22 Best City Breaks in the USA

Are you looking for the best city breaks in America? Read our list of top US cities now to plan your next weekend getaway or short break. Explore the best cities to visit on both coasts as well as in the heartland along with recommendations for the best things to do, when to visit, and the best place to stay. You may also like our post 33 Bucket List destinations to visit in the USA

Prior to having kids, we were more road trip kind of people. We didn’t stay long in towns and cities but preferred to camp and hike in national parks. We visited cities mainly to fly into our preferred destinations. But boy, having kids changes everything! Now we love going on city breaks to different US cities, staying in a comfortable environment, and checking out kid-friendly attractions like zoos, museums, and parks. 

Explore all USA City Guides here

We have taken a lot of city breaks in the past few years and some of them have been to the top cities in the country. We had fun in Times Square in New York and enjoyed beach time in Los Angeles. We biked the Golden Gate Bridge in San Francisco and went for a stroll along the Chicago Riverwalk. We had a romantic dinner at Larimer Square in Denver and fell in love with the beautiful balconies of the French Quarter in New Orleans. We saw the Liberty Bell in Philadelphia and the colossal arch in St. Louis.

We have also visited stunning museums and unique cultural attractions like the Museum of Jazz in New Orleans, the Field Museum in Chicago, the Denver Art Museum, and the Georgia Aquarium in Atlanta. And the food! We have eaten in Chelsea Market in NYC and at the Reading Hall in Philadelphia. We slurped on the sourdough clam chowder at Pier 39 in San Francisco and ate delicious Tex Mex at the Riverwalk in San Antonio. We drank and ate for hours at the famous buffets in Las Vegas. Want to share in our fun? Check out our list of best city breaks in the USA now!

Can you guess the best city breaks in America?

Top City Breaks in the USA

The United States is lucky to have a wealth of beautiful cities with prominent landmarks, historical attractions, iconic cuisines, and friendly locals for discerning visitors. You can easily plan a trip to most of these cities over a weekend or 3 days and see most of the famous attractions. Add in budget airlines and cheap airfare, and a city break also becomes a cheap holiday option. Here is our epic list of some of our favorite cities in the country which double up as excellent city breaks:

New York City

New York City is the ultimate city break not just for domestic travelers but also for visitors from across the Atlantic. The Big Apple has everything from famous museums and vibrant nightlife to iconic eateries and beautiful parks. Start your visit in Times Square, which is the tourist heart of New York City. Take your photo on the famous red steps, be transfixed by the flashing billboards, spot the Times Square Ball, and people watch. Times Square may be touristy but you can’t visit New York without seeing this #1 attraction. 

Other popular things to see in New York include the 9/11 Memorial & One WTC Observation Deck, Empire State Building, Rockefeller Plaza, Wall Street, Statue of Liberty, and Chinatown. For art and culture fans, see the stunning collection at the Metropolitan Museum of Art or Guggenheim Museum or MOMA. You can also see dinosaurs and other prehistoric animals at the American Museum of Natural History or witness the country’s maritime history at the Intrepid Museum. The city’s food scene is also legendary and draws visitors from across the world.

New York has lots of things to do for outdoor lovers as well. Take a stroll through Central Park and walk over its famous bridges or paddle in the lake. Or you can walk across Brooklyn Bridge and enjoy the city views from DUMBO. If you like climbing then head over to the Vessel and climb its many staircases while enjoying the views of the Hudson River. To plan your trip to the Big Apple, read our post on 37 Best Things to do in New York City.

New York as seen from Staten Island Ferry

Chicago, Illinois

Our favorite city ever! Chicago is a jewel of the Midwest. It is full of fantastic restaurants, shows, museums, and lakefront water views. While you can easily spend a week in the city without running out of things to do, the excellent public transport makes it easy to experience the best of Chicago over a long weekend as well. 

Chicago experiences all four seasons; the best times of year to visit are in late spring and early fall when the temperatures are milder. Summer and winter have more intense highs and lows but also lots of seasonal events like live music and festivals in the summer, and ice skating and holiday events in winter. In fact, Chicago in winter is a stunning panorama of dazzling holiday lights and icy Lake Michigan. 

