Affiliate Disclosure: The Rewards Mom may receive a commission from card issuers. Opinions, reviews, analyses & recommendations are the author’s alone, and have not been reviewed, endorsed or approved by any of these entities. All points values are estimates based on the time of this writing.

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Someone once told me they celebrate their anniversary more than any other occasion. Every year you don’t get divorced, you’re beating the odds.

Everyone gets a birthday every year. But staying married and continuing to choose each other year after year? THAT is something worth celebrating.

The problem is finding room in the budget. As your kids get older, life gets more expensive, and time with your spouse can easily fall to the bottom of the list. When the budget is limited, the anniversary trip is often the first thing cut so you can still take the kids somewhere.

I love points because they make it possible to prioritize time away together without giving up the family trip.

Here are some of our favorite destinations we’ve visited on couples trips using points, along with a few more on our bucket list. If you want to learn more about how points work, follow the links in the below section. It will give you a great start.

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New to Points? Start Here

The short version: cashback is simple, but transferable points are what unlock trips like these. Cards from Chase, Amex, Capital One, Citi, and Bilt earn points that transfer straight to hotel programs, usually at 1:1. So the points you’re earning on groceries turn into an overwater villa in Bora Bora.

The trick is knowing which bank transfers to which chain. Grab my free transfer partner cheat sheet. It tells you who all the banks transfer to on one page.

One pro move beginners miss: banks run transfer bonuses of 20-40% throughout the year. These transfer bonuses can easily turn 100,000 points into 140,000. Learn how transfer bonuses work before you transfer anything.

Starting from zero? Here’s the full beginner’s guide. Otherwise, just note the loyalty program under each property below.

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Couples Trips We Have Taken and Loved

I couldn’t rank these places if I tried because they’re all so different, and we loved each one for completely different reasons. We love exploring somewhere new, so we’re not the kind of couple who returns to the same anniversary destination every year. These are all places we’ve stayed as a couple, loved, and were able to book with points. They’re listed in no particular order, along with what made each one worth the trip.

Before we get into the list, remember that hotel cash prices and points rates can change dramatically based on your dates. The ranges below are meant to give you an idea of what is possible, not promise an exact price. Always search your dates before transferring any points.

1. Alila Ventana Big Sur

Alila Ventana Big Sur Alila Ventana Big Sur feels completely removed from real life, even though it is still an easy trip within the United States. The redwoods, ocean views and winding drive along the California coast make the trip feel romantic before you even arrive. It is considered a wellness resort, so the included meals are healthy, but they are also high-quality and delicious, with menus created by a Michelin-starred chef. The resort also has unique experiences you do not find everywhere, including Japanese baths, which are clothing optional, and an infinity hot tub overlooking the redwoods. Because the meals and many resort activities were included, we could check in, slow down and enjoy being together without watching the cost of every meal pile up. We stayed for two nights, and it felt like the perfect amount of time.

What it can cost: Cash rates are often around $1,800 to $4,000+ per night. As a Category 8 Hyatt property, standard rooms now range from approximately 35,000 to 75,000 points per night, depending on the date. A standard Hyatt free-night certificate generally will not cover this property.

What we paid: The cash rate for our dates was $3,450 per night, or $7,863 total. Instead, we paid 45k points per night (90k Hyatt points) and $0. We were there at the end of July.

2. JW Marriott Venice Resort & Spa

JW Marriott Venice Resort & Spa gives you two completely different versions of Venice in one trip. You can spend the day exploring the busy streets and canals, then take the complimentary boat back to a quiet private island with gardens, pools and room to breathe. We loved being close enough to enjoy Venice while having somewhere peaceful to come back to at the end of the day.

The resort grows vegetables and herbs in its own garden, produces extra-virgin olive oil from the island’s olive trees and has a gourmet restaurant led by a Michelin-starred chef. It felt romantic and secluded enough for a couples trip, but it also had so much space and so many family-friendly activities that we immediately wanted to return with our kids. There are pickle ball courts, a family pool, large grassy areas and even outdoor movie nights on a giant screen. We loved it as a quiet escape for the two of us, but it is one of the few couples-trip hotels we visited and left thinking our kids would love it just as much.

What it can cost: Cash rates often fall around $600 to $1,200+ per night in season. Marriott uses dynamic pricing, but award nights commonly land around 70,000 to 110,000 points. A Marriott free-night certificate may work when the nightly price is within the certificate’s value after adding up to 25,000 points. Whenever I book a Marriott hotel, I try to use free-night certificates or wait for a transfer bonus. Marriott often charges a high number of points per night, so transferring flexible points at the regular rate does not always give me the best value. A transfer bonus gives me more Marriott points for the same number of flexible points, which helps the redemption stretch further.

