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I believe in traveling like a local. I believe in traveling consciously, and considerately. I believe in making educated decisions about the way you spend your time and money.
If you can get more for less, then why not?
This page is everything I find useful when it comes to planning and booking a trip. From cheap flights, to good food, I’ve got an opinion on all of it.
Table of Contents
Quick Links
Here are the quick links. If you want an in depth explanation on how to use these links effectively, check out below.
Flights
Google Flights, Kayak, Skyscanner, Momondo, Scotts Cheap Flights
Accommodation
Airbnb, Booking, Hotel Tonight, VRBO, Avantstay, Kayak
Camping and RV
Hipcamp, The Dyrt, Outdoorsy, RVshare, Recreation.gov
Car Rentals
Expedia, Kayak, CarRentals, Turo
General Resources
Where to find good food
Activities & Fun
Airbnb Experiences, Tripadvisor, Time Out, Expedia
Nightlife
Travel Visas
Vaccine & Health Info
Travel Insurance
Blogs and Guides
Nomadic Matt, Anywhere We Roam, Wikipedia, Blonde Abroad, Rough Guides, AFAR, Pinterest,
WHERE TO BUY COOL TRAVEL GEAR
In Depth
Here is where I get down and dirty with my process for planning and booking trips, and I share useful tips and tricks I’ve picked up over the years. There are many ways to get what you need, and the methods you use may differ from what I use, and that’s cool too. Hopefully something here helps you find what you are looking for, whether it’s a great deal or a great meal.
if you feel overwhelmed by the endless possibilities that exist when planning a new adventure, then reading this article can help you focus your energy and find some direction.
Booking Flights
These days there are plenty of ways to find deals on flights. There are sites like Scotts Cheap Flights and Escape Flights which are very helpful for harder to find deals. These resources are great for finding deals for specific airports or destinations, but they are also helpful when you want to travel, yet don’t know where or when. You can just wait for a great deal to jump out at you. Maybe you didn’t think of going to Portugal, but when a $300 flight pops up, it suddenly seems like a great idea.
First Step
When should you start searching for a flight? Whenever you decide to go somewhere, look for flights right way. Not to book, just to start tracking the prices. The only way you’d want to book immediately, is if you already know what a good deal is for your start and end point. And if you track flights that much, you probably can skip this section, because you know too much.
There are many opinions about when the best time to buy is (52 days out on a Wednesday and blah blah blah). But the truth is, I have gotten great deals many months in advance, and even just a couple weeks in advance.
Your best bet is tracking the prices as early as possible so you can start to see things for yourself. Keep checking for at least a few weeks to see what it’s doing. In general, booking really far out isn’t recommended, and booking last minute isn’t recommended either. Somewhere in the middle is the sweet spot.
Aim for more than a month away but less than eight months out. There are good deals everywhere. Just find out for yourself, then you’ll feel good about the price you get regardless, because you’ll know you put some time and effort in to get the best deal you could.
The process I use for finding good deals typically starts with Google Flights. You can input your destination and the calendar pops up with the cheapest flights available each day.
If your dates are flexible, you can easily see the cheapest options. Then, fine tune it by adding filters, such as only nonstop, and including/excluding certain airlines, etc.
If you don’t have a place in mind, click “explore destinations” on the homepage. This pulls up a map that gives a quick reference to the best flight deals for many destinations leaving from your home airport.
Once I have an idea of prices, I will cross reference my findings with Kayak and Skyscanner. Frankly, it’s rare I find a big difference in prices between all of these sites, but it’s a good habit to get into.
Momondo is another travel fare aggregator that can be helpful. I only use it occasionally for insight into flight prices over the long term. Once you input a flight search there will be a button on the top right – “Flight Insights for Los Angeles to New York”.
It pulls up a handful of charts and statistics about flights to your destination to give you an idea of how good of a deal you are getting at any given moment.
My one caveat when using Momondo is to investigate the website you actually buy the tickets from. They do link to many reputable sites, but occasionally they link to lesser known websites that when you look into them, have questionable reviews. They may be totally fine, or maybe not. Just do a little research if you haven’t heard of the site by checking them on Trustpilot, Better Business Bureau or Sitejabber. I usually book directly with the airline or through Priceline, Orbitz or Expedia and have never had issues.
