Prepare to Take Your First One-Day Travel Trip Alone

Dec 2, 2024

How to Travel Alone for the First Time

I’ve been traveling alone for a long time because I find it relaxing. I know that it’s not the norm for everyone but this blog post is intended to teach you how to travel alone for the first time, ever or in a loooonnnggg time.

Of course, I’m biased but as a semi-empty nester I happen to think that solo travel is underrated. It feels empowering, adventurous but sometimes a little overwhelming. Preparing to take your first one-day travel trip alone is a great way to build your confidence and get you out of your comfort zone in your post-divorce life. A one day trip may mean you return home same day or just that you’re only gone for 24 hours.

Honestly it really doesn’t matter what your relationship status is but I recognize that sometimes it’s hard to get at away. There are times when money is tight, vacation time is low and the kids schedule is chaotic but you still a change of scenario.

You just need to get away even if its only for a day. Let’s get into some simple but practical tips for the best places to hang in the United States for when you’re traveling alone for a quick trip.

Why Taking a Trip to Do Nothing May Be Exactly What You Need

Southwest Airlines Rapid Reward Program requires a minimum of 20 flights annually to maintain A-List status for the following year. Usually, around October, I check my flight count to see how far away I am from keeping my A-list. 2024 was no different.

I go back and forth between, “Forget it, I’ll just let it go” and “I really want to keep my A-List status”. This year, I decided to keep it and booked a quick trick to St. Louis. I didn’t have any plans in particular, but it feels good to:

• Not pack a bag/lug a suitcase around
• Not worry about real plans
• Get a away for a quick break without breaking the bank
• Not have to worry about anyone else’s needs or plans
• Still sleep in my own bed

We often think of a good vacation as having a full itinerary with tons of new experiences. But when you get back home, you need a vacation from the “vacation.”

So, while a trip intended for you to do nothing may sound weird and possibly like a waste of money, this is less about money and more about peace of mind, convenience, and opportunities for rediscovery.

You can reach many of the destinations discussed in this post by plane, train, or automobile, but when we think about the most efficient way, it’s likely by plane, so that is what the focus is for this post. However, feel free to choose any method of transportation that works best for you.

One-Day Travel Tips for Solo Travelers

When to take your solo trip?

If you’re a newly divorced mom with minor children then it goes without saying that you might need to book the trip based on the custody/visitation schedule.

In addition, these trips should feel light. This means that it shouldn’t be a logistical nightmare. Booking on a typical off day or a planned vacation day is a good idea.

The other cool thing about solo trips is that you can usually sneak away without most people even knowing that you’re gone. To offset safety concerns, it makes sense to tell a family member or best friend but these are trips I often keep to myself from most people.

Tip #1: Travel on the cheapest days of the week

Book the trip on a Tuesday, Wednesday or Saturday. Why? Because flights are typically cheaper on these days due to lower demand. Most people don’t want to fly in the middle of week, unless its business travel and chopping up a weekend is rarely the preference. So if you can book a flight on one of those days, it’s a simple way to save money regardless of the airline. The bonus is that the airport is also less busy, obviously, so security lines are generally shorter.

If you’re coming back the same day then it’s the best value for a roundtrip flight. Alternatively if you do book on a Tuesday and come back on a Wednesday, it’s still typically a great value even with the overnight stay.

I’m no travel expert, but I typically book my flights 21-45 days in advance, more if possible. I only book last-minute flights in emergencies because you are going to pay through the nose every time.

Tip #2: Research parking prices

For most airports, it’s more economical to park offsite because on-site parking, when available, is more expensive. However, for same-day or quick turnaround trips, on-site parking may not be more convenient but reasonably priced.

Here’s a quick example. Economy parking (offsite) for Midway Airport in Chicago is $15 a day, even if it’s not a full 24 hours. For a big city, this is not a bad price.

