How to Take Your Dream Trip for Under $1,000

A few years ago, my partner and I took our dream trip. We rode the train from our home in Milwaukee all the way to Portland, Maine. We’d talked about it for years, batting the idea back and forth until one day we decided to go for it. We didn’t have the money for an extravagant trip, but that didn’t stop us. In fact, we did the whole thing for under $1,000. And in the end, it was a better trip because we had to stick to a budget. We had to get creative. And creativity usually leads to fun. Or at the very least, a great story. How did we take a cross-country trip without breaking the bank? I’ve got a few tips for that. 

Plan Ahead

The thing about taking a dream vacation on a budget is that you have to plan ahead. I’m not the type of person who likes to have every moment of my vacation mapped out, but years of travel have taught me that if you don’t plan a little, it’s more expensive in the long run. By researching deals and discounts in advance, you can save a lot of money.

For our trip to Portland, I relied on Groupon to find discounted activities. We ended up getting two for one admission to the Portland Museum of Art and the Victoria Mansion Museum. We also found great savings on a lighthouse boat tour and a fantastic deal at a waterfront restaurant where we were able to celebrate our anniversary with a lobster dinner. 

Don’t Splurge on Your Accommodations

Here is the thing about traveling, you are there to enjoy the place you are visiting, not the room you are sleeping in. So don’t worry too much about finding the perfect hotel. I love using sites like Airbnb, VRBO, and even Hipcamp. They lead to incredibly unique stays that don’t pop up in a general Google search. Stays that are often cheaper than a standard hotel. Our Airbnb in Portland was right in the heart of the city and just $55 a night. The best part? It was a historic rooming house with loads of character. Yes, we did end up sharing a bathroom with the other room on our floor, but if that isn’t your thing you can filter out that option and give yourself as much privacy as you need. The point is, we got creative with our accommodations and ended up staying in the center of the city. We not only saved money on a room, but we were able to walk everywhere (including from the train station), which meant we didn’t have to rent a car or spend money on Uber and Lyft. A huge win in our book because that meant we could spend the money we’d allocated for a rental car on something else. 

Don’t Eat Out Every Night

Without a doubt we spend the most money on food when we travel. We love to eat. And we love to eat good food. But when you’re on a budget and away from home how can you save money and not end up eating fast food every night? One word: Picnic. Picnics are the perfect way to save money and explore the city you are visiting. I’ve had picnic meals all over the world. On the steps of a church in Luca, Italy, on a bench overlooking the Brooklyn Bridge in New York City, on the back hatch of a car at a Civil War Park in Kentucky. In Portland we found a corner store and bought cheese and crackers, some fruit and a couple of beers and headed for the waterfront. We enjoyed a laidback meal while watching the fog roll in off the ocean. We lingered for more than an hour in the cool summer weather, people-watching, talking, and just listening to the sounds of a city that wasn’t our own. Picnics are a great way to save money on a meal while often enjoying some of the best views your destination has to offer, plus we took our leftover cheese and crackers back to our Airbnb to enjoy as snacks later. 

Walk Everywhere

If you are able, walk as much as you can. We were lucky in that Portland is an extremely walkable city and we spent a lot of time exploring it on foot. Walking not only saves money, it provides a chance to discover shops and restaurants that could be missed when whizzing by in a car. We discovered some of our favorite bars, record stores, and vintage shops in Portland this way. 

Of course, walking isn’t a possibility for everyone. But there are still great ways to get around without the expense of renting a car. Most midsize cities and larger have public transit or even bike share programs to help you get around. Do a little research before you travel, you may find that you can buy a bus pass for the duration of your stay. And of course, for those smaller trips there is always Uber and Lyft. 

Spend Wisely on Souvenirs

This doesn’t exactly have to do with saving money in the moment, but I promise you’ll thank me later. In Portland my partner and I started a tradition that still persists today. In lieu of buying weird trinkets or souvenirs that will break, we started buying coffee to take home with us. We both love coffee and love trying local coffee shops wherever we travel. In Portland we really enjoyed Speckled Ax Coffee and decided to buy a bag to take home with us. Since then, we’ve acquired coffee from LA, Palm Springs, New York, Johannesburg, San Francisco, Kansas City, Chicago and more. This tradition lets us extend our vacations, in a way. Every morning we sip coffee and remember the places we’ve been. 

Follow These Train Tips

I’d be remiss if I didn’t leave you with a few train tips. It can be really expensive in the United States to travel by train, so here are three things we did to cut the cost: 

1. We only took the train one way. 

We chose to take the train from Milwaukee to Portland and then found a cheap flight home from Portland. This saved us money as well as time. For us, taking the train was part of the vacation, so we enjoyed the thirty-some hour trip, but knew we didn’t want to spend money on it more than once. 

2. We sat up all night. 

Yes, yes. You heard me right. Sometimes your dream trip comes with some sacrifices. For us it meant not splurging for a sleeper car on the longest leg of our trip from Chicago to Washington, DC. Instead, we sat up all night. While I’ll admit, a sleeping car probably would have been more comfortable, sitting up all night wasn’t bad at all. Especially if you’re used to airplane travel. Just remember to bring a pillow, ear plugs, and maybe an eye mask. 

3. We packed snacks (and drinks!). 

Listen, Amtrak coffee only costs a dollar. If you want to drink it, by all means, go for it. But it costs a dollar for a reason, so save yourself (and your taste buds) the money and pack tea. Tea is my favorite travel companion. It’s easier on the stomach than coffee and it’s inexpensive if you buy it ahead of time. It’s easy to pack, and hot water is always free (just remember to bring your own travel mug). As for other snacks, the dining car is inevitably overpriced. I suggest packing things you’ll be able to eat throughout your trip. Peanut butter sandwiches, bags of pretzels or chips, granola bars, maybe even a couple of apples. Things that won’t spoil. Remember that you won’t be on the train forever and small meals like this are doable for a little while.  

Your dream trip doesn’t have to be expensive, whatever it is. We traveled across the eastern half of the United States from less than $1,000 and never once felt like we missed out on anything. On our way to Portland, we saw Chicago, Washington D.C. and Boston. We explored and ate and drank. Sure, our backs were a little sore after that all-night train ride from Chicago to DC, but in the grand scheme of things, that was all part of the adventure. No matter where you want to travel (or how) you can do it for less than $1,000, you just have to be willing to do your research, plan ahead, and get creative. So, find the cheapest flight, train ticket, or closest city you’ve never driven to and go. The world is big and it’s wild and it’s calling to you.  

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