Top 10 US Cities for Long Weekends
Updated: Jun 11, 2022
Almost all travel posts for the top 10 US cities include New York City, Boston, Miami, San Francisco and Los Angeles. This top 10 list will not. Not that I don't love to spend time in each of these cities (and I've visited each for work/fun easily over 200 times), it's more that we wanted to focus on some of the smaller, sometimes less traveled cities across America. I wanted to include places that have their own unique culture, food, outdoor activities, history and architecture. The "Big Five" listed above certainly have all of these aspects, but we'll cover our travels with them in other posts. Some of our favorite cities are not the typical cities people visit for long weekends, but they should be. A few are pretty far flung, but distance has never stopped me from flying for a long weekend (I once flew round trip to Shanghai for three days!!). These are the places that pop into my thoughts when I think of a great long weekend:
10. La Jolla, California
La Jolla is exactly the town you think of when you picture southern California. Beaches, ocean front communities, tall palm trees and lots of people watching. La Jolla is just a short drive up the coast from San Diego (a very nice city to travel in as well), and it has the small, beachy, locals only vibe you'll want to experience. The highlight of the area is La Jolla Cove and it's local resident population of pacific harbor seals and California sea lions. You can walk out onto the small beach and swim or snorkel with the seals and sea lions in close proximity. You will also most likely encounter them in close quarters up on the rocks as well. It's best to keep your distance and not disturb them, but they are amazing to watch. The area is also frequented by leopard sharks and the occasional otter. You can rent a kayak and even take a kayak tour into the cave. There are plenty of shops and restaurants within walking distance, but going up from the park is a fairly steep incline when walking.
Pros: Amazing wildlife, great views, great restaurants/bars, old school southern California
Cons: Limited parking, accommodation can be expensive, the seals are pretty stinky!
9. Nashville, Tennessee
Music City USA or "Nash Vegas" as it's become known is a great city to dive into live music, cold beer and spicy hot chicken. On the main strip of Broadway, you can't throw a stick without hitting live music or someone who thinks they are country music's next big star. Most of the venues have a long history and you can actually find a pretty wide variety of music and not just country. Everyone should purchase a pair of cowboy boots and bar hop down Broadway in Nashville at least once in their lives. And when you're hungry, head over to Hattie B's for the original Nashville Hot Chicken, which is exactly as it sounds: spicy, hot and amazing. Best with a cold domestic beer, don't get too fancy. Nashville has a pro football and pro hockey team if you're lucky enough to be in town during a game. And there are interesting historic sites, such as the full scale replica of the Greek Parthenon in Centennial Park.
Pros: Great live music, local southern food, reasonable accommodation, party culture
Cons: Crowded, The enormous swarms of women all dressed the same will get tiresome
8. St Augustine, Florida
The first of two cities in Florida on this list, St Augustine is distinctly different from most other Florida destinations. It's the oldest European settlement in the US, it's been a Spanish fort, trading post and a haven for pirates raiding the southern coasts. Most of the buildings in the historic area retain an older Spanish style of architecture and you can explore the large Spanish fort, Castillo de San Marcos within walking distance. The historic part of the city (the Spanish quarter, now called "Colonial quarter" and Old Town) makes you feel like you're back in 1700's colonial times, with dozens or local shops, BnB's, restaurants and pubs all done in colonial style. You can cross over the bridge of lions, famous for it's Italian inspired Medici lion statues and head to the beach on Conch island or Anastasia state park. Stop by the marina and have a cocktail and some fresh seafood at the Conch House, located on the marina. Check out the Cuban styled Columbia restaurant for beautiful atmosphere, mojitos and great food.
Pros: Very walkable, beaches aren't that crowded, amazing history and culture
Cons: Nearest airport is JAX over an hour away, Parking can be tough at times
7. San Antonio, Texas
Once the capital of Mexican Texas, San Antonio has become an enormous city in Southern Texas. The best place to spend a long weekend is around the Riverwalk area, where you'll descend down stone steps to find a winding river flowing through the city. The Riverwalk is lined with restaurants and you can even take a boat ride through the river. There's nothing like sitting on an outdoor patio at night, enjoying a margarita and admiring all the massive tree's illuminated with thousands of decorative lights as people and boats pass by. It's especially beautiful during the holidays as even more lights are added. As you climb out of the Riverwalk, you're a few steps away from the Alamo. This is a must see in San Antonio and you can easily spend a couple hours exploring the Alamo complex. A short Uber ride away is the Pearl area, filled with unique local spots and watering holes. San Antonio also has SeaWorld, several US Air Force installations and the NBA Spurs team. Austin is a little over an hour drive north, and if you're up for a road trip check out The Salt Lick BBQ for serious Texas BBQ in an amazing setting.