Onsite parking (no shuttle buses involved) at Midway Airport is $40 a day or $4 an hour. So, let’s assume I’m taking a single-day trip and want it to be as convenient as possible. So I calculate that I’ll need to park for about six to seven hours, which should cost about $28 if I choose hourly parking.

However, I learned (after I had already parked) that the Daily $40 lot only charges $20 to park for 4-8 hours.

Go figure!

Now, obviously, parking in Economy is still $5 cheaper ($15 versus $20) than parking onsite, but walking directly from the parking garage to the terminal, saving about 20-30 minutes, is absolutely worth $5.
Before you travel, check the website for information on parking at the airport where you will be flying in and out so that you can make a more informed/strategic decision.

Tip #3: Stick to travel hubs when possible

Living in the Chicago land area gives me a clear advantage when taking domestic or international flights. Chicago is a travel hub, and it makes it pretty easy to get to some of the best travel destinations in the world. However, I stick to the safest countries and cities for one-day or solo trips. Fortunately, this still leaves me with a lot of options.

In most cases, if you are traveling alone for the first time, the best places to go typically meet these three simple standards for me

• Short flight/time in the air
• Good culinary scene
• Easy airport to navigate

​The bonus is if they have a fascinating local culture.

The choice of destination airport is really important. When an airport is easy to navigate, it is less likely to be crowded, which means you can breeze through security lines. It also means that the overall trip feels more relaxing because the travel environment doesn’t feel chaotic. Small airports typically fit this bill; however, airports like Minneapolis and Phoenix aren’t terrible.

The other reason to stick to travel hubs is that you’re less likely to get stuck. Travel hubs offer many direct flight options and good alternative airline options should your flight be cancelled.

If you live far away from the travel hub, traveling to a hub city also offers convenience and security, especially if you need to return home by a certain day or time.

Lastly, travel hubs are often in major cities, which means you will likely have many great restaurants to choose from, an appealing cultural scene, and access to many modern amenities, like Uber and Lyft services.

The Best Places to Visit for Solo Travelers

If your previous travel was determined by your former partner’s preferences or your children’s sports travel schedule, then your first trip alone gets to be determined by you. You can book a group tour, meet new people, or create new experiences depending on what YOU like. From personal experience, sometimes it can feel so good waking up in a beautiful hotel room with no chores, laundry, or list of errands waiting on you the moment you get up.

Of course, staying overnight comes with an extra cost, but if you can curl up with a good book you can never seem to read at home, it might be the best thing for your sanity and overall wellness.

The cities I’m recommending below are places where I’ve had the best time, where I have genuinely good food recommendations, where the local people are kind, or where I just enjoy spending time.

Remember, be open to making new friends, pack light or not at all, and have fun! Preparing for your first trip alone can feel daunting, so give yourself some grace. If you decide that the best way to travel solo is an extended trip to Latin America, Western Europe, or South Asia, please go. The point of this post is not to restrict you. It’s to help you fulfill those “need to get away” moments, but here are just a few considerations.

Things to Do Alone in Chicago

It’s only fair that I start with my hometown and my favorite city in the US. I’m going to talk to you about it. Chicago has so much to choose from, and it’s one of the best places to visit in the summer. It has two major airports, and you can get to the heart of the city from either one pretty quickly using public transportation (the cheapest way to get around) or car services.

By the way, if you like hearing about food recommendations/ reviews, be sure to follow The FIIRM Approach on Instagram and Facebook to learn about my favorites as I travel to old and new destinations.

Why Chicago is Good for a Day Trip?

• Hub city
• Great place for foodies – deep dish pizza, hot dogs, steakhouses and so much more
• Scenic – Lakefront, iconic architecture
• Main Tourist attractions: Willis (I still call it Sears) Tower, Millennium Park, Museums, River Cruises
• Beautiful Hotels for a Relaxing Stay – Park Hyatt, Westin, Langham

Things to Do Alone in Los Angeles

Los Angeles is more charming and exciting than most cities. If you pay attention to social media, you know it’s known for its Hollywood glam, scenic beaches, and beautiful homes. If you live on the East Coast, it’s a long way to travel for a day trip, but if it’s a short flight, then I recommend it as an option. Honestly, though, I don’t love downtown LA, but that’s a personal preference.

