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Milestone Anniversary Trips: Where to go & What to Do

While we typically spotlight family-friendly destinations, especially those that will appeal to younger children, this piece is all about the adults!  

Read on to discover some continental and international destinations that make the perfect milestone anniversary trips. Yes, you and your special someone deserve to get away now and then on your own, so make it memorable! 

Continental Options Plus Hawaii

Beverly Hills, California 

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As a piece of iconic American history and glamor, Beverly Hills is a wonderful destination for a unique anniversary trip. While there are countless high-end restaurants and plenty of shopping opportunities on Rodeo Drive, there are also many activities to enjoy that won’t require you to take out a second mortgage to afford. 

Beverly Gardens Park, with its iconic roses, is one such location. Here, you can get the perfect shot of the Lily Pond and historic Beverly Hills Sign. In fact, this is one of the most photographed spots in the entire city! You can also print out a Happy Trails Walking Tour to explore the entire city on foot. 

While there are many high-end hotels to stay in when visiting this classic location, perhaps one of the most notable, and therefore worthy of an anniversary trip, is the famous Beverly Hills Hotel, a member of the Dorchester Collection. This hotel, which regularly hosted Elizabeth Taylor and Marilyn Monroe as guests, is still one of the most beloved and iconic hotels in the world. 

From its beautiful garden in the Polo Lounge to its banana leaf wallpaper and pink exterior, the Beverly Hills Hotel is a destination in and of itself. Thankfully, even though this is still considered a celebrity hotspot, all guests, even those who aren’t quite famous, are made to feel welcome.

While staying at this classic location, you might be tempted to stay put in your luxurious bungalow. However, if you do want to venture out, be sure to make your way up to Griffith Observation for views of the renowned Hollywood sign. If you don’t get a shot of this, did you even go to Hollywood?

Kaui, Hawaii

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If you want to find true paradise on this side of heaven, there is likely no other location better to visit than beautiful Hawaii.

Visiting the island of Kaui offers you an ideal mixture of the lush jungles and beautiful beaches. You can explore natural wonders by helicopter, boat, and/or foot or enjoy a variety of memorable experiences

There are countless places to stay when visiting Hawaii in general and Kauai in particular. One notable resort that is ideal for an anniversary trip is Ko’a Kea Hotel and Resort at Poipu Beach. This breathtaking resort was named one of the world’s most romantic hotels for good reason. 

This resort features its own restaurant, spa, pool, watersport access adventure center, and sushi bar, and even offers a Tesla experience, allowing you to reserve a Tesla for use during your stay so you can venture out and see all Kaui has to offer. 

The rich textures and vibrant colors of the island, along with the spacious guest rooms and suites, allow you to create a luxurious experience that is perfect for reconnecting and unwinding. You can stay in your room, on the beach, in your own private lanai, or go off-site to explore some of the nearby attractions.   

New York City, New York

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To list everything you could possibly do in “the city that never sleeps” would take up this entire list of anniversary trips. However, there are a few worth pointing out when you choose the “Big Apple” as your romantic anniversary destination. 

Be sure to see a Broadway Show after taking in a delicious dinner at any one of the many award-winning eateries in the city. Also, visiting the various New York museums, which are some of the best in the world, is a must-do activity when visiting the city, along with taking a trip to the iconic Central Park

There are countless places to stay when visiting New York, but one way to remain close to all the action is to stay right in Times Square by booking the Renaissance New York Times Square Hotel by Marriott.

The rooms themselves are nice, but the location is to die for as it is mere steps from so many New York activities. In addition, the hotel’s R Lounge, featuring floor-to-ceiling windows with amazing views of Times Square, makes it the perfect place to relax after a fun day in the city. 

While staying right in the heart of the city is fun, you can also venture out and do more during your visit. One suggestion is to book a photo tour photoshoot complete with the most amazing city as your backdrop. This part tour and part photo shoot will show you all the city has to offer and give you something to take home to look back on as well. 

In addition, nearby Hudson Valley features the Storm King Sculpture Garden, which is newly renovated and perfect to explore, along with the many dining options and boutiques within the Hudson Valley.