Pros: Riverwalk area is very walkable. Great BBQ and amazing Tex/Mex style food
Cons: Traffic can be brutal, Lot's of drunk people, homelessness is a problem
6. Albuquerque & Santa Fe, New Mexico
The land of enchantment and Breaking Bad. Albuquerque and Santa Fe are two of my favorite cities to visit and they are about an hour drive between the two. Albuquerque is much bigger than Santa Fe, but walking around in the old town amongst the adobe buildings, shops and restaurants feels like walking through time. Check out Church St Cafe, which looks very small from the outside, but is really a sprawling complex with outdoor seating and beautiful "old west" décor. The food in both towns is fantastic, especially for old school traditional New Mexican cuisine. People are obsessed with chili's here, and you'll be asked "red or green" when ordering pretty much anything. Act like a local and just respond by saying "Christmas", and you'll get a blend of both chili's. Santa Fe has an impressive plaza filled with local merchants and adobe buildings. There are tons of day trips you can make from ABQ, and getting out and seeing the vast New Mexico sky is an attraction itself. Try a day trip to the wild west and visit Lincoln, site of many of Billy the Kids exploits. Or take the long drive to White Sands national park and be amazed at the cool to the touch gypsum dunes. And if you do visit the Breaking Bad filming sites, the real owners of Walter White's house are not fond of visitors and are generally extremely rude to people standing in the street, let alone the side walk.
Pros: Spectacular outdoor scenery, Sandia Peak tram, unique culture and food
Cons: ABQ has some rough areas with high crime rates and drug involvement
5. Tucson, Arizona
If you love the outdoors, then a long weekend in Tucson is perfect for you. The city itself isn't really the main attraction, but the stunning desert surrounding Tucson absolutely is. Take lots of water, but hiking in Sabino Canyon or Saguaro national park should always be on anyone's list for visiting the Sonoran desert. Here massive Saguaro cactus take the place of trees, and you can see thousands when wandering the many hiking trails. We prefer to stay on the Oro Valley or Tanque Verde side of town, and there's lots of local favorites for delicious southwestern cuisine in this area. Tucson is not a very fancy town, it's a more laid back vibe than the city of Phoenix just over 100 miles north. Tucson is old west, laid back desert. If you time it during the right time of year, you can start your day with a hike in the desert, then drive up Mt Lemon to experience a completely different climate and even ride a ski lift over snow! For history buffs and aviation lovers, the Pima Air and Space museum is one of the largest collections of aircraft in the world. And you drive through the military's aircraft boneyard and see rows upon rows of aircraft sitting in the hot desert sun. For a unique day trip, Tombstone is a short drive south and worth an afternoon exploring the dusty streets of a former wild west gunfighter mining town.
Pros: Exceptional outdoor hiking and biking, real southwestern cuisine, beautiful views
Cons: Extremely hot in summer, thorns, spines & dangerous wildlife, some rough areas
4. San Juan, Puerto Rico
It's hard to find a more perfect destination for a long weekend than San Juan. It's not #1 on this list as it's a bit more difficult to get to than the other destinations, especially if you don't live on the east coast. Being in San Juan is like being in a foreign country, but with all the conveniences of being in the US. Puerto Rico is part of the US, so you don't need a passport to visit this island paradise if you're a US citizen. You can spend days wandering around the cobblestone streets and colonial Spanish buildings of Old San Juan. While you're exploring you may as well stop at bar where the Pina Colada was invented at Barrachina and order one (or three). You can't miss the massive El Morro Spanish fortress dominating the tip of San Juan's ocean front. On the other side of Old San Juan you can explore the largest Spanish fortress built in the new world, El Castillo de San Cristobal. There are plenty of resorts in San Juan with white sand beaches and crystal clear Caribbean water. But if you want a real Puerto Rican experience like the locals, head to La Placita at night where most of the tiny shops turn into miniature bars serving ice cold beer. Impromptu live music starts playing at many of these spots and the streets become a giant salsa dance floor. You'll mix with more locals than tourists and it's an experience you'll brag about to your friends when you get home. If you get really adventurous, hop on a small plane and fly out to one of the Spanish Virgin islands of Culebra and Vieques for unspoiled tropical beauty and a true island paradise off the beaten path.