Chicago is well known for both its museums and impressive downtown buildings, and no tourist should skip the architecture river cruise that is both entertaining and informative. An alternative is a stroll along the vibrant Chicago Riverwalk. The Art Institute of Chicago, Field Museum, and Shedd Aquarium are all nationally acclaimed and can each easily take up an entire day of exploration. Visiting these museums with the kids is our favorite family activity. Here’s a tip: Be sure to look into student and reciprocal museum membership discounts before you go!

Another essential attraction in Chicago is the Millenium Park. While the famous Cloud Gate sculpture – better-known as the “Bean” – is the main attraction here, other places of interest including the Crown Fountains, Lurie Garden, and concerts in the Pritzker pavilion are equally popular. Other things to see in Chicago include the Navy Pier, Willis Tower, and the Magnificent Mile. To explore other Chicago essentials including Garett’s and the Frank Lloyd Wright District, read our Chicago Travel Guide: 39+ Things to do in the Windy City.

Stephanie of Explore More Clean less

Chicago skyline on the Bean

Las Vegas, Nevada

If you like your city break to pack a punch in the form of incredible nightlife, glamor, and glitz then Las Vegas is perfect for you. Sin City is definitely not for the faint-hearted. With its casinos, gambling in big figures, and adult revue shows, Vegas is a whole different world. But even if you don’t indulge in any of this, the neon lights of Vegas and the attractions on the Strip are enough to charm you into never leaving the Sin City. 

Our favorite thing to do in the city is to explore the Las Vegas Strip and its casinos. The casinos display flamboyant architecture, beautiful artwork and decor, sculptures, lavish themes, and more. The casinos also have many free attractions and shows to entice visitors. Some of our favorite things to see on the Strip include the musical fountains of Bellagio, the false sky and the gondolas at the Venetian, the ride up the Eiffel Tower at Paris, the view across Brooklyn Bridge at New York New York, and the flamingo habitat at the Flamingo. To see all the nearby attractions, read our Ultimate Las Vegas Bucket List.

Where other cities have urban parks and green spaces for outdoor lovers, Las Vegas offers the whole of American Southwest for your admiration. If you have less than a day, then make the day trip to Red Rock Canyon or Death Valley. If you have more time, then plan a leisurely road trip to the Grand Canyon, Zion National Park, and Antelope Canyons. There are many national parks and natural areas in the vicinity of Las Vegas, so this is a perfect vacation for adventure lovers.

Las Vegas from above

San Francisco, California

When it comes to the West Coast, very few cities are as popular as San Francisco. The city has attracted hippies, entrepreneurs, and innovators since the 1950s. The city’s most famous icon is the Golden Gate Bridge, considered one of the engineering marvels of the century. Taking a photo of the Gold Gate Bridge shrouded in fog from one of San Francisco’s beaches is every visitor’s dream – which is not so difficult considering that the fog is present in SF year-round. In fact, it even has it’s own twitter account and a name – Karl, the Fog.

Apart from the bridge and the fog, San Francisco is most famous for its cable cars, pretty Victorian houses, the second-largest Chinatown, and the prison – Alcatraz. To visit Alcatraz, take a cruise from Pier 33. While you are at the pier, visit the Fisherman’s Wharf area and spot the sea lions lounging on the docks. This famous waterfront area has souvenir shops, stalls selling crabs and sourdough bread, cruise ticket booths, bike shops, maritime museum, aquarium, carousel rides, and even a Ben & Jerry’s. We recommend trying the famous clam chowder in a sourdough bread bowl – one of SF’s iconic dishes.

Read our San Francisco posts now to plan this part of the trip:
San Francisco 3 to 5-day itinerary ideas
17 Best Things to do in San Francisco on your first visit

Other popular things to do in San Francisco include shopping in Ghirardelli Square, walking down the crooked Lombard Street, admiring the view from Twin Peaks, and checking out the art museums. San Francisco is also a perfect starting point for road trips along the coast, either up towards the redwoods in Northern California or down via Big Sur and the Pacific Coast Highway. Or you can always visit the famous Yosemite National Park. 