Flight Hacks
One way to get creative with sourcing a good deal, is booking each leg separately. This isn’t new, but definitely worth mentioning, and Kayak offers this option right in the search. For example, buy a one way on Delta because it’s cheapest and then get the return on American because it happens to be cheapest.
You can also get creative with how you get to your destination. For example, a flight from Los Angeles to Antofagasta, Chile typically goes 11 hours south to Santiago, and then 2 hours back north to Antofagasta. But you can look into buying a ticket to Lima, which is an 8 hour flight followed by 2.5 more south to Antofagasta. It may be cheaper and shorter. Just leave enough time between your connecting flights if they are booked separately, and be aware that if you miss one, you are most likely screwed for both.
If flights to your destination seem expensive, look on a map at what other major cities are nearby, and start playing around with options to get there. For example, is a flight to Amsterdam too expensive from New York? See what happens when you fly to London and then book the final leg separately on a low cost European airline like Ryan Air.
Before Booking
In these (post?) Covid times, airlines policies are always changing. A lot are flexible with cancellations, but don’t make assumptions and end up screwed. Always read the fine print so you know your options.
I could keep going on and on about getting great deals, but there are many other articles that go deeper into how to get the best flight deals. These are just the quick methods I find work for me.
Booking Accommodations
There are so many places to stay these days. Between hotels, Airbnbs, RV’s, camping and glamping, how do you even begin to choose? I try to let the destination guide me.
What I mean by this, is that certain destinations are best suited for certain types of accommodations. If I am going to a small beach town for a summer vacation, renting a beach house is my first choice. Going to Las Vegas will be all about the big hotels. Going to New York? Hotels are expensive and small, so an Airbnb would probably get you more space for less money. And then, camping trips and trips with RV’s are in their own category.
Where to Start
1. Make a budget
2. Preliminary search of hotels and vacation rentals to understand the market
3. Start saving the places that you like
4. Research the places you like by reading reviews, amenities and location info
5. Book it!
1. First, come up with a budget. And then ask yourself how flexible that budget really is and if you are willing to pay a little extra for the right place. If my budget is $150 per night, I will set the price parameters to around $175. Sometimes the perfect place is $155 per night, not much more expensive, but you don’t see it because it’s outside the search parameters.
It is important to keep in mind all the extra fees as well. Resort fees and parking for hotels, and cleaning, service and occupancy fees on Airbnb. They add up fast, and can quickly push places out of budget.
That $193 per night Airbnb suddenly jumps up to over $300 per night after fees. Ouch.
And below, that $259 per night hotel is going to be a lot more expensive once you factor in the $46.60 per night resort fee, the 13.5% tax and additional 3% city tax. All of this is important to keep in mind when making your budget.
2. I always begin my research with a quick search on Booking and Airbnb. This gives me an idea of how far my budget will take me, and if there are better options in hotels or vacation homes. Sometimes the market for one or the other is terrible. Joshua Tree, for example, has few hotels and they are mostly not good. Yet, they have many awesome and affordable Airbnbs. A quick search on Booking and Airbnb will give you a good idea of what the best choices are for your trip.
If your dates are flexible, don’t enter any dates into the search bar, you will only be limiting yourself. You can fine tune exact dates later.
Sometimes I find a great place right away, other times I have to dig deep. And don’t be afraid to dig deep either. There are so many Airbnbs that you could be on page 15 and still find a beautiful place with a lot of great reviews.
3. Whatever website you use, save the places that stand out to you. My first search I only look at if it’s in my budget and if it looks cool. I dig deeper later. Take advantage of Airbnb Wishlists, or “heart” them on Booking. It is easy to get overwhelmed by the number of options, so having a small list makes it much more manageable.
4. Once you have your list of places, you can begin the more intensive research. First thing I look at is location. If you are in a small town this may not be a big deal, but in a city this can be an absolute deal breaker. You don’t want to spend an hour commuting to everything you want to do.
After location, I check out the reviews. This is arguably the most important part. It can have great photos, great location, but the reviews reveal what you really need to know. As you read them, keep in mind that sometimes people can be ridiculous. A bad review amongst a sea of good ones needs to be taken with a grain of salt. The same goes for a handful of glowing reviews amongst many mediocre or bad ones. The more you can read the better. Pay attention to the most recent ones too. There may be construction, closed amenities or new management resulting in slipping quality. All stuff worth knowing about.
If you have gotten this far, do a final check for amenities they have, and for any additional resort fees or service fees etc. Things like parking can be very important too.
