10 tips for planning a weekend, multi-city sports road trip

Me on an airplane sports travel trip

I’m willing to bet that for most people, the ideal sports road trip is a long and leisurely one. You know, multiple weeks spent out of town, going to half a dozen games or more, all while enjoying the spoils of the places their travels take them.

I’m also willing to bet that most people are like me: forced to balance their travel aspirations with all the trappings of life. Those include work, family, friends and other interests that don’t have to do with sports or travel.

For me — and, I’m assuming since you’ve gotten this far, for you as well — planning travel is usually one giant balancing act. The perfect itinerary has to pass through a series of checks to become attainable. Can I get this many days off? Will I be missing something important? Will my family or friends be able to come? Can I get the plane/train/game tickets?

And, of course, the all-important one: Can I afford this?

It’s a balancing act that I’ve been teetering on for more than 10 years — partly so that I can visit enough stadiums to keep this site humming, but more because I really enjoy doing this.

No matter how short the vacations are, traveling, going on sports road trips and experiencing new places are always worth it to me.

If you’re visiting Itinerant Fan, then it must be worth it to you, too. So this post is all about taking advantage of limited time to still visit stadiums and see games, while remaining conscious of time and budget.

I have taken at least one sports road trip like this every year since 2010. Despite the pandemic, I managed to get out there in 2020, also — my last trip was a two-city, three-day January visit to Winnipeg and Edmonton to check out their hockey arenas (Bell MTS Place and Rogers Place, respectively).

I’ll be drawing mainly from that road trip, as well as a four-city, five-day jaunt I took in 2019 to Milwaukee, Indianapolis, Columbus and Chicago, for this post. However, past experiences were valuable learning tools, as well.

With all of that in mind, here are my 10 best tips for planning a weekend-long, multi-city sports road trip. I hope that you can use this post to help you put your next trip together when travel and sports event attendance return to “normal” levels.

1) Go where the schedules take you

Let’s face it: You can’t plan a sports road trip if there aren’t any games to see. You have to work with what the schedules give you, which can often limit where and when you can travel.

If you are hellbent on seeing a particular game, team or arena, then you’re somewhat hamstrung — and the parameters of your vacation are already defined. Without it, though, you have more freedom to choose a place and keep your travel plans looser.

I have my favorite teams, too, but more often than not my sports road trips don’t involve any of them. I choose cities, stadiums and games that are interesting to me for a variety of reasons — usually, it’s because I haven’t seen a stadium and want to check it off my list, or because it’s an opportunity to meet up with an acquaintance.

Your variety of reasons might be different, but the gist of this tip remains the same: If you focus more on the fact that there is a game to see and less on which game it is, your sports road trip horizons will widen greatly.

Bankers Life Fieldhouse atrium sports road trip

2) Go where the bargains take you

OK, so you’ve identified a range of places you’d like to visit and games you’d like to see, and a timeframe in which to do it. How do you narrow it down?

For me, that choice is usually easy: Choose whatever’s cheapest.

By “cheap,” though, I take into account the entire package. Maybe the flights are inexpensive, but the tickets for the games you want to see are in high demand. Or game tickets are cheap, but it so happens that the city you’re visiting is hosting a major convention and hotel rates are through the roof.

Or, maybe you can hack your way into a less expensive trip. For example, when I visited Winnipeg and Edmonton, I used miles to book my outbound trip and return to Los Angeles. I paid full-price only for the middle leg of my journey, between Winnipeg and Edmonton — a total of about US$120.

In other words, I badly wanted to see those two cities, and doing so completed my checklist of NHL arenas in Canada. But I waited until I found the perfect balance of schedule, time and budget to go.

Before that, I had identified other windows to go, but unfortunately those cities can be prohibitively expensive to travel to, especially from California. So I used those opportunities to travel elsewhere while waiting for the starts to align with Winnipeg-Edmonton.

3) Know your sports trip geography

To visit multiple cities in one trip, proximity matters.

I know that’s not a huge revelation, but it’s a big help in saving money and time when you’re on a sports road trip.

Besides the two multi-city trips I mentioned above, other itineraries I’ve embarked upon in recent years include:

  • Oklahoma City-San Antonio
  • Nashville-Memphis
  • Atlanta-Tampa-Miami
  • St. Louis-Kansas City-Denver
  • Philadelphia-New York-Boston
  • Montreal-Ottawa-Toronto
  • Vancouver-Calgary-Edmonton

These, of course, are all groups of cities that are within reasonably close range (ie. a 1-hour flight or a 4-5 hour drive) of each other. Getting there from where you live might be somewhat expensive, but the travel you do within the trip itself doesn’t have to be — nor should it be.

Knowing the parameters of the cities you hope to visit, and the budget required to travel between them, will go a long way toward forming an itinerary that’s attainable and affordable.

Airplane wing sports travel

4) Find small ways to maximize your time

Knowing the nuances of sports scheduling — and using it to your advantage — can go a long way toward getting the most out of your road trip.

For example: Many Saturday games in the NBA, NHL and Major League Baseball are played during the day. Having Saturday evening free gives you more time in the city you’re visiting — or, it gives you an opening to travel to the next location before Sunday, a day on which the vast majority of sporting events take place in the afternoon.

Do you have a 9-to-5, Monday-through-Friday job and want to spend your weekend journeying somewhere to watch sports? Then look into opportunities to travel Friday night to get a head start on your itinerary.

Better yet, take a half-day so that you can catch an afternoon flight, and maybe that’ll give you the chance to see a game on Friday.