Golden Gate Bridge, San Francisco

Miami, Florida

Miami is a fantastic city break for a weekend getaway or an international vacation destination. Some of our favorite things to do when visiting Miami are hitting the beautiful white sand beaches, exploring South Beach’s vibrant Art Deco district, visiting Little Havana for Cuban coffee and pastries, shopping at Bayside Marketplace, and sampling the Caribbean cuisine of Little Haiti. The fantastic Vizcaya Museum and Gardens are worth a stroll to appreciate their beauty. For gorgeous views of the Miami skyline, take a cruise on Biscayne Bay.

Additionally, a number of side trip options can make your time in Miami even more memorable. For a laidback road trip consider driving to the nearby Florida Keys. To explore the marshes and mangroves and spot gators, manatees, and more, visit Everglades National Park. Or you can even take a ferry over to the Bahamas, for a more exotic vacation.

While planning your trip to Miami, bear in mind the hurricane season. It stretches from June to November but usually peaks in September. Also, summer in Miami is very humid and very hot. The best time to visit Miami is undoubtedly the winter as it is generally still sunny, warm and pleasant. Springtime is also an ideal time to visit because the heat and humidity are not in full blast mode yet.

If you really want to stay in the middle of the action, you cannot get more Miami than South Beach. An abundance of chain and boutique hotels can be found in this part of the city for a range of budgets. As well, the South Beach neighborhood is highly walkable with loads of restaurants, shopping, and bars for all tastes.

Rebecca of KwaFare

South Beach Ocean Drive

New Orleans, Louisiana

For a charming city break with mild weather and a range of attractions, consider New Orleans! This famous city needs no introduction. Founded in 1718, New Orleans has a unique mix of French, Spanish, and African cultures. On exploring New Orleans, you will find famous streets, historic buildings, and city squares. Read our New Orleans itinerary now to plan your trip.

The buildings in the French Quarter boast of beautiful architecture, large wrap-around balconies, and central courtyards that are iconic to the city. There are museums such as The Presbytère and the Cabildo where you can learn about New Orleans’ past or the New Orleans Jazz Museum which is dedicated to the genre’s origin in the city. This is also a great area to try out some of New Orleans specialty dishes like a po’ boy sandwich followed by the famous beignets at Cafe du Monde. And, of course, you should go to a jazz club on Frenchmen Street.

After exploring the French Quarter, you should visit the adjacent Treme neighborhood. Also known for its music and food, Treme – specifically Congo Square – is the birthplace of jazz in New Orleans. As much as it is famous for music and architecture, NOLA is also famous for its elaborate, above-ground cemeteries. Saint Louis Cemetery No.1 is the most famous and worth a visit as it is quite unique.

If you still have time, there are also many other things to do near New Orleans including a day trip to visit old plantation houses or an airboat tour to explore the swamps. The best time to visit New Orleans is from December to May when the weather is great and many events are happening throughout the city. The summer and fall are cheaper times to visit but temperatures can be high and there is a risk of hurricanes. If you visit during the Carnival season, you will be treated to parades and festivities culminating in one big celebration on Mardi Gras Day.

Suzi at Survey Suzi

Jackson Square, New Orleans

Portland, Oregon

Portland is one of the best places for a city trip in the United States, in fact, it is also an amazing urban retreat in the Pacific Northwest. Spend a quick 3 days in Portland, Oregon and you’ll be able to check out the foodie scene, explore the hiking trails, and see the quirkiness of the city. 

When in Portland, one of the most popular things to do is try out all the amazing food. There are tons of restaurants and eateries ranging from thai at Pok Pok to interestingly flavored ice cream at Salt & Straw to aromatic Stumptown Coffee and much more. 

Portland is close to the Oregon coast as well as the Columbia River Gorge, making it a great place to start your hiking trip in Oregon. You can hike along the coast in Cannon Beach or see the insanely tall Multnomah Falls. You’ll definitely get an opportunity to see a lot of the greenery that the Pacific Northwest is known for!

The best time to visit Portland is in the warmer months, between May and October, the temperatures are higher and less rainy in comparison to the winter months. But honestly, Portland is great any time of the year. Some of our favorite places to stay in Portland include the Courtyard by Marriott Portland Downtown and Crowne Plaza Portland Downtown Convention Center. 