5. Once the place you want has passed the test, book it! The prices of hotels may fluctuate a little bit, but Airbnbs most likely won’t. Nice Airbnbs tend to go fast, so don’t delay.
Whatever your preference is, just make sure you book as far in advance as possible. Especially for Airbnbs. The good ones usually seem to be snatched up months in advance.
VACATION HOME RENTALS
Airbnb is just about everybody’s first choice when booking a vacation home. Other than the high fees that add up quickly from service fees, cleaning and occupancy fees, it has tons of options and you can’t go wrong.
VRBO is another big player with tons of options, so when I have trouble finding an Airbnb sometimes I will search here.
Avantstay is a fairly new company in limited markets. Their focus is towards mid-range to high end homes that are great for larger groups. You will find some modest 3-4 bedroom homes, but you will also find massive 10 bedroom+ estates and even ones that can host 300 person weddings. What sets them apart from other vacation home rental sites is that they manage every single listing. This creates a consistent user experience regardless of where you are. They also work with a team of in-house designers who custom decorate each home, so they tend to be a little extra stylish.
HOTELS
I have always had a pretty similar experience using Booking, Hotels or Kayak. Booking tends to have vacation home rentals as well, so that’s a plus, although I have never booked one through them. You can’t really go wrong with any of them.
Hotel Tonight can have some great last minute deals. They have limited options, but what they have is carefully chosen, so you can usually count on a solid place through them. Just keep in mind that each booking is only for 2 guests and you can’t change that through the app. So if you are booking for more people you may want to look elsewhere or call the hotel to ask before you book.
Camping & Rv
Camping
Finding great campgrounds is slightly less straightforward. There is no one stop shop that I am aware of to see all public and private campgrounds.
I tend to prefer public campgrounds, as they are usually in the most beautiful places and they are the cheapest. Private campgrounds, like those you can find on Hipcamp, are great alternatives, but they tend to be $40-60 per night instead of the standard $15-30 for most public campgrounds.
My first stop when searching for campgrounds is The Dyrt. It is a great app for finding public campgrounds with reviews as well as some privately owned ones. You don’t book anything through the Dyrt, but it links to third party sites, typically recreation.gov.
If you know you want to camp in or near National Parks you can just go straight to Recreation.gov as well. If you like to read reviews, like I do, it’s nice to have extra opinions on The Dyrt as well.
That is typically where my search ends as I love the public campgrounds available around the US. But if you decide you want some other options, then Hipcamp has a variety of unique places. Sometimes it’s just camping in somebody’s backyard, and sometimes it’s a full blown, privately own campground.
RV
If you want to go the RV route I have seen great options on Outdoorsy and RVshare. When booking a trip in an RV there are many things to consider. First, where are you going with it and where do you want to pick it up? If you want to start in Los Angeles and then go to Mammoth Lakes, about 6 hours away, you can pick up the RV in LA, but then you are paying a ton for gas, and sometimes there is an extra charge for mileage on the RV. So the other option is finding an RV closer to Mammoth Lakes to cut down on those expenses. Unless of course part of the reason you want an RV is for the experience of driving it.
You also want to do your research on where you can park them. There are many places around the US where you can just park on BLM land and stay there for free. If you don’t need a hook-up this is a great option. Otherwise you want to plan ahead and book campgrounds with RV hook-ups if you need them.
There is a lot more to consider when renting an RV, so I will create a separate post soon.
Car Rentals
This is fairly straightforward, but there are definitely some important things to keep in mind. I always start off with a quick search on Expedia, Kayak or CarRentals. This will give you a solid idea of what it will cost to get a rental car. Depending on how far our you book, these prices may fluctuate a bit. They do use dynamic pricing depending on supply and demand. Track pricing for a few weeks and see if it changes before jumping right in. Unless it’s silly cheap up front. I booked a car in Mexico for $4 per day. It’s not getting much cheaper than that.
Often times when renting a car you don’t get to specify the exact car you get. It is usually a Toyota Camry, or something similar. If you want to get an exact car for your trip, or you simply wish to partake in the sharing economy you can try Turo. It is the Airbnb of cars. It works just like Airbnb, gives you many options for the exact car you want, and sometimes can be cheaper. Keep in mind you usually must return to the same place you picked it up since it’s just a person’s car most of the time. I have used Turo only once, but it was insanely easy and convenient. I didn’t even meet the person, just picked up the car from a grocery store parking lot and left it in the same place.