This 500-acre outdoor sculpture museum is a great place to visit if you are artistic or simply enjoy wooded areas, rolling meadows, and more. You can even rent a bike.  

Tucson, Arizona

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If your idea of the perfect getaway involves plenty of sunshine and wellness services like award-winning spa treatments, then visiting the Tucson area could be a great anniversary trip.

When in the area, make sure to visit Saguaro National Park, home to the nation’s largest cacti. Here, you will see enormous cacti silhouetted by the beauty of the magnificent desert. 

As another interesting location, consider stopping in at the Mission San Xavier del Bac, a recently restored adobe church built in the 1700s. This still-operational church presents a great example of beautiful colonial architecture and is worth exploring both inside and out.

The Miraval Arizona, an adults-only resort, offers an all-inclusive experience for “wellness in the Sonoran sun.” and is the perfect place to stay in Tucson.

Situated near the majestic Santa Catalina Mountains, this resort features many inclusive packages that allow you to focus only on each other when visiting, not on tipping or payments. Your experience, not the check, is of paramount importance, so much so that Miraval is a gratuity-free resort. 

Rooms at the Miraval are luxurious, and on-site amenities include transportation to and from the Tucson International Airport, culinary offerings including meals and snacks, an arrival gift, and a host of activities that can be arranged. 

Experiences at Miraval include aerial yoga classes, culinary classes, a zip line course, archery, equine activities, hiking, perhaps up Mt. Lemmon, and much more. The idea is to create restorative stillness, complete with the backdrop of the beautiful Sonoran Desert. 

Big Sky, Montana

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The fresh air, vast terrain, and rustic romance of Big Sky, Montana, make it an ideal destination for your anniversary trip. This is especially true if your anniversary happens to be in the winter, as this area features a top-notch ski resort, Big Sky Resort,  that even has a heated chairlift.

Of course, even in the off-season, which is not the winter for this area, there are activities to enjoy, like hiking, fly fishing, or visiting Yellowstone National Park. When visiting Big Sky, consider the Montage Big Sky, located just 45 minutes from Yellowstone, situated in the valley of the Spanish Peaks Mountain Range

Described as a location where modern design meets alpine charm, the Montage features luxurious accommodations, dining, a spa, and even ski packages. This Alpine oasis boasts a host of wellness treatments, including a luxurious indoor pool. 

Depending on the time of year you visit, Big Sky is perfect for snowboarding or skiing but also offers hiking and cycling opportunities. The Big Sky area offers the perfect backdrop to just get away from it all, to become refreshed, relaxed, and rejuvenated. There are unlimited outdoor recreation opportunities as well as many delicious eateries. 

Sea Island, Georgia

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As part of the Golden Isles of Georgia, Sea Island is a privately owned and unincorporated island, complete with a gated entrance for only resort guests and Sea Island club members. You reach it by a causeway from St. Simons Island. As such, you can be sure that this will offer the privacy and intimacy befitting an anniversary trip. 

When staying at Sea Island Resort, choose from a variety of properties. The Cloister, The Lodge, and Sea Island Cottages, which are all part of the property and offer a variety of experiences to guests. The Cloister features five miles of private beach, elegant rooms, and 50 acres of lush surroundings, with options of staying in the main building and wing, beach club, or ocean residents. 

The Lodge is a Forbes Five-Star Resort boutique hotel that is known as a small, intimate space big on Southern charm. It features 43 rooms, seven cottages, and a championship golf course. The Cottage rentals are another option, with three to eight-bedroom options. The cottages are perfect for seclusion and privacy. 

Private beach access, in-room dining, breakfast packages, a pool, butler service (at the Lodge), and more are just part of the standard level of service at the Sea Island Resorts. You can spend your whole vacation at the resort thanks to its dining options as well as shopping, spa, and other activities, including horseback riding on the beach.

If you do want to venture back off the island, though, you are located near St. Simons Island, Georgia, where there are a host of other activities to enjoy. For example, visit the St. Simons Lighthouse Museum and see the last of only five surviving light towers in Georgia. 

