If you get the big things right, the little things don’t matter. You have to be frugal before you can be reckless. Get the core four (flight, lodging, transportation, food) right, and then rely on the good habits you’ve developed to help guide your experiences throughout your trip.
Always save up the cash to pay for everything beforehand. I will never advocate for taking trips if you have debt or don’t have your finances in order. You aren’t doing yourself any favors.
Always start with the plane tickets. I like to search for my plane tickets on Google Flights. They have a feature where you can enter your weekend of choice and then explore destinations on the map. Credit Card hacking is great for getting flight discounts or free plane tickets.
The best way to score cheap tickets is to be flexible on your dates and times. I often fly out Friday night and take Monday off of work because flights coming back Monday evening are cheaper than flights coming back Sunday night. I try to fly out either really early to get a full day exploring or really late to get in a full day of work before leaving.
I don’t mind being flexible about layovers, but I always try to get a direct flight if possible. Often they are cheaper because airlines want to fill their flights, but I’ve found that even if it’s a bit more money, it’s worth the extra time I get to spend at my destination. It’s also much less stressful. If the first flight is delayed, there is no stress that a connection will be missed. There is also no stress that I will be stranded in a city if the second flight is cancelled. Google “Direct flights from *your city*” to see various travel options and the airlines that fly there.
If you do need to book a flight with a connection, don’t be afraid to get a long layover. I once had a 9 hour layover in Amsterdam and took the train in to explore the city for almost the whole day – yet another benefit of traveling light. You weren’t allowed to leave the airport if you had a checked bag, and there were no lockers of any kind. I would have been miserable exploring the city dragging along a rolling suitcase, and would have been even more miserable sitting in the airport that long.
Before booking, double check local hotels/AirBnBs just to make sure the prices are good for those as well. Then lock those low prices in. Forgo the insurance/upgrades. You should only be traveling if you’re in a financial place where losing that ticket money does not impact you, and most airlines will actually refund you or change your dates if you call them and explain any extenuating circumstances (like sickness or a death in the family).
Figure out what you want to do at your destination. At least a general idea. Google can help. Then make your hotel/rental and transportation plans around that.
Consider the length of your stay. Do you want to stay downtown or on the beach and spend the entire trip within the same two mile radius? Do you want to explore the whole island or mountainside? Do you want to move to multiple locations?
If you want to drive around the area, look for deals on car rental sites. You will need to find a rental car and a hotel or house that has good parking and easy access. You can generally find a cheaper place outside the main city area, which is fine if you have a car. Keep parking costs in mind though.
If you want to stay in the same area of the city, you should try to find a place that’s located near where you want to spend the bulk of your time and would likely be better off with taxis/uber or other public transportation and walking. Even if the place is a bit more expensive, remember that your time is worth money, and be mindful of the driving time. Don’t be afraid to walk further distances than you usually would. It’s a fun way to explore.
For a mix of both, see if you can stay downtown and rent a car for just one day of exploration. What is the most cost effective?
Caveat to a rental car: I won’t drive in foreign countries where I don’t understand the signs.
Thoughts on hotels/AirBnBs
I always book in safe areas, even if it costs a bit more. My life is worth more than money.
I look for places with free breakfast so that I can eat a large morning meal without worrying about how it will be acquired.
Free coffee/tea and other amenities are a plus, but make sure you only focus on the ones you will use. (I don’t bother finding AirBnBs with pools because I know I won’t use them. I’d rather be at the beach. Focus on finding the best price that meets your needs.)
Renting a room in a residential AirBnB usually means that you’ll be near grocery stores, drugstores, etc. which are very convenient. Think about how much time you’ll spend there (the answer should be “Not much at all, I’ll only be sleeping”) and see if renting a private room makes more sense. You shouldn’t have any valuables with you, so there’s no worry about anything being stolen.
Restaurants/Food
Make sure all your food experiences are ones you will enjoy. As a rule, I aim to only go to a restaurant once per day for the trip. It often falls somewhere between lunch and dinner time.
For the rest of my food, I try to coordinate beforehand or buy from a local grocery store when I arrive. You can pack sandwiches and snacks to bring with. I enjoy buying local fruits or groceries from the market. I appreciate getting to eat lunch the moment I’m hungry rather than stopping my activity to find food. I’m a picky eater as well, so that can make finding places more difficult. It’s never fun walking around hungry.
I always buy a disposable water bottle when I arrive at my destination and refill it throughout the trip and toss it when I get back to the airport. It is important to stay hydrated.
Remember... Frugal travel means taking ONE bag
It counts as your personal item. This bag should be easy to carry, sturdy, well-made and lightweight. Check any travel size restrictions for your personal item before buying a new bag. Having a smaller bag forces you to pack less. Anything you buy has to fit in your one bag on your way home.
See “Smart Packing for Frugal Travel”
If you want a souvenir, make sure it’s cost effective and something you will value
I have a collection of fridge magnets from everywhere I visit. It sounds cliché, but I buy one everywhere I go. I make it a game to search for the nicest one I can find as I wander around the city. They are lightweight and small, which makes them ideal for carrying around. They are easy to find in the airport or any tourist shops. They usually cost $2-$5 each. I am happily reminded of my trips every time I pass by the fridge. The magnets remind me to be thankful for and to appreciate my opportunities.
I also have a sand collection from my favorite beaches. I find inexpensive clear bottles with corks (some were gifts from my Buy Nothing Group) and have them prominently displayed in my living room filled with the sand I bring back. I carry an extra Ziploc bag if I know I’ll be visiting a beach, just in case. (*Note that if you take sand home, you should always put the bag of sand in a separate bin through the TSA checkpoint. They must test the sand for bombs. If you forget, they will have to pull the sand out of your bag and send both the bag and the sand through again before testing.)
I often buy postcards that I send to friends and family. I like to buy useful and thoughtful gifts as well.
I’ve also bought dresses, shirts, and other miscellaneous items that I still wear and enjoy. The important thing is that it’s something that will add actual value to your life, not just exist as a “nice-to-have” or as extra clutter in your household. Remember – you have to carry it around with you for the rest of your trip. Not only are you carrying it around for the rest of your trip, but you are carrying it around for the rest of your life.
What Reckless does NOT mean...
- Not being safe when you travel
- Ignoring safe alcohol limits (if you’re going to get drunk, do it at home instead)
- Spending with abandon – don’t just throw out all your frugal habits
The Reckless Part
I never worry about spending money on valuable experiences like museums, parks, shows, bus or boat tours, etc. If I genuinely think I will enjoy it, I am happy to do it. These trips and experiences add so much value and enjoyment to my life. If it’s something that costs money, I make the most of it by spending at least an entire morning or afternoon. That gives me time to really take in the experience.
There are many free activities as well anywhere you visit (including sitting on the beach and walking through the city), and I enjoy them equally. The habits I’ve developed – focusing on value maximization and seeking experiences that add real enjoyment to my life – make it easy for me to disregard fancy expensive tourist traps in favor of experiences with real substance and lasting impact. Once you develop good habits, it’s ok to be reckless because you are reckless within the “safe area” you’ve created for yourself.