Planning a 50th Anniversary Trip on Points
How to turn fifty years of partnership into the trip of a lifetime — without spending a fortune in cash.
Fifty years.
That's 18,250 mornings. Some of them easy, waking up to coffee already brewing. Some of them hard, in ways that don't need describing here. Eighteen thousand days of choosing the same person, through the decades that changed everything and the ones that didn't seem to change at all.
A 50th anniversary deserves more than a nice dinner. It deserves a trip — the kind of trip you've been talking about since you were young enough to think fifty years was an impossibly long time.
And here's the part that might surprise you: if you've been accumulating credit card points, hotel loyalty rewards, and airline miles over the years — even without realizing it — you may already have enough to make that trip happen. Not on a budget. Not cutting corners. The real trip. The one you've been imagining.
Let me show you how.
Start with the conversation, not the spreadsheet
Before we talk about points and programs and booking strategies, let's talk about the trip itself. Because the most important question isn't "How many points do I have?" It's this:
Where have you always wanted to go together?
Maybe it's Italy. The two of you standing on a balcony in Positano, watching the sun drop behind the coastline. Maybe it's Paris — not the Paris of a three-day European tour, but a week in Paris, walking slowly, sitting in cafés, discovering neighborhoods that aren't in the guidebooks. Maybe it's something entirely different. A river cruise through Bordeaux. A safari in Kenya. A quiet cottage in the Cotswolds where you do nothing at all for ten days.
Sit down together. Talk about it. The destination matters less than the conversation — because this trip is about the two of you deciding, together, what this milestone means.
Once you know where you want to go, everything else is logistics. And logistics, as it turns out, is what credit card points are remarkably good at solving.
Take stock of what you have
Most couples who've been managing a household for decades have more points than they realize. Here's a quick way to find out.
Check your credit card points
Log into each credit card account — or download the card issuer's app — and look for your rewards balance.
The most common places points accumulate:
- Chase Ultimate Rewards (if you have a Chase Sapphire, Chase Freedom, or Chase Ink card)
- Amex Membership Rewards (if you have an American Express Gold, Platinum, or EveryDay card)
- Capital One Miles (if you have a Venture, Venture X, or Quicksilver card)
- Citi ThankYou Points (if you have a Citi Premier or Double Cash card)
Don't forget: check both of your cards. If one of you carries a Chase Sapphire and the other has a Capital One Venture, you have two separate points balances working for you.
Check your loyalty program accounts
Next, look at your airline and hotel loyalty accounts. Even if you haven't been strategically earning, you may have balances from past flights and hotel stays.
- Airline frequent flyer programs (Delta, United, American, Southwest, and others)
- Hotel loyalty programs (Marriott Bonvoy, Hilton Honors, World of Hyatt, IHG One Rewards)
Add it all up
Write down every balance. You may be looking at something like this:
| Program | Balance |
|---|---|
| Chase Ultimate Rewards (her card) | 82,000 points |
| Capital One Venture (his card) | 45,000 miles |
| Delta SkyMiles (his account) | 23,000 miles |
| Marriott Bonvoy (her account) | 38,000 points |
| Hilton Honors (his account) | 54,000 points |
| Total estimated value | ~$2,400 to $3,800 |
That's a real example of what a couple might find after years of routine spending. And depending on how you use those points, that value can stretch significantly further — especially for business-class flights and luxury hotel stays, where the cash prices are high but the points prices are often reasonable.
Three anniversary trip blueprints on points
Let me walk you through three specific trip scenarios — each designed for a 50th anniversary celebration, each achievable with points that a typical couple might accumulate over one to two years of strategic earning (or may already have).
Blueprint 1: A week in Italy — Rome, Florence, and the Amalfi Coast
The vision: Five to seven nights across Italy's most iconic cities. A few days in Rome exploring ancient history, a few days in Florence soaking in art and food, and a finale on the Amalfi Coast with nothing to do but watch the sea.
Getting there — business class on points:
This is the flight that changes everything. Business class from the US to Rome typically costs $4,000 to $8,000 per person in cash. On points, you can book the same flight for a fraction of that.
- Using Chase Ultimate Rewards transferred to United: 60,000 points per person for business class to Rome on certain partner airlines. For two: 120,000 points.
- Using Amex Membership Rewards transferred to ANA (All Nippon Airways): ANA books Star Alliance partners. 88,000 points per person for business class to Europe. For two: 176,000 points.
- Using Capital One Miles transferred to Air Canada Aeroplan: 70,000 miles per person for business class to Europe. For two: 140,000 miles.
