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The best online resources for planning a trip

With hundreds of air travel companies, tens of hundreds of hotels at each destination, and prices that change several times per second, trip planning can be a nightmare, and getting a reasonable deal is not that straightforward. This page will teach you the secrets to booking a trip fast, with the most options, and the least hassle.

If you just don't have the time for it, there are a number of interesting services online that can do the work for you, such as Mygola.

As an example, we'll use Big Island, Hawaii, a somewhat challenging destination given its lack of public transportation and numerous attractions spread throughout the island.

Start with

  • check sunrise/sunset times at the destination(s)
  • check the predicted weather on Weather Underground (based on historical records for the period you are interested in): enter your destination, click "Trip Planner", then enter the dates.
    Example of predicted weather for Honolulu over Christmas
  • read the TripAdvisor PDF for the place, for a general idea
  • go through the TripAdvisor "To-Do" / attractions list to get an idea of what you want to see during your trip.
    Example for Kona, Big Island, Hawaii
  • you can easily place the attractions you want to visit on a Google Map. Sign into your Google account, go to maps.google.com and click "My Maps". This will let you visualize where you want to go and pick a place to stay that optimizes the distance to your destinations. You can also get directions, which help with estimating travel time among points of interest.
    Here's My Google Map Big Island, Hawaii.
  • read the Wikitravel pages for your destination. Start with the country (for general customs, dress code, and general aspects to be aware of), continue to the state/county/region page for local regulations and attractions outside a city, then end with the place for the locality you want to visit.
    For example, for Kona, you'd read the US page (learn that Americans have a gut aversion to Speedos, for example), then Hawaii (learn the law about driving mopeds), then Big Island to learn bout local points of interest, then finally Kona.
  • stay in touch with the local travel-related topics at TripAdvisor's forums, or ask your own questions.
    Here is the forum page for Kona.

The best online sites for travel planning

  • Kayak - a meta-search engine for flights, hotels, cars and vacation packages. Searches hundreds of other search engines, brings all the results together, and offers powerful options for filtering results, saving favorites, removing bad deals, sharing results in real time with a friend etc. The best, by far.
  • TripAdvisor - has reviews for hotels, restaurants, activities, tour companies etc. For condos though, use FlipKey or VRBO directly (see below in Where to stay.
  • Yelp - has reviews for pretty much any business in the US and UK.

How to book a trip

  • have everything ready to be booked at once, so you are sure the condo (hotel room) is available between your flights, and cars are available too. For example, in Big Island, HI, it's easy to not find any car available in high season, even though there are still accommodations and flights.
  • always check RetailMeNot for coupons. You can easily save between 5% and 10% on hotels with Orbitz.com coupon codes like fabsave5. Many other travel sites take coupons.
    Example coupons for Orbitz, Expedia, Travelocity

Where to stay

  • check for condos on VRBO and FlipKey - many are much cheaper than hotels and way larger, with real kitchen and other amenities
    • beware that the search options are very primitive: you can't search by available dates, nor filter by amenities
    • when filtering out candidates, look first for special length of stay requirements that you don't meet, such as "minimum 10 nights for Christmas period"
      • still, some owners will do you a favor and let you rent for fewer nights
    • you must e-mail the owner and inquire about a quote and availability because often enough, condos marked as available have been rented, but the owner didn't bother to update the status
  • CouchSurfing provides a very cheap alternative to staying at a hotel or condo - you stay at a CS member's house, and have a varying degree of privacy and access to bathrooms and other amenities. If all you need is a couch to crash on, Couchsurfing is great. You can also search for dedicated rooms, and sometimes you may find one with a private bathroom.
  • if are short on cash and you want to stay at a more or less random hotel, you can bid on Priceline or Hotwire, and get a hotel of their choice at your price. But first read http://www.betterbidding.com/.


  • for continental US flights, check Southwest separately, as they don't share prices with the search engines
  • after you booked the flight, when selecting seats, check SeatGuru for the best seats in that airplane
    • if traveling as a pair and there are 3 seats in a row, select the aisle and window seats. You can always offer one of these seats to the passenger who'll get the middle seat, but there's a chance nobody will want a middle seat and you'll have all 3 seats to your two selves.
    • if the booking site says you can't select seats at the time, come back one day later, and you may be able to select seats

Car rentals

  • check specialized sites first (e.g. Discount Car Rental Hawaii) before Kayak.com or other (meta) search engines
  • you can also find car rentals on Craigslist. You'll get a car with cosmetic blemishes, which won't make you look like a tourist, and you'll pay much less for it.
    Example: Kona car rental on craigslist
  • car rental reservations may be cancelled at very low fees, e.g. $10 for Budget, so reserve one anyway if your plans are uncertain.
  • if you don't really care about the type of car, and just want an inexpensive one, try Priceline's "Name your own price".