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Think of a second honeymoon as a do-over, your chance to book the trip you couldn’t afford after the wedding. If an overwater villa has been living on your Pinterest board, now could be the time. Hilton, Marriott, Hyatt, and IHG have resorts with overwater rooms you can book with points. The Caribbean even has a few overwater bungalows of its own. Familymoons are catching on, too, with resorts that once catered to couples adding perks for kids and grandparents.
Celebrating at sea instead? Amex’s Cruise & Yacht Collection is now live. Eligible Amex Platinum cardholders can get $100 to $300 in onboard credit on sailings of five nights or more booked through Amex Travel.
If you’d rather do Europe, Paris might not be on your list right now, but it could be next year. Air France-KLM Flying Blue released cheap business class award seats there from cities like New York, Chicago, and San Francisco, starting at 60,000 miles one way with dates through August 2027. Through Oct. 31, transfer bonuses from Amex and Rove make it even cheaper, at 48,000 Amex points or about 43,000 Rove Miles.
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🔔 Your flight got cheaper. Now what?
Ever stared at the same flight for days, wondering if you should book now or wait for a better price? You don’t have to time it perfectly. Since most major airlines no longer charge change fees, a price drop after you book can mean getting the difference back as an airline credit. The catch is you usually have to notice the drop and ask for it yourself.
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There’s no upfront cost, and if the price never drops, you don’t pay anything. When Junova does save you money, it charges 20% of the savings. For example, if a $500 flight drops to $350, you’d get a $150 airline credit and pay Junova a $30 fee. Fully refundable fares get a refund instead. Basic Economy fares and award tickets aren’t eligible.
If you want to try it, Departure Digest listeners get $25 in Junova credits with code DD.
✈️ Essential intel
Beginner’s guide
New to the points game? We break down how to earn miles and book flights and hotels for less so you can travel better without a trust fund. It’s the no-BS starter guide you’ll wish you had sooner.
What are destination dupes?
Destination dupes can mean lower prices, fewer crowds, and easier trips. Find alternatives to the Maldives, Mykonos, Aspen, Napa, and more.
🧳 Build your airport fit
💡 Runway tip
Award tickets don’t have to be all points. Paying cash one way and using points the other can sometimes be the better deal.
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📝 Transcript
Most honeymoons get planned right after the most expensive party of your life. So instead of booking the trip you really want, you book what you can afford. Lucky for you, there’s a do-over.
You’re listening to Departure Digest. Today, it’s second honeymoons, Amex’s new cruise program, and a business class points deal to Europe.
Planning a second honeymoon
Let’s start with that second honeymoon.
Think a big anniversary, a vow renewal, or just the trip you never took. The first time around, you were exhausted, broke, and still writing thank-you notes on the plane. And let’s be real, you weren’t listening to Departure Digest yet, so you probably weren’t being very smart with your points. This time, you’ve got more of them, and maybe a fancier credit card or two.
You also know each other a lot better now, like which one of you wants to snorkel and which one prefers to nap, so you can plan a trip for the couple you are today.
If you want to go all out, book the overwater villa from your Pinterest board. Let’s take the Waldorf Astoria Maldives, for example. It’s the holy grail of Hilton redemptions. Cash rates can top $3,000 a night. But you can also book a room there for 250,000 Hilton Honors points, or even better, with a free night certificate from a Hilton credit card. And it’s not just Hilton. Marriott, Hyatt, and IHG all have resorts with overwater rooms you can book with points. You’ll just want to budget for the boat or seaplane transfer and the food, which is priced like you’re stuck on a deserted island, because, well, you basically are. My rule of thumb is to use points for the flights and the room, and save your cash for the one splurge you’ll talk about for years, like a private dinner on the beach.
Then there’s the question of who’s coming. Some couples are returning to their honeymoon spots with the kids, and sometimes the grandparents. Call it a familymoon, which is sweet, right up until a toddler cannonballs into your private plunge pool. And resorts have caught on. Plenty of places that used to be all about couples are now adding things for little kids, teens, and grandparents. Even the Waldorf in the Maldives has a kids’ club and a waterpark.
If your points balance is smaller, you don’t have to go halfway around the world to make it special. The Caribbean is a great place to start, especially at an all-inclusive, or better yet, an adults-only one. And yes, there are overwater bungalows there too. We rounded up a few gems in our destination dupes guide, which we’ll link below.
Wherever you end up, don’t be shy about telling the hotel it’s your anniversary when you book. You could get champagne, a room upgrade, or other fun surprises.
Amex’s Cruise & Yacht Collection
And if you’d rather celebrate at sea, Amex’s new Cruise & Yacht Collection is now live. It covers a long list of cruise and yacht brands, including the Ritz-Carlton Yacht Collection and Virgin Voyages.
If you have an Amex Platinum card, you can get $100 to $300 in onboard credit, plus a special amenity, on eligible sailings of five nights or more.
The catch is you have to book through Amex Travel to get the perks.
Flying Blue’s business class award deal
Okay, and before I let you go, I’ve got a flight deal, because not every honeymoon happens on a beach.
I know Paris isn’t exactly at the top of anyone’s travel list right now, but hear me out, because you can book this for a trip a few months from now.
Air France and KLM’s Flying Blue program released some cheap business class award seats to Paris from major cities like New York, Chicago, and San Francisco, for flights through August 2027. They start at 60,000 miles one way, plus about $350 in taxes and fees.
It gets better, though. Flying Blue partners with most of the big points programs, so you can usually move your points over at a 1:1 ratio. But through Oct. 31, Amex and Rove are both running transfer bonuses.
Amex is giving you a 25% bonus, so that 60,000-mile seat costs just 48,000 Amex points. Rove’s bonus is even bigger, at 40%, which brings it down to about 43,000 Rove Miles.
To book, log in to Flying Blue, select Book with miles, and enter your departure city and Paris. Leave the date blank and hit search, and you’ll see the price for each day.
Transfers can’t be reversed, so check availability first. Then head to the rewards page in your Amex or Rove account, choose transfer points, and pick Flying Blue. Voilà!
And that’s a wrap for this week. If you’ve got points sitting around, maybe this is your sign to book the honeymoon you wanted the first time. Have a great weekend.
Departure Digest is the voice memo from your savviest travel friend. We track travel news and points math so you never make an expensive mistake.
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