Constance at The Adventures of Panda Bear 

Portland skyline

Seattle, Washington

If you are looking for the best city break in the US, a long weekend in Seattle is highly recommended! This easy to navigate, walkable city, offers many great eats and attractions to visit even within a short timeframe. Known for its rainy days, pack your umbrella no matter when you go – or don’t, if you want to fit in with the locals! August is your best bet if your heart is set on sunny days.

The historical Pike Place is a must-do on your itinerary. In fact, it’s so tasty that you may want to add it twice! Consider a tour of the Market with a group such as Eat Seattle Tours. They will educate you on the history of Pike Place and how it came to be the landmark that it is today. The tour includes samples from several of the best restaurants and personal interactions with the market staff. Clam chowder, smoked salmon, or fresh chocolate, anyone?

The Seattle Center is just a short monorail ride across the city and offers the panoramic Space Needle views with its glass floors. It also sits right next to the Chihuly Garden and Glass Museum which is filled with glass exhibits that will exceed your expectations. Head over to Pioneer Square for an Underground Tour of the original city of Seattle which lies beneath the streets and is filled with juicy secrets and comedic anecdotes. If skyline views are your weakness, Kerry Park offers them in abundance and are best seen at sunset.

If you would like to see more of what Washington has to offer beyond the city streets, rent a car for a few hours and head to Snoqualmie Falls. This picturesque mountain town is filled with sweet candy shops, a quaint train station, and of course, postcard-perfect views of the cascades from above as well as from the boardwalk at river level.

Seattle has many hotels to choose from; The State Hotel is a beautiful choice downtown. The city has something to offer every visitor, whether it is coffee, nature, restaurants or history. You’ll find it the perfect place for a city getaway!

Sierra of Free to Travel Mama

Seattle skyline

Los Angeles, California

Los Angeles is the ultimate city break. The second-largest city in the country is famous for its movie star sightings, filming locales and studio tours, famous museums, art galleries, farmer’s markets, and of course the famous Southern California beaches. LA’s culinary scene is also world-class and the city continues to attract all kinds of travelers. The city experiences mild weather which makes it a year-round destination. See our Los Angeles itinerary post to plan your LA trip. 

Start your visit at the Hollywood Walk of Fame and spot your favorite movie stars on the pavement. See the Kodak Theatre and Chinese Theatre. Take a picture with the Hollywood sign. See Madame Tussauds and take a photograph with the street buskers. Take a tour of the movie studios and take a look behind the scenes. See the beautiful Walt Disney Concert Hall designed by Frank Gehry. 

Take a stroll around beautiful Griffith Park and visit the Griffith Observatory. The Observatory has many interesting exhibits and is housed in a beautiful building. You will also see beautiful views of Los Angeles from the courtyard of the observatory. Visit the Museum Row on Miracle Mile and step inside whichever you fancy. The Broad and LACMA are two of our favorites. Other things to do in Los Angeles include the Getty Center and Villa, Venice Beach, Santa Monica Pier, Musso & Frank Grill, etc. 

Almost as famous as it’s attractions, are Los Angeles many day trips. Take your car out on a spin to Malibu, Laguna Beach, Santa Barbara, or the Santa Ynez Valley wineries. Or head out to the desert and stay in a spa resort at Palm Springs. For a quirky destination, visit the nearby town of Ojai. In the winter, ski on the slopes of Big Bear. 

To spend a day on the water, take a ferry to Catalina Island or Balboa Island. For balloon rides, wineries, and other attractions consider a trip to Temecula Valley. If theme parks are your thing, then spend the day at Disney parks in Anaheim or visit Universal Studios. Los Angeles also makes the perfect start for a stunning California road trip

Los Angeles as seen from Griffith Park

Denver, Colorado

Denver is one of the most underrated cities in the country. It is full of culture, good food, and has excellent views of the Rockies. You can go hiking among the wildflowers in the summer and go skiing in winter – Denver makes a great year-round tourist destination. Denver also has a great nightlife scene, making it popular with visitors of all ages. 

