Top 5 Weekend U.S. City-Breaks

Why don’t we travel more often? Usually the excuses boil down to two main concerns, getting the money and the time to do it. So we’ve put together our top 5 favorite U.S. cities (in no particular order) that are perfect for spending just 2-3 days in. Best part? There are frequent flights to each of these locations, meaning the cost of these flights is lower and you can accomplish what you want over just a weekend! Concerns are solved, now get to booking!


No, you don’t have to LOVE country music, but it does help if you do!

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Nashville is a very clean city and everyone is overly friendly. Spend your Saturday walking down Broadway St, which is fully lined with bars & restaurants buzzing with live music and tons of people no matter what time of day it is. The Stage and Tootsies are great honky-tonk bars where you can see the next big country star before his/her fame kicks in. Keep going to the end of the street and check out ACME bar’s roof deck to enjoy views of the river and sunshine.

The Gulch is another great area of Nashville (~20 minute walk from Broadway or short cab ride), with less of a touristy feel. This area is close to Vanderbilt University, and you’ll get more of the college student, trendy-vibe here. Check out Kung Fu Saloon in this area which is an indoor/outdoor bar featuring an indoor arcade and outdoor games like cornhole and giant-sized Jenga.

If you’re a big country music fan, check out the Country Hall of Fame. And if you happen to go during hockey season, you must see a Predators game! Nashville has made news throughout the country for their rowdy crowds, catfish throwing escapades, and random celebrity performance surprises in-between periods!

Bachelor or bachelorette? Put this place on the top of your list for your bash! Although you will see several grooms/brides-to-be while you’re there, it’s an ideal location due to the warmer temperatures, very safe reputation, and low prices.

San Francisco


Famous for its steep hills, cable cars, and beautiful Pacific oceanfront with views of Alcatraz and the Golden Gate Bridge, this city doesn’t disappoint. Enjoy some Philz coffee, which is the Bay area’s new Starbucks while walking around Alamo Park. This high altitude park gives you views of the Painted Ladies (colorful homes next to each other) with a skyline view of the city and bay. Next, head to Lombard Street, which is famously filmed for the extremely windy, downhill road. Continue making your way to the water and stop at Pier 39. Grab some lunch and see the sea lions wrestle each other, enjoy street entertainment, and hop on the two-storied merry go-round!


After lunch, it is essential you walk the 15 minutes to Ghiradelli Square for their famous ice cream you can smell from a mile away. The line will look long, but they are efficient there and it’s worth the short wait.


Drive/bike over the Golden Gate Bridge, and when you see the majority of tourists pulling off at “Vista Point” for pictures, keep going. Take your next exit on Alexander Ave, and loop around for a higher-up, stunning, and less crowded view of the bridge and city. Continue out of the city to Sausalito for dinner. If you’re driving, it’s worth the toll back into the city, and if you’re biking, it’s worth the extra mile or two (but definitely take the ferry back!). This adorable town is full of quaint shops, oceanfront restaurants, million dollar houses in the hills, and million dollar boats in the bay. Grab some dinner at Salito’s on the deck for a gorgeous sunset and delicious Alaskan King Crab legs!


If you feel happy with what you covered in the city in a day, there are amazing destinations within an hour’s drive such as Napa Valley, Sonoma Valley, or Muir Woods. These wine valleys and national monument will make you feel a million miles from a city and may be the perfect way to unwind before your trip home.


chicago bean up close

Chi-Town, or the Windy City, is one of my favorite places to visit due to the constant changes and things to see. The sky-scraping architecture is stunning, and despite being in the midwest, you get a coastal feel due to the unending sights of Lake Michigan.

Spend your morning walking along the riverfront, stopping for breakfast to watch boats pass you by in the narrow river. You can people watch as Chicago-natives jog past, tourists meander through, and musicians choose a spot to entertain passersby.

chicago river

Check out “The Bean”, the centerpiece in Millennium Park. This huge, reflective bean gives a mirrored view of the skyscrapers behind you, plus a distorted version of you! For a spectacular view looking down on the Bean and entire downtown, grab a drink at Cindy’s rooftop.