Why LA is Good for a Day Trip?

• Hub city – LAX can be a beast though
• Good place for foodies – Celebrity-owned restaurants and trendy cafes. My Personal Fav is Griddle Cafe on Sunset Blvd.
• Scenic – Ocean, Beaches, Mountains (everything you need to see in one place!)
• Main Tourist attractions: Arts District, Rodeo Drive, Santa Monica Pier; great museums and Hollywood studios
• Beautiful Hotels for a Relaxing Stay – There are so many options: The Garland & Hollywood Roosevelt are a just a couple of options

Things to Do Alone in New York City

New York City is not everyone’s first idea for their first solo adventure. I get it. However, if you’re open to a new adventure, then you’ll appreciate that NYC is full of excellent options for solo travelers.

Why NYC is Good for a Day Trip?

• Hub city- LaGuardia was recently renovated and it’s beautiful!
• Good place for foodies – Celebrity-owned restaurants, NYC-style pizza, hot dogs, and culturally diverse food. My Personal Fav is Cuts & Slices in Brooklyn.
• Cultural Scene is rich!!!
• Main Tourist attractions: Manhattan, Times Square, Broadway, Central Park, The Metropolitan Museum of Art
• Beautiful Hotels for a Relaxing Stay – This one is tricky. While there is no shortage of hotels in NYC, I’ve yet to stay at one that felt very relaxing however, Trip Advisor recommends – The Knickerbocker and The Dominick Hotel

Things to Do Alone in Atlanta

Atlanta has a little bit of everything—southern charm, big-city amenities, and a thriving sports/arts/culture scene. It is a slower city than New York and Chicago, but not slow enough to put you to sleep when you arrive. Navigating the city can be a challenge sometimes because of traffic, and even though there is a train station connected to the airport, it’s not the most public transportation “friendly” city.

Why Atlanta is Good for a Day Trip?

• Hub city – while the airport is huge, there are many amenities within a short drive from the airport.
• Decent place for foodies – Brunch & Soul food options. My Personal Fav is Poor Calvin’s in Atlanta.
• Cultural Scene is rich!!!
• Main Tourist attractions: Piedmont Park, Atlanta Botanical Garden, Coca-Cola Museum, The Battery Atlanta and National Center for Civil and Human Rights
• Beautiful Hotels for a Relaxing Stay – The Whitley; Loews Atlanta Hotel

Things to Do Alone in Denver

​Denver has an artsy, hip vibe. It’s a beautiful city with amazing views of the mountain and a thriving arts and music scene.

Why is Denver Good for a Day Trip?

• Hub city
• Decent place for foodies – No personal favorites but that just means I need to take another trip
• Main Tourist attractions: Denver Botanic Gardens, hiking, Rocky Mountain tours, local breweries or world-famous Beer Trail
• Beautiful Hotels for a Relaxing Stay – Great boutique hotels; The Oxford Hotel and The Catbird Hotel

Things to Do Alone in Dallas

Dallas is a big city! It’s loaded with history, culture, and, of course, old-fashioned Southern hospitality. If you can make it to Dallas on a short flight, then having a brief love affair with the city is easy.

Why Dallas is Good for a Day Trip?

• Hub city
• Good place for foodies – BBQ and Soul Food are a must. My Personal Fav for a sweet treat is Cookie Society. The brisket at Hurtado is AMAZING!
• Main Tourist attractions: The Sixth Floor Museum; NorthPark Center; Dallas Museum of Art
• Beautiful Hotels for a Relaxing Stay – The Joule; Fairmont Dallas; Thompson Dallas
  

Things to Do Alone in Phoenix

The weather alone is a reason to visit Phoenix in the spring and fall. Summers are pretty intense, and it’s quite chilly at night in the winter, but it’s still a great place to relax and enjoy beautiful scenery.

