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As the days get shorter and colder, Miami makes a tempting escape, with warm weather, beach time, rooftop cocktails, and plenty to fit into a quick getaway. Our ideal 48 hours starts at the pool and moves on to a sushi happy hour, a beach day, the murals at Wynwood Walls, and a dressed-up night at Kiki on the River. We also share points-friendly hotel options, including a look at the former W South Beach, which is reopening as a Waldorf Astoria in 2027.

Just because you can put that poolside bar tab on points doesn't mean you should. Hilton is starting to let elite members use points for room service and other charges at checkout, and American Airlines is rolling out its own miles-and-cash bookings. Both are convenient, but you'll usually get more for your points by saving them for a regular award night or flight.

And for all the NYC Marathon runners, Delta is handing out free treats near baggage claim at JFK and LaGuardia on Oct. 29 and 30, then offering early boarding and a shout-out at the gate on Nov. 1 and 2.

Timeline

0:00 Start Here

0:19 How to Spend 48 Hours in Miami

2:28 When Paying With Points Isn't Worth It

3:45 Delta's NYC Marathon Perks

4:30 Sign-Off

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Advertiser Disclosure: Departure Digest may receive compensation through our partnership with advertisers when you click on links to offers on this page. Opinions expressed here are the author’s alone, not those of any bank, credit card issuer, airlines or hotel chain. Terms apply. The information is valid at the time of posting.

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Thanks to a new Amex Airbnb partnership, you can now book Airbnbs through Amex Travel and earn bonus points on those stays. And if you have The Platinum Card® from American Express or The Business Platinum Card® from American Express, your up-to-$600 annual hotel credit is now called the lodging credit and now covers eligible Airbnb Luxe homes, too. Those stays can also come with up to $250 for Airbnb Experiences. The bad news is that starting in 2027, you’ll need to book at least two nights to use the credit, so say goodbye to the one-night fancy hotel splurge.

In other Airbnb news, the company is cracking down on checkout chores. For bookings made on or after Nov. 20, hosts can’t make you strip the beds or take out the trash, which seems fair when you’re already paying a cleaning fee.

Meanwhile, Air China just launched a Copenhagen-to-Reykjavik flight. It sounds like a typo, but it’s a great example of a fifth freedom route. These flights can get you a much nicer seat on a shorter trip, and they can be cheaper, too. We explain what they are and how to book them.

Timeline

0:00 Start Here

0:17 Amex Travel Adds Airbnb Stays

1:45 Airbnb’s New Checkout Chore Rules

2:38 What Are Fifth Freedom Flights?

4:15 Sign-Off

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Advertiser Disclosure: Departure Digest may receive compensation through our partnership with advertisers when you click on links to offers on this page. Opinions expressed here are the author’s alone, not those of any bank, credit card issuer, airlines or hotel chain. Terms apply. The information is valid at the time of posting.

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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.

Timeline

0:00 Start Here

0:21 Planning a Second Honeymoon

2:37 Amex’s Cruise & Yacht Collection

3:04 Flying Blue’s Business Class Award Deal

4:28 Sign-Off

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Advertiser Disclosure: Departure Digest may receive compensation through our partnership with advertisers when you click on links to offers on this page. Opinions expressed here are the author’s alone, not those of any bank, credit card issuer, airlines or hotel chain. Terms apply. The information is valid at the time of posting.

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Business class comes with plenty of goodies, but not everything at your seat is yours to keep. The noise-canceling headphones and bedding stay on the plane, while amenity kits, toiletry gift sets, pajamas, and slippers can go home with you. A few airlines almost expect you to take something, from a decorative Qatar Airways pillow and Virgin Atlantic's cheeky airplane-shaped salt and pepper shakers to KLM's gin-filled ceramic Dutch houses.

For a souvenir with mouse ears, some Costco locations are selling a two-day Disneyland Park Hopper ticket with Lightning Lane Multi Pass and a $60 dining card for about $330. That could save roughly $170 compared with Disneyland's regular price. Sam's Club members can also get 10% off $300 Disney gift cards from Nov. 6 through 8.

And in case you missed it, the Plaza Hotel in New York closes in January 2027 for at least four years to restore its facade. That makes this holiday season the last one for Palm Court tea or Kevin McCallister's 16-scoop sundae until at least 2031.

Timeline

0:00 Start Here

0:21 What You Can Keep From Business Class

2:16 Costco and Sam's Club Disney Deals

3:54 The Plaza Hotel's Four-Year Closure

4:45 Sign-Off

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Advertiser Disclosure: Departure Digest may receive compensation through our partnership with advertisers when you click on links to offers on this page. Opinions expressed here are the author’s alone, not those of any bank, credit card issuer, airlines or hotel chain. Terms apply. The information is valid at the time of posting.

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Southwest is overhauling Rapid Rewards in January 2027, and the Companion Pass takes the biggest hit. Credit card welcome bonuses will no longer count toward it, and the full pass will only come with Southwest's new top status. Occasional flyers can pick up smaller rewards, like bonus points or preferred seats, on the way there. The airline also shared an early look at its upcoming Southwest Icon Lounges, which start opening in late 2027.

Already booked a flight? The price you paid might not be final. If your fare drops after you book, you can often claim the difference as an airline credit, as long as it isn't basic economy. The hard part is noticing. That's where Junova comes in. It tracks eligible flights booked directly with major U.S. airlines and handles getting the savings back for a 20% fee.

For a bigger splurge, Delta is giving Delta One, its long-haul business class, a makeover this fall, starting on flights from Los Angeles. Expect a wagyu burger, sorbet paired with Champagne Taittinger, Blanton's bourbon, and new Missoni amenity kits.