International Trips 

Seychelles, Africa

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If remoteness is key in choosing your destination, you likely won’t find a better option than Seychelles Island. This super remote location is nearly 1,000 miles off Africa’s east coast. While the beloved Maldives merit much of the praise, those in the know say that a visit to Seychelles is even more applicable for a true getaway.

Admittedly, this is not a budget-friendly option as this location has never been “cheap” to visit. In addition, the Seychelles is not on any cruise itinerary as a stop. However, that is what gives this beautiful location immense appeal when it comes to creating the perfect anniversary trip. 

There aren’t many choices in terms of hotels in the area due to the travel time it takes to get there. The best place to stay is probably the Four Seasons Resort Seychelles. This picturesque retreat is situated on the southwest coast of Mahe’, overlooking the bay of Petite Anse.

The Four Seasons resort features 67 stilted suites (a few of which have direct private beach access)  and villas that will have you living in the trees as they are designed to mimic treehouses. Your hotel room situates you in luxury with a jungle canopy of jackfruit, mango, coconut, and cinnamon trees. 

An expansive outdoor living area, glass-walled bathrooms, open-air showers, a private gym,  and infinity-edge plunge pools take this adventure to a whole other luxurious level. Considered a romantic hideaway set amongst a tropical paradise, this location has it all including several fine dining options or even room service. 

Patagonia, South America

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If you and your most important person both enjoy being active and enjoying all nature has to offer, then a visit to the last frontier of South America to Patagonia could be the perfect anniversary trip.

You can do multi-day hikes in Chilean Patagonia or day hikes in Torres del Paine National Park, known as the World’s 8th Natural Wonder. There are even driving tours of the park if that is more your speed. 

In addition, you can opt to see much of the park’s natural beauty via a glacier tour on a boat. There are several options to consider when staying in this area as far as accommodations. Obviously, if you plan on multi-day hiking, then you can stay at little lodges located on the trails.

However, if you want the best of both worlds, combining the love of nature and all the area beholds with luxurious accommodations, then Singular Patagonia is probably the best option. 

As a member of the Leading Hotels of the World, this Puerto Bories Hotel, offers an atmosphere of extreme refinement situated amongst the unparalleled natural beauty of Chilean Patagonia for the perfect fusion of relaxation and nature. 

Situated just a mere 5-minute drive from the town of Puerto Natales, you can easily access many excursions, some of which are in the famed Torres del Paine National Park.

In addition, right on the hotel grounds and declared a National Monument in 1996, you can tour the Cold Storage Plant at Puerto Bories. This museum-hotel provides an immersive experience into the history of the location as well as providing a luxurious stay with amazing amenities. 

All rooms in The Singular feature incredible views of the Patagonia fjords and are themselves extremely spacious and comfortable. Luxurious features like Egyptian cotton linens, room service, heated floors, custom furniture, and more add to the elegance of the space.   

Paris, France

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There couldn’t be a list of best anniversary trips for milestone anniversaries without the inclusion of the most romantic place on earth, Paris, France. The city of light features the Eiffel Tower, rich food served in candlelit bistros, along with many world-famous landmarks, and an abundance of rich wines, making this a must-add to our list. 

Due to the area’s appeal, there are many hotels and/or resorts to choose from when staying in the area. However, one of the most glamorous and luxurious options, worthy of a milestone anniversary trip, is the La Reserve Hotel and Spa Paris. This five-star, glamorous hotel is the ideal indulgent anniversary splurge. 

Nestled within an early 20th-century mansion located near the Champs-Elysees, this hotel is designed to make you feel as if you are a private guest in an aristocratic home. The hotel features notable amenities like working fireplaces, marble busts, gold lacquered woodwork, spacious guest rooms, and burgundy velour, all creating a chic look throughout the entire space. 

The hotel suites range in size from 540 to 1,830 square feet. They boost large sitting rooms, private terraces, and, most impressively, dining room views of the Eiffel Tower. Dining options are, of course, noteworthy as well, including the Le Gabriel, with two Michelin-star chefs. 

