrive in New Orleans the day before your tour and stay at The Roosevelt. This is one of the best hotels in the city with clawfoot tubs and luxurious art deco interiors. It dates back to 1863 and is only a short walk from Bourbon Street.
7. Cappadocia, Turkey
Some couples are looking for beachy travel ideas for their 20th-anniversary trip. This recommendation won’t be for you! Cappadocia is the ideal destination for spouses searching for magical, fairytale-esque scenery with a surreal, desert landscape.
The quintessential Cappadocia experience is taking a hot air balloon ride at dawn. Book it for your first day, as the weather may force you to rearrange!
Visit the rock-carved churches and Göreme Open-Air Museum, a UNESCO site. Wear your Indiana Jones fedora and explore the ancient cave dwellings of underground cities like Kaymakli and Derinkuyu.
Where to stay: The boutique Museum Hotel offers couples a romantic place that still feels authentic to Cappadocia. Rooms are carved from caves, and bathrooms are wall-to-wall marble. Enjoy a fine dining experience at the hotel’s traditional restaurant and hot air balloon views from the rooftop terrace.
8. Bora Bora, French Polynesia
Visiting French Polynesia is a dream destination for many couples. You may think romantic anniversary trips to exotic destinations like this are out of your reach. But there are direct nine-hour flights from Los Angeles and San Francisco to Tahiti. It’s only the next island over!
Bora Bora is a great place for relaxing and romantic activities. Enjoy a picnic on quiet, pristine beaches with views of Mount Otemanu. Dine on a floating platform at sunset, gazing into the eyes of your partner.
Hop on a Jet-Ski tour or a boat tour around the islands. Swim in the sea with the sharks and sting rays. Depending on where you stay, your resort can probably arrange all of these activities.
Where to stay: Take the chance to stay on a private island by booking Conrad Bora Bora Nui. Stay in one of their overwater bungalows with stylish Polynesian décor and private plunge pools. The island of Motu To’opua is only 20 minutes by boat from the airport, but still feels secluded.
9. Lake Michigan, Illinois
You might not expect to see Lake Michigan in a list of 20th-anniversary travel ideas, but it’s perfect! Stay on the Illinois side to enjoy a picturesque lakefront dotted with charming, small towns.
Take a romantic stroll through Lake Forest Beach with views of the dunes and the lake. Take your spouse for an intimate dinner at Le Colonial. Visit the gift shops in Lake Forest’s Historic Market Square. Just down the road is the Chicago Botanic Garden, which is just beautiful in summer!
Where to stay: The half-timbered façade of the Deer Path Inn looks like it was plucked from the English countryside. This elegant 1929 inn offers couples open fireplaces, afternoon tea, and traditional British pub fare. It’s the perfect spot for the ultimate cozy, romantic stay.
10. Iceland
Everything about Iceland makes it an ideal location for a romantic escape. The dramatic waterfalls like Goðafoss, the geothermal springs, the bakeries on every corner… It’s a safe, relaxing place with otherworldly landscapes like nowhere else on Earth.
Book a two to three-week adventure driving around Iceland’s Ring Road in summer. Or, visit in winter and enjoy a snowy city break in Reykjavík. Book a tour of the natural sights on the Golden Circle Route and soak in the Blue Lagoon. Cross your fingers that you’ll spot the northern lights together!
Where to stay: Book The Reykjavik EDITION hotel. It’s in a prime location by the harbor with a rooftop bar overlooking the city. Rooms have chic, minimal decor and floor-to-ceiling windows. There is even an onsite bakery!
11. Cape Town, South Africa
Cape Town has a gourmet dining scene, beaches, and proximity to a wine region and game reserve. Talk about a memorable place to spend your 20th wedding anniversary!
In the city, take the cable car up to Table Mountain. Witness incredible views across Cape Town and the South Atlantic Ocean.
Couples with space in their itinerary should spend a few nights in the Stellenbosch wine region. Adding on a safari isn’t out of the question either. Aquila Private Game Reserve is just over two hours away from the city and home to the Big Five!
