November is an underrated time to travel since most folks are already kicking their holiday spirits into high gear. But wouldn’t it be nice to go on a little vacation before the insanity begins? Or maybe you just want to experience a city in a new light or have the travel-itch after staying indoors the last few years (few years?!).
Either way, we highly recommend taking some time to (safely) explore, enjoy some gorgeous weather, or simply get away with friends, family or yourself during this off-season travel period.
So, before Mariah Carey fully defrosts (🎵 I-I-I… 🎵), here are our top picks for a November weekend getaway.
For Great Wine and Better Weather, Visit: Sonoma County, CA
Most people think of summer when they plan to visit Cali, but we are pretty much set on fall as the best time to visit the state. In Sonoma, about 30 miles north of San Francisco, the weather in November is just flawless, with average temps in the mid-60s – just enough for a light jacket and perfect for wine tasting tours (we recommend getting a vineyard pass), exploring rolling hills and canyon trails, and taking in those golden California sunsets.
Cabernet Sauvignon season begins in November, so book a tour and then head into town for holiday strolling and shopping for some gifts for your friends and family (and a little something-something for yourself, too).

For Pre-holiday Joy, Visit: Chicago, IL
Less crowds, perfectly chilly weather, crisp leaves, art and culture, incredible food – what’s not to love about Chicago in November? We’ll wait. Seriously though, we think this may be a secret Chicagoans keep in order to preserve the beauty these locals get to experience in November.
First off, these folks KNOW how to do the holiday season the right way. The magical Christkindlmarket, based on the 16th century Christkindlesmarkt in Nuremberg, Germanya, is a German outdoor holiday market with authentic and unique shopping with plenty of things to look at – and eat. Feast on German schnitzel, warm pretzels, beer, sausages, and strudel and find tons of adorable hand-crafted gifts like cuckoo clocks and hand-painted wooden figurines.
When the snow flurries begin to fall, step inside of the Art Institute of Chicago to get warm and peruse the nearly 300,000 artworks including the main collection with plenty of must-see pieces from Georges Seurat, Monet, Manet, Renoir, Van Gogh, and Degas (swoon!). Don’t forget to stop by Millennium Park and pay a visit to The Bean! There’s just too much to do in this lively city, and we cannot recommend it enough.

For Romance and Culture, Visit: Florence, Italy
Florence is not only ranked as one of the most romantic cities, but it just is too perfect for visiting in fall for many reasons. One is the weather: crisp autumn temperatures in the 60s make for an invigorating experience. Combined with sunsets that cast glowing tones in oranges, deep pinks, and warm yellows over the Duomo, Florence is truly a magical place to be in autumn (and an impeccable international destination if you’re looking to get outside the U.S.).
For a delicious meal with a killer view, try the Golden View ristorante which boasts sweeping views of the Ponte Vecchio and the Arno River, as well as a private wine cellar for tastings (Florence is known for their Chianti). In between hazelnut gelato and lots of pasta, be sure to take in all the famous artwork, from the frescos in the Church of Santa Maria del Carmine to, of course, Michelangelo’s immaculate marble statue of David at the Galleria dell’Accademia. Salute, Firenze!

For Warm Weather and to Get Away from it All, Visit: Tulum, Mexico
If you are looking for a warm-weather vacation to escape the chills of November, have we got a oh-so relaxing destination for you. Tulum has risen in popularity over the last few years, and we can’t help but see why. The #1 Best Places to Visit in Mexico boasts Turquoise waters and white-sand beaches that beckon international travelers. In November the weather is deliciously dry and temperate making for perfect beach relaxing and enjoying the cerulean Mexican waters.
While you’re there, adventure awaits you. Explore the ancient, hidden Mayan ruins which have been preserved for centuries, or sink into the dazzling nightlife at Kin Toh bar AKA the Treehouse where you can enjoy a gastronomical experience while tucked away into your romantic “nest” booth. For a truly luxurious experience, try the spa at the Instagram influencer hot spot, the El Pez hotel, complete with seascape balcony rooms and dreamy accommodations. On second thought, BRB while we go book our flights!

For a Classic Autumnal Experience and Shopping, Visit: NYC
Autumn in New York, why does it seem so inviting? Queue up the Billie Holiday and pretend you’re in a rom-com because you are the main character every day when in NYC in November. No matter what you choose to do – whether ice skating at Rockefeller Center, seeing the Radio City Rockettes perform their classic holiday dances, or taking in all the glittering lights of the city from a rooftop bar with cocktails – you are guaranteed to never run out of fun in the city that never sleeps. Can you dream of anything more perfect than strolling down the city sidewalks with leaves falling to your feet while you’re bundled in a sleek wool coat eating a steaming hot dog from a street corner vendor? WE THINK NOT.
P.S. it’s a little-known fact that you can snag a sneak peek at all the Macy’s Thanksgiving Day Parade floats the night before on the Upper West Side! And if you are still there at the end of the month, don’t forget to check out the annual Central Park Christmas Tree Lighting on November 27 or the Rockefeller Center Christmas Tree Lighting Ceremony on December 1. Oh, and maybe grab a little Frrrozen Hot Chocolate from Serendipity 3 – just for nostalgia’s sake.
Whether you are looking for a quick weekend trip to explore a new city or a chance to get away from it all before the holidays begin, November is an underrated time to hop on a plane and take a vacay into new lands.
With all the options we’ve given you – you will surely have plenty to scratch your pre-holiday travel itch. Happy (and safe) travels, Donnas!
