My Family’s Unorthodox Approach to Traveling

My family was never fond of planning ahead. For those that dread tedious planning, read this article on our very minimalistic forte. Even more, learn how to do this while on a budget!

Steps to planning

Booking a flight

My best advice is to go with the flow. Usually, when my family travels when determining where we are going to go we are pretty flexible. Depending on the time, some places are more or less expensive than others. Also, we choose the exact dates based on the price, which saves a lot of money. If you have your heart set on one place, by all means, pursue it, but if you are just excited to simply go on a vacation- book cheap flights! Last year my family wanted to go to Greece, but the tickets were really expensive. Instead, we booked flights to Madrid for only 300 dollars each. 

Tip: Flight prices fluctuate throughout the week. The same seat will be more expensive on a Saturday than a Tuesday night! A great site to look at is or book directly with airlines because it is usually cheaper. 


After booking a flight, my mom and I get together and research the area. We look up top tourist destinations, cute towns, cities, best beaches, etc. We make a list of our favorite places and their distance from the airport/major city that we are flying into. This is when we establish if we are going to stay in the area, go to different islands, or visit different cities. This past summer we were planning on doing a road trip to Southern Spain. When we realized we really wanted to visit Valencia, we decided that it would be too much driving and would not be able to do both. Instead, we decided to take a boat from the port in Valencia and go to the Balearic Islands.


I might sound crazy, but if you want to travel as I do, don’t book all your hotels ahead of time! 

Book a hotel in the city you fly into for that night (or if you want to spend more time there, book the hotel for a couple of nights). Then plan as you go. We usually have a couple of cities/places we definitely want to visit, and we book hotels there as benchmarks for our trip, but other nights we just drift around. It is a little risky, but it's always a ton of fun, and we always make the most out of our vacations. This way we can take the suggestions of locals and travelers about their favorite places to go and spend time there. Also, if we like someplace a lot we can stay there for longer than expected instead of being tied down. It’s also important to note that you don’t have to stay at expensive hotels. We usually book air bnb’s which are much more cost-effective. We always have the hotel and air bnb apps and we always pay for worldwide data so that we can book hotels on the road. 

A Fun Story: You have to act wisely if you decide to not book hotels in advance. It isn’t for everyone. One time we visited Tropea, Italy during a national holiday, so it was packed. We couldn’t find any airbnbs. My dad asked a couple of people if they knew where we could stay. We were brought to a family's house that rent out an empty wing of their home. We stayed there and really got to experience the Italian culture. They had a farm and we even got to make tomato sauce with them. 

Types of Trips We Go On

A Laid Back Caribbean Trip

Usually, during school break my family takes a trip to somewhere tropical, to get away from Boston’s brutal winter. We usually stay at a resort for our entire trip when we visit places like Mexico, The Dominican Republic, Puerto Rico, etc. We always try to have a cultural experience even during these types of trips so we usually rent a car. This gives us the freedom to visit lots of cool places. For example, in Puerto Rico, we went to a market and ate at a restaurant full of locals. In Mexico, we went to nearby cities and went swimming at a bunch of cenotes. Also, resorts usually offer snorkeling excursions, trips to nearby islands, boating, surfing, etc. so take advantage of that. 

A Road Trip

These types of vacations are usually very spontaneous. We use the template I explained above when planning these types of vacations. We stop at several different cities and locations and usually only spend a couple of days at each location. Be prepared for lots of driving, but it will be tons of fun. My favorite road trip was when my family flew into Milan. We were able to hit several cities in Northern Italy, Monaco, and Switzerland.

A Small Range Vacation

This is what we did in Majorca. We booked one hotel for the entire time here. Driving from one side of the island to the other is about 1 hour. While we stayed in the capital, Palma, we left every day and drove around half an hour each day for a different city or beach. This type of vacation is still spontaneous, but you have a definite place to stay every night. 

Open your eyes up to new worlds, peoples, and ideas. This traveling approach may not be for everyone, and there are plenty of other ways to see the world. Nevertheless, I love how I travel as it ensures the most culturally authentic experience.

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