Celebrating your anniversary is a chance to look back on all the amazing memories you and your partner have shared together throughout the years. However, it can be tough to decide on how exactly you’d want to celebrate. Though you could opt in for a classic dinner date, why not level up your celebration and go on an anniversary trip!
Luckily for you, we’ve got the inside scoop on some of the best US anniversary trip destinations. From popular hot spots to hidden gems, these destinations are sure to impress! Let's get right into it and turn your anniversary into something truly special!
How To Choose The Right Anniversary Trip Destination For You & Your Partner
When choosing the right anniversary destination for you and your partner, start by determining what kind of experience you both want.
If you’re both craving downtime and itching to relax, a trip to a resort in Hawaii might be exactly what you need. But, if you both thrive on new experiences and can’t sit for long, any destinations with many activities might be a better fit.
Budget is also another important consideration.
A trip to the Amalfi coast might be something on your bucket list, but it may not be feasible right now due to your budget. The good news? There’s plenty of other alternatives that won’t break the bank. Additionally, making simple choices such as preparing your own meals and choosing a cozy cabin over a luxury hotel can make your dream trip possible.
Ultimately, the goal is to plan a trip that reflects your relationship, and what matters to you both, not others.
Anniversary Trip Planning Tips
Here’s some helpful tips and tricks to plan your anniversary trip as smooth as possible.
1. Schedule downtime. When planning your trip, resist the urge to pack every minute with activities. Having downtime can give you and your partner space to reconnect, relax, and remember why you’re both taking this trip in the first place. Allow yourselves to linger over coffee, take an unplanned stroll, or simply enjoy each other's company without an agenda. You deserve the rest.
2. Make dinner reservations ahead of time. If you’re wanting to hit up the hottest restaurants near your destination, book it well in advance, especially during peak times including New Years Eve. Even for casual spots, consider placing online orders for pickup to save time and reduce stress.
3. Mix it up! During your anniversary trip, use it as an opportunity to try something new together. Seek out activities and places that push you slightly outside of your comfort zone. Whether that’s an Italian cooking class, a sunrise hike, or exploring a new area, these shared “firsts”can become some of your most cherished memories.
4. Pack Smart. When getting ready for your trip, think carefully about what you'll need based on your destination and trip length. Take some more time to research the climate and typical activities, as you won't need a heavy jacket for Costa Rica, but you'll definitely want one for Montana in Winter. You can pack many versatile pieces that can be mixed and matched, and consider whether a carry-on will suffice or if you'll need a larger suitcase for longer stays.
5. Consider The Time Of Year You’ll Be Traveling. Last but not least, your travel dates will significantly impact the cost and experience. Off-peak seasons usually mean cheaper flights and hotels, but there's often a trade-off. For instance, visiting Scottsdale in the middle of summer will save you money, but walking outside will feel like you’re in an oven. So, choose wisely. Find the sweet spot that balances your budget with comfortable weather and the experience you and your partner are seeking.
25th Anniversary Trip Ideas
Aspen, Colorado
For the adventurous couple who loves the outdoors, Aspen is the perfect destination. Pack your snow boots and hit the slopes for some skiing or snowboarding during winter time. You can also choose to hike or bike through the mountains during the summer and take in the stunning scenery. Year round, this destination is packed with fun activities and perfect for adding excitement to your anniversary celebration.
- Best for: the adventurous couple that loves the outdoors and mountain scenery
- Trip length: 4-5 days
- Budget: $$-$$$
- Best time to go: November-March for the ski season; June-September for hiking and other outdoor activities
Where To Stay
The Little Neil and Hotel Jerome offer the ultimate luxury Aspen experience with world-class amenities and peak elegance. Budget-conscious travelers can base themselves in nearby Glenwood Springs or drive into town for a 20 to 40 minute adventure, as it's closer than you think!
Where To Eat
Treat yourselves to an extraordinary celebration dinner at Matsuhisa for world-class sushi or Element 47, where refined American cuisine meets an impressive wine list. For a more relaxed mid-range vibe, White House Tavern serves elevated comfort food, while Meat & Cheese offers artisanal farm-to-table small plates perfect for sharing.
What To Do
Make your way to Aspen Mountain or Snowmass for legendary winter skiing, or conquer the iconic Maroon Bells trail during summer! For pure romance, soak together in Glenwood Springs' natural hot springs just 40 minutes away, then stroll through downtown Aspen's boutiques and galleries or explore the scenic trails around the Recreation Center.
Miami, Florida
If you and your partner love a little bit of glamor and sun, Miami is the place for you. Hit up the famous South Beach for some fun in the sun. Afterwards, the two of you can indulge in some delicious Cuban cuisine in Little Havana, and dance the night away at some of the hottest clubs in the country.