Where to stay: Venture to Stellenbosch and book the five-star Clouds Estate adults-only resort. It’s a small guesthouse with only seven rooms nestled within a 12-acre vineyard. Open your curtains to a stunning view of the Hottentots Holland Mountains and relax in one of two outdoor pools.
12. Napa and Sonoma Valleys, California
Both a short drive from San Francisco, Sonoma Valley and Napa Valley are fun, convenient places to celebrate your 20th anniversary. Visiting vineyards and wine tasting is a must in these world-famous wine regions.
Toast to your milestone several times over at the Domaine Carneros vineyard in the Napa Valley. They’re known for pinot noir and Chardonnay varietals. Head to Sonoma Valley for Château St. Jean, where they grow every grape from merlot to malbec. Turn it into an anniversary vacation you’ll never forget with a hot air balloon ride at sunset.
Where to stay: If you and your spouse prefer to stay in Napa, Auberge du Soleil is perfect. This world-renowned five-star resort has unobstructed views of the valley and a Michelin-starred restaurant. Farmhouse Inn in Sonoma Valley blends luxury and rustic charm with its bright barn-style cabins.
13. Cyclades, Greece
Plan an island adventure on not just one Greek island, but three. Paros, Naxos, and Santorini are Cyclades Islands just a short ferry ride apart. Enjoy the whitewashed houses, blue-domed churches, and beautiful beaches on a memorable trip with your love.
Wander along the charming cobblestone streets of Naoussa in Paxos. Visit the ancient Temple of Apollo in Naxos. You won’t have to miss out on wine tasting in Greece either. Santorini’s vineyards – Santo Wines Winery and Domaine Sigalas are fantastic – are the cherry on top of a romantic Grecian getaway.
Where to stay: The cliffside Katikies Hotel in Santorini is hard to beat. Bright minimalist rooms complement the white streets of Oia. Some suites have infinity pools where you can enjoy the iconic sunsets over the Aegean Sea away from the crowds!
14. Puerta Vallarta, Mexico
There are so many great resort destinations in Mexico. With fine dining and luxury hotels, Puerto Vallarta is a fantastic destination for couples who have spent 20 years together!
Book a private sunset cruise in Banderas Bay with views of the Sierra Madre mountains. While in the nearby Riviera Nayarit, visit the small colorful town of Sayulita. Book a horseback ride along the beach or in the jungle of the mountain’s foothills.
Some resorts here offer so many amenities, you may not want to leave! Expect golf courses, tennis courts, pools, bars, restaurants, and spas.
Where to stay: Choose the more secluded Four Seasons Resort Punta Mita. It’s in Riviera Nayarit, around an hour from Puerto Vallarta. Sleep in modern beachy casitas surrounded by tropical gardens and soft-sand beaches.
15. Maui, Hawaii
The Hawaiian Islands are a go-to destination for couples looking for romantic travel ideas. It has everything! Sunsets, beaches, resorts, fine dining… Everything you and your spouse might want in an anniversary vacation.
Maui is a great option for incredible scenery. Rent a car and drive along the Road to Hana, stopping at every waterfall and black sand beach. Book a 60-minute helicopter ride – an experience you both won’t forget! Head to the Upcountry wine region for a tour at Tedeschi Winery.
Where to stay: While Maui doesn’t have many all-inclusive resorts, The Ritz-Carlton offers couples tons of optional amenities. Include dining credits, spa treatments, and excursions like all-inclusive packages in your booking. Organizing everything in advance is an ideal way to enjoy a stress-free trip in a romantic place.
Celebrate your Special Anniversary on a Romantic Trip
Every anniversary is a milestone worth celebrating, but your 20th is an extra-special occasion. It’s the perfect excuse to plan a romantic stay that reflects your journey and spend quality time together. Choose a tropical paradise like Bora Bora, a city break in Cape Town, or a winter wonderland in Iceland. Choose the best vacation destination for you! These 20th-anniversary trip ideas offer something for every couple.
About the author: Kirsten is a family travel expert who has been traveling with kids for over 20 years. She has been featured in Travel & Leisure, Parents Magazine, AFAR, Vogue, NBC, Lonely Planet, and Thrillist, to name a few. Kirsten is also the content creator behind Kids Are A Trip, an award-winning site for planning family vacations.