Travel Planning (Part 2): Where to Stay and What To Do

Successful trip planning can be a complex and involved process.  Check out this four part guide on how to put together an excellent vacation!

Now that you’ve decided where to go in Part 1 of the series…the next step is deciding where to stay and what to do while you’re there!

What to Do

Though it may seem backwards, I decide what things I’m interested in doing before I decide where to stay.  This gives me the opportunity to identify what areas I’m going to be frequenting at my destination and pick a hotel (or vacation rental…or campground…or whatever) that is convenient to my plans.

At this stage, I’m not making an itinerary (see Part 3).  Just a list of anything and everything that I might be interested in.  Museums, exhibits, historical sites, cool architecture, tasty looking restaurants, meeting locations for any tours, etc.  If you’re travelling as a group, it’s a good idea to have everyone make a list of things that they might be interested in doing while they’re there.

Finding Ideas of Things to Do

So where do you find ideas of things to do on your vacation?  Pretty much everywhere!

Internet: The internet has definitely made travel planning a whole lot easier!  A wealth of information and ideas is just a click away.  Check out tourism websites for your destination…Pinterest…travel forums…blogs…etc.  You’re sure to come up with a ton of incredible ideas of things to do no matter where you’re traveling.

Books: Travel guidebooks are still a great resource for ideas of things to do on your trip.  Though the information in them isn’t as up to date as internet-based resources, sometimes it’s nice to be able to flip through a physical book full of glossy photos, maps, and travel tips…all in one handy location.  Without a need for wi-fi.  If you don’t want to purchase a book, don’t forget about your local library!

Friends and Family:   Have any of your friends or family been to your destination before?  If so, ask them about their trip.  What was their favorite thing that they did while they were there?  Their least?  Did they like where they stayed?  Firsthand experience can certainly be invaluable…but always remember that everyone has their own interests and travel style.

Generating a Map

Now that you have a list of things that you might be interested in doing, it’s time to generate a map.

You can either do this literally—by dropping pins in the locations on a map (either virtually with something like Google maps or physically by marking up a paper map)—or figuratively by familiarizing yourself with the area so that you know in general where things are located.  The exact address isn’t the point here, you’re not going to generate directions from one place to another from this (though you could if you built a custom map of locations). This step is to get an overall idea of the areas of the destination that you’re interested in visiting.  Which comes in handy both when choosing where to stay and when planning your itinerary.

Choosing Where to Stay

Once you know where you’ll be spending time at your destination, that’s when to choose where you’re going to stay.

No matter what type of lodging you choose (hotel, vacation rental, campground, etc.), you’ll want to know where that’s located in relationship to the activities that you want to do while you’re there.  There’s nothing worse than picking a hotel and then discovering that it’s all the way across the city from everything you’re planning on doing…or typing ‘hotel in Washington D.C.’ into your search engine and getting 300 results to sort through.

By mapping out your areas of interest you can better make decisions about what lodging locations best fit your needs…narrowing down your search results and making sure you’re not surprised about travel times after you’ve already booked.

Pros and Cons of Locations

One of the most basic decisions about where to stay is also one of the most important.  Do you stay central to your activities…or further out?  On the surface, that seems like a simple, straightforward question.  Closer seems better.  But you’d be surprised how many times people actually opt to stay at a distance from where the attractions they plan to visit are located!

The main driver behind a decision to stay further out is often cost.  Hotels and other forms of lodging close to desirable areas are often much higher priced than those options at a greater distance.  Sometimes compromises need to be made.

Central locations:  Staying in a central location offers easy access to attractions, restaurants, and other amenities.  Even though a few things on your list may be located further out, you’ll minimize the amount of money and time you need to spend on transportation to and from activities.  However, you’ll likely pay a premium for these rooms.  But no need to worry about getting home if you decide to stay out late.

Distant locations:  In addition to often being less expensive, staying out of the main tourist zones of a destination can also often provide a slightly less hectic atmosphere if that’s what you prefer.  However, these areas are often not located near many of the activities that visitors want to see, so that’s going to require transportation of some sort.  Destinations with great public transportation systems often make this relatively easy, especially if you stay near a well-connected station.  However, consider the cost of transportation passes and the time needed for any commuting (as well as what time you’ll likely to be travelling—rush hour on the subway is never much fun!).  If there isn’t public transportation, how will you get where you need to go?  Will you rent a car?  If so, what is the parking situation near your activities?  Uber/Lyft?  All these expenses (of money and time) need to be considered to determine if the lower cost of the hotel room is actually a savings.

The beautiful Palmer House Hotel in Chicago

Hotel Choices in Action

Here’s a quick look at how I decided where to stay for a few of my trips.

Boston:  While I haven’t gone on this trip yet, so I can’t tell you exactly how the decision played out…but I knew I wanted to stay in the general historic downtown area.  Pretty much everything on my list of things to do was located in this small, walkable region.  But…I also knew I was going to take a day trip to Salem by commuter rail…leaving early and returning late.  I liked the idea of being close to North Station where I could easily catch the train to Salem…and the area is so compact that I’d still be within easy walking distance of most of my other activities.  As I’m going to be spending much of October on the road (in inexpensive chain hotels), I knew I wanted something a little special…but nothing that would break the bank.  Thankfully I was lucky enough to catch Hotel Indigo Boston Garden running a special.  Right next to North Station.  Within walking distance of most attractions on my list.  Convenient subway access for those places that aren’t easily walkable.  Granted I expect this is a very busy area of the city…but I’m only there for a long weekend, so that shouldn’t be an issue.

London:  My last trip to London, I was in town for about a week…and the places on my list of things to do were relatively spread out over several areas of the city.  Because I was there for a longer period of time, I wanted somewhere relatively quiet and budget friendly.  Thankfully London has a great public transportation system and I had already loaded my Oyster card, so I knew that staying a short distance away from the main tourist zones wouldn’t really be a problem.  I was also coming in from Paris on the Eurostar…which meant I’d be arriving at St. Pancras…and after a full day of travel (even fuller than I expected thanks to a mistake on my passport!) I knew I didn’t really want to have to trek halfway across London to get to my hotel if possible.  That’s when I discovered a lovely row of houses in Bloomsbury converted into multiple hotels…all located on a quiet street with a garden.  Walkable to St. Pancras, tube stations, and a couple places on my list of things to do.  In the end, I choose the Harlingford Hotel as they offered a single room and breakfast (because I’m not very good about grabbing breakfast on the go in London).

Chicago:  I knew from the beginning that this was going to be a super quick weekend trip.  Time was of the essence.  I didn’t want to be spending anymore of my precious minutes travelling than absolutely necessary.  I wanted to fly in…take the L to my hotel…then be able to explore on foot from there.  And, since there was really only one reason for this trip (to see a musical production), I wanted to be as close as possible to the theater.  All these things added up to staying downtown.  Downtown hotels in Chicago are *expensive.*  Way outside my budget for a weekend trip.  Thankfully, most of them cater to business travellers…and there isn’t much business travel right before a major holiday….  Which meant that I could score a deep discount on a room at the incredible Palmer House around Thanksgiving.  Close to an L stop.  Right next door to the theater.  Walking distance to other attractions that were already on my list of things to do.  And absolutely stunning (which made a weekend trip feel extra special)!!!

Travel Planning (Part 3):  Building your Itinerary