Apples To Angels

How You Can Take A Coast-To-Coast Train Trip For $289 In Train Fare


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Seeing the country by train is a dream.

But you’ll find, particularly with America’s train system, that schedules can be difficult to line up. And who wants to plan logistics?

Apples To Angels makes a coast-to-coast trip easy to do - because the planning is already done

With this post, we tackle where to go, what to do, and how to get there - and we ensure that train schedules line up perfectly so you can take the trip of a lifetime. Apples To Angels is a week-long, self-guided experience on the outRise app that takes you coast-to-coast on Amtrak. At the time of this publishing, you can book all train fare below for $289. 

The best part? outRise is a self-guided app, so Apples To Angels is a self-guided trip. That means this trip happens on your terms, on your time. On the outRise app you'll find turn-by-turn directions to each stop in this experience, including insider notes, photos and more.

This post will take you through the self-guided Apples To Angels adventure day by day, to help you get a feel for what the trip is all about.


Itinerary (summarized)

Day 1: New York City (Empire State Building)
Day 2: New York (Central Park + overnight train to Chicago)
Day 3: Chicago (Skydeck + overnight train to Flagstaff)
Day 4: Flagstaff (arrive at night)
Day 5: Flagstaff (Grand Canyon)
Day 6: Flagstaff (Route 66 + overnight train to Los Angeles)
Day 7: Los Angeles (Manhattan Beach)

What To Book In Advance (summarized)

Train Tickets*

Day 2: New York City > Chicago (depart @ 3:40pm) [book here] - $90
Day 3: Chicago > Flagstaff (depart @ 2:50pm) [book here] - $138
Day 6: Flagstaff > Los Angeles (depart @ 8:38pm) [book here] - $61

*Before booking train, please double-check that schedules align. Train schedules are subject to change.

Hotel Rooms

Day 1: Stewart Hotel (NYC) - 1 night
Day 4: Hotel Monte Vista (Flagstaff) - 2 nights
Day 7: The Wave Hotel* (Los Angels) - 1 night

*optional - if you’re going to stay the night in Los Angeles


Day 5: Budget Rental Car (2 days)


Apples To Angels: The Experience

Day 1 (New York City)

Today you get into NYC. Maybe you fly in, maybe you rented a car, or maybe you even got a head start on your cross-country train trip and took the train to NYC. However you arrived, check into the Stewart Hotel, which, for the location and quality, is one of the most reasonably priced hotels in NYC.

If you’re looking for a budget-friendly alternative, check out the West Side YMCA or the Vanderbilt YMCA, which both offer dorm rooms (hostels) or budget-friendly private rooms.

NYC Pizza

From here, you’re probably hungry - right? Of course you are. You’re in New York City. One of the best spots near the Stewart for a slice of NYC pizza is Bravo Kosher Pizza. 

Empire State Building

After filling up, head to the viewing deck of one of the most iconic skyscrapers in the world - the Empire State Building. From here you’ll be able to catch the cityscape at nighttime (or earlier in the day if you’d like) from the viewing tower.

Keep In Mind...

Keep in mind - the last elevator up is at 8:15, so you should get in line before 7pm. There are actually two observatories - the 82nd floor and the 103rd floor. Tickets to the 82nd floor observatory are $42/adult, while visiting both the 82nd & 103rd floor are $75/adult (purchase tickets here -


Day 2 (NYC - Chicago)

Central Park (Train To Chicago @ 3:40pm)

After grabbing breakfast at the cafe of your choice, head over to Central Park for a stroll through the city’s largest greenspace. Your train leaves at 3:40pm, so you’ll want to give yourself plenty of time to walk back and head to Penn Station.

Train To Chicago

After getting to Penn Station, you’ll hop on the 3:40pm train for an overnight train to Chicago.


Day 3 (Chicago - Flagstaff)

Feeling rested after your overnight trip? Good - you’ve got a busy afternoon. You’re coming back to Union Station at 2:50pm for your train to Flagstaff, so you may want to put your luggage in a temporary locker - which you can rent with sites like Bounce.

