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Off Peak

Off Peak, no. 2: the Christmas market sweet spot is two weeks long and almost nobody books it

Weekdays between December 1 and 15 get you fully open markets, 20 to 40 percent lower hotel prices, and none of the crush. The window closes hard on the 20th. Confirmed 2026 dates inside.

Sep 17, 2026 · 4 min read
Five states where declining the rental counter's coverage can leave you uninsured
Terms & Departures

Five states where declining the rental counter's coverage can leave you uninsured

The standard advice is to decline everything because your credit card covers it. That advice is right about damage and wrong about liability, and in five states the gap is real.

Sep 14, 2026 · 3 min read
Tulum re-check: we promised to revisit this. The verdict holds.
The Overrated Index

Tulum re-check: we promised to revisit this. The verdict holds.

In July we cancelled Tulum three days after Mexico announced a federal rescue plan, and said we would rather write the comeback post. Seven weeks later, we cannot. Here is what the data shows.

Sep 10, 2026 · 3 min read
The clause that decides your medical claim was written before you bought the policy
Terms & Departures

The clause that decides your medical claim was written before you bought the policy

Travel insurers review your medical history for 60 to 180 days before your purchase date. What they find there, not what happens on your trip, determines whether a medical cancellation gets paid.

Sep 07, 2026 · 3 min read
Second City, no. 1: Paros is not a cheaper Santorini, and that is the point
Second City

Second City, no. 1: Paros is not a cheaper Santorini, and that is the point

Every list tells you to swap Santorini for Paros. We cleared Santorini six weeks ago, so we cannot pretend it is a straight substitution. Here is the honest version, with the ferry math.

Sep 03, 2026 · 3 min read
The cleaning fee is charged per stay, not per night. That is the entire game.
Terms & Departures

The cleaning fee is charged per stay, not per night. That is the entire game.

Same rule that fixed hotel fees covers vacation rentals, and the total is now honest. But the fee is structured so that short stays subsidize long ones, and one platform earns a commission on the fee itself.

Aug 31, 2026 · 5 min read
Off Peak, no. 1: the Caribbean's best week is the one people think is dangerous

Off Peak, no. 1: the Caribbean's best week is the one people think is dangerous

Hurricane season pricing runs through November 30. Actual hurricane risk collapses by mid-November. That two-week overlap is the best price-to-risk window on the Caribbean calendar, and it's bookable right now.

Aug 27, 2026 · 4 min read
Basic economy got worse in 2026, and the changes were announced quietly
Terms & Departures

Basic economy got worse in 2026, and the changes were announced quietly

Three major rule changes landed between December and May, all of them subtractions. What basic economy costs you now, airline by airline, and the two situations where it's still the right buy.

Aug 24, 2026 · 4 min read
The Amalfi Coast isn't overrated. The trip everyone books is.
The Overrated Index

The Amalfi Coast isn't overrated. The trip everyone books is.

The coast is as good as advertised. The default itinerary, Positano in August, is the most expensive way to see the least of it. Same coastline, 30 to 50 percent cheaper, with the fistfights at the bus stop optional.

Aug 21, 2026 · 3 min read
Your "free" travel insurance depends on which card you tapped
Terms & Departures

Your "free" travel insurance depends on which card you tapped

Premium cards really do include trip cancellation coverage. The catch isn't the coverage, it's that paying with the wrong card, or splitting the bill across two cards, can void it entirely.

Aug 10, 2026 · 4 min read
Lisbon: CLEARED, with one condition. It's a month.
The Overrated Index

Lisbon: CLEARED, with one condition. It's a month.

Same city, same trams, same pasteis. Book it for early October instead of August and the price drops roughly a quarter while the lines shrink. The board's second CLEARED, and the condition is a calendar entry.

Aug 06, 2026 · 2 min read
The resort fee didn't die. It moved upstream.
Terms & Departures

The resort fee didn't die. It moved upstream.

A federal rule now forces hotels to show the fee in the advertised price. It caps nothing, bans nothing, and changes exactly one thing: where the number hides. Here's how to read the new label.

Aug 03, 2026 · 3 min read