Things to keep in mind
– Read the reviews for the company you use. Sometimes the customer experience is horrendous and will leave you with headaches long after you dropped off the car. I always go with well known brands like Hertz or Enterprise. Better to pay a little more up front rather than have them holding funds and making things up about damages to the car.
– Always take a ton of pictures of the car. Damaged areas and undamaged ones too. You don’t want to be stuck fighting them about whether or not a new scratch was from you. To really cover your ass, do this at the end as well. Sometimes you won’t have an agent walk around the car with you upon return, so if you have photos at the beginning and end you are much more likely to be safe.
– Get insurance, or better yet, have your own. Check with your credit card company to see if they have car insurance included. Your own auto insurance may cover you entirely or partly as well. Another option, is looking into third party providers. These tend to be cheaper than buying it through the company. If you want to keep it simple, go through the company. Just keep in mind you might not need everything they are selling. So know what you have before getting there and being pressured into things you don’t need.
– Adding drivers may increase the price, so do so only if you need to. Often times a spouse may be included with no charge.
– Renting from a location at the airport will usually be more expensive. More convenient, yes. But decide if you want to save a little money, or have things be easier.
– Always return the car with the same amount of gas, or more. You’ll get hit with extra fees if it’s too low. Take note of nearby gas stations as you drive out so you don’t have to search when coming back.
– Read the fine print on your rental agreement. You usually can’t cross international borders or go on dirt roads, so if you do that and something goes wrong, you are now responsible.
– Use a credit card, not a debit card for the hold they require.
General Resources
Finding Good Food
Eating is important, and for some of us, it’s everything. So how exactly do you find a good meal anywhere you go? The internet of course. Actually, in an ideal world you will have some personal recommendations of where to go by locals. But for those times when you don’t have that luxury you will need to turn to sites such as Yelp, Tripadvisor and Google Maps. There are plenty of other resources you can use, but many of them are country or city specific.
Websites such as Eater, Infatuation and Thrillist are great for a place like Los Angeles, but they may not exist where you are going.
Whenever possible, ask people you encounter where they recommend eating. Ask Airbnb hosts, Lyft drivers, employees at the grocery store, anybody. Get locals talking about what they like. Then do a little research on top of that to see if their recommendations check out.
I like to start my search for a great restaurant based on a specific neighborhood. If you are in a town or even small city you may be able to do a general search, like “best restaurants Big Bear Lake” and quickly search through all the restaurants since there aren’t many.
If you are in a large city, you have to get a lot more specific. Searching “best restaurants Los Angeles” is going to bring back tons of options that may not be close to you. That search term tends to bring back a lot of expensive results as well. If you want a more modest meal you need to add more search terms such as “cheap” or “affordable” etc.
It is important to keep in mind that reviews need to be taken lightly. Google Maps reviews tend to be higher than on Yelp or Tripadvisor. A restaurant with nearly 5 star rating on Google Maps may be only 3.5-4 on Yelp. People tend to review more critically on Yelp, from my experience. Cross reference between a few sites if you want to be safe.
Activities, fun & Nightlife
So you’re going somewhere new and want to find fun stuff to do. How do you make that happen? You most likely have a few things you know you want to do or have heard of, but you will probably have to dig a little to find what you are looking for.
Mention a trip to New York and you may immediately think of Times Square, The Statue of Liberty and Central Park. Sure, they are things worth seeing, but there are way better things to do (although Central Park is truly great. Times Square, not so much). Finding cool stuff to do somewhere new is one of the hardest parts of traveling. That’s not to say you aren’t likely to have a lot of fun doing just about anything, but if you want to maximize your fun and go beyond the basic touristy activities you may have to dig a little deeper.
Activities & Fun stuff
I usually start with a generic search “things to do in New York”, “must see in New York” or “travel guide New York”. It gives you a quick overview of what main stuff to see. Occasionally there will be something that really stands out or something lesser known that finds it’s way into a top ranking article on Google.
Tripadvisor, Time Out, Expedia and The Culture Trip tend to pop up frequently. Although, it really depends on where you are going. This works well for the US, but other countries are likely to have different results.
Reading through those results will typically spark an idea for other things I’d like to do. For example, flea markets or art galleries. From there you can narrow your search and look for “best flea markets NY” or “art gallery openings NY.” Continue on down the rabbit hole and you are likely to find cooler things to do than the most basic tourist attractions.