To get an even higher view, head over to the John Hancock building and take the elevator up to the 96th floor Signature Room for 360 degree views of the city from the highest point you can get (without the need for a helicopter). Ladies: the best view is actually from the women’s restroom – so whether you have to go or not, get yourself in there!

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If you like to shop, head to Michigan Ave for non-stop storefronts. Beware – there is a clothing tax of 10.25% in Chicago! So make sure you love it before you buy it. If it’s nice out and you’d prefer to soak up the sun, head to North Avenue beach where you can rent kayaks, jet skis, or just sit back and watch some volleyball games.

In the evening, head to Roof on the Wit for more great skyline views and a modern, classy atmosphere. For more of a casual atmosphere, get yourself to Wrigley Field for a game and experience one of the oldest ballparks in America.


New Orleans

new orleans balconies 3

New Orleans is a city you must visit for three reasons: the food, the music, and the architecture (fine and maybe to give out/receive some beads if you really want). Expect to hear jazz music resounding from each street corner. Be ready to eat any type of food fried, my favorite was crocodile legs. Enjoy the buildings that are unlike any others in America, full of color and cast-iron balconies for a signature New Orleans look.

Head to the French Quarter in the morning and you’ll suddenly feel like you’re in Europe. This is the oldest area of the city, and the gorgeous architecture shows it. Buildings boast their original Spanish & French designs, and you have the opportunity to tour these homes or simply enjoy the many boutiques that line the streets. Line up at Cafe Du Monde for a signature New Orleans beignet (pronounced Bin-Yay), which is basically an even more delicious take on fried dough.

new orleans french quarter

Walk down the famous Bourbon Street which has endless amounts of bars, restaurants, and musicians on the street. You may see people holding a crawfish boil right on the sidewalk and selling this traditional New Orleans dish to people walking by.  This street is extremely famous for the Mardi Gras parade which is held two weeks before Ash Wednesday each year. If you like to party, you want to be here!

Frenchman Street is the not-so-touristy Bourbon Street. Take out the neon lights, add in more locals, and there you have it. Live music will be playing each night of the week, bars will be slightly less expensive, and the atmosphere is much more enjoyable.


boston skyline

Famous for its history as one of the oldest American cities, Boston has a gorgeous design with old-English charm on the coast of the Atlantic Ocean and built around the Charles River. Due to early settlers, the city was built by roads created from horse and carriage, meaning you won’t find the standard city grid-like set up here!

Get yourself to Dunkin Donuts, New England’s signature coffee franchise which can literally be found on every block. With your caffeine kick, stroll down Newbury Street which is famous for its luxury retail stores. If you’re not into spending hundreds of dollars on a tank top, focus on the stores on the far end of the street, and expect more high-end options as you get each block closer to Boston Common. Spend some time wandering around Boston Common, a gorgeous garden surrounding the State House with its signature golden roof.

boston common

Continue from Boston Common to Faneuil Hall, which has a strong British influence and is lined with cobblestone streets and pathways. It’s a very quaint area with a food/gift market in which you can find almost anything! Restaurants and bars come alive at night, and street performers are always entertaining.

From Faneuil Hall, get yourself to the North End which is Boston’s Italian area. This small picturesque neighborhood is full of Italian restaurants, and the food is top notch. You’ll notice a line of people for blocks, and they are all waiting to get into Mike’s Pastry for amazing dessert. The line moves amazingly fast – so don’t miss out!

Boston is a city famous for it’s sports teams so depending on the season you are there, get yourself to Fenway Park or the Boston Garden!


An easy way to see all of the city is to follow the “Freedom Trial” which is 2.5 miles along downtown Boston highlighting historic sites from the battle with the British, this will take you to almost all of the major destinations in Boston!


Are you doing a weekend city-break this summer and want advice on where to stay and what to do? Reach out at any point!




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