Pros: No passport/currency conversion for US, amazing warm culture, immersive history
Cons: A bit of a further flight, some areas still recovering from Hurricane Maria
3. New Orleans, Louisiana
The Big Easy, Nola is a fantastic city to spend a long weekend. The newly opened airport and addition of several low cost carriers makes getting to New Orleans even easier. Everyone should experience New Orleans at least once in their life for the incredible food, beautiful French inspired architecture, amazing culture and the "Laissez les bons temps rouler" attitude. The French quarter is a must see, and Bourbon and Royal streets are crammed with bars, restaurants and plenty of street performers. But to really experience Nola, you have to get away from the tourist area of Bourbon St. One of favorite activities is strolling the less visited back streets in the quarter or the garden district and just taking in the beautiful homes and gardens. We've stumbled upon residents opening their windows and serving free drinks more than once. For live music, you should experience Frenchmen street for music venues and mix with the locals for some of the best jazz music around. There seems like there is always something happening in New Orleans and you can stumble into countless festivals and concerts. It's also the best city to eat your way through, with so many amazing restaurants. My favorites are crab cheesecake at The Palace Cafe, the boudin stuffed pork chop at The Court of Two Sisters and the oysters and seafood platter at Peche. Drinking is a way of life in New Orleans, and it's easy to spend an afternoon chatting it up while drinking sazeracs and vieux carre's while spinning slowly around on the carousel bar at Hotel Monteleone. If you do go during Mardi Gras, go the week before the final weekend to experience the parades and atmosphere without the massive crowds.
Pros: Amazing food, live music, beautiful French styled homes, serious partying
Cons: New Orleans can be a very dangerous place, with high crime rates, be careful!
2. Key West, Florida.
The southernmost point in the continental US is one of the most unique cities in all of America. The eclectic mix of people that don't fit in elsewhere, fit in perfectly in Key West. You may be in the state of Florida, but Key West is it's on it's own pace and it's own set of rules. Bar hopping on Duval street and drinking in the same watering holes as Hemingway and Buffett is an experience all should partake in at least once. Make sure you get away from Old Town and Duval street for a while and explore the other parts of the island. There are great locals spots on nearby Stock island for fresh Conch fritters and cold beer like Hogfish bar and grill. Key West time is best when it's spent on the water, snorkeling & diving the offshore reefs, kayaking the mangroves or floating with tropical drink in the water. Stroll around Mallory square before sunset and mingle with the many street performers and tourists and wait for the spectacular sunset celebration. Restaurant choices go from fairly cheap local spots to extremely fancy, expensive one in a lifetime dinners at places like Latitudes on sunset key. With the year round warm weather, tropical palms and exotic flowers, and laid back conch culture, you'll be one of the many who ask themselves: "Why don't I sell everything and move here?". You should! And if you need more convincing, check out more details and activities for Key West here.
Pros: Warm weather, turquoise Caribbean ocean, eclectic people watching and culture
Cons: Can be seriously hot, parts of Key West (old town) have many, many drunk people
1. Charleston, South Carolina
We may be a bit biased when it comes to our home town of Charleston, but having now visited all 50 states and almost every major city in the US, Charleston is still the nicest (in my opinion). It's a beautiful city, with intact colonial styled building painted in pastel colors with huge open porches and hidden well manicured gardens. The downtown area is very walkable and even after living here our entire lives, we still love walking around the quite streets below Broad st and admiring the stunning homes and history. Charleston has become a culinary hotspot, and world class chefs are opening and experimenting with new restaurants all the time. Despite other cities claims (looking at you Savannah), the original and best sweet tea, shrimp & grits, and she crab soup are found in the Holy City. Make sure to try them at Poogans Porch and 82 Queen. And if you come during oyster season, try to attend an oyster roast or make sure you get a pot of fresh steamed oysters at Bowens Island or Red's Icehouse. Best with a cold beer. Fantastic long sandy beaches surround the Charleston peninsula with Isle of Palms and Sullivan's Island on one side and Folly Beach on the other. If you need more convincing on coming to Charleston, read our guide here for plenty more experiences you won't forget. Come soon, as the secret of why Charleston is the best US city for a vacation weekend is definitely out and sadly the culture is starting to change a bit. Come see it before it's gone.