Start your visit at the Denver Art Museum. Housed in a beautiful, contemporary building, the museum has a vast collection of modern and contemporary, Native American, and New World art. Then see beautiful downtown buildings such as the Denver Public Library and the Colorado State Capitol before taking a walk along the 16th Street Mall. This pedestrian mall is the place to be in Denver. It’s beautifully landscaped and lined with fashion brands, hip restaurants, pubs, and souvenir shops. This is also the best place to see the 4th of July fireworks in Denver. 

Another must while in Denver is the beautiful Union Station. This historic train station has been transformed to be the hub of Denver with food courts, boutiques, and a bar. Denver’s outdoor attractions are legendary. Watch a concert at the famous Red Rock amphitheater or go paddleboarding in the city’s parks. Denver has a great biking trail while the Denver Botanic Gardens are beautiful year-round. And of course, you need to see the Denver Broncos play at the Sports Authority Field. Read our post on Best Things to do in Denver for more attractions.

16th Street Mall in Denver

Washington DC

Washington D.C. is one of the best city breaks in the United States. It is brimming with history, museums, culture, and a robust restaurant scene. Even if you have been to DC before, it is possible to have a completely different trip on your next visit because of the sheer amount of things to do.

While on a trip to DC, you must see the monuments at the National Mall, the White House, the US Capitol building, the free Smithsonian museums, and the Washington National Cathedral. You can also take a stroll through charming Georgetown, visit George Washington’s home at Mt. Vernon, catch a sporting event, or hang out at a number of different festivals that occur in the city throughout the year. 

Foodies will love the international food scene in D.C. You can find almost any type of cuisine and there is no shortage of interesting cafes, restaurants, and bars. D.C. also has a thriving food truck culture! You will find all kinds parked near the National Mall on the weekends.

The best time to visit DC is in the spring. Around late March/early April the city turns pink with cherry blossoms and pink magnolias. Those blooms are followed by blooming redbuds, dogwoods, and azaleas. The cherry blossoms are world-famous and when you see the Tidal Basin at peak bloom, you will see why!

Staying near the DC Waterfront is a good central option to see most of the main attractions. If you want a bit more character try staying in Georgetown or Old Town Alexandria. If you want to save some money, try staying in the Rosslyn area of Virginia and take the metro into the city.

Lindsey at Abroad Wife

Cherry blossoms at the National Mall

Boston, Massachusetts

Boston is one of the most historic cities in the U.S., and it’s brimming with interesting sights and attractions. Whether you’re a history buff, a foodie, an outdoors lover, or a luxury traveler, you’ll find plenty to love about Beantown. 

One of the top things to do in Boston is walking the Freedom Trail, which will take you to many of the city’s most famous sights and introduce you to the area’s history. To get a totally different perspective, ride to the top of the Prudential Tower and take in the 360-degree views. Make some time for people-watching at the Boston Common and window shopping on Newbury Street as well, and if you’re looking for something outdoorsy, rent a kayak on the Charles River or head to Middlesex Fells for a hike.

The Boston area is made up of numerous neighborhoods and suburbs, each with its own unique identity. The North End, Back Bay, and the South End are the most popular for travelers, but hipster suburbs like Cambridge and Jamaica Plain also have a lot to offer. For the most convenience, look for accommodations near the Red or Orange lines of the MBTA (“The T”). 

Fall is hands-down the best time of year to visit Boston. You’ll avoid the sweaty heat of summer and the frigid snowstorms of winter, plus you’ll be treated to New England’s famed fall colors. For the very best leaf-peeping opportunities, time your trip for mid-October. 

Jennifer of Passions and Places

Boston downtown


One American city break that often goes overlooked is Philadelphia. It’s a fantastic city with a lot to offer anyone who visits. Philly is more manageable than New York City and comes without the sticker shock of high prices. Philadelphia is a lot more fun than Washington, DC and still provides world-class museums and loads of American history. There are just so many things to do in Philadelphia, here’s where to start.