👉 Get $25 in Junova credits with code DD: https://www.junova.ai/?ref=DD

Timeline

0:00 Start Here

0:17 Getting Money Back When Your Fare Drops

2:15 Delta One's Onboard Makeover

3:07 Southwest's Rapid Rewards Overhaul

4:43 Sign-Off

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Advertiser Disclosure: Departure Digest may receive compensation through our partnership with advertisers when you click on links to offers on this page. Opinions expressed here are the author’s alone, not those of any bank, credit card issuer, airlines or hotel chain. Terms apply. The information is valid at the time of posting.

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An airline may no longer owe you a hotel if a last-minute mechanical problem leaves you stuck overnight. Starting Oct. 19, the Department of Transportation won’t count certain repairs, onboard medical emergencies, and a few other disruptions as the airline’s fault, which is what triggers meal vouchers and hotel stays. Refund rights aren’t changing, and trip delay coverage on many travel cards can reimburse meals and a hotel, whatever reason the airline gives.

If a foldable phone is on your wish list, the iPhone Duo opened for preorders on Oct. 16. It starts at about $2,000 and folds down to roughly the size of a passport. It’s eSIM-only, and at that price, card phone protection is only a partial safety net.

Marriott is leaning into marathon season with race packages at a handful of hotels. At the JW Marriott Essex House New York, that means pasta specials before the New York City Marathon on Nov. 1, a free drink when you show your medal, and some rooms overlooking the finish line. Plus, JetBlue’s new first class is now on sale for flights starting in December, with fares from $249 one-way between LaGuardia and Fort Lauderdale if you book by Oct. 16.

👉 Top cards for trip delay protection: https://go.departuredigest.com/delayperks

Timeline

0:00 Start Here

0:20 The DOT’s New Flight Delay Rules

1:56 Apple’s Foldable iPhone Duo

3:33 Marriott’s Marathon Perks

4:30 JetBlue’s New First Class Now on Sale

4:48 Sign-Off

———

Advertiser Disclosure: Departure Digest may receive compensation through our partnership with advertisers when you click on links to offers on this page. Opinions expressed here are the author’s alone, not those of any bank, credit card issuer, airlines or hotel chain. Terms apply. The information is valid at the time of posting.

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Flying business class for the first time? Before you head to the airport, check your baggage allowance and whether your ticket gets you into a lounge. Once you're onboard, there are a few things worth knowing, too. That pre-departure glass of champagne isn't a given, and the rules around the call button can depend on which airline you're flying. If you're offered pajamas, go ahead and change. Just leave your bare feet out of the lavatory.

On the hotel side, Marriott Bonvoy is testing a new upgrade list in its app, giving some members a look at their spot in line and how many upgraded rooms might be available. It’s only at a small number of hotels for now, but Marriott says it’ll expand to more than 250 hotels in the U.S. and Canada by November. We like the transparency, but the app won’t tell you what room you’re actually in line for.

Plus, Margaritaville at Sea is selling an all-you-can-cruise pass for two adults starting at around $2,500, good for unlimited sailings through Dec. 31, 2027. It could be a great deal if you plan to cruise often, but there are some restrictions, and taxes, fees, and gratuities still apply.

Timeline

0:00 Start Here

0:21 How to Fly Business Class for the First Time

2:03 Marriott's Airline-Style Upgrade List

3:14 Margaritaville at Sea's Unlimited Cruise Pass

4:44 Sign-Off

———

Advertiser Disclosure: Departure Digest may receive compensation through our partnership with advertisers when you click on links to offers on this page. Opinions expressed here are the author’s alone, not those of any bank, credit card issuer, airlines or hotel chain. Terms apply. The information is valid at the time of posting.

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Flights from New York to Madrid for $300 round trip, with a checked bag included? Deals like this have become rare, but Thrifty Traveler Premium's cash and points alerts can help you find them. Premium costs about $130 a year, and one or two good deals could cover it if you're flexible about where you go.

Meanwhile, Amex dropped big news for its Centurion Lounge network. Newark's lounge opening has been pushed to 2027, but the delay comes with an upgrade. It'll now be more than 30,000 square feet, making it the largest Centurion Lounge yet, complete with a gelato terrace that might even make flying out of Newark worth it. London Heathrow is also getting a second location, and Houston's lounge is nearly tripling in size. Before any of that opens, though, Philadelphia's lounge closes this week for renovations and isn't expected to reopen until the end of 2027.

Even more surprising, Southwest could be eyeing Dreamliners, wide-body jets built for long-haul routes. It'd be another big shift for an airline that only recently added assigned seats and stopped letting bags fly free. We'll believe a Southwest flight to Rome when we're boarding it. And if you'd rather spend New Year's Eve in flip-flops than snow boots, Andrea Bocelli and Ludacris are both headlining in the Bahamas.

👉 Get $20 off your first year of Thrifty Traveler Premium with code DEPARTUREDIGEST: https://thriftytraveler.com/a/departuredigest

Timeline

0:00 Start Here

0:17 A $300 Round Trip to Madrid

0:51 How Thrifty Traveler Premium Works

2:14 Amex's Biggest Centurion Lounge Expansion

3:16 Southwest Eyes Long-Haul Routes

4:00 New Year's Eve in the Bahamas

4:33 Sign-Off

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Advertiser Disclosure: Departure Digest may receive compensation through our partnership with advertisers when you click on links to offers on this page. Opinions expressed here are the author’s alone, not those of any bank, credit card issuer, airlines or hotel chain. Terms apply. The information is valid at the time of posting.

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