The Worst and Best USA City To Visit For Every Month In 2019

The new year is already off and running with a bevy of events, festivals, activities, things to do, and places to see across the USA. Before you start packing and heading out to destinations near and far, take a minute or three to check out which cities offer travelers the maximum in vacation fun and frolic during a specific month and which cities to avoid.

Since one of the goals of traveling is to get your money's worth by exploring, sampling, interacting, and participating in the venues, landscapes, and activities available, be sure your vacation destination won't leave you high and dry, wet and soggy, or hunkered down in a hotel room. Whether it's due to too many tourists resulting in long lines and endless waiting, unfriendly seasonal weather and situations, or spring breakers partying hard on local beaches, you'll want to make the most of your travel itinerary.

To get an idea of what you can expect from January through December in cities offering the opportunity to enjoy your time, whether it's for a day, weekend, or longer, peruse the following list of suggestions. The list will also include USA cities for each month that, for a variety of reasons, may be better suited as a vacation destination at a later date, or, maybe not at all.

24 January (Best) - Maui, Hawaii - From Sunrise to Sunset, it's all good


It's Hawaii; what more is there to say? Tropical weather, sun-drenched beaches, stunning sunsets, whale watching, and unlimited water activities make Maui a "best of" city for winter travelling. Not only do you have access to miles of beach, there's also the mountains for hiking lush landscaped trails.

The only "must have" items for this winter wonderland is a pair of flip flops, shades, a beach towel, and your most flattering swimming attire with a pair of hiking boots thrown in for good measure. Winter is considered "high season" so make your reservations early.

23 January (Avoid) - Flagstaff, Arizona - Picture postcard perfect... if you like snow

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Chilly cool doesn't quite describe what you can expect when travelling to Flagstaff during the winter. Think more along the lines of being stuck in a deep-freezer where the temps dip in and near the teens on the thermometer. Estimated temperatures for January are around 43 degrees for the high and 17 degrees for the low.

There are plenty of opportunities for going outside and making a snowman or snow angels. Other than that, things to do are limited. If you like it cold, Flagstaff won't let you down. If you don't, well, then avoid avoid it.

22 February (Best) - Cashiers, North Carolina - Southern hospitality rocks

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Situated amidst the Nantahala National Forest, you'll feel like Robin Hood as you make your way around Cashiers lush landscape of waterfalls, meandering rivers, and scenic views of the Blue Ridge Mountains. The city is quaint with cozy restaurants and inns and an array of things to do from hiking and fly-fishing to a round of golf.

The busy season is May-October when the population of this visual oasis exceeds 25,000. During February and the off-season, you can enjoy the tranquility of Cashiers with only around 2,000 others. Very nice.

21 February (Avoid) - Minneapolis, Minnesota - Brrrr...that's all there is to say about it

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If you think Flagstaff's temperatures are unfriendly during the winter, Minneapolis tops the charts. While the city has plenty to offer, it also offers a lot of snow and nighttime lows of 12 degrees. That's up 6 degrees from January. If you're heading to Minnie, bring your skis.

Otherwise, find a nice cozy hotel or bed and breakfast where you can snuggle up in front of a roaring fire with a cup of hot chocolate and enjoy the quietude of snowflakes as they gently cover the city and you, too, if you venture outside.

20 March (Best) - Black Hills, South Dakota - Pure pedal power

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For those looking for a snow-filled adventure, the annual 28 Below Fatbike Race that takes place along pristine snow-covered trails in the Black Hills is a memorable experience. The race begins in Spearfish and is the only time the US Forestry Service allows access to the trail. The 50k loop is a challenging race for experienced bikers.

Enjoy the beauty along the trail as you push the pedal to the max, relax at the end of the race at the after party, and cozy up at the end of the night at the Spearfish Canyon Lodge.

19 March (Avoid) - Fort Lauderdale, Florida - Spring has sprung when spring breakers arrive

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Yes, Fort Lauderdale is in the beautiful subtropical state of Florida where the skies are as blue as the ocean and the sugar sand runs for miles. It's also one of the premier destination locations for students on spring break.

If you don't mind crowded anything and everything, young adults whose goal is to "party hardy" into the wee hours of the morning, scantily clad sun-worshipers, loud music, and a nearly unlimited number of creative beverages, then Fort Lauderdale is the place to be. Otherwise, avoid at all costs.

18 April (Best) - Sanibel Island, Florida - A pristine sandy oasis not in the desert


April is the last month of Sanibel Island's peak season and one of the most perfect times to enjoy all there is to see and do. Although prices will be higher, it's worth it to stroll the beach at sunset in idyllic weather. Another advantage of visiting in April is the avoidance of being in Florida during hurricane season.

When in Florida, do as the natives do and that is enjoying the sound of the waves against the shore, dine on the freshest seafood, indulge in your favorite libation, and just "chill". There's no hurry and no worry when the Gulf of Mexico is at your toe tips.