Philadelphia is full of American history. The essential sites for visitors include Independence Hall, the Liberty Bell Center, and the Betsy Ross House. You can visit Christ’s Church and sit in the same church pew that George Washington did. Philadelphia’s amazing museums display the best in art and science; most popular being The Philadelphia Museum of Art and The Franklin Institute Science Museum. Families with kids love to visit the Please Touch Museum and the Philadelphia Zoo – it’s actually the oldest zoo in the nation.

The best time to visit Philadelphia is in the spring and fall months. During the shoulder season, you have smaller crowd sizes and moderate temperatures. It’s the best of both worlds! While in Philadelphia there are three neighborhoods that you should consider staying in. They’re all in the city center and the first is Rittenhouse. It’s a posh neighborhood with high-end hotels, shopping, and restaurants. Many visitors love to stay in Old City, an area known for the historic buildings and attractions that are older than the country itself. The third area to consider is the Gayborhood/Midtown Village. It’s a trendy section of Philadelphia known for charming local shops, delicious restaurants, and coffee shops.

Derek of Robe Trotting

Philadephia City Center


Charleston is an incredible city along the South Carolina coast. There are so many things to do and incredible sites to see in Charleston that it’ll make your head spin! Let’s start with the top 3 things to do in Charleston. First off, head to the beach. Charleston is home to miles and miles of shoreline, so do yourself a favor and spend some time along the Ocean. We recommend Folly Beach, since there is a wonderful little town to get some fresh seafood. Which brings us to item number two: eat fresh seafood. Ask a local what is in season, and the catch of the day will make for an incredible local meal. 

Third, head to downtown Charleston. Walkthrough the streets and explore one of the city’s many parks. If you have a car, here is a bonus fourth item: the Angel Oak. Just outside Charleston is the oldest (and most beautiful) tree East of the Mississippi River. It is worth the trip!

The best time to visit Charleston is in the Spring, ideally from April to June. The weather won’t be too hot at this time, and the plants will be lush and green. We recommend staying either near downtown Charleston or in Folly Beach. We opted for the beach life and had a wonderful time – every morning was spent watching the ocean waves crash on the shore and every evening was for ocean-side strolls.

Julie of Ruhls of the Road

St. Michaels Church and Broad Street in Charleston

San Diego

If you’re looking for the perfect city break in the US, you absolutely cannot go wrong with sunny San Diego, California! Boasting one of the best climates in the country — with perennial sunshine and year-round good vibes — San Diego also has a lot to offer visitors and is an essential place to visit in Southern California.

San Diego is perhaps best known for its expansive beaches and it really has some of the best in the state. If you want to have a beach day, you have numerous options available to you. Head to Mission Beach for a classic Southern California vibe, complete with a beachside amusement park and wooden roller coaster. Pacific Beach is also a fantastic option for more of a local feel. If you want to feel as if you’ve stepped back in time to the 1970s, then make sure to head to Ocean Beach, the least touristy of the three and home to the beautiful Sunset Cliffs State Park.

If you’re more interested in museums and culture, then make sure to visit Balboa Park, which is filled with countless museums and is also home to the world-famous San Diego Zoo. If you want to learn more about San Diego’s seafaring heritage, then make sure to head to the Maritime Museum located in the downtown area.

San Diego also has a hopping restaurant and craft beer scene, so it is a great destination for both foodies and beer connoisseurs alike. If you have more time, drive down to LA or go on an amazing Southern California road trip to Joshua Tree National Park. All in all, San Diego really has something to offer everyone and you cannot go wrong with a trip of any length to this beautiful California city.

Maggie of The World Was Here First

San Diego skyline

Nashville, TN

If you are looking for a city break that is loaded with options for both day and night, plus family-friendly as well, Nashville is a great option any time of the year! 

Nashville is the country music capital of the world, so there’s no surprise that you will have endless opportunities to enjoy all things music when you visit. Even if you don’t love country music, you can’t help but get caught up in the excitement. 

Many of the famous Honky Tonk venues have live bands every night of the week. Several also hold free line dancing lessons each night, which is one of those things you have to try. Even if you are uncoordinated like me! A night at the famous Grand Ole Opry is a must-do Nashville attraction too, with concerts all year at the auditorium. You may see a future superstar before they become a household name.