Ride in style while you’re out there and rent an exotic car to tour around the city. Don't forget to visit the Wynwood Walls for some amazing street art and unique dining experiences like the Hiyakawa Japanese omakase experience. We also recommend renting out jet skis to splash in some adventure to your trip.
Best for: Couples who love sunshine, nightlife, and a touch of luxury
Trip length: 3–5 days
Budget: $$–$$$
Best time to go: March–May for great weather; December–April for peak energy
Where To Stay
South Beach is perfect for walkable beaches, nightlife, and iconic Miami vibes. Brickell offers sleek hotels with rooftop views for a modern feel, while Coconut Grove is ideal for couples wanting a quieter, romantic escape.
Where To Eat
Savor classic Cuban dishes in Little Havana, then book an anniversary-worthy dinner at Joe’s Stone Crab or Zuma. For something unique, the omakase experience at Hiyakawa is unforgettable.
What To Do
Spend your days beach lounging or exploring Wynwood’s art scene, then add adventure with jet skis or a sunset cruise. Dress up for glamorous nights out in South Beach or Brickell.
San Francisco, California
For a romantic West Coast anniversary trip, San Francisco is a must-visit destination. Take a romantic stroll through Golden Gate State Park and catch a glimpse of all the lovely sights. Book a ride on the famous cable cars and go up and down the steep hills located all across the city.
You could also enjoy the delicious food offered within different neighborhoods. Make sure to visit Cole Valley and check out Zazie, a French American diner where you can get some of the best french toast in the bay area. Afterwards, you can take a trip down to the Sutro Baths and end your day with a lovely view of the sea! For couples looking to extend the romance, these same activities make for an unforgettable San Francisco honeymoon, blending iconic sights with cozy neighborhood charm.
Best for: Couples who love culture, scenery, and food-forward travel
Trip length: 3–4 days
Budget: $$–$$$
Best time to go: September–October for clear skies and fewer crowds
Anniversary moment: Watching the fog roll over the Golden Gate Bridge at sunset
Where To Stay
Union Square keeps you central to shopping, dining, and transit, while Nob Hill offers classic romance with elevated city views. Couples seeking a quieter vibe may enjoy boutique hotels in neighborhoods like Pacific Heights.
Where To Eat
San Francisco’s culinary scene shines in neighborhood gems like Zazie for brunch and Tartine for pastries. For a special anniversary dinner, book a table at Gary Danko or Quince for refined, unforgettable meals.
What To Do
Ride the iconic cable cars, stroll through Golden Gate Park, and explore coastal landmarks like Sutro Baths. A ferry ride to Sausalito makes for a relaxed and scenic afternoon together.
Taos, New Mexico
If you're looking for a unique and artistic destination, Taos is the place to consider. This small town in northern New Mexico is home to a vibrant arts scene, with numerous galleries, museums, and festivals throughout the year. Stay in a cozy adobe casita, take a hike in the nearby mountains, and visit the iconic Taos Pueblo for a glimpse into Native American culture.
This is a wonderful destination to get away from it all and unwind together in the sunshine. Remember to pack in your great quality sunscreen to make sure you’re prepared for any sunbathing!
Best for: Couples seeking creativity, culture, and a peaceful escape
Trip length: 2–4 days
Budget: $–$$
Best time to go: May–October for warm days and festival season
Anniversary moment: Watching the desert sunset from an adobe patio
Where To Stay
Cozy adobe casitas and boutique inns offer warmth, charm, and a strong sense of place. For more privacy, mountain lodges just outside town provide serene desert views.
Where To Eat
Taos blends Southwestern flavors with local ingredients and artistic flair. The Love Apple is a favorite for an intimate, candlelit anniversary dinner.
What To Do
Browse art galleries, visit Taos Pueblo, and hike nearby mountain trails. End your days soaking in nearby hot springs or stargazing under clear desert skies.
Kauai, Hawaii
If you're looking for a tropical destination, Kauai is a great choice for an anniversary trip. This lush and beautiful island is known for its stunning scenery, outdoor adventures, and laid-back vibe.
A popular activity you can book is taking a helicopter tour of the island. This is the best way to take in all the views and see Hawaii like never before! You can also visit any of the sandy beaches along the coast and lay out in the sand as you listen to the waves crashing for a peaceful experience.
Best for: Couples craving tropical romance and outdoor adventure
Trip length: 5–7 days
Budget: $$$
Best time to go: April–June or September–October
Anniversary moment: A helicopter flight over waterfalls and emerald cliffs
Where To Stay
The North Shore offers lush scenery and a quieter atmosphere, while Poipu is known for sunny beaches and resort-style comfort. Both areas provide stunning backdrops for an anniversary stay.