Where to stay:
- Rome (3 nights): The InterContinental Rome Ambasciatori Palace or a Marriott property like the St. Regis Rome. Points costs range from 40,000 to 70,000 points per night depending on the property and season.
- Florence (2 nights): The St. Regis Florence (Marriott) or Hotel Indigo Florence (IHG). Points costs range from 35,000 to 60,000 per night.
- Amalfi Coast (2 nights): Cash booking may be more practical here, as points-bookable properties on the Amalfi Coast are limited. Budget $400 to $600 total for a beautiful coastal hotel — worth every dollar for the setting.
Approximate points needed:
- Flights: 120,000 to 176,000 points (depending on airline program)
- Hotels: 150,000 to 260,000 hotel points (depending on properties)
- Estimated cash outlay: $800 to $1,500 (taxes, fees, Amalfi hotel, meals, trains between cities)
What it would have cost in cash: $12,000 to $18,000 for two people, including business-class flights.
Blueprint 2: A river cruise through Southern France
The vision: Seven nights gliding through the vineyards and medieval villages of Provence and Bordeaux. Someone else drives the boat. Someone else cooks the meals. All you have to do is wake up in a new place each morning.
The reality of cruises on points: River cruises can't typically be booked directly with points — Viking, Avalon, AmaWaterways, and most river cruise operators don't participate in loyalty programs. However, points can cover significant portions of the trip.
How to use points for a river cruise:
- Pay for flights entirely on points. Business class to Paris or Lyon using the same strategies as Blueprint 1: 60,000 to 88,000 points per person.
- Use a credit card travel portal to apply points toward the cruise cost. Chase Ultimate Rewards, Capital One Miles, and Amex Membership Rewards all allow you to book travel (including cruises) through their travel portals, using points as payment.
- Through the Chase travel portal, 100,000 Ultimate Rewards points = $1,250 to $1,500 toward a cruise (depending on whether you hold the Sapphire Preferred or Reserve).
- Through Capital One, 100,000 miles = $1,000 toward travel purchases.
- Book pre- and post-cruise hotel nights on points. A night or two in Paris before the cruise and a night in Bordeaux after — booked with Marriott, Hilton, or Hyatt points — adds to the experience without adding to the cash cost.
Approximate points needed:
- Flights: 120,000 to 176,000 points
- Cruise offset: 100,000 to 200,000 credit card points through travel portals
- Hotel nights: 60,000 to 100,000 hotel points
- Estimated cash outlay: $3,000 to $5,000 (remaining cruise balance, excursions, incidentals)
What it would have cost entirely in cash: $15,000 to $22,000 for two people.
Blueprint 3: An African safari — the bucket list trip
The vision: A week in Kenya or Tanzania. Sunrise over the Serengeti. Elephants crossing a river. Sundowners on the savanna. The kind of trip that people describe as life-changing and mean it.
Using points for a safari:
Like river cruises, safari lodges typically don't participate directly in hotel loyalty programs. But the strategy is similar: use points for the components that do accept them, and let cash cover the rest.
- Business-class flights to Nairobi or Dar es Salaam. Using Amex Membership Rewards transferred to Ethiopian Airlines' program or ANA: approximately 75,000 to 90,000 points per person. For two: 150,000 to 180,000 points.
- Pre- and post-safari hotel nights in Nairobi or Cape Town. The Hyatt Regency Nairobi (15,000 Hyatt points per night) or the Hilton Nairobi (40,000 Hilton points per night) are excellent options. Two nights for two people: 30,000 to 80,000 points.
- Apply credit card points toward safari lodge costs through travel portals. A seven-night safari at a mid-range lodge in Tanzania runs $5,000 to $10,000 per person. Even 100,000 credit card points applied through a travel portal offsets $1,000 to $1,500 of that cost.
Approximate points needed:
- Flights: 150,000 to 180,000 points
- Hotels: 30,000 to 80,000 hotel points
- Safari offset: 100,000 to 200,000 credit card points
- Estimated cash outlay: $6,000 to $12,000 (remaining safari costs, internal flights, tips, incidentals)
What it would have cost entirely in cash: $18,000 to $30,000 for two people.
If you don't have enough points yet — how to get there
Looking at these blueprints, you might be thinking: "We're close, but not quite there." That's perfectly normal. Here are three realistic strategies for building up your points balance in the months before your anniversary trip.
1. Time a credit card sign-up bonus strategically
Credit card sign-up bonuses are the single fastest way to earn a large number of points. If your anniversary is eight to twelve months away, you have time to earn a sign-up bonus and plan your bookings.