Beyond the music, there are plenty of great places to eat and cultural experiences to have. Head down to the Gulch to see some of the coolest street art, including the iconic #whatliftsyou angel wings. Then grab a bite to eat at the popular Biscuit Love nearby.

If you need a break from the hustle and bustle of the city, a short drive away you can visit one of the Plantation homes in Nashville, such as Belle Meade or the Hermitage. Here you will learn some of the darker histories of the city. For accommodation, try the Omni Nashville Hotel or stay at one of the many amazing private Airbnb rentals as we did. 

Holly of Four Around The World

Nashville has some of the best music!

Portland, Maine

Portland, Maine will win you over during your time there, whether you’re visiting for a week or for a weekend. With a population of more than 65,000 people, Portland somehow manages to have a small city vibe. Incredibly walkable and a foodie city at its heart, the city has a charming personality and a rich history you’ll love exploring.

One of the best things to do in Portland is to visit the six famous lighthouses that are accessible from the city center. They’re each unique in their own way. If you can’t get to all of them, the two best ones are Portland Head Lighthouse and Bug Lighthouse.

Next, explore the foodie side of the city and take advantage of the fresh and delicious seafood. The lobster in Portland is one of the best in the country, you won’t want to miss out! Take a walking foodie tour to eat your weight at some of the city’s best restaurants or jump aboard the Lucky Catch lobstering tour on Casco Bay and catch your own.

In addition to great food, Portland also has 300+ microbreweries – more than any other state! Maine Brew Bus runs great 3-hour long tours that include tastings at three spots and are a great (and responsible) way to visit the best breweries. Time permitting, take a tour of the islands on Casco Bay ferry or hang out around Portland’s beautiful waterfront. The best time to visit Portland is between June and September. Most of the attractions don’t open until the end of May when the cold weather starts to wind down.

Ioana of The World Is My Playground

Eat fresh seafood in Portland

St. Louis, Missouri

If you are driving from the east coast to the west coast or vise versa, you will want to make sure that you pass through “the Gateway to the West.”, the city of St. Louis. St. Louis sits right on the mighty Mississippi River and, honestly, is one of the most beautiful cities to drive into.  

St. Louis is known for the iconic St. Louis Arch that sits along the Mississippi River. The 630-foot stainless steel arch is actually a part of the Gateway Arch National Park. It is also the tallest arch in the world. Did you know that you can ride an elevator to the top of the arch? At the top, there are small windows from which you have a beautiful view of the Mississippi and St. Louis. At the bottom of the Arch there is a great underground museum called the Museum of Westward Expansion with many exhibits about westward expansion and the Lewis & Clark expedition.

In addition to the famous Mississippi River, downtown St. Louis has a number of sights and is quite walkable.  St. Louis has a rich baseball history, so attending a Cardinals game is a great activity. We also enjoyed visiting the famous Anheuser Busch brewery.  They have a number of tours and a great tasting area for lounging, food and even some live music.  

Other things to do in St. Louis include visiting the Old Courthouse, exploring the grand Union Station, and enjoying a night out at Laclede’s Landing Riverfront area. We visited St. Louis during the spring, and found it to be a lovely time of year to visit because it wasn’t too hot or humid, yet we had wonderful sunshine and warm weather. As for where to stay, we found a great Airbnb in a historic part of town which enhanced our experience and made it quite an enjoyable weekend getaway.

Josh of Peanuts or Pretzels

San Luis Obispo

If you’re looking for a city break in the US that’s also an excellent place to relax, you can’t go wrong with a visit to San Luis Obispo. This city sits on the central coast of California and is delightful all year round…although spring and fall are two of my favorite seasons to visit.

A visit to San Luis Obispo (SLO) offers a variety of entertainment options, from shopping in the cute downtown shops to enjoying the famous weekly Farmers’ Market on Thursdays. The market has lots of fresh produce and delightful handmade products for sale and is worth a visit. While in SLO, you must also explore the local Mission San Luis Obispo de Tolosa – it is a part of the founding heritage of San Luis Obispo from the year 1772. If you love charming cities, then this is the perfect place to visit!