Where To Eat
Fresh seafood and island-inspired cuisine are highlights throughout the island. A sunset dinner at Beach House Restaurant is a perfect way to celebrate.
What To Do
Take a helicopter tour, relax on secluded beaches, and hike Waimea Canyon. A Na Pali Coast boat cruise adds unforgettable views and adventure.
Napa Valley, California
Next on the list is Napa Valley, California. For the wine-loving couple, this destination is a no-brainer. Take a scenic drive through the vineyards, book a wine tasting tour, or enjoy a romantic dinner at one of the many Michelin-starred restaurants in the area.
And if you're feeling adventurous, why not take a hot air balloon ride over the valley? The views are breathtaking, and it's the perfect opportunity for a memorable photo opportunity.
Best for: Wine-loving couples and food enthusiasts
Trip length: 2–4 days
Budget: $$$
Best time to go: April–June or August–October
Anniversary moment: Sunrise hot air balloon ride over vineyard-covered hills
Where To Stay
Boutique inns in Yountville or St. Helena keep you close to wineries and dining. Vineyard resorts offer spa amenities, privacy, and scenic views.
Where To Eat
Napa is famous for farm-to-table cuisine and Michelin-starred dining. Splurge on an anniversary dinner at The French Laundry or Bouchon.
What To Do
Enjoy wine tastings, scenic drives, and spa days in Calistoga. A hot air balloon ride adds a truly memorable anniversary experience.
Asheville, North Carolina
Asheville is the perfect destination for a cozy mountain getaway! Situated in North Carolina's Blue Ridge Mountains, this quaint town offers visitors an abundance of artistry and culture. Enjoy craft brews from one of its many breweries or savor tasty farm-to-table cuisine for a truly unique dining experience.
Get lost on the Appalachian Trail and enjoy the peaceful atmosphere of being on top of a mountain. There’s something special around every corner here! Relax after your adventures with some time spent cozying up by the fire in a nearby cabin and cook up some delicious s’mores!
Best for: Couples who love mountains, creativity, and cozy vibes
Trip length: 3–4 days
Budget: $–$$
Best time to go: September–October for fall foliage
Anniversary moment: S’mores by the fire after a mountain hike
Where To Stay
Secluded mountain cabins offer privacy and romance, while downtown boutique hotels keep you close to Asheville’s food and arts scene.
Where To Eat
Asheville’s farm-to-table dining scene shines with fresh, seasonal flavors. Cúrate is a standout choice for a warm, celebratory dinner.
What To Do
Drive the Blue Ridge Parkway, hike scenic trails, and explore local breweries. Visiting the Biltmore Estate adds elegance and history to your stay.
Chicago, Illinois
Chicago, the vibrant metropolis nestled along the shores of Lake Michigan, is an incredible destination in the United States that guarantees an unforgettable anniversary celebration. This dynamic city seamlessly blends culture, architecture, and culinary delights, offering a plethora of experiences that will create lasting memories.
Embrace the city's energetic spirit by taking a romantic stroll along the Magnificent Mile. This upscale shopping district offers a mix of luxury boutiques, department stores, and charming cafes. Treat yourselves to a shopping spree or indulge in a couples' spa retreat to relax and rejuvenate amidst the bustling city.
Best for: Couples who love architecture, dining, and city culture
Trip length: 3–4 days
Budget: $$
Best time to go: May–September
Anniversary moment: Cocktails with skyline views from a rooftop bar
Where To Stay
River North puts you near dining and nightlife, while The Loop offers easy access to museums and landmarks. Both areas are convenient and walkable.
Where To Eat
Chicago’s food scene ranges from iconic deep-dish to world-class fine dining. Celebrate with an anniversary dinner at Alinea or RPM Italian.
What To Do
Take an architecture boat tour, stroll along the lakefront, and explore Millennium Park. Rooftop bars are perfect for evening celebrations.
New Orleans, Louisiana
A city known for its rich cultural heritage and vibrant atmosphere, New Orleans offers an intoxicating blend of romance and excitement for couples celebrating their anniversary. Let the rhythm of this captivating city sweep you off your feet as you immerse yourselves in its unique charm.
Begin your journey by indulging in the delectable Cajun cuisine that New Orleans is renowned for. From gumbo to jambalaya, the flavors of the city will tantalize your taste buds and create a culinary experience like no other. Don't miss the opportunity to savor fresh seafood and beignets at the famous Café du Monde, a local favorite for authentic cuisine.
