9 Anniversary Trip Ideas–Planning The Perfect Celebration

9 Anniversary Trip Ideas–Planning The Perfect Celebration

Jason and I will be celebrating our 30th wedding anniversary this year and we decided to book a trip to Costa Rica to celebrate. We’ll spend eight days in this tropical country, most of it in the Monteverde Cloud Forest. Over the years, we’ve planned many epic adventures for celebrating anniversaries and mostly, they’ve been very successful. But choosing the right destination isn’t always easy, so I thought I’d help with anniversary trip ideas. I’ll share nine romantic and fun destinations along with a few planning tips.

Anniversary Trip Ideas--Wendy and Jason in Florence, Italy
Wendy and Jason in Florence, Italy

Choosing The Destination for Your Anniversary Trip

Before selecting any destination for your anniversary trip I recommend asking yourselves these two questions;

  1. How long can we be away from home?
  2. How much do we want to spend?

A short weekend getaway can definitely be romantic, especially if you’re on a tight budget. When our kids were young, this was often the best option for us, both for the sake of budget and childcare. But if this is a significant anniversary year, you may want to allow more time and give yourselves permission to spend more money. Whatever the decision, it’s important for both of you to be on the same page. 

Next, think about how you want to spend time on your trip. Do you want to relax and chill, or are you looking for some adventure? If work has been stressful and you both need a break, finding a charming bed and breakfast in a charming little town might be just what the doctor ordered. Or maybe you want to spend time together trying something new. There’s no right answer, but again, it’s important to review your options in advance.

Wendy and Jason in Sequoia National Park
Wendy and Jason snowshoeing in Sequoia National Park

Money Saving Tips For Your Anniversary Trip

Your romantic getaway doesn’t have to break the bank. So here are a few ways to save some money without sacrificing the experience. We’ve used all of these tips and tricks over the years and saved a considerable amount of money.

  1. Travel mid-week instead of on the weekend.
  2. Compare booking a package with reserving each portion of the trip separately. 
  3. Use credit card points instead of cash. 
  4. Look for deals through websites like TravelZoo.
  5. If booking airfares, compare all your options through Google Flights or SkyScanner.
  6. Plan free or low cost activities like hiking, biking, and kayaking. Many cities offer free-walking tours as well.
Food tour in Madrid
Wendy and Jason on a food tour in Madrid, Spain

Anniversary Trip Ideas In the United States

If you want to travel within the United States, the options for a romantic escape are endless. And whether you want a beachside, mountain top, or big city destination, we've got you covered.

Catalina Island, California

If you’ve decided on an oceanside, weekend getaway then Catalina Island is perfect, because whether you want to relax or stay active, this place delivers. Jason and I had the chance to stay at the recently remodeled Atwater Hotel last year and loved it. Everything you’ll want to do is within easy walking distance; tours, the beach, restaurants, and shopping. 

If you’ve decided upon a relaxing weekend, then head to the Descanso Beach Club, reserve two chaise lounges, order a tropical drink, and simply chill for the day. When you get hungry, the onsite restaurant serves delicious food.

For the more adventurous, book one of the many activities or tours offered on the island including ziplining, kayaking, rock climbing, and more. Jason and I took the Bison Expedition and explored the rugged backcountry of Catalina for over two hours. We bounced along dirt roads searching for wildlife. Occasionally we stopped to appreciate the scenic views. And since ours was the last expedition of the day we were treated to a sunset over Avalon Harbor.  

When you’re ready for a really romantic dinner, do what we did and head to Avalon Grille. The food was delicious and the service spot on.

Catalina Casino
Catalina Casino

La Jolla, California

Earlier this year Jason and I were looking for a completely relaxing getaway for a few days and decided that La Jolla fit the bill. This seaside section of San Diego has an upscale charm that includes plenty of fine dining, high end shopping, and great resorts. And while it could be an adventurous destination, for us, this is the place we go to chill.

After years of visiting La Jolla and staying at many of the area hotels, we’ve settled on the Hilton Torrey Pines as our favorite. Most of the rooms have balconies with a view of the world-famous Torrey Pines Golf Course. If we’re in the mood for a hike, Torrey Pines State Park is within walking distance. But one of the reasons we’ve come to love this hotel is it’s location next to Torrey Pines Lodge, a luxury resort with an elegant restaurant and gorgeous spa. Essentially, we stay at the Hilton for about half the price of the Lodge, but avail ourselves of services at both. In fact we’ve found the side door of the Hilton that connects to the side door of The Lodge (maybe I shouldn't be sharing this!).

