Key West, Florida
Key West takes the top spot on the list. Not only is it an amazingly charming little place, the weather in November is perfect, and the restaurant / bar scene is enough to keep your belly full throughout the day and your mind and body entertained into all hours of the night.
Before you make reservations, here are a few things to consider. Key West is home to some of the coolest Bed & Breakfasts in the country. In fact, when I travel to Key West, B&B’s are the only type of lodging I’ll stay in. As for my top picks, check out Frances Street Bottle Inn, Ambrosia Key West Tropical Lodging, and the Island City House Hotel. That’s not to say that there aren’t dozens of awesome places to choose from, but the three I just mentioned round on the top spots on nearly every list, including mine.
When in Key West, be sure to hit up Duval Street for some all-day / all-night entertainment. In addition, head down to Sunset Pier for an incredible dose of people-watching and fun. While there, stick around for the sunset (pictured above), and then head back to Duval to finish the night with some live music and dancing.
There are two things that I absolutely love about Aspen in late November. First, the skiing is incredible. Second, the mountains are crowded but not to the point of being unbearable. In fact, since most people spend the Thanksgiving holiday with family and friends, the end of November is the ideal time to hit up Aspen.
Now, Aspen is full of beautiful hotels and boutique lodges, and if skiing / snowboarding is high on your priority list then you will need to find something that’s close to the mountain. After all, no one wants to wake up and Uber it to the slopes, so my top three choices for Aspen accommodations are Hotel Jerome – Au Aberge Resort, The Limelight Hotel, and The Little Nell. I won’t lie. All three accommodations rest on the higher end of things, so if you’re looking to save a few bucks, check out places like the Aspen Mountain Lodge or The Inn at Aspen.
New Orleans, Louisiana
The Big Easy has witnessed a resurgence as of late, and there’s no better time to check out the city than in late November. For many reasons, the season is at a lull, which means tourists aren’t roaming the streets in abundance and rates on airfare and hotels are quite reasonable.
For those who have never been to New Orleans, you can expect a melting-pot culture populating a city that’s been built around Creole style architecture laced with deep Southern undertones. In addition to the beauty that surrounds you, music fills the streets as musicians line sidewalks and pack the halls of local watering holes. Seriously… if you can’t find a live band playing somewhere in New Orleans at every given moment of the day then you’re not paying attention.
For those who have been to New Orleans, you know what you’re getting yourself into though you may be on the lookout for hip, new places to stay. If that’s the case, here are three to consider. First, check out the Audubon Cottages located in the French Quarter. It’s a little pricey, but well worth the extra cash. In addition, you might want to take a look at Hotel Mazarin. Staying there won’t break the bank, and you’ll find yourself resting in a comfortable room that’s within walking distance to pretty much everything. Last but not least, consider spending a few nights at the Windsor Court Hotel, a place that boasts incredible views of the Mississippi. Personally, I’ve never stayed there, but I know people who have and they swear that they won’t stay anywhere else in New Orleans.
In addition to its famous seaside cliffs that often serve as a springboard to hours of fun, Negril is relatively inexpensive, and most can spend the entire day eating, drinking and smoking for about $40. Here’s the trick. Stay at one of the Oceanside resorts, but don’t spend all of your time on property. In fact, I encourage you to venture into town, and away from your resort, at least a few times during your trip. Not only will you find some of the best roadside food stands in the world, you’ll walk amazing little markets, meet some incredibly friendly people and experience the true culture of Jamaica. Now, some people will tell you to be careful when walking the streets. That’s good advice. You should always stay alert, but you won’t have too much to worry about if you keep your hands in your pockets and a smile on your face.
Circling back for a second, let’s talk about places to say in Negril. My top choice is Tensing Pen Resort. My wife and I stayed there for a week or so on our honeymoon, and I’m not kidding when I say that I never wanted to leave. Another resort in Negril worthy of your time and attention is The Cliff Hotel. The rooms are beautiful, the staff is awesome and the on-property food will make you forget about Thanksgiving dinner at moms house.
When in Negril, just relax and enjoy the vibe. Venture away from your resort on occasion, hit up seven-mile beach, do some cliff diving at Rick’s Café, eat local food, and have an awesome time.
Napa Valley, California
OK – I’ll admit it, Napa is more than a little trendy and not very cheap. But hey, if you’re going to skip out on Thanksgiving dinner then you should do it in style!
Napa Valley, as you all know, is the center of the American wine universe. In addition, it also plays home to what can arguably be called the prettiest countryside in the United States. When there, enjoy wine tours, fancy dinners, hot-air balloon rides, a plethora of R&R and some good old fashion driving. The truth is, San Francisco Airport is probably your best bet, and you’ll want to rent a car to get to Napa. That’s cool, though. Trust me. There’s no better way to experience the beauty around you than by driving through it without a care in the world.
If you’re looking for a place to stay, check out Wine Country Inn located in St. Helena. This boutique establishment is surrounded by vineyards and serves as the perfect vacation destination if you’re looking to relax in a romantic setting. Next on my list of places to stay in Napa is Meadowood Napa Valley. Boasted as the “ultimate luxury resort,” Meadowood features cozy cottages, world-class golf, unbelievable resort-style accommodations and all the amazing wine you can handle. Last but not least, and this one’s for those looking to spend more money on wine than lodging, check out the Chablis Inn located on Solano Avenue in Napa. Rooms run around $150 / night, and that leaves plenty left over to splurge on the other things you love.
It’s Time for a New Type of Thanksgiving
This Thanksgiving, and everyone thereafter if I can help it, I’m taking my family on a trip to someplace incredible. As for where you’ll go this Thanksgiving, it is my hope that this article has inspired you to break from the norm and travel to someplace awesome, as well. That’s not to say that your family’s home isn’t awesome, but let’s be real. You work hard for a living, and your vacation should be a stress reliever not a stress inducer.
Thanks so much for taking the time to read. Travel safe, and please take care of each other along the way.