Yes, you can take that trip:
A guide for those who don’t travel much
A photo you saw in a book as a child, the postcard you received from an aunt, the city from your favorite movie, or how a friend talked and talked about the best dinner they ever had on their vacation–we all have places in our mind that we’d love to visit “someday.”
Life is precious, why not make that someday become tomorrow? If you don’t know where to start, start here.
This guide is for those who are new to traveling, whether you’ve never left the country or are ready to do something other than the same vacation year after year.

7 Rules to Travel By
Where to stay
If this is your first time traveling to a new country, you might default to booking a hotel. Staying at a hotel is great, but Airbnb is also a budget-friendly option for finding a comfortable place to stay.

Deciding between a hotel or Airbnb
If you’re unsure where to start, start with your budget. Do a search for hotels and see what the price ranges are and then do the same thing on Airbnb. This might give you the answer you need, however, more likely it will be a bit more nuanced.
As a general rule of thumb, if it’s 2 nights or less, I’ll book a hotel. If it’s 3 nights or more, I look for an Airbnb that meets my needs.
Another factor could be group size. Depending on the country, rooms with two queen beds may be hard to find. If your party is 3 adults or more, it might be more affordable to find an Airbnb than booking two hotel rooms.
Hotels are more ideal for:
- Shorter stays
- Convenience of housekeeping, meal service (depending on hotel), bellhop, concierge
- Easy check-out procedures, for example you don’t have to take the trash out
- Storing luggage before check-in and after check-out
- Using credit card points or reward points
Airbnb rentals are more ideal for:
- Longer stays
- Groups
- Saving money on eating out by using the kitchen, storing leftovers, etc.
- More room to relax
- Getting a glimpse of daily living
- Budget-friendly travel
For selecting a resort, I could use guidance. Resort stays are not my area of expertise, so if you have some recommendations, please share them in the comments!
Booking an Airbnb for the first time
If you’ve never booked an Airbnb, you might be pleasantly surprised how easy and fun it can be. More times than not, it is cheaper than a hotel and more comfortable. Below are some tips to help you get started.
Enter your initial search requirements: city, dates, number of people. You’ll get a wide range of results, but next you need to go to Filters to narrow down the search for what you need.
- Type of place: select Entire Home if you want a place all to yourself
- Price range: while it’s nice to find a deal, I will increase the minimum price per night to eliminate undesirable rentals
- Bedrooms vs beds: often you’ll find the number of beds is greater than the number of bedrooms as sofa beds or futons in the living room count as a bed. When traveling with friends or family, I always select 2 bedrooms.
- Amenities: if I’m staying longer than 4 days, I will want a washing machine
- Self check-in: if I’m getting in very late, then I’ll select this option. Otherwise, it doesn’t really matter.
- Host language: the Airbnb app has an auto-translate feature for messages between hosts and guests. I’ve never had an issue with a host not speaking English, so I don’t think this filter is necessary.
Now that you have a list of places that meet your requirements, it’s much easier to find the perfect place to stay. I prefer searching via the map view, so I expand that and zoom in.
Here are things I typically look for:
- Outdoor spaces or beautiful views
- Proximity to transit or walkability to sites
- Pay attention to the cancellation policies, they differ by host
- Fees can change by host, so one place might be cheaper per night but the total might be more expensive
- Read reviews thoroughly to find things that may not be in the description. Is there an elevator? Is the wifi fast enough to support work activities? Is there loud street noise at night? Do they let you check in early or store your bags?
- Discounts for longer stays (1 week or more)
And if you can’t find what you’re looking for in the description and reviews, you can always message the host prior to booking with any of your questions.
Selecting which neighborhood to stay in
Honestly, there’s no exact science here. But usually you don’t want to stay in the heart of the tourist zone in big cities as it’s going to be more expensive, harder to find good places to eat, and crowded. If you’re only staying for one or two nights and want to maximize the number of sites you see, then this could make sense.
Otherwise, I suggest doing your research on the best neighborhoods to stay in. A simple Google search could do the trick–I like to read blogs from other travelers who share their first hand experiences.
I look for slower-paced neighborhoods that are walkable to the main sites, have transit options, and have a mix of locals and tourists. In smaller towns, this is not necessary as the entire town is probably a good choice, but in larger cities, this is my preference.
My favorite resources
I’ll update these regularly, so be sure to check back.

Essential apps:
- Google Maps – for finding and saving sites, stores, and restaurants or for navigating local transit options. Don’t forget to save my maps of favorite places.
- Google Translate – this app can translate signs and menus using the camera feature, listen to audio, or record and play your phrase in a different language
- WhatsApp – commonly used app to send messages or make calls to people around the world
- Mobile Passport Control (if you don’t have Global Entry) – when returning to the U.S., use this app to zip through customs
For getting from point A to point B:
- Rome2Rio.com – one of my favorite sites, Rome2Rio is especially helpful when you’re not sure if it’s better to take a train or a flight (or sometimes a bus). Your search results will show the easiest and cheapest travel options.
- FlightConnections.com – if you know you want to fly and are not limited to one airline, this is a great website to see your options for visiting other cities that are one flight away
- SeatGuru.com – for help selecting the most comfortable seats on your flight
- Google Travel – if you’re unsure where you want to go, you can use the Explore option to see prices for destinations from your home airport. Use Google Flights for tracking ticket prices, knowing if it’s a good time to buy, or searching for cheapest travel days.
- Hopper (mobile app) – for tracking prices of flights and knowing if you should buy now or wait
- Roame.Travel – if you have credit card reward points, this site finds the best deals on flights regardless of loyalty program
- Watch this video for “24 flying hacks” that covers everything from websites to use, packing tips, and how to make your flight as comfortable as possible
For booking unique experiences:
- Airbnb Experiences – select the Experiences tab to discover local activities. It can be a mixed bag, but I’ve booked some great cooking classes, personal tours, and cocktail bar experiences through Airbnb.
- Viator – a Tripadvisor company, I find this site easier to navigate than its parent company to find unique local experiences and not just Cheryl’s favorite playground to take the kids. Personally, I’ve booked excellent wine tastings, day trips, and tours via this site.
For research and planning:
- The king of European travel, Rick Steves, is one of my favorites. I recommend looking at secondhand book stores and thrift stores to purchase his distinctive blue and gold travel guide books–the history of places doesn’t change so the year published doesn’t matter much. His website is also packed full of helpful information and he has many videos on YouTube and streaming services.
- YouTube might seem like an obvious choice but is sometimes overlooked. There are so many incredible travel YouTubers that share tips and recommendations for whatever kind of trip you’re planning. Make sure to save notable places onto your Google Map!
- ThePointsGuy.com – more than just tips on using loyalty points, this website is full of airline news, travel tips, and resources like this guide for first-time and frequent travelers
- If you’re going to Europe or the U.K. for the first time, check out my blog post for additional tips

How can I help?
I hope this guide helped you get started in planning your next trip, but if you find you still need a little extra guidance, I’m happy to help.
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