They’re often little things, but schedule tweaks like that can open up surprising windows of opportunity to squeeze in another game or even city. Which brings me to…

5) Sleep on the plane

I live on the West Coast, so when traveling to the East Coast, I typically have two choices: 1) Fly during the day and give up pretty much the entire day because of the time difference, or 2) take a red-eye.

You may feel strongly about red-eyes, and I don’t blame you. I sometimes fail to get much sleep on overnight flights, and I’d be lying if I said it didn’t affect my mood and desire to do much once I arrived at my destination.

But to me, it’s a small sacrifice to make when the trade-off is having a few extra hours to check out a city or see an extra game.

If you’re an East Coaster considering a sports road trip out west, that of course means you’ll have to decide whether you want to take a red-eye back home. Perhaps staggering into work bleary-eyed on a Monday morning is not worth it to you, and that’s perfectly understandable.

However, if maximizing your time on a trip is important to you, then red-eyes are something to consider.

6) Pack only what you need

If you’re going to be away from home for only two or three days, this shouldn’t be difficult. Bring your fan gear, but coupled with a few changes of clothes, you probably just need a duffel or overnight bag.

And if that’s the case, you don’t have to check any luggage in when you arrive at the airport. That can be a key time-saver, particularly when you reach your destination city. And it multiplies the more stops you make on your journey.

Another thing to consider: If your sports road trip involves an NFL game, ditch your normal carry-on bag and use the clear bag that fans carry into NFL stadiums for things like your phone charger, sweater, snacks and so on. 

If you travel for sports often, try this fun exercise while waiting at an airport on a fall weekend: Look to identify the people who are traveling because of NFL games. Other than their jerseys or fan gear, quite often the dead giveaway is the fact they’re carrying a clear bag around. And you might be surprised by just how many of them you see.

7) Stay where the stadiums are

This, also, is a somewhat obvious suggestion that deserves a qualifier. Hotels are acutely aware of what type of events are going on in their city, especially sporting events that bring in an influx of guests.

Once an event like this is confirmed, the hotel rates will always be adjusted accordingly. Not surprisingly, this is not a time when they’ll slash prices hoping to drive up demand — it’s already there.

This is especially true in NFL cities, and rates at brand-name hotels will go up almost as soon as the upcoming season’s schedule is released, usually in mid-April.

Sometimes it helps to speculate when it comes to hotel rates. If you’ve identified a weekend to travel, but game schedules haven’t been finalized, make a hotel reservation anyway. Just make sure that it’s one that doesn’t require a deposit or a cancellation fee, so that you can adjust if need be.

OK, all that being said, the benefits of staying near the stadium should be fairly clear. Being able to walk to the game eliminates other travel expenses, such as parking, or even car rental. You’re already in the middle of the action as soon as you step out the door. And you’ve saved a significant amount of time to do other things, such as tailgate or find a pregame party at a nearby restaurant.

Some venues, of course, are not in tourist-friendly areas and don’t have nearby lodging options. That’s OK — at least you can budget accordingly knowing in no uncertain terms that you’ll have to factor transportation into your plans.

Fans at stadium sports travel

8) Be precise about what you plan to do

Maybe you’re not a rigid time-planner. I’m far from one myself.

But I find it does help to plot out other things I want to do during my visit so that I don’t feel like I’ve missed out on something important even with such a short visit to a city.

One example: During a three-day visit to New York City and Buffalo in late 2019, I charted out every meal I wanted to eat for the entire trip. Why? Because there were specific restaurants I wanted to visit at both stops — especially in Buffalo, where I wanted to try many of their unique dishes.

Charting your plans out may seem unnecessarily tedious, but it helps you ensure that you’ll have time for everything you want, whether that involves food, museums or other attractions.

9) Don’t let travel delays get you down

Early on a Friday morning in February 2019, I sat in the terminal at Milwaukee’s General Mitchell Airport waiting for a flight to Chicago O’Hare, where I would grab a connecting flight to Indianapolis.

I had a ticket for the Pacers game that evening at Bankers Life Fieldhouse, with tipoff at 7 p.m. (Eastern). But at 6 a.m. (Central), I got some bad news: My flight out of Milwaukee was canceled. The next one would be in the late afternoon, and after connections, I would arrive in Indy around 8 p.m.

Missing part or even all of the Pacers game suddenly became a real possibility, and I had already purchased a ticket.

Without belaboring the story, it ended happily enough. On the airline’s dime, I took a bus from Milwaukee to O’Hare (the two airports are only about an hour’s drive apart, not including stops), caught an earlier connection, and arrived in Indy in mid-afternoon.

I made the Pacers game without issue (because I stayed in a hotel blocks away from the arena — see tip No. 7). In the end I missed out on only one thing I wanted to do, which was visit the Indianapolis Motor Speedway.

Believe it or not, I enjoyed the hustle. I truly believe that how much you enjoy travel depends on how well you handle disruptions to your best-laid plans.

I still have never had to eat a game ticket on account of a travel delay (knock on wood). However, I’ve always gone into these itineraries with the attitude of, “I hope I don’t miss my game, but if I do, grin and bear it and make the best of it.”

To paraphrase one famous travel writer, always assume you’ll have the chance to come back.

10) Above all, the game’s the thing

And be sure to enjoy it! Whether it’s seeing that bucket-list stadium, hanging out with your family or your buddies on a vacation, or watching your favorite team in a venue that’s not theirs, there’s always value in traveling for sports. 

No matter how small your window is in which to do it.

I’d love to hear about your experience with this type of sports road trip, too! Leave a comment below or send me an email at hi@itinerantfan.com to let me know what you think.

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