Why Phoenix is Good for a Day Trip?

• Hub city
• Decent place for foodies – Amazing Mexican and fine dining options. My Personal Fav is Steak 44
• Main Tourist attractions: Desert Botanical Garden; Camelback Mountain; Wrigley Mansion
  
• Beautiful Hotels for a Relaxing Stay – So many resorts and day spas to choose from!
  

Things to Do Alone in Seattle

Seattle is breathtakingly beautiful. It’s a cool city to visit for coffee, music, and rain lovers! Although it’s a big city, it doesn’t feel overwhelming, even though there are a lot of people who live there.

Why Seattle is Good for a Day Trip?

• Hub city
• Good place for foodies – Amazing Mexican and fine dining options. My Personal Fav is Pink Door
• Main Tourist attractions: Pike Place Market; original Starbucks, Glass Museum, Space Needle, Bainbridge Island
• Beautiful Hotels for a Relaxing Stay – Hotel Theodore, Edgewater Hotel

Things to Do Alone in Nashville

Why is Nashville Good for a Day Trip?

• Not a hub, but the airport is easy to navigate
• Good place for foodies – Southern Food, Hot Chicken and BBQ.
• Main Tourist attractions: Grand Ole Opry; Broadway; National Museum of African American Music
• Beautiful Hotels for a Relaxing Stay – Conrad Hotel, Noelle Hotel

Things to Do Alone in Minneapolis

Now, you may not want to venture to Minneapolis in the heart of the winter unless you really like cold weather, but it has other cool things going for it. The people and culture remind me of Denver in a lot of ways, and I think it’s ideal for a first solo travel adventure.

Why is Minneapolis Good for a Day Trip?

• Hub airport
• Decent place for foodies – No personal favs.
• Main Tourist Attractions: Mall of America, Walker Art Center, lake views, Sculpture Garden
• Beautiful Hotels for a Relaxing Stay – JW Marriott, Hewing Hotel
  

Things to Do Alone in Washington D.C.

I absolutely love D.C. It’s one of the most culturally rich cities because of its history, food, and social scenes. Now, the rodent situation I could do without, but nobody’s perfect! 

Why Washington, D.C. is Good for a Day Trip?

• Hub Airport – Reagan is very easy to navigate.
• Great place for foodies – I have too many favorites to name, but The Hamilton, Residents, Kitchen and Kocktails are a few that come to mind
• Main Tourist Attractions: There are way too many to name but here are few – National Mall, any Smithsonian museum, Rock Creek Park
• Beautiful Hotels for a Relaxing Stay – JW Marriott, Hewing Hotel

Time for FIIRM Hero Action: Travel Alone for the First Time

This blog post was intended to provide the best tips for preparing for your day trip alone and to help you understand the little things you can do to have a good experience traveling alone for the first time.

Life will always get in the way of us doing all the things we want to do, but I encourage you to make time to sneak away so that you can increase your confidence and comfort with traveling alone. It doesn’t need to take a lot of time.

You can take a page from my book. My last solo trip to St. Louis, took about six hours. Every trip doesn’t need to be a long weekend or require travel specialists to coordinate. All I needed was me, myself and I.

If you’re not already following The FIIRM Approach on Instagram, let’s connect so that you can hear firsthand about restaurant recommendations in our Finicky Friday food features.

You might discover your favorite new place or find the next city to visit when you need to sneak away for a fantastic meal.

The kids will be fine. The laundry can wait. It’s time to create new memories in small towns or even foreign countries.

You can also check this FIIRM Hero blog post – New Experiences Don’t Have to Cost You a Lot of Money, or research Facebook groups that share ideas on solo travel.

Travel smart. Keep it light. As my friends and family always say to me – Safe travels.