What we paid: The cash rate for our dates was ~$1,200 per night. Instead, we paid 85,000 points for one night post cruise around Italys boot. We were there the beginning of September.

3. The St. Regis Rome

The St. Regis Rome gave us that classic, over-the-top European hotel experience that felt perfect for an anniversary trip. It opened in 1894 under César Ritz and has hosted everyone from royalty and heads of state to celebrities and diplomats. There is so much history throughout the hotel, including the original elevator, huge Murano glass chandeliers, the grand staircase and the Ritz Ballroom. It has been beautifully updated, but it still feels like you are staying somewhere that has been part of Rome for more than 130 years- because it has!

The location also made it easy to explore Rome during the day and come back to a hotel that still felt like part of the trip. One of my top five travel experiences ever was sitting in that lobby eating a caprese salad prepared tableside while an incredible pianist played and sang “Volare.” I know that sounds like such a small thing compared to everything there is to see in Rome, but it was one of those moments I will never forget. The entire hotel felt special, but that evening in the lobby is what made the stay truly unforgettable for me.

What it can cost: Cash rates are often around $1,000 to $2,000+ per night. Marriott award prices are dynamic, with recent rates commonly around 100,000 to 140,000 points per night. An 85,000-point Marriott certificate could work on a lower-priced night after adding up to 25,000 points, but many dates will still be too expensive.

What we paid: The cash rate for our dates was $1,115 per night ($2,230). Instead, we paid 75,000 points per night (150,00 points) for 2 nights pre Italian cruise. See notes above about Marriott points tips. We were there the end of August.

4. The Ritz-Carlton O‘ahu, Turtle Bay

The Ritz-Carlton O‘ahu, Turtle Bay gives you a completely different O‘ahu experience from staying in Waikiki. We stayed there before it became a Ritz-Carlton, so the fact that you can now book it with Marriott points makes it even more appealing. We loved being on the quieter North Shore, where the trip felt centered around the ocean, sunsets and being outside instead of shopping and city crowds. There is plenty to do around the resort, but it is also the kind of place where sitting by the water for a few hours feels like a perfectly good plan. The food was excellent too.We spent zero time near Waikiki on that trip, and it still solidified O‘ahu as our favorite Hawaiian island. We explored some of the resort areas near Aulani and could not believe how crowded they felt, with so many hotels packed together. Turtle Bay felt completely different. In our opinion, this is THE place to stay if you are going to O‘ahu. I would happily come back every year, and I cannot wait to experience it again now that it is a Ritz-Carlton.

What it can cost: Cash rates are often around $800 to $1,500+ per night. Recent Marriott award availability has started around 102,000 points per night, with busier nights pricing higher. An 85,000-point Marriott certificate could cover a lower-priced night after adding up to 25,000 points.

What we paid: $700 cash in 2020, but helped supplement with Capital One points at the time. Now, we would use Marriott points.

5. The Ritz-Carlton, Half Moon Bay

photo from Marriott- we stayed here pre blogger so I didn’t have any photos of the hotel

The Ritz-Carlton, Half Moon Bay is one of our favorite examples of a trip that does not require flying across the world to feel special. The hotel sits right on the cliffs overlooking the Pacific, with coastal walking trails, firepits and sunsets that make the entire stay feel romantic. It is close to San Francisco, but it feels much more like a quiet coastal escape than a city trip.

What it can cost: Cash rates are commonly around $900 to $1,500+ per night, especially on weekends. Marriott award rates are dynamic, but recent availability has started around 100,000 points, with a recent median near 103,000 points. An 85,000-point Marriott certificate may work on a lower-priced night when combined with up to 25,000 points.

What we paid: The cash rate for our dates was $1,200 per night ($2,400). Instead, we paid 85,000 points per night (170,00 points). See notes under JW Marriott Venice for Marriott points tips. We were there the beginning of August.

6. Hyatt Carmel Highlands

Hyatt Carmel Highlands is all about the location and view. It sits above the coastline near Point Lobos, with easy access to Carmel-by-the-Sea and some of the most beautiful stretches of Highway 1. We loved having a fireplace and ocean view to come back to after exploring the coast. We stayed here pre Alila Ventana Big Sur so we could squeeze every moment we could out of that stay.