Visiting the Eiffel Tower is obviously a must-do activity when visiting Paris. However, there are many other romantic ways to spend the days when visiting, including visiting Monet’s house and gardens, seeing world-class art in the Muse’e de l’Orangerie, or row boating in Bois De Vincennes

Hakone, Japan

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Hakone is just a quick day trip away from the famous Tokyo but far enough removed to offer traditional Japanese inns and lots of hot springs and other natural attractions. It’s also near Mount Fuji volcano, Lake Ashi, and the Hakone Shrine, which is a beloved shrine featuring a very noticeable fire-engine red gate.

There are many transportation options to choose from, meaning that even if you are staying anywhere within Hakone, you will be able to access many activities, restaurants, and noteworthy attractions.

There are several inns, resorts, and hotels in the Hakone area that are worth visiting. However, for this particular getaway, being a milestone anniversary getaway, I particularly liked the Hakone Retreat Villa, which doesn’t allow children under the age of 12. 

As the only hotel in Fuji-Hakone-Izu National Park (Japan’s most visited National Park), the Hakone Retreat Villa offers private hot springs baths, beautiful woodland views, wood-burning stoves, and minimalist decor, all with a rustic, chic feel.

When staying here, you will be served traditional Kaiseki courses, but with a creative modern flair, or choose French cuisine cooked in a wood-burning oven. 

If you would rather be closer to the action and able to walk from your hotel to the city, then you might instead prefer the Yoshimatsu, which is located mere steps from Lake Ashi. Due to its central location, you can easily access the city and explore. 

Rooms here feature beautiful lakeside views and include access to several hiking trails, some featuring original stone pavement. When on your walk, look up to the snowy peaks and enjoy this tranquil retreat to nature. Japanese gardens, outdoor hot springs baths with a view of Mount Fuji, room service of traditional kaiseki ryori dinner, and quiet, intimate rooms are all part of what is offered at Yoshimatsu. 

Amsterdam, Netherlands

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If you would prefer spending your time in historic settings with an abundance of art and culture to enjoy, then a trip to Amsterdam could be a good fit. The Stedelijk Museum, the Van Gogh Museum, and the Rijksmuseum call Amsterdam home and make a pretty great collection of activities. 

For the even more romantic at heart, you can visit the Cafe’ Papeneiland, a historic brown cafe, and its famous, world-renowned apple pie. Of course, enjoying a science cruise down the canals is also a super sweet way to spend your time in this picturesque city. 

Pulitzer Hotel, which includes 25 golden age canal houses that are joined together and have been renovated into a chic property with great drinking and dining options, is an ideal place to stay when visiting Amsterdam. This historic location is home to more than four centuries of Dutch heritage.

Situated among the city’s beloved canals, the Pulitzer Hotel offers a perfect combination of modern design and traditional Dutch craftsmanship. The rooms and suites differ in size, views, and layout, but they all feature a celebration of Dutch heritage. This, combined with the luxurious touches and the inviting settings, has been carefully designed to provide comfort to all who visit. 

While only available in the winter, through the months of December and January, one of the most romantic activities to enjoy in Amsterdam is the Amsterdam Light Festival.

You can enjoy this amazing experience either by boat, bike, or on foot. This is a free event that is best described as a winter festival complete with unique spectacles in the form of light exhibitions, light sculptures, and more.  

Ibiza, Spain

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Considered an island chic getaway, a visit to Ibiza, Spain, offers more than meets the eye. Yes, there are many tourist activities along the main areas of this Balearic island; however, if you venture out ven a bit, you will find yourself surrounded by rambling orchards, wild forests, and sleepy hill villages. 

While visiting any time of the year is a good idea, spring offers a unique experience thanks to the almond trees that are in full bloom this time of year. The glorious white and pink blossoms create a swatch of beauty over the entire valley. 

Known as one of the best hotels in Ibiza, the Cas Gasi is a great option for your anniversary stay. The Cas Gasi also happens to provide the best front-row seats in the area to the natural show of spring foliage, thanks to the fact that this property spills down a hillside covered in carob, fig, and almond trees. 

The hotel is described as being secluded yet offering low-key luxury. It also features a privileged location for the most beautiful beach experience on the entire island. This, along with the serene swimming pools, fusion cuisine, regular yoga sessions, and wabi sabi-inspired design, makes it a great choice for such a monumental celebration. 