Pros: Downtown is easily walkable, amazing food, real southern culture, history
Cons: Hot & humid summers, wait times at restaurants, lots of tourists sometimes
Bonus: Las Vegas, Nevada
Las Vegas was originally not on this list, back when we first published our favorite weekend destinations, but everyone should experience it at least once, so we've added it to the list. Personally, I like to stay somewhere on the Las Vegas strip as it's close to the airport and you can walk to just about all the attractions. We also really like downtown Las Vegas around Fremont St, and there are several new hotels/casinos in the area that are really nice. Walking the Vegas strip is always entertaining, and you can see some unique and free experiences like the Bellagio fountains, the Mirage volcano and the Sirens of the Seas pirates show at Treasure Island. There are plenty of local spots off the strip to check out, but for a weekend, you can have everything you need on The Strip. Las Vegas has become very expensive in the past few years, and the pandemic did little to curb this. Drinks, food, hotel rooms and even parking are now priced very high! During the week you can find some attractive deals, but weekends have become very expensive.
Pros: Nightlife, entertainment, some of the best casinos and some top-notch restaurants
Cons: Crowded, a lot of drunken partiers, expensive
A couple other cities we really love, but are harder to get to:
It was really hard to narrow down our favorite spots for long weekends and we left off a few that we love, like Miami, Savanah, Pittsburgh, Washington DC. I originally had the following cities in mind as they are worth a long weekend visit, but a further distance than others:
Alaska is everything you imagine it will be, and then amplified by 1000%. Anchorage is nice, but it's more of a gateway to other sites in Alaska, like the Kenai peninsula and Denali National Park. It's a long flight to Anchorage, but the scenery and experiences are completely worth it! It's about a two hour drive from Anchorage to Seward in the Kenai, but it's a drive filled with amazing views of the inlet, mountains and glaciers. Once in Seward, you have the opportunity to jump on a tour boat and see Resurrection bay, with a great chance of seeing Killer Whales, Humpback and Minke Whales, Steller Sea lions and many other aquatic wildlife. If you're lucky enough to be in the Kenai during one of the salmon runs, the fishing is some of the best in the world. Throw on some waders and head out onto the Kenai River for amazing chances at trophy sized fish, but always be very bear conscious as their are both black and grizzly bears in the area.
Pros: Spectacular scenery, wildlife & nature, unique culture and history
Cons: Fairly remote, expensive lodging (outside of Anchorage), homelessness is an issue
Isolated in the middle of the Pacific ocean, Honolulu would have made our top 10 list if it wasn't so far to reach. But the long flight is absolutely worth it, especially if you live on the west coast of the US. There aren't many places as aesthetically gorgeous as Hawaii, with it's crystal clear warm water, white coral sandy beaches and lush tropical jungles. Honolulu is a major city, and with all major cities has some of the same problems experienced on the mainland, such as terrible traffic. But it's tough to get angry about traffic when you're on one of the worlds most beautiful tropical islands. Honolulu has lots to offer for a great long weekend, and Waikiki beach is at the top. Waikiki is exactly what you think it is, long strands of sugary sand beaches and azure clear oceans teaming with tropical marine life. It's also lined with multiple hotels and resorts, so there are plenty of restaurant options and high end shopping. Life's pretty good sipping Mai Tai's at the Pink Palace hotel on Waikiki beach. And if it's your first visit, you should take the plunge and be a huge tourist an go to a Luau, it's a great experience and very entertaining. If you want to try something more local, one of our favorite little local shacks is Hula Dog, a Hawaiian take on the hot dog with guava and mango relish in a taro bun. There are also a lot of great hikes to get lost in the jungle, and the scenery makes you feel like your in Avatars Pandora.
Our favorite is the Aiea Loop trail, where you have some incredible views of some of some of the valleys, but you may also spot rare birds and a the crashed wreckage of a WW2 bomber. Just make sure you bring lots of water. An even more immersive experience into Hawaii's history can be had at the Pearl Harbor Battleship Arizona memorial. There are lots of exhibits, and the Arizona memorial is a somber experience, but well worth it to understand the sacrifices made by so many.
Pros: Breathtaking natural beauty, beautiful beaches, great food, history and culture
Cons: Long flights, expensive lodging, crowds of tourists, homelessness is an issue
What are your favorite US cities for a long weekend? Leave a comment below and let us know!