A True Chicago Meal (Italian Beef)

Once you’ve dropped your bags, fill up on a Chicago classic. And no, I’m not talking about deep dish. 

It’s funny - a lot of Chicagoans aren’t all that crazy about deep dish. But do you want to know what every Chicagoan actually loves? Italian beef. So you’re going to hit a classic Italian Beef joint for this Chicago staple. Want to order like a pro? Get it dipped - that’s when they dip the entire sandwich in au-jour. It’s wet, it’s juicy, and it is so Chicago.

Once you’re full-up on Chicago grub, hit the Skydeck.


Heads Up...

**Just a heads up - this is the most “schedule-tight” portion of the trip. Please be sure to check the wait time, and ensure that you have enough time to go up (you’ll spend ~20 minutes up there, and it will take you ~20 minutes to get down) and get back so you don’t miss your train. The Skydeck is less than a 10 minute walk from Union Station, but make sure you give yourself plenty of time.

In Case That Doesn't Work Out...

If the wait for the Skydeck is too long, a great alternative is the Chicago Riverwalk, which is only a ½ mile north of the Skydeck. It’s a gorgeous mile-long walk along Chicago’s legendary Chicago River to beautiful Lake Michigan (keep in mind the 1 ½ mile walk back to Union Station from Lake Michigan).**

Chicago’s Skydeck is located on the 103rd floor of the Willis Tower and it gives you a bird’s eye view of one of America’s biggest and oldest cities. The best part? There’s a plexiglass box you can step out into - with a plexiglass floor. So you can see THROUGH THE FLOOR, 103 floors up. Come on - be brave! Step out there for the photo there, kiddo!

"chicago Skydeck" by ukdamian is licensed under CC BY-NC 2.0

Train To Flagstaff (Train Leaves @ 2:50pm)

After the Skydeck, head on back over to Chicago’s iconic Union Station to catch your 2:50pm train to Flagstaff. This is the longest leg of your trip - 30 hours - so settle in! Try to get a seat on the west side of the train (to easily catch the sunset out your window) and make sure you’ve brought plenty of snacks :D

Go West...

If you’ve never been on a long-distance train here in the US, they have this thing called “the viewing car”. It’s a car made mostly out of windows so you can see everything you’re passing. It’s magic. Hurtling through the heart of the country at night, staring up at the blazing stars against the night sky when you’re not even quite sure what state you’re begin to understand why American Indians of Great Plains developed such a respect for their home and this spot in the world.

This is certainly the most “romantic, traveling by train to the West” leg of this trip.


Day 4 (Flagstaff)

Arrive In Flagstaff

After arriving in Flagstaff, you’re probably pooped from your trip. Check into your room at Hotel Monte Vista (3 days, 2 nights) for some well-deserved Zzzz’s.


Day 5 (Grand Canyon)


Phewwwww what a great night’s sleep (I hope)! Time for breakfast. 

Just a 5 minute walk from your hotel is the best breakfast spot in town. Now don’t let the name fool you - “Tourist Home All Day Cafe” is anything but a tourist trap. Locals love it - and you will too. Pastries, coffee, steak and eggs, vegan friendly options, the whole bag. 

Fuel up - today is one of the highlights of the trip.

Rent Your Car

If it’s not too hot, you can consider walking the mile to Budget Rental Car to pick up your rental. But it’s Flagstaff, so it’s probably going to be pretty hot. I recommend hopping in an Uber to get there.

Stock Up

After grabbing your car - but before going to the Grand Canyon - go next door to Fry’s Food & Drug to grab water and snacks. Seriously. It’s a long day, and it’s the dessert. You need lots and lots and lots (and lots) of water.

 And now, it’s time for the Grand Canyon!

Grand Canyon

You May Cry A Little When You See It...

The Grand. Canyon.

Stories of people crying when they first see it are anything but rare.

When you arrive at Grand Canyon National Park, you’ll need to pay a $35/car entrance fee. Well worth it to see one of the natural wonders of the world, don’t ya think? While there’s parking in Grand Canyon Village, do yourself a favor and park in the Grand Canyon Visitor Center. From here it’s a short walk to Mather Point, one of the iconic vistas of the Grand Canyon. 