One of the coolest things about this hotel is that it opened in 1917, before Highway 1 even existed. This part of the coast was much harder to reach back then- we’re talking horse and buggy. It still does have the historic feel, but it has been renovated, so our room was nice and clean- but you can only do so much to a hotel that was built in 1917. You are really staying here for the views, though. Because it was built so long ago, the hotel sits in a location that would be extremely difficult to recreate under today’s California coastal development rules. It is right on the cliffs with these wide-open views of the Pacific that you are not going to find at a newer hotel, and the grounds are immaculate. We thought it was completely worth it. The entire coastline was so pretty, and the view was what made the stay feel special.

What it can cost: Cash rates are often around $500 to $900+ per night. It is currently a Category 6 Hyatt property, so a standard room ranges from 20,000 to 40,000 points per night under Hyatt’s current award chart. A Category 1-7 Hyatt free-night certificate can cover an eligible standard room when one is available.

What we paid: The cash rate for our dates was $732 for one night. Instead, we paid 29k Hyatt points and $0.

7. Bellagio Las Vegas

Photo from MGM resorts

Bellagio is one of those hotels where the location becomes part of the trip. We loved being right in the middle of the Strip, watching the fountains and having restaurants and shows within walking distance. Las Vegas is also one of the easiest couples trips to make as short or as elaborate as you want. You can fly in for two nights, eat well, see a show and be home before it becomes a major vacation. Most people don’t realize you can book this with Marriott points.

What it can cost: Cash rooms commonly run around $250 to $600+ per night, while event weekends can be much higher. Marriott award pricing is dynamic, with a recent median near 56,000 points per night and a broad range of roughly 30,000 to 100,000+ points. Remember that the nightly resort fee, currently around $60 with tax, may still be charged on an award stay. A Marriott certificate may work when the award rate falls within its value plus the permitted top-off.

What we paid: The cash rate for our dates was around $400. We use a free night certificate instead.

8. Mauna Kea Beach Hotel, Autograph Collection

Mauna Kea Beach Hotel, Autograph Collection is the Big Island hotel I remember most for the beach. It sits on crescent-shaped Kauna‘oa Bay, and while beaches in Hawaii are public, the beach in front of the hotel felt wonderfully private when we were there. The water, soft sand and uncrowded setting were the entire reason the stay felt so special. Guests still rave about the beach, along with snorkeling right off the shore and watching manta rays feed under the resort’s lights at night. The hotel was originally created by Laurance Rockefeller in 1965, and it has always had a quieter, more timeless feeling than the enormous resorts nearby. It also just completed the largest renovation in its history, with every room and suite reimagined, new pools, updated restaurants and expanded family and wellness spaces. We loved it as a couple, but with the renovated family pool, kids’ club and easy beach days, I would absolutely bring our kids back too.

What it can cost: After the renovation, cash rates often start around $1,100 to $1,300 per night and can climb above $2,000. Marriott prices awards dynamically, and current award nights start around 97,000 points, with recent pricing centered close to that amount and higher dates reaching well above 100,000 points. An 85,000-point Marriott free-night certificate may cover a lower-priced night after adding up to 25,000 points. The hotel now charges a nightly resort fee, including on points stays, so include that in your comparison.

What we paid: [ADD YOUR POINTS, CASH AND DATES]

9. Hilton Waikoloa Village

Hilton Waikoloa Village might be the largest resort we’ve been to. It covers 62 oceanfront acres, with a saltwater lagoon where guests regularly spot turtles and tropical fish, multiple pools, a waterslide, boats and a monorail that carries guests between the lobby and room towers. We thought the property itself was incredible, even though we did not love the food. In my opinion, the grounds, lagoon and family activities are the reason to stay (but we didn’t have our kids with us) while the size of the resort, slow transportation and expensive onsite dining can be frustrating. If we came back with our kids- we would plan more meals at Kings’ Shops or Queens’ Marketplace and let the kids spend their time snorkeling in the lagoon and going down the waterslide. It feels almost like Disney built a resort in Hawaii, but it was never a Disney property.

What it can cost: Cash rates commonly fall around $300 to $700+ per night, before the resort charge and parking. Standard Room Rewards are usually priced around 100,000 Hilton points per night, while premium-room rewards can be much higher. A Hilton Free Night Reward can cover one night when a Standard Room Reward is available. Learn how Hilton points and free-night rewards work here.

What we paid: Cash price was $525 for our date. We paid 50,000 Hilton points.

