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10 Best Vacation Cities for Architecture-Loving Contractors

10 Best Vacation Cities for Architecture-Loving Contractors

If you’re a contractor who appreciates great workmanship, getting away from the 9:00 to 5:00 (or 7:00 to 7:00) opens up the opportunity to experience some of the best architecture America has to offer. The nice thing is, excellent architecture tends to be close to great food and entertainment, making it easy to take along your spouse and/or family. Our top 10 best vacation cities for contractors who love architecture and construction all have a special place in the hearts of our team.


Vacation Cities for Contractors Who Love Great Architecture and Construction

#10 San Francisco, California

10 Best Vacation Cities for Architecture-Loving Contractors } San Francisco

San Francisco has some issues they need to work out, but once they get it together, there’s some fantastic construction and architecture to check out. The big highlight is the Golden Gate Bridge. There’s also an interesting mix of modern and Victorian styles among residential areas. For the traveling contractor, it’s seeing how builders deal with the challenging geology, elevation changes, and potential for earthquakes that make it worth seeing.

#9 Chicago, Illinois

10 Best Vacation Cities for Architecture-Loving Contractors | Chicago

Another city that has some issues, Chicago is fascinating as an architectural destination. Skyscrapers dominate the downtown area. While many are modern and reach high, it’s some of the original skyscrapers worth taking a hike and looking for. There are several pre-1900 designs still standing, including the DeWare Building (1862), the Rookery (1886), and the Second Letter (1889).

I recommend a walk down the riverside to the lake if it’s a nice day. Just be sure to take a jacket—I was walking on a calm, clear 80° day, and in 15 minutes, clouds rolled through the skyscrapers, the temp dropped below 60° and the wind picked up to 25 MPH!

#8 Las Vegas, Nevada

10 Best Vacation Cities for Architecture-Loving Contractors | Las Vegas

If you like to gamble and love a party that never ends, Las Vegas has to be on your list. While the architecture is more recent than some of the cities on our list, it’s absolutely incredible! Where else are you going to find a pyramid in the desert without going to Egypt? Be sure to check out the inside of the Venetian and pop into the Venus Garden of Ceasar’s Palace to be impressed by how its building design drowns out the sounds of the city.

#7 New York, New York

10 Best Vacation Cities for Architecture-Loving Contractors | New York

There’s no question that skyscraper lovers have to visit New York at some point. With some of the oldest and newest skyscrapers (with more in development), it’s a testament to builders’ ingenuity, bravery, and perseverance. Not only is it iconic to American architecture, but there’s also a massively diverse group of people that made them happen, from the design and foundation to the steelwork and first flipping of the breaker.

#6 Philadelphia, Pennsylvania

10 Best Vacation Cities for Architecture-Loving Contractors | Philly

If your love for construction and architecture includes an affection for history, Philadelphia is a great destination. Similar to San Fransisco, there’s a blend of modern and Victorian styles along with the classic English rows (AKA Philadelphia rows) building style. Be sure to book your stay at the Loews Hotel that’s an easy walk away from Philadelphia’s impressive city hall—both will get your builder’s heart racing.

#5 St. Augustine, Florida

While a lot of the downtown area has a touristy/amusement park feel, St. Augustine is the oldest city in the United States and it has the oldest masonry fort in the country. The Castillo de San Marcos began construction in 1672 and played a large part in our history. There’s plenty to see from the outside for free, but it’s worth the $15 entry fee to get a better look at the coquina limestone construction and read about the history. Kids under 15 are free with adult admission.

#4 New Orleans, Louisiana

Despite annual threats from hurricanes, New Orleans rebuilds and restores in a way that shows off its rich French, Spanish, Creole, and Caribbean heritage in its building design and colors. The French quarter downtown is a must-see before heading uptown to visit the Garden District for New Orleans’ impressive collection of Antebellum designs along with mansions built with Greek Revival and Georgian architecture.

#3 Cape Elizabeth, Maine

If you’re on the hunt for impressive construction, a trip to the Northeast for a lighthouse road trip is well worth your time. Top on our list is the Portland Head Light at Fort Williams Park in Cape Elizabeth. It’s the classic craggy rock outcropping location set on 90 acres with a beautiful home and keeper’s quarters attached. Part of what’s so fascinating is the lighthouse’s age and history—it was built in 1787 for just $750.

The site is open year-round from sunrise to sunset and it’s worth the effort to be there for the sunrise.

#2 Charleston, South Carolina

Charleston, South Carolina is an iconic and idyllic example of what coastal construction should be. Similar to sections of New Orleans, there’s a healthy influence of Antebellum design mixed with other late 1800s styles. As you walk or drive through town, you’ll notice the wide range of Victorian and Greek Revival architecture alongside Georgian, Federal, and even Italiante.

Be sure to make time for a trip down the waterfront where you can see some of the classic 19th century Southern mansions along Battery Row.

#1 Washington, DC

There may be no greater city for building and monument architecture than Washington, DC. The entire downtown area is full of some of the finest of work of its time. Even the layout of the city and its streets are worth studying. And why not? It was and is the capital of our country and a symbol of the freedoms we enjoy.

Bonus: Lakeland, Florida

Aside from the fact that PTR is headquartered in Lakeland, we also have the largest single collection of Frank Lloyd Wright architecture at Florida Southern College. Most of it is still in use. From the Annie Pheiffer Chapel to the water dome and the esplanades, it’s a must-do trip for fans of Wright.

While you’re here, hit up Palace Pizza downtown for the best pizza and Italian dishes that locals line up for, or give Nineteen61 a shot if you’re looking for something more formal and upscale. Lastly, we can’t forget to recommend eating at the excellent, if eclectic, Joinery which overlooks the beautiful Lake Mirror. Be sure to make time to walk around our downtown lakes and drive out to Circle B Bar Reserve to see some of Florida’s famous alligators.

What’s your top travel destination? Let us know in the comments below!


While you’re here, check out our buying guides to find the best tools across a ton of categories.

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