17 April (Avoid) - Los Angeles, California - Congestion forward, backward, and all around

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Overall, anytime you're traveling to Los Angeles and you'll be out and about seeing the sights via a car, plan on sitting in traffic. It doesn't really matter where you're heading in LA, you'll be competing for road space with commuters as well as other travelers.

Los Angeles has the dubious honor of being tagged as the top congested city in the U.S. in a study conducted by INRIX. The analytics by the company show drivers in LA spend about 102 hours a year sitting in traffic. Be prepared.

16 May (Best) - Nashville, Tennessee - Music to your ears in Music City

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If you're into music, country music that is, then Nashville is a music lover's dream come true. When spring is in the air, so is the music in Nashville along with beautiful weather. The city offers a menu of great music, incredible eateries both traditional with down-home cooking as well as upscale la de da dining options.

Music fills the air from honky-tonk style to moody blues on street corners or in one of the many bars lining the avenues or out-of-the-way holes in the wall. There's Graceland, the Grand Ole Opry, the replica of the Greek Parthenon, Belle Meade Plantation, and so much more. Yee-haw!

15 May (Avoid) - Las Vegas, Nevada - What happens in Vegas stays in Vegas; at least you hope so!


Why choose May as a bad month for visiting Las Vegas? There are a couple of reasons. While the weather is moderate with warm days and tolerable nights, it is considered the shoulder season. This means there are deals galore to be had for the asking. If a budget-friendly vacation is what you're hoping for, Las Vegas becomes a tempting tidbit for saving on inexpensive (cheap) flights and hotels. But let's face it, LV is not cheap nor is it a place to go with limited funds.

With casinos surrounding you 24/7 along with star-studded shows, nightclubs, and restaurants picking at your pockets, you may want to rethink your itinerary and bypass Sin City.

14 June (Best) - Detroit, Michigan - Motor City has the pedal to the metal


It's well-known that Detroit City has had some hard times, but changes to the Motor City have been underway resulting in a lot of progress to this once vibrant city that still has an awesome glow. Projects have been completed and there are more to come to ignite the brilliance of the city landscape and all it has to offer. If experiencing the transformation of a city sounds interesting, plan a visit and enjoy some of the new additions like the parks and biking lanes along a 3.5-mile stretch of the riverfront.

By summer, Atwater Beach will be rocking with sun, sand, retail venues, and a floating food and beverage barge. The Central Business District is getting a massive makeover and new hotels and historic buildings have been transformed into boutique hotels and upscale restaurants.

13 June (Avoid) - New Orleans, Louisiana - Rain, rain go away

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Whether it's your first time or the 10th time you're visiting the Big Easy, there's always something old or new to add to your vacation itinerary. From strolling through the French Quarter and checking out the nightlife, music and cafes on Bourbon Street to enjoying the ambiance of Jackson Square with a fresh hot beignet and a steaming cup of coffee. There are tours on land and steamboat outings on the Mississippi.

All activities are designed with tourists in mind and spending time outdoors. Problem being, June is the rainiest month with an average of 11 to 13 days of precipitation plus the month is heavy with humidity. If you visit, pack an umbrella.

12 July (Best) - Anchorage, Alaska - Become one with the landscape

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Alaska is one of the many destinations in the US that offers beauty, adventure, diverse landscapes, and an abundance of interesting places to go, assorted activities to do, and interesting things to see. Hop on the Seward Highway for a scenic drive, visit the Alaska Zoo, observe wildlife at the Alaska Wildlife Conservatory, or take a hike or two at Chugach State Park or venture down the Tony Knowles Coastal Trail.

While July has sizzling temperatures in the majority of states, Anchorage enjoys a cool 60 to 70 degrees, which makes outdoor adventures much more enjoyable.

11 July (Avoid) - Atlanta, Georgia - A serving of Hot Lanta, anyone?

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While Atlanta can keep you busy from pretty much around the clock, July is probably the month you'll want to avoid for two reasons. One, Hot Lanta is just that; super-hot and humid so you'll feel like a dishrag and two, prices are at their highest between June and August.

If you want to get your money's worth, this isn't the month to do it. Plus, you have kiddos out of school and crowds and lines at Six Flags, Stone Mountain Park, and Zoo Atlanta, to name just a few of the "hot" spots for travelers.

10 August (Best) - Chicago, Illinois - Nashville isn't the only "music city"

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Chicago has so many things to see and do from The Miracle Mile to the Navy Pier. The city offers a menu of restaurants, bars, nightlife, cultural venues, museums, and is home to the blues. One thing that adds to the list making Chicago a "best" choice for 2019 is it will be hosting Lollapalooza, as it does every year in Grant Park.

If you can't make the festival, never fear, tunes are available at Buddy Guy's Legends Blues Club. Pull up a seat and listen to cool music that says it all in words and wailing harmonicas and guitars. If you're a music lover, add Chicago to your list of travel destinations.

