Trip Planning

A lot of friends ask me how I find all the cool places we stay at. In this post I’ll introduce a few of the sites that I use for researching and booking places to stay.

TripAdvisor is probably the site I use most heavily when researching trips. I’m sure most people are familiar with it, but it’s a site that ranks hotels, restaurants and attractions based on user reviews. I use it primarily for researching hotels. I’ll look up a specific hotel that I’m considering, which I may have found elsewhere, as well as looking at the hotel rankings for a city or area I’m interested in. For example, I recently used it to check out hotels in St Augustine. There are various useful filters, for example this was for a trip with my partner Paula over Valentine’s weekend, so I filtered to just show the “romantic” hotels and ended up booking the top one on that list, Casa Monica. I don’t go purely off TripAdvisor rankings though, I do read the reviews in quite a bit of detail to try to work out which place would best suit what we’re after on a given trip – and of course cost comes into it too! Also I often find useful tips on TripAdvisor for a given hotel – which rooms to ask for, where to go for dinner, etc.

Tablet Hotels is a site that I use quite a lot to find cool boutique hotels. A lot of the nicer hotels that we’ve stayed at in the past few years I’ve found through Tablet. Some of their properties are pretty expensive, but in a lot of cases they’re comparable to the costs of more boring chain hotels – there is quite a price range, but based on my experience so far, their hotels are always cool and interesting. Tablet is just an agency, so hotels are not exclusively with them – you can book through Tablet, or via other means. Usually I have found Tablet prices to be competitive with (generally the same as) other booking routes, though on our recent trip to Trancoso, I booked one of the hotels I found on Tablet for half the price on Expedia. But this is the exception rather than the rule. They have an optional paid membership called Tablet Plus, which costs $195 a year, and gets you various perks including room upgrades when available (at some but not all hotels), and other things like free drinks/breakfasts/Internet depending on the place. If you think you’ll use Tablet quite a bit it’s worth considering, I have received some nice room upgrades through this. You can use this link to sign up for Tablet’s private sale email, which sends you special offers before they are generally available.

Hotwire is another site I use a lot, which approaches this from a whole different direction than the previous two. They offer discounted deals for hotels or car rental, but you don’t know in advance the name of the hotel or rental car company. I use them quite a bit for both hotels and cars, in certain situations. For example, if I’m staying in Manhattan I often use Hotwire to book a hotel, as hotel rates there tend to be so crazy. I can usually get a 4 star hotel for $150 to $200, and they usually have 3 star hotels for closer to $100, which is much cheaper than booking direct, in most cases. If I’m staying in New York I’m usually not going to be spending much time in the hotel anyway. I’ve used Hotwire in London a number of times too. They often have incredibly cheap deals on hotels by Heathrow Airport, which I’ve used quite a few times – though recently I prefer to stay in central London, I’ll write a post on traveling in and out of Heathrow shortly. I have also used Hotwire fairly often for rental cars – in most cases I don’t have a strong preference which company I use, and often they do have good deals.

Airbnb is a site I’ve used quite a bit recently, where individuals rent out rooms in their homes, or their whole home. I used to think of them mainly as a low budget alternative to staying in a hotel, but these days they have a wide price range and a lot of very cool and interesting places to stay – and all across their range you are likely to get something that is a much better deal than a comparable hotel. I recently used this to book a couple of stays at an extraordinary apartment at the top of St Pancras Clock Tower in London. It’s definitely worth checking out airbnb as an alternative. In most cases you won’t find airbnb places on TripAdvisor.

VRBO is another site somewhat like airbnb, in that it lets home owners rent out their homes directly. It’s been around a bit longer and is a little more “old school” – it doesn’t handle all the booking and reservations in a consistent way like airbnb does. But in some situations I’ve found it useful. I was just booking a house to rent for a few days in Santa Fe, and VRBO had a much bigger choice of places than airbnb there.