If you plan to leave the hotel then head to Prospect Street--the main thoroughfare of La Jolla--for a nice selection of restaurants and shopping. Personally we enjoy Duke’s. Their seafood dishes are quite good and the view of La Jolla Cove is spectacular. Try to make reservations just before sunset.

Vegas Strip
The Vegas Strip

Las Vegas, Nevada

Sin City is the opposite of quiet and relaxing, but Jason and I have celebrated many anniversaries in Las Vegas and always love it. So if you’re looking for plenty of action for your getaway, plan a trip to Vegas.

We’ve stayed at a dozen different hotels on The Strip over the years, but our favorite is definitely The Cosmopolitan. Not only do we love the large, stylish rooms, but the selection of restaurants is unparalleled (afterall, travel is really about eating!). I recommend splurging on a room with a terrace and a view of the Bellagio Fountains. After dozens of trips to Vegas, I’m still not tired of the fountains. When you get hungry head to Secret Pizza, Eggslut, China Poblano, or Hattie B’s Hot Chicken. And if you want to sip a drink in a gorgeous and unusual setting head to the Chandelier Bar where you’ll be surrounded by draped crystal beads.

Jason and I aren’t gamblers, so we’re not in Vegas for the slot machines or card tables. Instead, we go for the shows and restaurants. Among our favorite restaurants for dinner are Mon Ami Gabi at Paris, Giada’s at The Cromwell, and Jaleo at The Cosmopolitan. In the show category we have many to recommend including anything produced by Cirque Du Soleil, Absinthe at Caesar’s Palace, and the Blue Man Group at The Luxor.

If you’re visiting Las Vegas outside of the summer season, and you enjoy hiking, set aside a half day for Red Rock Canyon National Conservation Area. Encompassing more than 195,000 acres and featuring 19 marked hiking trails you could spend years exploring this geologically unique reserve. But just choose one trail and explore the colorful rock formations that dominate the park.

Wendy and Jason dining in New York City
Wendy and Jason dining at Tony D Napolis in New York City

New York, New York

Romance and New York City may not sound compatible at first, but stay with me. This is one of the dining and theater capitals of the world. Any kind of food you want can be found in NYC along with a wide variety of plays and musicals. In my mind, those are the makings of a great anniversary trip. And when you add in all the museums, attractions, and shopping, this city is an excellent destination.

However, New York City is not a budget destination. Hotel rooms alone can be bloody expensive. So this might be a splurge, but definitely worth it. For our last trip to New York we opted to stay in the Financial District near the 9/11 Museum and the World Trade Center. We selected this location because it put us within walking distance to some of the places we wanted to go including the museum and the Statue Of Liberty. We had a great time exploring this part of the city, but for my next trip I’ll probably choose a different neighborhood so we can learn even more about this complex American city.

When visiting New York it’s critical to make advanced reservations for everything, and for the most popular attractions, pay a little extra for front-of-the-line passes. And if like us, you get tired of public transportation, use Uber or Lyft instead. Sometimes it’s nice to be picked up exactly where you are and be dropped off exactly where you’re headed.

Park City, Utah
View of Park City Utah from the top of Bald Mountain

Park City, Utah

Jason and I don’t ski, but we have discovered that ski destinations make great summer vacations. We’ve been twice to this upscale resort town in Utah, and will be returning for the third time soon. The selection of stylish resorts, farm-to-table restaurants, and a charming town center filled with art galleries makes Park City perfect for an anniversary celebration. If you enjoy hiking there are hundreds of miles of trails of all levels.

For our last trip--and upcoming trip--we selected the Chateaux at Deer Valley. In winter, this is a seriously pricey option, but good deals can be found in the summer. The rooms are cozy and comfortable while the resort offers a pool, outdoor games and fire pits, and a lovely restaurant. The ski lifts and a few hiking trails are just a short walk from the resort’s entrance. For views of the entire region take the Sterling Lift to the top of Bald Mountain. When it’s time to eat, head to one of Bill White’s eight establishments including Grapo Wahso, and Chimayo. Or make a reservation at Glitretind, a Scandanavian inspired venue located inside the Stein Eriksen Lodge.

TRS Turquesa Hotel
TRS Turquesa Hotel in Punta Cana, Dominican Republic

Anniversary Trip Ideas–International Destinations

If you have more time--and typically more budget--an international destination can be a great anniversary celebration. In the current travel climate, be sure the destination you want to visit is open. And if it is, check out all their tourist requirements. Finally, be sure your passport is current and will not expire for at least six months from the time of your travel.