10. A Mediterranean Cruise Through Italy or Greece

Cruising has become one of our favorite ways to see Europe as a couple because we can visit several places without packing up and changing hotels every few days. We cruised through Italy, and Greece is next for us. In both cases, we booked within 90 days of departure and found a significantly lower prices. Points give us the flexibility to take advantage of those last-minute prices because we can use them to find affordable flights and cover the expensive hotel nights before and after the cruise. Most cruise lines will also let you hold a reservation for 24 hours, which gives you time to make sure you can find reasonable flights before committing. The tradeoff is that you are choosing from the cabins that are left, so you may not get your preferred room or location. The cruise fare itself is not always the highest-value use of points, but points can still take a huge bite out of the total cost of the trip.

What it can cost: Mediterranean cruise prices vary widely, but a seven-night sailing can easily run $2,000 to $6,000+ per couple before flights, excursions, gratuities and onboard extras. Cruise lines do not have a traditional hotel-style award chart. Depending on the rewards you have, you may be able to book through a travel portal or redeem flexible travel rewards against an eligible cruise charge. Read more about using points for a cruise HERE

What we paid: Inside cabins for both were $1200 for 10+ nights. In both cases, we asked for upgrades when got onboard. When available, you can get better rooms for huge discounts.

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Couples Trips Still on Our List

11. Conrad Bora Bora Nui

Image credit: Hilton

Conrad Bora Bora Nui is one of the most popular aspirational Hilton redemptions for a reason. The water, mountain views and overwater villas look incredible, and it feels like the definition of an anniversary trip. I am torn on making this a couples trip, though, because the snorkeling and marine life are exactly the kind of things I would love for our kids to experience too. Bora Bora may end up being romantic, a family trip or somehow both.

What it can cost: Cash rates frequently run $1,000 to $2,000+ per night. Standard Room Rewards are often around 120,000 to 130,000 Hilton points per night, while premium-room prices can jump to more than one million points. A Hilton Free Night Reward can cover one night when a Standard Room Reward is available, regardless of the property’s points price. Learn how Hilton points and free-night rewards work here.

12. Conrad Maldives Rangali Island

Image credit: Hilton.com

Conrad Maldives Rangali Island is on our list because it combines the overwater-villa experience with incredible snorkeling, two islands and an underwater restaurant. Like Bora Bora, this is another trip I could easily imagine taking with or without our kids. The room may be covered with points, but the seaplane transfer, food and activities can still make the Maldives expensive, so this is one where I would plan the entire budget before booking the award stay.

What it can cost: Cash rates often range from $1,000 to $2,500+ per night. Standard awards are often around 130,000 Hilton points, while premium rewards can be far higher. Hilton Free Night Rewards may be used when a Standard Room Reward is available. Transfers to the island are a separate cash expense. Start with my complete Hilton guide here.

13. JW Marriott Masai Mara Lodge

Image credit: Marriott.com

JW Marriott Masai Mara Lodge may be the most expensive points property on this list, but an African safari is one of our biggest travel goals. The rate includes meals, select drinks and game drives, which matters when you compare it with other luxury safari lodges. I love that this would not just be a beautiful hotel stay. The wildlife and daily game drives would be the entire reason for the trip.

What it can cost: Cash rates often run $3,000 to $5,000+ per night for two people. Recent Marriott award pricing has commonly been around 200,000 to 236,000 points per night, with a recent median near 212,000 points. Marriott free-night certificates are not a realistic option at these rates, but points could still offset a trip that would otherwise cost tens of thousands of dollars.

14. Waldorf Astoria Los Cabos Pedregal

Image credit: Hilton.com

Waldorf Astoria Los Cabos Pedregal is high on our list because it feels secluded without requiring an enormous international trip. Every room has a private plunge pool and an ocean view, and the resort is close enough to downtown Cabo that we would not feel trapped at the hotel. This seems like the perfect option when we want a warm, romantic trip but only have a few days.

What it can cost: Cash rates are often around $1,000 to $2,000+ per night. Standard Room Rewards commonly price around 140,000 Hilton points per night, while premium rewards can cost several times more. A Hilton Free Night Reward can be especially valuable when a Standard Room Reward is available. Learn more about booking Hilton hotels with free-night rewards here.

15. Park Hyatt Paris-Vendôme

Image credit: France.fr

Park Hyatt Paris-Vendôme is the kind of hotel I would choose when the destination matters just as much as the room. It is close to the Louvre, the Tuileries Garden and some of the most walkable parts of Paris, so we could spend our days exploring and still come back to a hotel that feels like part of the anniversary trip. Paris is expensive, which is exactly why using points for a central luxury hotel can make such a difference.

What it can cost: Cash rates often run $900 to $2,000+ per night, with an annual average around $1,300. As a Category 8 Hyatt property, standard rooms currently range from 35,000 to 75,000 points per night. Standard Hyatt free-night certificates generally will not cover Category 8 properties.

