Side Dishes Travel

5 Steps to Planning a Short Vacation

How to Vacation like a Boss

arAt the end of a vacation, no one wants to say they wished they had more time to see [insert tourist attraction]. However, the last thing you want to do is jam pack your itinerary and not experience your destination “in the moment.” But, Brian, how can I do this?

Ultimate Guide to Maui

Sunrise on Mt. Haleakala

Plan, plan, plan. Is it that easy? No. You need to research your destination. Figure out what you want to see, and plan your trip accordingly. I love planning and logistics. So when we go on vacation, I am the travel agent planning every minute of the trip.

Two years ago, Fatima and I went to London for the weekend. Yes, that sounds douchey. But we were there for business and had to be back in the office on Monday morning. Once the business part of this trip was over, we only had 48 hours to explore. And we did.

Vacation in London Like a Boss

Westminster Abbey

Plan your vacation on your own terms

Before we continue, I’m not saying you should plan 48 hour trips everywhere. Ideally, we’ll take at least a week off to travel (see our guide to Maui). However, sometimes you’re stuck with pockets of free time between trips or business meetings. You should make the most of that time! When we were planning our trip to Hawaii, we wanted to stop in LA. Fatima’s never been. Since we were heading west already, this was our opportunity to stop in LA. So we flew out and planned to explore for 48 hours. Check our our guide to Los Angeles.

Whether you’re going for 48 hours or two weeks, these tips will help plan your vacation.

Los Angeles and Hollywood - Liliesandloafers

The Hollywood Sign

Step 1: Make a list of places to see and know your audience

Why are you going? What do you want to experience? What do you want to see? Who’s going with you? If you were to visit New York City, I would say Times Square, The Empire State Building, and Central Park should be on your list of places to see.

Who are you traveling with? Kids, friends, family? Take that into consideration. That will determine if you’re walking all day or taking taxis. Fatima and I know our limits. If we are traveling with family, we’d have to tailor it to them.

Vacation in London Like a Boss

Tower Bridge

In Los Angeles, we knew we had to see the Hollywood sign, walk of Fame, and one of the studios. Round this out with a few local, trendy eateries, the Santa Monica boardwalk and that was the basis of our trip.

Step 2: Research your destination, ask questions, and add to your list

Whether or not you know what you want to see, you should research your vacation destination. This may reveal a new discovery or help you make a list of additional things you want to see. Ask your friends. Gather their thoughts. Do not use Facebook recommendations (sorry for the shade :)).

Vacation in London Like a Boss

Big Ben

Step 3: Pick what you want to do and prioritize it

Look at your list and pick out the things you want to do. Prioritize them into two lists: “must-see” and “would love to”. Your must-see places are the cornerstones of your trip. These may involve reservations or allocating more time to see them. In London, this was King’s Cross Station (Harry Potter), Buckingham Palace, Kensington Palace, Parliament, and Tower Bridge. Your “would love tos” are the places you will try to go to along the way, but if you run out of time, they get cut.

Vacation at Platform 9 3/4 Like a Boss

Platform 9 3/4

We had a few things on our Los Angeles “would love to” list that we never got to see. One of those was the Los Angeles County Museum of Art. Our rationale for visiting? A picture perfect instagram moment of the street lamps. We ran out of time and decided it wasn’t worth the detour.

Los Angeles - Liliesandloafers

We sat on that couch!

Step 4: List each activity’s time commitment and group by proximity

This will help you plan and manage your timeline. Activities needing more time will be planned as such. In London, this was so helpful. Knowing what was in close proximity on the way helped us see so sights in that beautiful city in 48 hours.

Vacation in London Like a Boss

Hyde Park gardens

Step 5: Put your research into action

Layout your trip’s “must-sees” day by day. Account for extra time between activities for traffic or other unforeseen things. Maybe the Queen emerges from the palace, so you stay a little longer to take photos. Look at your itinerary and layer in your “would love tos”. Putting these things down on your phone (list in notes app) or written in a notebook will help you on your trip.

Ultimate Guide to Maui

Seven Sacred Pools

Bonus: Be in the moment

In between looking at your plans, put the phone down and be in the moment. Yes, get that selfie to remember your trip, but in moderation. Fatima and I had so much fun on our trips because we experienced it without our heads in our phones.

However, we had an exception: if the other person was in the bathroom, you could be on your phone. But when we were together, we were present. When you’re in a time crunch, make the most of the time you have.

Ultimate Guide to Maui

Turtle Town Snorkeling

Bonus #2: Bring your sneakers 🙂

Ultimate Guide to Maui

Bamboo Forest

Our London Itinerary with Google Maps

Seriously, bring your sneakers. You’re going to need them. Surprisingly and unsurprisingly, Central London is quite walkable. However, their transit system is fantastic. It took a few minutes to understand in what directions we needed to go, but we got around really quick. Our hotel was located in Mayfair; Buckingham Palace and Parliament to the South, Kensington Palace to the West, SoHo and West End to the East, and King’s Cross Station to the North.

We did most of our adventures on Day 1. We were flying out late on Day 2, so we needed to jam as much as possible in the first day.

Day 1:

  • Crosstown Doughnut & Coffee Bar – Wake up and have a sugary, caffeinated start to the day. These donuts were so goooood.
  • Platform 9 3/4 (Kings Cross Station) – for the Harry Potter fans, this is a must stop. The line for the photo opportunity gets longer as the day goes on, so get here by 8am. We were there a few days after Alan Rickman passed away.
  • Westminster Abbey, Big Ben, and Houses of Parliament – the tube station lets you off right across the street from Big Ben. What a sight! But walk away from the water and head to Westminster Abbey. Take a tour if you wish! Walk around Parliament. Walk towards Big Ben and the bridge adjacent to it. Want a good picture? Walk about 1/4 of the way down the bridge. A better picture is on the other side…
  • London Eye – You can’t miss this. The lines are long, and going around will take loads of time. This is a SKIP, unless you have time to wait and go around.
  • Borough market: food! – Walk along the river and side streets to Borough Market. It’s a bit underwhelming, so completely skippable. But head here to grab a quick bite.
  • Tower of London – Continue to walk, soon, you’ll be able to walk along the river. And there you’ll see Tower Bridge. Walk across and you’ll see the Tower of London. This is another tour stop! So take a tour and see the crown jewels. It was about 3pm when we got here, so we decided to skip and walk around.
  • St. Paul’s Cathedral – Continue to walk. Walk through the streets, take a picture in every red telephone booth. Head to St. Paul’s Cathedral. It’s beautiful, massive. Great photo opportunities.
  • Lamb & Flag  This is the oldest pub in London. Stop here for a drink before dinner.
  • Balans SoHo Society – Balans SoHo Society had great food. It’s right around the corner from Lamb and Flag. This area of London is popping at night.
  • Market Square Pub – This pub was around the corner from our hotel. It was cozy, lively, and convenient.

Day 2:

  • Buckingham Palace – Wake up, grab breakfast and walk to Buckingham Palace. If you can see the Changing of the Guard, do it!
  • Red Lion – Just around the corner behind St. James Palace, is this charming oub. Grab a bite and a pint before heading to Hyde Park.
  • Kensington Palace and Hyde Park Gardens – Walk through the park leading up to Kensington Palace. Walk through the gardens, along the fountain, until you see Kensington Palace appear in the distance. This will take at least two hours of your time. Take your photos. Maybe Meghan Markle will make an appearance…
  • SoHo Kitchen and Bar – Head back to SoHo for one last bite to eat. SoHo Kitchen and Bar is fantastic!

Lilies and Loafers London Vacation

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