Punta Cana, Dominican Republic

Right before the world shut down in March of 2020 I had the chance to visit Punta Cana in the Dominican Republic. Specifically I had the chance to stay at two different adults only resorts in this city. Whether you need an escape from your own kids, or like us, your kids are grown and you no longer require pools with slides and kids meals, an adults only resort is a great option for anniversary travel. 

I spent two nights at the TRS Turquesa hotel, the adults only portion of Grand Palladium Punta Cana Resort. This large, sprawling resort is located on the water and offers a long stretch of white sand beach to stroll any time of the day. This alone would be perfect for a romantic trip with your loved one. But it gets even better. As an all-inclusive resort you can eat at any of the dozens of restaurants on the property with a variety of international cuisines. To work off all that food head to the gym or take one of the organized yoga classes. At night enjoy live music at several of the bars and clubs. But perhaps my favorite part of the whole resort were the large, beautifully appointed suites that included an unlimited mini-bar. 

For one night I stayed at the TRS Cap Cana Hotel, a smaller adults only resort. Here there are never any kids--just adults having a really good time. This more intimate resort offered a few restaurants, a large pool area, daily classes, and nightly entertainment. I’d recommend either resort for a romantic anniversary getaway.

La Place Royale In Quebec City, Canada
La Place Royale In Quebec City

Quebec, Canada

I’ve been to Quebec twice, once to it’s capital city of Montreal, and once to Quebec City. Both are worthy destinations, and if you have enough time, could be combined into one trip. Both are great destinations for foodies, so if that’s a major focus of your anniversary trip, then this province of Canada is for you.

As the second most populous city in Canada, Montreal has endless neighborhoods to explore, sights to enjoy, and restaurants to dine. We spent a week here and just scratched the surface. We opted to stay in Old Montreal where the city was founded in 1642 as Forte Ville-Marie. This is home to cobblestone streets, ancient buildings, and Notre-Dame Basilica. If you enjoy museums like we do, head to the Museum of Fine Arts. Then be sure to save time to eat your way through this French inspired city. One way to do this is at one of the markets; Marché Atwater or Jean Talon Market. 

Quebec City is steeped in European charm, food, and culture. Everywhere you turn there are historic and well preserved buildings, some dating back to the mid-1600’s. Everyone speaks fluent French and will greet you with “bonjour.” This is a part of the country that considers itself Quebecois first and Canadienne second. I visited this city alone, and was really wishing Jason had been able to join me so we could both appreciate it’s romance together. But even without Jason, I fell in love with the food scene in Quebec City. No matter what else you do, book a food tour to really understand and appreciate how shops and restaurants in this town are proud to offer items that combine their Native, French, English and Canadian heritage. I stayed in the Old Port neighborhood at Hotel Le Germain Quebec and really hope to return there one day.

The Lee Family in Costa Rica
The Lee Family zip-lining in Costa Rica

Costa Rica

I’d be remiss if I didn’t include Costa Rica, especially since it’s the destination we’ve selected to celebrate our 30th anniversary. We took the whole family to Costa Rica a few years ago and fell in love with this Caribbean country. It’s relatively small with a laid back vibe while also being packed with natural wonders. 

For our first trip here we stayed in Playa Esterillos, located South of the city of Jaco. Our resort was small but perfectly positioned right on the beach. Each day we walked out of our room, across a small lawn and onto the sand to admire the expansive view of the Pacific Ocean. While the kids kept themselves entertained (they were both in highschool) Jason and I walked for miles along the sand hand in hand. Twice we ventured out of the resort; once for a ziplining tour and once to explore the nearby national Park, Manuel Antonio. We found that accommodations, activities, and food in Costa Rica were far less expensive than a similar tropical destination like Hawaii.

If you’re looking for anniversary trip ideas, I hope this article has helped. Or maybe it’s sparked an idea for a completely different destination. No matter where you decide to go, be sure to focus on the importance of your relationship and use the time to reconnect with the one you love.

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This Post Has 2 Comments

  1. Linda (LD Holland)

    We have an anniversary coming up and we planned a bit of a splurge few days away. So many of these U.S. destinations would not have worked this year. But keeping these as good future ideas. We are indeed visiting both Montreal and Quebec City on this trip so great to see them on your list. And yes, we plan to eat our way through both cities. Happy Anniversary!

  2. Laureen

    All excellent ideas and something for every taste and budget. Fun!

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