How to Plan your Dream Vacation:

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How to Plan like a Pro:

The big question, how do I plan a fun trip like this? I’m going to break it down in a few easy steps but the real key is to stay organized, stay within your budget and remember it’s a vacation…have fun!

1. Choose your Destination:

Choosing your travel destination can be daunting if you’re like me and have an extremely long travel bucket list. Typically, I choose where I want to visit based on my budget, vacation hours and the time of year I will be visiting. Make sure before you move forward with any plans, research the weather in the destination you’re visiting. For example, I love the Caribbean but I won’t visit between August and November because it’s hurricane season.

2. Set your Flight Alerts: (6 months before trip)

One of the first things I do when I want to take a trip is to set Google flight alerts. If the vacation is flexible, I’ll typically set alerts for a few different dates around the time I’d like to travel, to find the best deal. I use Google Flights charts for the cheapest months to fly to your destination. Once you find a great deal or affordable price on a flight, BOOK IT! To learn detailed tips and tricks on finding cheap flights, visit my article on flights (link).

3. Choose your Crew:

The group that you travel with can make or break your trip. As well as you think you know someone, you don’t know them until you’ve travelled together. Going on a trip is so much fun but it's also, exhausting, and frustrating when you’re navigating a new culture. You need people you trust and have fun with. Start small and pick a group of people who have similar interests and live life at the pace that you do. If you love schedules, being on time, and planning out your every day, pick people who are similar or at least open to it. If you want to relax, hang out and take the day as it comes, travel with people who are like that instead. You might have noticed that in most of my photos, I have a consistent group who I travel the world with but it’s not always fun and games. Traveling requires patience, compromise and willingness to try new things. When you choose your crew, don’t expect perfection, it's a vacation, try and relax and take each adventure as it comes.

4. Delegate your Tasks:

I’m a planner, and that often comes with the expectation that I plan everything. It’s ok to take on the planning role but remember, you’re not your friends’ travel agent or party planner. If you have the gift of leadership and planning, delegate tasks amongst the group. One easy way to do that is to host a quick meeting about the trip to discuss what you want to do and where you want to go. Try and come up with some guidelines as a team so you make decisions that everyone is happy with. Below is an example of how our friends delegated our recent trip to Europe:

Destinations:

  • Rome
  • Florence
  • Naples
  • Positano
  • Ibiza
  • Barcelona

Expectations:

  • Housing: $50/ night/ person or less/ each person wants their own bed
  • Activities: We want to try all the classic tourist spots but less touristy bars

Delegation of Tasks:

You can delegate however you’d like, but an easy way is to give everyone the opportunity to have some say regardless of what their delegated tasks are.
  • Elisa: Find things to do in Rome, book our stay
  • Brad: Find things to do in Naples, Book our stay
  • Anthony: Find things to do in Positano, Figure out a way to get there
  • Sandy: Find things to do in Florence, book our stay
  • Tennyson: Find things to do in Barcelona & Ibiza, book our stay

5. Book your Flight(s):

If you haven't found that sweet deal you were looking for, try booking your flight mid week for a bit of a lower price. Once you are about 3 months away, the prices only begin to rise so book your flight ASAP. Usually to make sure I’m on the same flight as my crew, I will book my flight first and email it to the group for the option to book the same one.

6. Book your Stay:

If you decide to delegate tasks, make sure to give your group a deadline of the day they need to book. You should have something booked at least 2 months ahead of time. I would book after you buy the flight because it’s easier to get your money back from a booking if you don’t find the flight you want. The most cost efficient option is to stay in an Airbnb but hotels are a great option if you are concerned about safety. If you are traveling with friends, I would recommend staying in a hostel. Hostels are cost efficient and a fun experience if you've never been to one. They are like large dorm rooms where you can rent a bed & a locker for about ¼ of the price of a hotel or airbnb. If you do plan a hostel stay, be sure to pack a lock to lock up your items since you will most often share a room with other travelers that you don’t know.

7. Do your Research:

I said it before but I’ll say it again, make sure you research the weather! The last thing you want is to visit a country where the weather keeps you indoors throughout your entire vacation. Checking the weather also helps you to know what to wear! Before you visit a new country, always do some research on the laws or major cultural differences that might be different from what you are used to. Just because you’re a visitor doesn’t mean you’ll get a pass if you break the law. A quick example of a law you might not know is in Singapore, you can’t feed the pigeons or chew gum! Not sure how true that is but I still didn’t do either. An example of a cultural difference is that in Ethiopia it’s extremely offensive to refuse coffee or a meal that’s offered to you when you visit someone’s home. I try and abide by cultural norms when you’re in another country out of respect.

8. Download the Google Map & Map out Top Activities:

This is especially important if you have limited time in a country. First, download the maps of each location you’re visiting through Google Maps on your phone. This is important because even if you pay for data, there’s a chance you won’t have solid service everywhere you visit. Second, map out all of the top locations you want to visit, to get a better idea of how far they are from each other. This way, you can easily plan your days based on what’s in the same location, rather than running around the city wasting good travel time.

9. Call your Credit Card Companies:

First of all it’s really helpful if you have a credit card with no travel fees or else you’ll have to plan for those fees in your budget. You should call all the credit/ debit cards that you plan to use and let them know you will be traveling. If you don’t, you run the risk of them pausing your card due to fraud.

10. Make a Packing Checklist & Pack:

You can take a look at my packing checklist and to find the ultimate packing list. The weather and your activities will play a huge part in what you decide to bring. You’ll also want to make sure to have good walking shoes unless you’re spending your vacation at a resort on the beach all day!

11. Prepare for the Flight:

It sounds silly but the last thing you want, is to spend all that time preparing for this amazing trip, pack all the right things and then find out you’ve exceeded the weight limit for your flight. It happens people! We purchased this inexpensive luggage scale and always UNDER pack so that we have room to bring back gifts. We also pack the lightweight scale to measure our luggage before we head home. Finally, don't forget to pack a bag for your plane ride. Below you'll find a few essentials that I bring on every flight:
  • Headphones with a jack (not wireless)
  • Phone charger
  • Snacks (I bring cup of noodles & just ask for hot water)
  • Water bottle (fill it after security & before the flight)
  • Small blanket (optional but definitely helpful if you get gold easily)
  • Hand sanitizer
  • Chapstick (it gets super dry on long flights)
  • Mini lotion
  • Downloaded movies on my phone
  • A book

12: Arrive Early to your Flight:

This is harder than it sounds and I always try to pack at least the day before a trip so that I’m ready for that flight and not rushing. Try to arrive 2 hours early for international flights and at least 1 hour early for domestic flights. Typically airlines will email you the option to check into your flight early online which is a great way to skip the lines and go straight to security upon arrival to the airport.

And away you go...

Phew… you’re done with the planning and ready to roll! Remember that if your plans don’t work out exactly as you expect, don’t lose sleep over it. Your plans are just a way to make the most use of your time & to stay safe. If you still feel like you need a bit of help, feel free to reach out to me through email if I can help answer any other travel planning questions.