Over the last 20 years, I've planned and booked 99% of the trips I've taken. I've used plenty of free services, and paid for help when needed. Below are the companies I've used in the past and am still confident recommending today. — Dave, Founder, GoBackpacking.com
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Kayak is the first place I go whenever I want to search for flight prices. It's fast, easy to use, and gives comprehensive results. Their price trend graphs are also helpful.
Skyscanner lets you set the destination to “everywhere” and get a sense of everywhere you can fly from the city you're leaving. Use it when you're not sure where you want to go.
AirTreks specialize in RTW and multi-city tickets. I used them to help me book my first four flights of my RTW trip, allowing me to focus on other things before leaving home.
Transportation
Rail Europe is the #1 distributor for European train tickets and rail passes. Multi-use tickets save time and money.
Japan RailPass is a must-have. Get access to all JR national trains in Japan, including bullet trains, for 7, 14, or 21 consecutive days.
Uber is my preferred ride app because I can use it at home and abroad. Get a free ride when you sign up with my promo code: uberdavelee
Tours & Sightseeing
G Adventures is the global leader in small group tours, with an emphasis on adventure travel and sustainability. Most tours are one-to-two weeks long. 700 tours worldwide.
Get Your Guide is an easy way to book tickets to popular sites in advance, plus they offer tons of half and full-day tours. I'm a fan of their skip-the-line tickets for European attractions.
Viator is another leading online sightseeing and tour booking site. Site features 100,000 things to do and millions of user reviews. A TripAdvisor company.
Accommodation
Booking.com offers every kind of accommodation, including hostels, hotels, and B&Bs. If I'm not sure what I want, I start here.
HotelsCombined is an excellent resource if you know you want to stay in a hotel. When we polled Go Backpacking's readers, HotelsCombined was a top choice for booking accommodation.
TripAdvisor has it all: hotels, flights, restaurants, tours. And the millions of customer reviews to help you make the best choice.
Hostelworld is the best place to search for hostels, whether you're using the website or mobile app. I rely on the user reviews, making sure to only stay in hostels with an 85% or higher rating.
Airbnb is perfect for when you need a break from hostels. Depending on the country, I either rent a room or apartment. Becoming an Airbnb host can help you earn money to travel.
Couchsurfing existed before Airbnb, and allows members to stay at one another's homes for FREE. I couchsurfed a dozen times during my 'round the world trip from 2007-9, and still use it today. It's a great way to meet locals.
Travel Insurance
World Nomads is one of the most budget-friendly travel insurance options available. You can purchase a policy while traveling, which is helpful on long trips.
SafetyWing is a startup offering travel and medical insurance specifically designed for digital nomads. Comparable policies are significantly less than the competition.
Allianz Travel Insurance is another trustworthy option, although it tends to be a little more expensive than World Nomads.