But if you also enjoy the outdoors—mountains and beaches and all the fun that can be had in the sunny California weather—then SLO is also the place for you! Bishop Peak is a famous local hike that will give you excellent views over the city and the surrounding areas, while nearby beaches like Pismo and Avila provide no end of fun in the water.

If this sounds like the type of city break for you, then be sure to stay at the Madonna Inn—a local landmark in and of itself, with each room decorated in its very own unique style. Your visit to San Luis Obispo will certainly be unforgettable and you’ll want to return time and time again!

Abi at Happy Go Abi

View of SLO from Bishop’s Peak

Billings, Montana 

It’s little by city standards, but there are so many fun things to do in Billings, Montana. Whether you are into history, good food and drinks, active play, or outdoor activities, you’ll find what you are looking for in Billings. 

We always try to include one or more museums in our visits. The Yellowstone Art Museum showcases modern Montana (and Western) artists. The Yellowstone County Museum is chock full of Native American beadwork and projectile points, as well as displaying a two-headed calf. And the Moss Mansion is a turn-of-the-century mansion featured in movies and T.V. shows. 

For outdoor fun, we enjoy the view of the Yellowstone River and Billings from Four Dances Natural Area, guessing the meaning of the pictographs at Pictograph State Park, and witnessing William Clark’s (of Lewis and Clark fame) signature at Pompey’s Pillar National Monument.

Billings has a great downtown filled with a surprising food scene. You can take a self-guided brewery and distillery tour, eat farm to table meals, and explore the Western cuisine. 

For family fun, we recommend a stroll through ZooMontana, bouncing at Get Air! trampoline park, and splashing around at The Reef Indoor Water Park. You can stay at the Big Horn Resort, which is home to The Reef. We also like to stay at The Northern in downtown. 

Mel of Traveling Mel

Beautiful Billings


Milwaukee is continuing to grow in popularity as a city that’s worth checking out and we couldn’t agree more. You can always find something to do no matter what time of the year, but we highly recommend paying a visit in the summer, as summers in Brew City are hard to beat. 

Believe it or not, Milwaukee is home to the world’s largest music festival, spanning over 11 days with 11 stages at the end of June and into the start of July. Not only will you get your concert fix, but Milwaukee’s best restaurants will have food stalls on the festival grounds, so it’s a great place to sample the city’s best food! 

Don’t worry – we didn’t forget about the beer! Milwaukee is the city that beer built and today there are so many breweries to visit. We highly recommend Lakefront Brewery for its tour, known as one of the best tours in Milwaukee. 

Other notable stops in MIlwaukee include the Harley Davidson Museum, Pabst Mansion, Milwaukee Art Museum, and the Historic Third Ward. As for the best places to stay, we highly recommend either the Pfister Hotel located in the heart of downtown or the Kimpton Journeyman Hotel, in the Third Ward area.

Adam at Milwaukee Insider

Summerfest, Milwaukee

Naples, Florida

On the southwestern coast of Florida  – on the western edge of the Florida Everglades – lies Naples, Florida, one of the most popular vacation spots in the United States. Situated on the Gulf of Mexico, Naples is easy to get by land, sea, and air — via Regional Southwest International airport (RSW) just 30 minutes away. 

Naples offers visitors year ‘round sunshine and warm weather, beautiful white sand beaches, endless shopping, golf courses galore, and a vibrant restaurant scene. Everything from fine dining, local seafood, and low key food truck fare is on the menu at over 700 eateries. 

The cultural and performing arts scene also makes Naples a great destination — just about any time of year visitors can enjoy performances (many of them free of charge) ranging from concerts in a local park, jazz on the beach, and live performances from a range of international talent. 

Stay at the luxury Inn on Fifth for the best location in the city right on Fifth Avenue South, where you’re surrounded with excellent shops, restaurants and the beach just blocks away.

There’s a lot to offer on a short city break, but one of the favorite things to do in Naples among visitors and locals alike is simply to catch a fiery sunset at the Naples Pier, a perfect way to end your visit.

Lori or Travlin Mad

Sunset on the beach at Naples

Did you like our post on the best city breaks in the USA? Did we miss out on any of your favorite cities? Let us know the answer in the comments.