In addition to the picturesque beaches, Ibiza also offers other activities for you to enjoy on your trip. For instance, Dalt Vila is a fortified old town full of rich cultural history. This unique and interesting site is even considered a UNESCO World Heritage Site. There are three official tour routes through the town, or you can just wander around on your own. 

Another noteworthy activity to consider is riding bikes for a tranquil experience through Formentera. To get to Formentera and its green track, sparkling waters, and sandy shores, take a ferry from the southern coast of Ibiza, out of Ibiza Town’s main port. Once you arrive, you can rent a bike from various places on the island. 

Svalbard, Norway

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For an even more secluded and romantic spot, why not consider visiting the very northernmost inhabited region of Europe at Svalbard, Norway?

In Svalbard, located between the North Pole and mainland Norway, during certain times of the year (between April and August), you can experience 24-hour daylight, a time called the “midnight sun.” This means that your little getaway together would seemingly not end as the daylight goes on and on. 

If you prefer the night, though, you can always opt to visit during the “polar night” time, when the darkness lasts for 24 hours (January and February).

During this especially romantic time, you can partially see the aurora borealis. However, if your goal is to experience the northern lights, your best time to visit will be from autumn to mid-April. 

While a literal arctic paradise, the city of Longyearbyen in Svalbard is a cosmopolitan city with many restaurants, modern hotels, and even Scandinavia’s largest wine cellar. When dining in Svalbard, you can enjoy locally sourced delicacies like Arctic char, Atlantic cod, Svalbard reindeer, and Svalbard grouse, all served with mushrooms and herbs fresh from the tundra. 

In addition to enjoying fine wine and interesting dining options, you can also enjoy many unique activities in this area, like snowmobile tours, museums, galleries, the arctic wilderness, ice caves, and more.

Always prioritize guided tours and use local guides for safety, as these areas can be dangerous. Keep in mind that this is the polar bear kingdom! 

As mentioned above, there are several hotels to choose from in the Svalbard, Longyearbyen area. However, one of the best is the Svalbard Hotell Polfareren. This boutique hotel offers snug charm with a rustic atmosphere, all with a high level of service and offering modern furnishings. 

The hotel lounge features a polar library, along with a bar and refreshment area. The reception area is staffed around the clock to help guests organize activities and learn more about the region. Breakfast is included in your stay, along with complimentary WiFi. 

Cong, Ireland

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This particular adventure is the fulfillment of a dream for me personally. Now, if you haven’t somewhere deep inside wanted to live as royalty in a castle, then you can appreciate this destination for other reasons.

However, personally, Cong, Ireland, and the Ashford Castle Hotel could not be a more perfect anniversary destination.

First off, Cong is situated in the southwest region of Ireland and is a tiny village that is perhaps best known for being the filming location of The Quiet Man, starring Maureen O’Hara and John Wayne. I haven’t personally seen this film, but still, it’s neat that this unique town was the backdrop. 

Aside from its classic movie backdrop history, Cong also features some of the most ancient stone monuments and circles in all of Ireland. The Cong area is full of medieval wonders and ancient sites, not the least of which is the 12th century Cong Abbey and the castle, the Ashford Castle

Speaking of castles, you can actually stay in this unbelievable setting yourself and live like true royalty during your stay at Ashford Castle Hotel. Within this beautiful hotel, situated within the 800-year-old castle, you can choose from 83 rooms that have been individually designed and detailed. 

The castle setting provides the ideal backdrop for a true wellness experience as you can enjoy Ireland’s Best Hotel Spa, which was awarded by the World Spa Awards.

The over 350 acres of ancient woodlands and rolling hills that surround the castle are perfect for horseback riding, falconry, fishing, clay shooting, cycling, archery, lake cruising, kayaking, and other unique and interesting experiences

Staying in this amazing location will often include a full Irish breakfast, as well as access to the Ealu, which is the state-of-the-art health and fitness center on-site, including a sauna, steam room, pool, jacuzzi, and gym.

This, along with private wine tasting, dinner, four-poster beds, on-site boutiques, a bakery, and a gift shop, makes visiting Ashford Castle in Ireland a dream come true.