Best for: Couples who love music, food, and rich cultural experiences
Trip length: 3–4 days
Budget: $–$$
Best time to go: February–May
Anniversary moment: Live jazz in a candlelit French Quarter bar
Where To Stay
The French Quarter offers historic charm and walkability, while the Garden District provides a quieter, romantic atmosphere with beautiful homes.
Where To Eat
Cajun and Creole cuisine take center stage in New Orleans. Commander’s Palace is a classic choice for an elegant anniversary dinner.
What To Do
Listen to live jazz on Frenchmen Street, take a Mississippi River cruise, and wander historic neighborhoods hand in hand. These experiences will transport you back in time while creating unforgettable memories together, blending the romance of centuries-old architecture with the vibrant energy of a city that never stops celebrating life.
Malibu, California
Nestled along the sun-kissed shores of Southern California, Malibu stands as an incredible anniversary destination in the United States to offer an unforgettable celebration. Known for its breathtaking coastal beauty and laid-back luxury, Malibu exudes a romantic charm that sets the stage for a truly memorable experience.
Indulge in the culinary delights that Malibu has to offer, from upscale oceanfront restaurants to charming seaside cafes. Explore the iconic Malibu coastline by visiting the famed Malibu Pier, where you can enjoy stunning views, indulge in beachside picnics, or try your hand at fishing. A truly wonderful place to celebrate your special milestone together.
Best for: Couples seeking coastal luxury and relaxation
Trip length: 2–3 days
Budget: $$$
Best time to go: May–October
Anniversary moment: Sunset picnic overlooking the Pacific Ocean
Where To Stay
Oceanfront resorts offer luxury and panoramic views, while private beach rentals provide intimacy and seclusion.
Where To Eat
Malibu’s dining scene blends fresh coastal flavors with upscale ambiance. Nobu Malibu is a must for a romantic oceanfront dinner.
What To Do
Stroll the Malibu Pier, lounge on the beach, and hike coastal trails. Scenic drives along the Pacific Coast Highway set the tone for romance.
New York City, New York
Come explore the romance that is New York City! This city has it all – history, art, culture and a melting pot of different food. Take an iconic walk through Central Park and take in this urban paradise. It’s the perfect spot to have a picnic and enjoy some nature within the city.
You can plan ahead and book tickets for one of Broadway's top-notch shows. Head over to the top of the legendary Empire State Building and see New York for all its glory. NYC will be sure to captivate your heart nonetheless and give you many opportunities to make your anniversary trip special.
Best for: Couples who want iconic romance and endless options
Trip length: 3–5 days
Budget: $$–$$$
Best time to go: April–June or September–December
Anniversary moment: A Broadway show followed by a moonlit Central Park walk
Where To Stay
Midtown offers unbeatable access to shows and landmarks, while SoHo or the Upper West Side provide charm and quieter streets.
Where To Eat
New York’s food scene spans the globe, from casual eats to legendary fine dining. Celebrate with a romantic meal at The River Café or One If By Land, Two If By Sea.
What To Do
Enjoy a Central Park picnic, catch a Broadway show, and take in skyline views from the Empire State Building. Museum visits and evening strolls complete the experience.
Anniversary Trip FAQs
Below is a list of the most commonly asked questions for anniversary trips.
What are the best anniversary trip destinations for a weekend?
The best weekend anniversary trips are places that are easy to get to and offer a mix of great food, relaxing activities, and one or two standout experiences. Cities, wine regions, and cozy mountain towns work especially well for short stays.
What are the best anniversary trip destinations on a budget?
Budget friendly anniversary trips often focus on experiences rather than luxury. Destinations with free outdoor activities, walkable neighborhoods, and affordable lodging options can feel just as romantic without a high price tag.
Where should we go for a first anniversary trip?
A first anniversary trip is a great opportunity to choose somewhere that feels special but not overwhelming. Look for a destination that balances romance with fun, giving you time to relax, explore, and celebrate without over-planning.
What is the best time of year for an anniversary trip?
Spring and fall are often ideal because they offer comfortable weather, fewer crowds, and better pricing. That said, the best time ultimately depends on the destination and the type of experience you want to share.
How far in advance should we book?
Booking a few months ahead is usually enough for most trips. If you are traveling during peak season or planning a milestone anniversary, booking earlier helps secure better options and reduces stress. Make sure to book accommodations and restaurant reservations as early as possible, especially for popular experiences and beachfront hotels that fill up quickly during the spring and fall seasons.
Start Planning Your Anniversary Trip Today!
No matter what kind of anniversary trip you're looking for, there's a unique destination in the US that's perfect for you and your partner.
Ready to start planning your trip? When you book with Celebration.com Travel, you can rest assured that every single detail of your trip will be handled with care. Fill out our interest form to connect with a travel agent today!