The problem is that the best guides are rarely the ones you can find through a quick google search. When I lived in Australia, the big ones that people recommended were Broadsheet and The Thousands (which seems to have disappeared sadly). But I didn’t find those before I went. So the deeper you can go, the more solid info you may find. Pinterest, Reddit and other message boards are good for this as well.
Airbnb Experiences is good for random experiences where you are likely to get a much more unique and local perspective on things.
Events
One of the best ways to find cool things to do, is search for events. Whether it’s an art fair, a food festival, a concert or movie screening, some of the most unique stuff you can do will be going to a cool event. That is where you are likely to find locals too. Time Out is again, a good starting point, but don’t limit yourself. Dig deep, go beyond the first page of Google. Search for things like “free events NYC”, “upcoming events NYC” and see where it takes you. Once you browse the initial offerings, you are likely to come up with something more specific you might like, such as food, art or shopping events.
Music
For nightlife, I like Resident Advisor. This is largely for great electronic music with a lean towards the underground scene. So if you like to go out and dance to great techno or house music this is an awesome starting point.
It is difficult to recommend general guides, because the best ones tend to be location specific. Here are a few more of my favorites for NY and LA music:
Oh My Rockness – Indie music mostly
Sofar Sounds – An interesting concept, and a great way to go somewhere random and meet locals. You buy tickets to an intimate live music experience at often undisclosed locations and you don’t know how you will see. They are often local, lesser known artists, but great musicians nonetheless. They may be in somebody’s private backyard or living room, or in a coffee shop or bar. It’s a total wild card, but a lot of fun.
If you love music festivals, then Music Festival Wizard is a great place. This is also a great reason to travel somewhere new, especially for a road trip.
Visas, Insurance & Health
Visas
For visa requirements when traveling, I tend to just Google “visa requirements for Bolivia” or something similar. Often times the official website for the country will pop up and I always check there first.
Another convenient option is Online Visas. You input your home country and get a handy map and list of all the Visa requirements for each country. This is especially useful if you are hitting multiple countries in one trip.
Vaccinations & Health
When traveling to certain less developed countries you may encounter vaccination requirements to enter. In South America, Africa and Asia there is a lot of this. Vaccinations for things like Yellow Fever or Typhoid. There is nothing worse then arriving to a new country just to be denied entry because you aren’t vaccinated. Covid 19 vaccination requirements are becoming a thing as well.
The CDC is the number one source for all of this info as well as other health advisories.
Travel Insurance
I have personally almost never travelled with travelers insurance. Many believe this is a cardinal sin. As I get older I am more open to it. But when I was in my 20’s I was on a tight budget and that seemed like an expense worth passing up. Of course it is one of those things that is easy to pass up, but the second you need it you are beyond happy to have it.
Even though I didn’t take my own advice for years, I still recommend it now. World Trips and Insure My Trip are two great options. Insure My Trip searches multiple providers to offer you the best rates, so I would recommend starting here.
The only company I have actually used before was World Trips. I didn’t need to make a claim fortunately, so I can’t speak to what happens if you actually have an issue while traveling. But the rates were affordable and the reviews good.,
Other Blogs & Guides
Anytime I go anywhere I read a bunch of blogs and website to get multiple perspectives. I expect you to do the same. No one person has all the answers. These are some of the ones I most enjoy reading and find the most useful.
Nomadic Matt – Just about everybody knows this one and for good reason. He has been around forever, has info on so many places, and it’s pretty thorough.
The Blonde Abroad – Another heavyweight in the blogging world. Her articles have a lean towards single female travelers, but she has so much content and is quite thorough that anybody can get something from here.
Anywhere We Roam – A beautifully designed blog with stunning photos. A lot of content on Europe.
Hand Luggage Only – Lot’s of well designed content with a ton for the UK.
AFAR – The same as the travel magazine. Continually putting out solid content.
Rough Guides – the place I tend to go when looking for more classic travel guides.
Maptia – Great travel stories and photography.
Pinterest – a great place to search for travel guides from lesser known and harder to find blogs. Just because they don’t appear at the top of google doesn’t mean they don’t have valuable information. I find Pinterest to be a great place to find a larger variety of content from lesser known creators.
* The first two photos are not mine. Credit: Andrew Neel, Filippo Peisino
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