Looking for a new way to celebrate the most wonderful time of the year? When it comes to the holiday season, these cities have a lot more to offer than just small-town charm. From memorable décor and festivals to magical train rides and boat parades, you’ll find it hard not to feel festive while gathering with friends and family in one of these five cities.


There’s a reason America’s Sailing Capital is consistently ranked one of the top cities for celebrating the holidays. Annapolis decks out its many 18th-century buildings in garland and lights to create a winter wonderland that makes visitors feel as if they’re visiting a Christmas past. While there are many celebrations to join in on, simply strolling the streets – often snow-covered – will put you in the spirit of the season. 

Still have some holiday shopping to do? On select Thursday nights in December, popular retail spots along Maryland Avenue, State Circle, Main Street, Market Space and more will stay open until midnight to give you extra time to shop for everyone on your list. You can also celebrate the holiday season while satisfying your sweet tooth with tons of local chocolate vendors and holiday shopping opportunities along West Street during the Annapolis Chocolate Binge Festival on December 2.


The Blue Ridge Mountain city brings magical memories to the holiday season for revelers of all ages. Whether you’re enjoying the Christmas lights on a horse-drawn carriage ride or wrapping up your holiday shopping at one of the many boutiques and studios downtown, Asheville allows you to embrace the excitement of the season without the crowds of a big city.

Traveling with little ones? Head to Chimney Rock – ranked by USA Today as one of the top 10 places to catch up with Santa – on December 1 and 8 to see the big guy gear up for his Christmas Eve mission as he warms up with a climb up the rock. For a more sophisticated celebration, catch Christmas at Biltmore. Complete with over 50 impressive Christmas trees, the Biltmore Estate – one of America’s largest homes – and its over-the-top traditions will breathe new life into your holiday routines from early November to January 6, 2019. You can also hop on a horse-drawn carriage or hayride (available on the weekends) and take in the unrivaled holiday displays that make up magical Main Street during the Forest City Christmas Lights, November 22 through January 1, 2019.


Easy access to the ski slopes is not the only aspect attracting crowds to Durango, Colorado during the winter season. This historic mining town mesmerizes all ages with its magical lights, memorable events and small-town coziness. Plus, with sleigh rides, dog sledding, snowmobiling and ice skating at your fingertips, it’s the perfect escape for those looking to stay active during their holiday getaway. 

Traveling with fans of The Polar Express? Hop aboard the historic Durango & Silverton train for a memorable ride inspired by the beloved holiday story, November 16 through January 3, 2019. Then, head to Animas Museum’s Christmas Bazaar and get a taste of Durango’s history while stocking up on special gifts and souvenirs on November. 30 and December 1.


Who says you need snowflakes to savor the holiday spirit? While Naples, Florida is better known for its white-sand beaches rather than snow-covered branches, this island town takes celebrating seriously when it comes to Christmas. After all, it was named one of America’s Best Beach Towns for Christmas by Coastal Living.

If you truly need to see snow to celebrate the season, head to Third Street South any night November 20-24 to see the snow fall, plus live music, carolers and shopping opportunities during the Celebration of Lights. Or, switch things up by taking your celebrations to the sea when you observe one of the five – yes, five – annual boat parades happening around the city throughout December.


This California beauty is another beachside city known for stepping up its game during the holidays. Whether you’re getting in the spirit while taking a festive stroll around Balboa Village or finishing your holiday shopping at Fashion Island, you’ll find it hard not to make jolly memories in Newport Beach.

Get in on all the action when you go on a holiday lights cruise, happening nightly throughout December, and check out all the decorated waterfront estates competing in the Ring of Lights competition. Or, take in the views from land during the 110th Annual Newport Beach Christmas Boat Parade, December 19-23, one of the largest holiday boat parades in the world. In the mood for more traditional holiday hoopla? Head to nearby Winter Fest at the OC Fair & Event Center December 20 through January 6, 2019 featuring ice tubing, fireworks, carnival rides, light mazes and Orange County’s largest outdoor ice rink under the stars.

Ready to experience the holiday magic for yourself? Keep your gift-giving budget in check when you save on your airfare and hotel accommodations this season using Vacations by Marriott. You’ll also earn Marriott Rewards® or SPG® points to put toward future stays in the new year.