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6 Places That Are at Their Best in December, and How to Book Them for Less

Whale season in Maui, Christmas markets in Vienna, Réveillon dinners in New Orleans. Six trips where December is the right month to go, with the timing and booking details that keep the cost down.

By ROSE Rewards Editorial Team

Published · 6 min read

December is the most expensive month of the year to travel in the week before Christmas, and one of the better-value months in the two weeks before that. That gap is the whole strategy of this guide. The six places below are at their best in December for a specific reason (whales, markets, dry season, a holiday tradition), and each one comes with the booking detail that most affects what you'll pay.

DestinationWhy DecemberBook aheadPassport (US citizens)
New York CityHoliday windows, markets, the treeHotels for weekendsNo
MauiStart of humpback whale seasonHaleakalā sunrise, 60 days outNo
Cancún & TulumDry season beginsChristmas–New Year weekYes
ViennaChristmas marketsOpera seats; standing room same dayYes
New OrleansRéveillon dinners, City Park lightsRéveillon tablesNo
San JuanLong Puerto Rican holiday seasonHoliday-week hotelsNo
At a glance. Details and sources for each are below.
A snowy New York street with a lit Christmas tree and holiday crowds
01

New York City

New York, USA

The city's holiday season is mostly free to experience: the Fifth Avenue windows, the tree at Rockefeller Center, the markets at Bryant Park and Union Square. What costs money is the hotel, and that's where timing matters.

Why December: Decorations are up from the start of the month. Rates typically rise week by week toward Christmas, so the first ten days of December usually offer the same city for less.

Worth doing

Know before you go: Midtown on a December weekend is crowded enough that a 15-minute walk can take 40. Plan the big sights for weekday mornings.

Sunset over Makena Beach, Maui, with waves on the shore
02

Maui

Hawaii, USA

Warm water and long beaches when most of the mainland is cold. The draw that makes December specifically worthwhile is wildlife.

Why December: Humpback whales migrate from Alaska to Hawaiian waters for the winter. Sightings build through December, and NOAA notes the population that winters in Hawaii is one of the best-studied in the world. Early December avoids the sharp price rise of Christmas week.

Worth doing

  • Watch for whales from the shore in Wailea or Kīhei in the morning, when the water is calmest
  • See Haleakalā at sunrise (reservation required) or at sunset (no reservation required)
  • Snorkel Molokini Crater on an early boat, before the afternoon wind
The Tulum ruins above a turquoise sea on Mexico's Riviera Maya
03

Cancún & Tulum

Riviera Maya, Mexico

Turquoise water, Maya ruins on a cliff and freshwater cenotes in the jungle, all within about two hours of each other.

Why December: The dry season begins, bringing more sunshine and lower humidity than summer. Winter also typically sees less sargassum seaweed on the beaches than the warmer months, though it varies by year.

Worth doing

  • See the Tulum ruins at opening time, before the heat and the tour groups
  • Swim in a cenote; many ask you to shower off sunscreen first to protect the water
  • Take the ferry from Cancún to Isla Mujeres for a day

Know before you go: Christmas and New Year's week is peak season here. If your dates are flexible, the first two weeks of December are noticeably calmer.

Lights over Vienna's Christkindlmarkt on a winter evening
04

Vienna

Austria

The Christmas markets are the reason to go in December: lit squares, mulled wine, roasted chestnuts and a coffeehouse on every corner when you need to warm up.

Why December: The main markets run through to around Christmas, and the market at Schönbrunn Palace continues as a New Year market into early January.

Worth doing

  • Wander the markets at Rathausplatz, Spittelberg and Schönbrunn Palace
  • See an opera from standing room: the State Opera lists standing places at €13–18 (2025/26 prices), sold from 10 a.m. on the day
  • Ride trams 1 and 2, which between them cover most of the Ringstrasse, for a sightseeing loop at a transit fare
The New Orleans skyline reflected in the Mississippi River at night
05

New Orleans

Louisiana, USA

Few US cities have holiday traditions as specific as New Orleans: Réveillon dinners, the lights in City Park and live music every night of the week.

Why December: Many restaurants serve Réveillon menus through December, a multi-course holiday dinner tradition at a fixed price. Celebration in the Oaks lights up City Park from late November to January 1; check the calendar, as it has closed on Christmas Eve in past years.

Worth doing

  • Book a Réveillon dinner in the French Quarter
  • Catch live music on Frenchmen Street, where venues are smaller than on Bourbon Street
  • Ride the St. Charles streetcar past the Garden District
Colorful colonial buildings with wooden balconies in Old San Juan
06

San Juan

Puerto Rico

Caribbean warmth and colonial streets, and because Puerto Rico is a US territory, no passport is needed for US citizens flying from the mainland.

Why December: Puerto Rico's holiday season is one of the longest anywhere. Parrandas (caroling parties that move from house to house) run through December, and the season doesn't really end until the San Sebastián Street Festival in mid-January.

Worth doing

  • Walk Old San Juan and the walls of El Morro in the late afternoon
  • Try the holiday staples: lechón, pasteles and coquito, the coconut eggnog
  • Take a night kayak tour of the bioluminescent bay in Fajardo

Know before you go: Planning a day at El Yunque rainforest? Check the US Forest Service site before you go: access rules for the main road have changed several times in recent years.

How to pay for a December trip without overpaying

December award prices for flights and hotels move with demand, just like cash prices. Two habits make the biggest difference:

  1. Price the same dates in cash and in points, then work out what each point is worth on that booking. Our guide to whether your travel points are actually saving you money walks through the one-minute calculation.
  2. Move your dates by a day or two away from the weekend before Christmas and New Year's Eve. Both cash and award prices tend to drop on either side of those peaks.

The bottom line

Pick the destination for the reason that makes December special there, book the time-sensitive piece first (Haleakalā permits, Réveillon tables, holiday-week hotels), and travel in the first half of the month if you can. For the hotel itself, the hotel planner gives a rough idea of what a night costs in points before you commit.

Questions people ask

What is the cheapest time in December to travel?

Generally the first two weeks of December, before school holidays begin. Prices for both flights and hotels typically rise sharply in the week before Christmas and around New Year's Eve.

Do I need a reservation to see sunrise at Haleakalā?

Yes. Reservations open on recreation.gov 60 days in advance at 7:00 a.m. Hawaii time, with a portion released two days before each date. Sunset does not require a reservation.

Do US citizens need a passport for San Juan, Puerto Rico?

No. Puerto Rico is a US territory, so US citizens flying from the mainland don't need a passport. Bring a valid government photo ID for the flight.

Sources

  1. National Park Service: Haleakalā sunrise reservations
  2. Bryant Park: The Rink at Winter Village (admission and rental prices)
  3. The Morgan Library & Museum: Charles Dickens's A Christmas Carol
  4. NOAA Fisheries: Humpback whale
  5. Travel Mexico Solo: Tulum airport (TQO) guide
  6. Vienna Tourist Board: Christmas and New Year's Eve in Vienna
  7. Wiener Staatsoper: Standing room
  8. Visiting Vienna: Christmas market glossary (mug deposits)
  9. New Orleans City Park: Celebration in the Oaks
  10. New Orleans RTA: Fares and passes
  11. US Customs and Border Protection: Travel for US citizens

Prices, dates and program rules change. We checked these sources on November 9, 2026; confirm with the provider before you book or buy.

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