Dublin, Ireland

Welcome to Rudderless Travel

First time here?

Yes. Alcohol!
Because no great love story started with someone eating a salad!!!

Things To Know About Me

I work full time with children with special needs.

Read more about that HERE

30+ Countries Visited

4 Continents Visited

First Country Ever Visited - Barbados (It's where my folks are from)

Born & Raised In Toronto, Canada

I was once a hip-hop artist with a successful Moet Drinking Career

**Please Note** One of these statements in mildly exaggerated 😉

planning a short trip

About Me

Hey there, My Name is Christopher Rudder, and I’m so glad you found my travel website. 

I am a short trip, mini-break, business travel, weekend getaway, stopover and layover specialists who uses my skills in videography and editing, photography, podcasting, and writing to tell stories and create itineraries for Rudderless Travel.

I’ve visited about 60+ cities and towns in about 30+ countries while working full time. I mention cities because while I may be away for two weeks to a month, I planned short trips and stopovers to maximize how many places I see during that time. 

Read more about me HERE: Being Rudderless With Christopher Rudder

My Travel Style

My travel style was born out of necessity. I had a burning need to see and explore this fantastic and vast planet but I was restricted by the amount of vacation time I had. The average person has two to three weeks of vacation. So instead of spending all of my time in one or two cities, I wanted to maximize the number of cities and countries I visit by spending an average of two to three days per city.

If you include long weekends, you might have more vacation time than you think.

Taking a short trip is one of my favourite ways to travel because they allow me to travel extensively despite having a limited amount of vacation days. In addition, when done correctly, short trips are like a travel hack – a way to hack your way to travelling more!

All that said it order for you to enjoy your short trip thoroughly you’ll need a little bit of Acceptance and a lot of Planning & Logistics.

Short Trip Travel Styles

The Difference between short trips and a long trip can be defined as a short trip that takes place within a day (12 hours) up to a week. This includes 24, 48, 72 & 96-hour trips or 1-4 day trips.  
A long trip is when you spend an entire week, 2 weeks or a month in a particular city or region.

Weekend Getaways

A weekend getaway is defined as spending a weekend in your backyard, province, state or region or internationally.

Weekend: Leave Friday afternoon and return Sunday evening.
A Long Weekend: Leave Thursday evening and return Sunday evening or leave Friday evening and return Monday evening.
(In Canada, we have about eight long weekends in one year give or take depending on whether you have Good Friday and Remembrance Day off as well as where Christmas, Boxing Day and New Year Day fall on the calendar.)
A great strategy is to add one of your vacation days to a long weekend which gives you an extra day. Two days for travelling and two full days to explore the destination.


stopover is a destination added to your flight itinerary before continuing to your final destination. Stopovers are shorter than your overall trip and last more than 24 hours.
Here’s an example of a stopover: Toronto → Reykjavik → London.
Instead of going to London directly, you can stopover in Reykjavik for a few days at no extra cost. Using Airwander, you can search a wide choice of stopovers to see if you can fit a possible stopover in your next travel itinerary. 


Layovers are connection points between destinations that are less than 24 hours.
Here’s an example of a layover: Toronto → New York → Dublin
Your final destination is Dublin, but you may have a layover for up to 24 hours in New York. 

Flights with layovers are usually the cheapest option. Still, the average person can’t handle staying in an airport that long so they end up spending more money for a direct flight – often overlooking the possibility of exploring the destination. Also in most cases, using a program like Airwander, you can turn a layover into stopovers, explore a new destination and leave for your next destination rested.

That said, for a layover to be possible, you need to consider these factors:

  • length of the layover
  • distance from the airport to the city center
  • time of day
  • size of the airport

Keep in mind that you will need to leave the Connecting Flights area, and when you return, you will need to go through customs and security again.

Business Travel

Who says business and pleasure can’t mix. If you’re already visiting a different city or country you might as well see what else that destination has to offer. From business-specific accommodations to things to do and places to eat when not working

Day Trips

Adding a day trip to a neighbouring city, town, village and in some cases country is a great way to extend your cultural experience in the country you are visiting. If you’re already in a big city, getting to another city, town or village can be as easy a hoping on the local train. 

Be sure to check train times as the number of trains travelling between destinations for the day may vary.

The Science Of Short Trips


You will need to be honest with yourself in accepting the fact that you will not be able to see everything a city has to offer in two days. Hell, I’ve lived in Toronto my entire life, and I’m still discovering the city’s little nooks and crannies. Also, museums, art galleries, concert halls & theatres, depending on your interest, are usually the first to face the chopping block as they take up the most time.

Think of it as getting your feet wet – you can always come back.

planning a short trip


For a short trip to be successful, you simply can not arrive in a city and hope for the best. Planning is key! Open up that notes app or go old school with a pen and paper and after going through my website start researching: Other travel blogs, tourism boards, travel companies (Trip Advisor, Culture Trip, Expedia, Viator), YouTube.  

Be sure to take note of:

  • Interests & Must-See’s
  • Days & Hours of operation 
  • Address & Phone Numbers
  •  Website & Social Media
  • Payment options (Stockholm is a cashless society for the most part )
  • Length of tours and guides (walking tours, brewery/distillery tours)


Logistics is essential because when you don’t have much time in a city, navigating quickly and efficiently becomes critical. As I mentioned before, planning is necessary because you can not be wasting time trying to figure out what you want to see on the day you arrive. 

Likewise, logistic is about knowing where everything is and the most efficient way to get from point A to point B.

planning a short trip


Gone are the days of paper maps, but you should still keep a paper version for emergencies. (phones die or worst get stolen – as mine did in Paris). Even those cheesy city maps that you pick up Tourist Information Booths – both in the city centre, airports, train stations and hotels/Airbnb. 

Just keep in mind that nothing screams tourists more than holding a map – be careful. 

Before you arrive at your destination, use your digital map (Google Maps) to pin the location of everything that you want to see and do for each day of your visit. Using your map and your planning notes, create an itinerary based on hours and days of operation, distance and proximity to each other, the best route between points and the time required to see and do each activity.
Don’t forget to include your arrival point (Airport, Train Station, Ship port and the location of your accommodation. 

Choosing accommodation that is close to the majority of the things on your list is a huge time saver but might be more expensive.


Majority of city tourism boards include info about their local transportation system and getting around. Familiarize your self with the way their transit system works, where can you buy tickets or reload cards

In most cases, the name on the front or side of the train is the last stop in the train’s direction.   

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    Christopher Rudder, Owner & Content Creator of Rudderless TRVL
    - Read more about me HERE!

    For me, travel doesn’t have to mean taking weeks, months or years off work. You don’t need to move across the world to say you’ve “travelled“.

    Travel can be a weekend away down the coast from your home, exploring your own backyard - for me, that's my 48 Hour Toronto Itinerary, my province Road Trip Ontario or a short flight to the next state, province or country.


    Some of the links in this post are affiliate links. If you purchase a product, I may earn a commission. This commission comes at no extra cost to you. Please remember that I never recommend a product just for the commission — I only recommend something I genuinely believe in, trust and/or use personally. The small income I make here will help in maintaining this blog. Thanks for your support