No one likes to think that they paid too much for something. Everyone
likes a deal. But when it comes to travel, how do you get the best
deal? How do you save on flights, hotels, cruises, tours…?

It has a lot of it has to do with research, tools and timing.

Here are some tips and resources to help you get the best deal possible.

Booking a flight
Start monitoring flights and options (trying to find the best route and
price combination) three to four months before you plan to travel.
There seems to be a price sweet spot – if you book too early, the
airlines are still banking on customers coming through and so don’t
discount fares; if you book too late, they take advantage of your
procrastination.

Buy on Tuesday – that’s what I’ve read most recently though a year
ago it was buy early in the morning on Wednesday. This will change so
it can be part of what you monitor as you’re tracking prices.

When booking a flight:

• Keep your fly dates flexible.
• Look for the best connections vs. price.  Some of the options can
  be quite crazy. The best price I found for my trip to Chile flew me
  from Toronto to NYC to Barcelona to Santiago. I may like to save money 
  but I’m not that cheap.
• Book carefully watching the flight details and layovers. On a long
  haul flight, you likely have options and your layover could be in the
  middle of the night or early in the morning for the same price.
• All else being equal, maximize your points.
• Always collect points even if you don’t think you travel enough to
  take advantage of them. There are other ways of accumulating and
  spending points and you don’t know what the future holds.
• Be mindful of extra fees.

Rosemount Inn and Spa in Kingston, Ontario

• There are many booking engines. Just Google cheap flights and you’ll
  find lots. Use a couple when looking for the best fare and compare the
  results with the airline’s fares by going to their site directly.
• I recently heard about dynamic pricing. This is where online vendors
  gather information from your browser and modify their prices. Not
  all vendors do this but it was suggested that you check prices with
  both your regular browser and a secondary browser that you set up
  not to accept cookies.
• You know that little box that asks you for a promotion or coupon
  code which you never have? Well, sometimes you can get one just by
  Googling for it. You can also go to PromotionsCodes.com or FabulousSavings.com.
• Get a refund if you paid too much. Yapta.com
  will track the price of your ticket to see if it gets discounted
  further. I signed up and entered my trip to Chile. From what I’ve read,
  most airlines will issue a refund if the difference is $150 or more.

Booking Accommodation
Booking accommodation varies greatly depending on whether
you’re going budget or luxury or somewhere in between. Here are some
useful resources:

• The booking engines that you use for flights are happy to book your hotel as well.
• TripAlertz
  is like Groupon for travel. Simply sign up for free and receive their
  deals. If you buy one of their special deals you’re guaranteed their
  special price and, if the right number of people buy the deal, you get
  the Epic Price.
• Sniqueaway.com, Tablet Hotels, Jettsetter.com
  require you to become a member then offer special discounts typically
  on high end properties. With Sniqueaway you need to be invited. Google
  “Snique Away invite” to get a form to complete and become a member.
• Look for hotel reviews. This is especially important if you’re booking budget accommodation. Check Tripadvisor.com
  or the ratings on your Hostel booking site to see what people have
  said about the location. Don’t read just a couple of reviews, read
  many. And watch the dates of the reviews, they can be very out of date.
• Get a look at where your hotel or hostel is located and the surrounding area using Google’s Street View.

At the Hacienda Tres Rios resort on the Riviera Maya, Mexico.

Tours, resorts and cruises

This is the type of travel that frustrates solo travelers because we
are often overtly penalized for traveling alone with the brutal “single
supplement”. Here are a few thoughts and tips on the matter.

• Google “single supplement waived” to find the latest deals.
  Unfortunately, there are fewer and fewer as the travel industry heats up
  again.
• Be flexible. Book late. Accept a roommate. Ask to have the
  supplement waived. Work with your tour in any way possible to have the
  supplement waived.
• If you manage to get a really good deal – a deal that is even good
  with the single supplement – try to forget that they still hit you with
  it.
• Join sites like TripAlertz in hopes of getting that really great deal.
• Choose tour and cruise companies that support solo travelers like Norweigan Epic or Gap Adventures.

Janice Waugh publishes Solo Traveler, the blog for those who travel alone. The blog offers solo travel stories, tips, safety advice and destination ideas as well as a couple of free ebooks including Glad You’re Not Here: a solo traveler’s manifesto.