As summer winds down, you may be on the beach somewhere thinking about what to do with that last week of vacation you still have for 2021. Or, you may have spent the summer at home. In any case, autumn is a great time to travel. The crowds are gone, the weather is still nice, and it just feels great to get another trip in before hunkering down for the winter. Here are a few thoughts about where to go and what to do in each of the remaining months of the year.
Bodie Island Lighthouse, Nags Head, NC. Photo by Kyle Calhoun on Unsplash
September: Now that the Boys of Summer have gone (check out this great, slowed-down version of my favorite song), you’ll have just about any beach almost all to yourself in some terrific seaside locations. The Outer Banks of North Carolina are a hundred mile string of barrier islands, from Corolla and Duck in the north down to Hatteras Island and Ocracoke Island in the south. This is the time and place to rent a vacation home for a week, when the prices are half or less of what they were in the summer season. The sun is still hot, the water is still warm, and there’s plenty to see and do. Mix in some of the best fresh seafood around at great prices, and you’ve got yourself a great late summer beach week.
If you’re a tennis or golf fan, the weekend of September 24-26 features the best international team competition in each respective sport. The Laver Cup, which has supplanted the Davis Cup as the premier team event in tennis, features all the great players from Europe vs. the rest of the world. This year, it’s in Boston at the TD Garden, home of the Boston Celtics. Hotel and ticket packages are still available. For golf fans, the Ryder Cup is a definite bucket list item. The 43rd biannual edition will be held at Whistling Straits in Kohler, Wisconsin, featuring the best US players against their European counterparts. Hotel and ticket packages are still available for this event as well.
Blue Ridge Mountains, western North Carolina. Photo by Wes Hicks on Unsplash
October: It’s prime leaf-peeping season from Virginia to North Carolina, and what better way to see the spectacular fall foliage then by taking a road trip. Take the Skyline Drive, a 105 mile trip along the crest of the Blue Ridge mountains in Virginia from Front Royal in the north to Rockfish Gap, the southern terminus. Park and jump onto one of dozens of trails to admire nature’s beauty up close. If you’re a camper, the Shenandoah National Park features several well maintained campsites. If you prefer a roof over your head, check out the B&B’s and inns that dot the valley. And don’t forget to visit one of the wonderful wineries in the area.
If you go in late October, continue south along the Blue Ridge Parkway, which picks up where the Skyline Drive ends in Rockfish Gap and covers nearly 500 miles through the Great Smoky Mountains National Park, ending near Cherokee, North Carolina. Asheville, NC is near the southern end of the Parkway. Asheville is a mecca for arts, crafts, craft beer, and afficionados of The Biltmore, one of America’s great mansions. You can stay right on the property with the rest of the Vanderbilts or check in at one of Asheville’s highly rated hotels and inns.
Golden Gate Bridge, San Francisco. Photo by Maarten van den Heuvel on Unsplash
November: We think this is the best time to visit San Francisco. The weather is warm (although still cool at night), and it’s not crowded. Take a tour of Alcatraz (make sure to reserve at least a month in advance), enjoy the day at Golden Gate Park, and take a drive up to Sausalito for lunch. But it’s the wonderful neighborhoods of San Francisco that give the city its unique character, from Chinatown to North Beach (the Italian restaurants here are bellissimo) to Fisherman’s Wharf to the original hippy hangout of Haight-Ashbury. This is the place to use your Marriott Bonvoy points to splurge (for little or no cost) at the likes of the Westin St. Francis, the St. Regis, the W, the Ritz Carlton and many more.
Of course, if you crave for one last blast of summer warmth, South Beach or the Florida Keys are the places to go. Beaches, pools, nightlife, diving, snorkeling, nightlife, daylife. . .it’s all there under the still-strong Florida sun. If the nightlife still wins the day, check out South Beach is the pick, where you should stay at the hotel with the coolest pool you can afford, like The Delano or the W. For a more laid-back getaway, head south another 100+ miles to the Keys, America’s Caribbean outpost. From the dive spots just off Islamorada and Key Largo to the funky fun in Key West, this is one of the best destinations to leave the rest of the world behind.
Aruba lights
December: Take a trip to do your Christmas shopping in Chicago, where you’ll feel the chill of winter with plenty of places to drop in and warm up. Mrs. E and I particularly enjoy shopping the Magnificent Mile, which offers a wonderful selection of brand name and anchor retail stores, and looks magical under the holiday lights, especially if a light snow is falling. And when you’ve shopped until you’re ready to drop, head over to Three Dots and a Dash, an authentic tiki bar that will warm you up for the evening. Dinner? Daughter R and her husband Dave love Girl and the Goat in the West Loop for phenomenal global cuisine. We’re partial to Le Colonial, where you’ll find the best French-Vietnamese fusion anywhere outside of Saigon. And Gibson’s Steakhouse on Rush Street is the quintessential stop for every carnivore. Best of all, hit all three for the triple crown of Chicago cuisine!
Alternately, if you are still craving a beach in December, Aruba is a magical tropical wonderland. While every month is a good month to be in Aruba, it’s worth mentioning that the locals decorate spectacularly for the holidays, from mid-November through to January, and they go all-out. There’s something fun about being on a spectacular beach island that is fully dressed in holiday attire. We’ve written extensively about Aruba. . .check out our recommendations from our Aruba Trip Report, 2021 – Part II.
Wherever you go, and whatever you do, it’s time to start planning now. If you have any questions, feel free to contact us at phil@theexceptionaltraveler.com or leave a comment below.