9 August (Avoid) - Orlando, Florida - Stifling humidity and massive crowds!

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While Orlando is a great city to visit with a plethora of attractions, dining, outdoor adventures, parks, and just about anything else imaginable, it's also home to Walt Disney World. This isn't to say Mickey's house isn't a fabulous theme park; it is. What isn't fabulous is the Florida weather, festivals, and August crowds.

Weather-wise, it's hot, hot, hot mixed with humidity that's stifling. Then there's the stormy weather, which is not theme-park friendly. Add to that, peak season pricing comes to an end, so budget-friendly families hold out till August, which means crowds.

8 September (Best) - Breckenridge, Colorado - All roads lead to Oktoberfest

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September is definitely the time to experience a "Rocky Mountain" high in Breckenridge when the city celebrates Oktoberfest. The forest landscape provides the perfect backdrop and atmosphere for sampling a variety of flavorful German cuisine specialties, music, activities for all ages, and an assortment of cool and refreshing beer.

At the fest, you'll please your palate with over 36 vendors featuring tasty food and brew. You'll also get to take part in German-themed games or show off your dancing skills doing the polka. Don't forget your lederhosen!

7 September (Avoid) - New York City, New York - Start spreading the news...there's people traffic!

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How can NYC be a bad choice? The answer is simple. The fall season (along with spring) is one of the busiest times for travelers to make their way to the Big Apple. If you're planning a night on the town at Radio City Music Hall, a day tour of the Empire State Building, a ferry ride to Staten Island, fun at Coney Island, tea at the Ritz-Carlton, or shopping along Fifth Avenue, you can plan on long lines and wait times at attractions, expect already booked hotels, and know ahead of time that prices on everything will be higher.

6 October (Best) - Salem, Massachusetts - Take a magical mystery tour into history

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What better place to celebrate Halloween than in the city known for its witches and its infamous witch trials? You've got it. Consider Salem as your October destination. The city is long on history when it comes to diabolical doings and witchery and during Halloween, there are plenty of events to bring the past back to life. If you find Salem and its history interesting, tour The Witch House (pictured above). This is the actual home of Judge Johnathan Corwin, who took part in the infamous Salem witch trials in 1692.

5 October (Avoid) - Asheville, North Carolina - Bring your piggy bank

via:Adventurous Kate

North Carolina is one of the most beautiful states on the planet whether your plans include hiking in Pisgah National Forest, visiting the North Carolina Arboretum, or touring the historic Biltmore mansion. Asheville is southern hospitality personified. From wildlife and waterfalls to art galleries and breweries, there's something for all ages.

Why, then, is it a city to avoid in October? First, fall colors are like a magnet that draw droves of tourists to see the palette of colors, and because October was rated by CNBC in 2018 as the third most expensive city to visit (3 nights plus airfare for two) in the USA. Maui came in second and New York City was first. That's some serious competition!

4 November (Best) - Savannah, Georgia - A blend of charm and mystery

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The south is all about hospitality and history and you'll receive double doses of both when visiting Savannah. Take a horse-drawn carriage drive through the city or hop aboard the Old Town Trolley for a tour. Take a leisurely stroll through Forsyth Park's 30 acres in Savannah's historic district or peruse art at the Telfair Academy.

A visit to the serene Bonaventure cemetery and the Cathedral of St. John the Baptist is a must. Enjoy traditional down-home cooking as well as creative cuisine at the annual Savannah Food & Wine Festival.

3 November (Avoid) - Seattle, Washington - Raindrops keep falling on my head...

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Soggy is the best word to describe Seattle in November. The month is dreary, depressing, and ultra-wet. While taking a ride on the Seattle Great Wheel probably isn't the best idea, a visit to the Pacific Science Center or Chihuly Garden and Glass will keep you inside and dry.

If a lot of rain isn't a deterrent while you make your way around the city and won't prevent you from having a good time, that's fine just come prepared with galoshes, umbrella, raincoat, or rain poncho and you're good to go.

2 December (Best) - Jackson Hole, Wyoming - Crank up the snowmobile

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Jackson Hole provides a vacation of a lifetime during the winter because it's the offseason, which means multiple deals resulting in vacation savings. Add to that there will be less traffic and fewer people, which means you'll have a much more in-depth vacation than you would during the summer. While visiting, you'll have access to snowboarding, skiing, dog sled tours, and wildlife observation. You can take a trip Yellowstone with the only available transportation in winter - snowmobile or snow coach.

1 December (Avoid) - Aspen, Colorado - Bring extra cash

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Money, money, money is what you'll need if you plan to tackle the slopes in Aspen. This popular ski vacation destination, which is a popular haunt for well-known celebs, is not budget-friendly. There are plenty of things to do like visit the Aspen Art Museum, the Wheeler-Stallard House, and the Wheeler Opera House along with choosing a high-end resort.

From the city's fine dining restaurants to exclusive boutiques, prices are higher and with an influx of travelers making Aspen their base of operations for skiing, you can expect long wait times plus shell out some extra dough.

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