Oyster.com

Ask most people to picture a Hawaiian beach and they'll describe Waikiki without realizing it. White sand, a hotel a few steps from your towel, water warm enough to float in all afternoon. That's real. It's also one very specific version of a Hawaiian beach vacation. The four main islands don't just have different sand and different hotels standing behind it.

New York is set to add more new hotel rooms than any other American city this year, the second year running it has led the country on that count, and the property everyone is still talking about is 94 years old. The Waldorf Astoria reopened in July 2025 after an eight-year renovation that shrank its room count from 1,400 to 375 and left a $50,000-a-night penthouse at the top. That’s the state of New York hotels right now.

"All-inclusive" promises the same thing everywhere: one price, no surprises at checkout. What that price buys changes enormously from resort to resort, and matching the right property to the right traveler matters more than chasing the lowest quoted rate. A family with two exhausted parents wants a water park handling the entertainment. A couple marking an anniversary wants quiet and a decent wine list. Someone counting every dollar wants premium liquor included without a shock at checkout.

The villa has a private heated pool, the kids are wiped out from a day at the parks or the beach, and on Friday evening you walk to a shul for shabbos night minyan, then back at the villa sit down to a Shabbos seudah you cooked in a kosher-kept kitchen you trust. In Florida that is not a fantasy or a workaround. It is the expectation. This is the one state in the country where being frum makes the vacation bigger rather than smaller, because the communities here were built by people just like you.

Caribbean bookings are 21 percent ahead of last year’s right now, in the thick of hurricane season. Squaremouth, the insurance marketplace that tracks this kind of thing, says it comes down to two numbers: hotel rates are down, and named storms mostly aren't showing up. While NOAA calls for 7 to 13 named storms this year, 2 to 6 hurricanes, and Colorado State predicts 9 named storms and 4 hurricanes, only two storms have formed so far.

With just a couple weeks left before Labor Day 2026, the options are quickly running out. Hot spots are gone, and some other options are now running into college football season. To find a great place for you procrastinators we asked three questions: Is it a fair price, are rooms genuinely still available, and is there a real reason to be there beyond checking a long weekend off the calendar? Two places fit the bill.

Everyone already knows the September math. The Mediterranean's greatest hits, Santorini, the Amalfi Coast, the French Riviera, cool down from their July highs while the water stays warm and the rates drop 25 to 35 percent. Which is exactly why it’s no longer a secret. Three other corners of Europe also experience steep drops in rates with noticeably fewer people going. Adobe Stock | Noradoa San Sebastián in September is still swimming weather.

The U.S. Forest Service estimates fall tourism brings roughly $8 billion to New England's economy every year. Most of that money gets spent on rooms, and most of those rooms get booked before the leaves have even started to turn. Travelers who wait for a confirmed peak-color forecast are, by definition, booking last. Fall foliage doesn't arrive on a single date. It moves like weather, because it is weather.

Kayak's newest travel survey found that 84 percent of younger travelers say they would rather take a trip to a small town rather than a big city. Lower prices and thinner crowds were the top reasons. None of this is news to those of us in the travel industry. The small town next door to the famous city has been the better trip for decades.

Searches for Jaipur are up 107 percent year over year, the second-biggest jump of any destination on Skyscanner's 2026 travel trends report. Only a Costa Rican province beat it. That kind of number usually means one of two things: a destination that just got a direct flight, or one that finally caught up to what it always had. Jaipur is the second case, and what it always had was some of the best hotels in the world, sitting inside actual royal palaces, for less than a mid-range room in Rome.