After Mather Point, hop back in your car to hit Yavapai Point - one of the most clear and expansive views of the Grand Canyon. You’ll also be right next to the Yavapai Geology Museum, where you’ll be able to learn about the geology behind the Grand Canyon.


One Of The Most Epic Sunsets On Earth...


Sunset At The Grand Canyon

If you’re still up for it, and it’s near sunset by now, you HAVE to check out Hopi Point for a sunset. It is, without a doubt, one of the most epic sunsets on Earth. 

"Hopi Point 2" by toddwendy is licensed under CC BY 2.0


Have you thanked me yet for telling you to pack snacks? Seriously. They’re a must. But you need a real meal after this incredibly long day, so head to Pizzicletta to chow down on some wood-fired pizzas, along with a great selection of beer and wine. 

Keep the rental car for the night - you’ll need it to explore one more attraction tomorrow morning. 


Day 6 (Flagstaff - LA)


You’ve got all day to hang out in Flagstaff today. Whatever you choose to do, I’d wear active clothes and leave your bags at the hotel after checkout (they’ll hold them until you get back tonight). 

Free Day In Flagstaff

Up For A Hike?

If you’re looking for suggestions - how about a hike? Flagstaff is nationally-renown for its hiking - one of the best in the area is Fatman’s Loop, which is a moderately difficult 2.4 mile roundtrip hike where you’ll get absolutely stunning vistas. If you hike, just remember...BRING WATER!

"Fatmans Loop Trail" by Coconino NF Photography is licensed under CC BY-SA 2.0

Route 66

Before returning your car, make sure to hit Pete’s Gas Station, which is an old-school gas station turned museum. It epitomizes the romantic, “Route 66” notion, and is a great spot to hit before leaving Flagstaff.

Train To Los Angeles

After returning your car, grab an Uber back to your hotel where you’ll get your bags and walk the 3 minutes to the Flagstaff train station for your overnight train to LA, leaving at 8:38pm.


Day 7 (Los Angeles)

Los Angeles & Breakfast

It’s Day 7 of your trip - and you’ve arrived on the west coast - time to celebrate with some breakfast! Head to Grand Central Market which, at this time of day (you’re arriving at 8am), will be your best bet for a breakfast nearby. It’s ~1 mile away, so if you’re traveling with a backpack and want to stretch your legs, this is a great chance to go for a stroll.

Grand Central Market is home to a ton of LA food vendors, but for breakfast you have to go with Eggslut. Yes, Eggslut. The breakfast place with a name as powerful as its flavor. 

Getting To Manhattan Beach

After breakfast, you have a couple options. You can head back to Union Station and take public transit to get to Manhattan Beach (if you do this, get a 1-day Metro pass for $7) which will take you ~2 hours, or you grab an Uber for ~$30. Heads up! If you do public transit, make sure you select the “public transit” option when navigating in your maps, as that will help you line up time schedules.

Manhattan Beach

You Made It...

However you did it, you’ve finally made it to Manhattan Beach and the Pacific Ocean! It’s not quite time to check into your hotel yet, so spend some time with your toes in the sand at Manhattan Beach. Alternatively, if you take an Uber, you can get dropped off closer to your hotel (the Wave Hotel) and drop your bags there before hanging out at to Manhattan Beach until it’s time for check-in.

Sunset Over The Pacific

Whether you’re staying the night at the Wave Hotel, flying out of LAX or taking the train out that night, make sure to catch an epic west coast sunset on Manhattan Beach. 

You did it - you’ve covered from where the sun rises in the east coast all the way to where it sets here in the west. All in a week. And you’ve seen some of the best that America has to offer along the way.

Take a second to let that sink in….


Apples To Angels is the adventure of a lifetime, and it’s hard to believe it all fits into a single week. But make no mistake - it does! So pack your bags, get your tickets, and take the trip of a lifetime - available now on outRise!

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