16. Alila Napa Valley

Photo credit: Hyatt.com

Alila Napa Valley is an adults-focused resort in St. Helena with vineyard views, fireplaces and easy access to Napa Valley wineries and restaurants. I like that it would feel like a real getaway without requiring a long flight or a week away from the kids. This would be an easy long-weekend anniversary trip built around good food, a spa treatment and doing absolutely nothing on a strict schedule.

What it can cost: Cash rates generally start around $850 and can climb above $1,500 per night. It is a Category 8 Hyatt property, so standard rooms range from 35,000 to 75,000 points per night under the current chart. Standard Hyatt certificates will not usually cover it.

17. Park Hyatt Sydney

Photo credit: Hyatt.com

Park Hyatt Sydney has one of those locations that makes the hotel feel inseparable from the destination. It sits between the Sydney Opera House and Harbour Bridge, so even an ordinary morning at the hotel would come with one of the most recognizable views in the world. Australia and New Zealand are both are our list, but another one we might want to take our family with us to.

What it can cost: Cash rates are often around $900 to $1,500+ per night. It is currently a Category 7 Hyatt property, with standard rooms ranging from 25,000 to 55,000 points per night. A Category 1-7 Hyatt free-night certificate can cover an eligible standard room when availability exists.

18. Zemi Beach House, Anguilla

Photo credit: Hilton.com

Zemi Beach House is on our list for the beach alone. It sits on Shoal Bay, which is known for clear water and soft white sand, but the resort is small enough to feel quieter and more personal than a giant Caribbean complex. This looks like the kind of trip where we would swim, eat, read and finally stop checking the time.

What it can cost: Cash rates often exceed $1,000 per night and can climb toward $1,800 or more in high season. Standard Room Rewards have recently ranged around 110,000 to 140,000 Hilton points per night. A Hilton Free Night Reward can cover the night when standard reward space is available. This is another reason Hilton free-night rewards can be so valuable.

19. Impression Moxché by Secrets

Photo credit: Hyatt.com

Impression Moxché by Secrets is adults-only and all-inclusive, which makes it perfect for the kind of couples trip where the goal is to make almost no decisions after checking in. The suites, rooftop pools and included restaurants make it feel more elevated than a typical all-inclusive. We usually love exploring, but every once in a while, a trip where food, drinks and activities are already handled sounds pretty great.

What it can cost: Cash rates for two people are often around $1,000 to $1,500+ per night. It is a Category F Hyatt all-inclusive, so the current five-tier award chart ranges from approximately 45,000 to 85,000 points per night for two guests. Check your dates before transferring points.

20. Miraval Arizona Resort & Spa

Photo credit: Miraval resort and spa

Miraval Arizona would be a completely different kind of anniversary trip. It is adults-only, mostly device-free and built around wellness experiences, classes, outdoor activities and time to slow down. Meals, many activities and a nightly resort credit are included, so the points rate covers much more than a room. I could see us loving the chance to try something new together while being forced to disconnect from normal life for a few days.

What it can cost: Cash packages for two people can range from approximately $1,500 to $3,000+ per night, depending on the dates and package. Miraval uses its own Hyatt award chart, and pricing for two guests is higher than the single-occupancy rate. Under the current five-tier structure, expect roughly 52,500 to 112,500 points per night for two people. Most Hyatt free-night certificates cannot be used for Miraval stays.

A Quick Note About Free-Night Certificates

Just because I’ve mentioned these a few times above- free-night certificates can be one of the easiest ways to book an expensive anniversary hotel, but they do not all work the same way. Hilton Free Night Rewards can be used at many high-end properties when a Standard Room Reward is available, without a published points cap. Marriott certificates have a set points value, and you can currently add up to 25,000 points, so the nightly award price still matters. Hyatt certificates are tied to hotel categories, which means you need to confirm that the property falls within the certificate’s category limit.

If you want to use free-night certificates for one of these trips, start with my how to maximize free night certificates and my Guide to Hilton Honors. They explain how to earn them, how to search for eligible rooms and what to check before you make the rest of your travel plans.

Final Thoughts

I do not think an anniversary trip has to be a once-in-a-lifetime vacation every year. Sometimes it is a few nights in Las Vegas or along the California coast. Other years, it might be the trip to Bora Bora, Greece or Africa that you have talked about forever. The point is making room for time together, and points can make that possible without automatically giving up the family trip. Once you learn how to earn the points, the hardest part can be finding a babysitter!

If you don’t know how to earn this many points- make sure to start with my Beginner’s Guide to Points and Miles.