Example: The Chase Sapphire Preferred regularly offers 60,000 to 80,000 Ultimate Rewards points after spending $4,000 in the first three months. If you're already spending $1,300 per month on groceries, gas, and regular expenses, you'll meet the threshold through normal life — no extra spending required.
Two cards between the two of you (one Chase, one Amex or Capital One) could yield 120,000 to 180,000 points total. That's enough for two business-class flights to Europe.
2. Consolidate your points
If you each have rewards cards, check whether your points can be combined. Chase allows household point transfers between Sapphire cardholders. Capital One allows transfers between household members. Amex Membership Rewards points can be pooled within the same account.
Combining your points into one larger balance opens up booking options that neither balance could achieve alone.
3. Put your everyday spending to work
For the months leading up to your trip, channel your regular spending through your highest-earning credit card. Groceries, gas, dining, insurance premiums, utilities that accept credit card payment — all of this earns points.
A couple spending $5,000 per month on a card that earns 2 points per dollar generates 10,000 points per month — 120,000 points over a year. That's meaningful, and it doesn't require spending a single dollar more than you normally would.
Making it special: The details that matter
A 50th anniversary trip is about more than flights and hotels. It's about the moments. Here are a few ways to use points and smart planning to add touches that make the trip truly memorable.
Book a room with a view — on points
When you're booking your hotel on points, don't automatically choose the cheapest room category. Check the points cost for a room with a balcony, a water view, or a higher floor. The difference in points is often modest — 5,000 to 15,000 additional points — but the difference in experience, for a trip like this, is everything.
Imagine waking up on your anniversary morning and stepping out to a balcony overlooking the Arno River in Florence. That's not a luxury. That's the whole point.
Use the hotel concierge to arrange something special
When you book at a higher-end property — an InterContinental, a St. Regis, a Kimpton, a Hyatt — you have access to a hotel concierge. Before your trip, email the hotel directly and mention that you're celebrating your 50th anniversary. Ask if they can arrange:
- A bottle of wine or champagne in the room upon arrival
- A restaurant reservation at a special venue
- A recommendation for a meaningful local experience (a private wine tasting, a sunset boat tour, a cooking class for two)
Hotels love hosting celebrations. Many will go out of their way to make the occasion special — sometimes at no additional cost.
Write a letter
This isn't a points strategy. It's a life strategy. But I'm including it because it matters.
Before the trip, write your partner a letter. Not a card — a letter. Tell them what the last fifty years have meant. Bring it with you. Read it to them over dinner in Rome, or on a balcony in Paris, or on the deck of a river cruise somewhere in Provence.
No points program in the world can give you that moment. But points can get you to the place where the moment happens.
A timeline for planning your 50th anniversary trip on points
| When | What to do |
|---|---|
| 12 months before | Have the conversation about where you want to go. Take inventory of your current points. Decide whether you need to earn more (and if so, consider a strategic credit card). |
| 10 months before | Start booking flights. Business-class award seats to popular destinations fill up far in advance, especially for dates around holidays or summer. The earlier you search, the better your options. |
| 8 months before | Book hotels. For points bookings at premium properties, availability can be limited. Lock in your dates and room type now. Most loyalty programs allow free cancellation up to 24 to 48 hours before check-in, so there's no risk in booking early. |
| 6 months before | Handle logistics. Ensure your passports are current (renewal takes 6 to 8 weeks, longer if expedited). Research visa requirements for your destination. Purchase travel insurance. |
| 3 months before | Plan the details. Restaurant reservations, special experiences, day trips. Email the hotel concierge to mention the celebration. |
| 1 month before | Confirm everything. Recheck your flight and hotel reservations. Download airline and hotel apps. Download offline maps and translation apps for your destination. |
| 1 week before | Pack. Breathe. You've planned this well. |
One more thing
Robert — one of our WanderWise members — sent me a photo a few months ago. He was sitting in a safari lodge in Kenya at dawn, coffee in hand, watching elephants cross a river. He was traveling solo, a few years after losing his wife. The note he sent with the photo said: "I can't believe I almost didn't do this."
I think about that note often. Not because it's sad — though it carries sadness. I think about it because of the word "almost." Almost didn't do it. Almost waited too long. Almost let the logistics win.
You have each other. You have the time. And — whether you know it yet or not — you probably have the points.
Don't almost.
The bottom line
A 50th anniversary trip on points isn't about being frugal. It's about being strategic with resources you've already accumulated — so that you can invest in what actually matters: the experience, the memories, and the person sitting next to you.
Business-class flights, beautiful hotels, once-in-a-lifetime destinations — all of it is more accessible than you think. The points are there. They've been accumulating quietly while you were busy living the fifty years that brought you here.
Now it's time to use them.
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