Whether you're just looking for inspiration or already have your next destination in mind, the best vacation planning sites will help you find your way.

It’s been said that some people spend more time planning their vacations than thinking about how they will save for retirement. I certainly wouldn’t recommend that.

A decent amount of forethought, however can lead to increased savings and fun—not to mention less stress.

Whether you’re an obsessive planner or just looking for a pre-fab itinerary, we’ve got you covered. Our list of the best booking sites for vacation planning will help you figure out where to go, what to do there, and how to save money on everything you need for your trip.

The best sites to help you research and plan a trip

Maybe you already have a destination in mind, but if you need help choosing, these sites offer ideas and inspiration. They can also help you plan your itinerary once you know where you’re going.


Like its more famous sibling Wikipedia, Wikitravel is a free, user-created travel guide for just about any potential vacation spot on the planet. Articles are arranged geographically instead of in categories like “attractions” and “restaurants.” That means you search for the place you’re interested in visiting, and then you can read about what’s there. If there’s not a guide for the town or city of your choice, you’ll see all of the articles that mention it.

For more personalized help, some destinations have “docents”—volunteer guides available to answer your questions. There are also “talk” pages (the discussion tab at the top) where you can ask a question or start a conversation.

Wikitravel is a great first stop on your vacation planning adventure. You can’t make any reservations through the site but you’ll find plenty of information, including a Wikipedia-style history of your destination.

Trip Advisor

Trip Advisor is more than your average booking site. You can find a hotel here, but you can also look for a vacation rental. This broad category includes beach houses, condos, villas, woodsy cabins, and any other time of home rental you can think of.

Once you settle on a destination, Trip Advisor fulfills the promise of its name with travel guides and directories of nearby restaurants and attractions.

But Trip Advisor’s best feature may be its user participation. In addition to reviews and ratings of everything on the site, there are destination forums where you can ask anything from “where to pop the question” to “what to do during a five-hour layover here.” The friendly and helpful advice makes it feel like your friends are helping you plan your vacation.


Dreaming of a longer, more adventurous trip? Bootsnall specializes in “round the world” vacations.

Their online booking tool, called “Indie,” allows you to plot out, price, and book multi-destination flights. But even if you’re not looking to spend a year on the road, there are many helpful travel guides covering every continent.

There’s also an extensive community section with forums, traveler profiles, and a page to post your trip itinerary for feedback and advice.

Lonely Planet

There are more than a few iconic blue Lonely Planet spines on my bookshelf. As a brand with an “off the beaten path” mentality, I always felt less touristy toting the books around foreign cities to help plan my trips.

If you’d rather carry a digital guide, download Lonely Planet’s free “Guides” app. It comes with maps, phrasebooks, a currency calculator, and lots of good advice on what to see and do on your trip.

You can also find that kind of information on their website. And if you want to start booking your trip as you plan it, Lonely Planet can help you find vacation basics like flights, car rentals, and hotel rooms, as well as add-ons like travel insurance, sightseeing packages, and other travel products.

The best booking sites for travel packages

This is probably the set of sites you’re most familiar with—where you can rent a car, book a flight, reserve a hotel room, and seek out other travel services.


Expedia may be the most well known site that provides it all: hotels, cars, vacation packages, and more.

If you haven’t used it in a while, take a look. Expedia has added new features to its site including “Cruises,” “Vacation Rentals,” and “Things to Do.” In fact, it now resembles TripAdvisor.

Unlike TripAdvisor, Expedia offers extra discounts on hotel prices to “members” who sign up for its email list. Expedia membership also comes with the chance to earn Expedia+ points in addition to any rewards points you earn through travel rewards programs and credit cards.

Other convenient features include “Bundle Deals,” which allow you to quickly price combinations of hotel/flight/car rental and other vacation packages.

The “Scratchpad” saves your browsing history in one location so you can glance at all of your choices as you narrow the list. And the Expedia app keeps you updated on your reservations.


Trip Hobo calls itself “the world’s smartest trip planner.” It helps you create smoothly planned travel itineraries for an extremely broad range of cities—14,000 worldwide.

If you’re not sure what you want to do, you can browse a gallery of other users’ itineraries.

Once you select a destination, you can take full control of the planning or use the “Suggest me a plan” function to view TripHobo’s recommendations. The site’s command of details and logistics is nearly unrivaled.


Kayak may be the best site to visit if you want simplicity.

As with Expedia, you can compare and book flights, hotels and car rentals—as well as less-covered options like train tickets.

You can also search for vacation packages in a range of prices. And extra discounts are offered to Kayak members.

However, Kayak focuses on these core services instead of detouring too much into activities and attractions or alternative accommodations. This makes it a great site to use if you already know what you want from these basic categories.


Today’s travel sites can do much more than just book your ticket or hotel room. With the Internet as your travel agent, vacation planning is enjoyable and stress-free.

Which site is your favorite for researching and booking a trip? Have fun deciding where you’ll go next, and tell us about it in the comments.

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About the author

Elizabeth Spencer
Total Articles: 42
Elizabeth Helen Spencer is a personal finance and travel writer based in the Philadelphia area. She holds an MFA in Creative Writing and still nurses a secret fiction writing habit on the side. When not writing for work or pleasure, she loves to sweat it out in a hot yoga class and find new books to read. Elizabeth lives with her husband and two children and has reached the conclusion that "having it all" is a myth.