Tips for First-Time and Seasoned Travelers Alike

Beinvendidos fellow travelers! My husband and I have been traveling for close to two decades now, first as a duo and now as a family of four. We have traveled both domestically and internationally, and we have traveled on solo trips, just the two of us to trips and with groups as big as 16 people trips. Over the years, we have learned so many things along the way, from best tips for booking flights to arriving at the airport. This blog can help you along the way when organizing and booking your next trip. Whether you are a first timer traveler or a seasoned traveler, I hope to leave you with tips and tricks for planning your next vacation.

Disclosure: This post may contain affiliate links, meaning I get a commission if you decide to make a purchase through my links, at no cost to you.

Picking a Destination

We are a family that loves adventure, culture, food, and relaxation so when it comes to landing on our next destination, at times we find this to the be the most difficult part of the entire planning process. Things that influence our decision making process include:

• TIME of year we are traveling. It is important to research your destination of interest to see if that is a good time to travel there. Things to consider include weather, high tourist season versus low season, and/or travel warnings
• How MANY days we can get away. Depending on the time of year, some times we can only afford to get away from our jobs and the kids from school for a few days, whereas other times of year, we can plan a longer trip. Typically if we only have a long weekend (3-4 days) or short week (5-6 days), we will travel more domestically with flights less than 5 hours. However, during summertime, we can usually plan for longer 8+ day vacations and plan to visit destinations further away.
• BUDGET! This should probably be the first item on the list!! And is usually the biggest factor that impacts where we decide to go. Buying flights for a family of four can take a big chunk of the budget so many times when we start planning, we research flights to that location first. Cost of flights will often dictate where and when we are going. Additionally, traveling during high seasons is almost always more expensive than during shoulder or low seasons. High season does not always mean during summer, but many high seasons follow school breaks, including winter break, spring break, and of course, summer break. If you can avoid traveling during the common times schools are out, this can be a huge money saver.
• ACTIVITIES of interest. Lastly, you need to decide what kind of vacation you are looking for. Things to consider for this would include a relaxing versus adventurous vacation, variety of activities offered or low key or minimal activities offered by the location, a warm destination by the ocean versus a cooler destination in the mountains, exploring the city or exploring the sea, etc. Although for us this is not as big of a factor because I believe you can make any destination as exciting and adventurous or as relaxing and low key as you want, this is something many may want to consider when choosing your next vacation location.

Planning

You have picked your destination and now it is time for planning, organizing, and booking!! Depending on the trip and destination, you may consider using a travel agent if the trip is going to be more complex with multiple flights and transfers or you may be able to manage the bookings yourself if you are super organized and/or it is a less complicated trip. At first it may feel very overwhelming to plan and book; however, following a few easy steps can help make this process more smooth.

• RESEARCH, research, research! After I pick my destination, I try to do as much research on that destination as I can. Much of my research is conducted on Pinterest, reading blogs, just like this one, featuring itineraries, do’s and don’ts, and recommendations. I try to learn all the things about the destination. First starting with attractions offered by the location (i.e., excursions landmarks, proximity to other attractions) and then moving to hotels and resorts, and lastly places to eat.
• BUILD an itinerary. After some research, you can start to build an itinerary of the things you would like to do on this trip. I like to write all the ideas down in a planner. I use the Clever Fox Travel Planner, which has lots of room for organizing a monthly, weekly, and daily itineraries, packing lists, checklists, and fun stickers to decorate . Although there are digital options, I like to have a paper/pen version so I can take it with me without needing cell service and I can also take a picture of each itinerary to have handy without having the actual book with me! I write down the details of hotels, places to eat, and places to see. For my family, a good rule of thumb is to have a few days of excursions or activities and a few days of chill and relaxation. I usually alternate these to give us some much needed rest in between the more active days. If we visit multiple locations on a trip, I also try to plan the days and activities in proximity to each other based on the city we will be staying for that part of the trip. For example, when my family went to Puerto Rico, we planned our kayaking, exploring of Old San Juan, and touring the rainforest on back to back days because they were all located on the East side of the island. Keeping in mind the timing of excursions and proximity to where you are staying will really help to make your trip smooth, avoiding jumping back and forth between locations. Once I have an idea of what we want to do and where we want to see, I organize this into a day to day itinerary. This further helps you decide which airport to fly into and which hotels to book. Keep in mind, you may need to look at hotels and flights simultaneously as the cost of flights may dictate where you start your trip.

Booking

Now the booking can begin! The first things we book are flights, hotels, and possibly a rental car.

• TRAVEL packages through wholesale marketers, such as Costco or Sams Club is a great place to start. They have great discount options for booking resorts, hotels, flights, and rental cars. You do have to be a member to take advantage of their deals though. Many of the options they offer are high end and we have always loved the quality of products we have booked. Another route we go is to use our points earned through our credit cards. You can book directly through your bank of the credit card (i.e., Chase, American Express) or you can transfer your points to the company and book directly with them. Typically your credit card will list which businesses they works with for these transfers. In many cases your points go further when you transfer to the company and book through them directly.
• CHOOSING a flight can be a bit time consuming if you want to get the best deal. A great trick for looking for different options is to use Google Flights or Kayak which will find the cheapest flights to that destination showing you multiple airline prices. Another good tip is to leave your dates flexible. Almost all search engines have this option so you do not have to pick specific dates, but rather just a month or several weeks you want to search. When flying more domestic flights under 8 hours, my family’s favorite airline is Southwest Airlines. Their flights are typically affordable and comparable in price to flights offered by other major airlines. They offer free checked-bags, family boarding, and flexibility, making them a great choice for families flying with littles. The biggest factor influencing our choice to choose Southwest Airlines (SW Airlines) is their flexibility with changing your flights. If you are unfamiliar with SW Airlines, they allow you to rebook a flight, if your plans have changed or even if the price becomes cheaper after you have already booked. My husband will typically book a flight with SW Airlines and then check every month or even sometimes every week to see if the price has changed. We have saved tons of money by doing this!
• BOOKING your stay can also take some time. There are many options when it comes to choosing a hotel. Once I have researched Costco and our credit card for ideas, I typically go to Trip Advisor to see reviews and gather additional information that the direct website may not include for a specific product. Things to consider when doing your research:
  • all-inclusive versus a non-all-inclusive resort
  • current packages or offers from the hotel (i.e., breakfast included)
  • within walking distance to certain attractions
  • amenities offered
• PLANNING your excursions or activities is a fun part of the booking process! With all of your research, you should have an idea of what you want to see and do. Similar to the hotels, I like to do a little more digging on Trip Advisor or Travelocity to read reviews and get more details of what is included in the tour. Even if you are not into an adventurous activity, there are many activities that are low key (i.e., food tastings, wine/beer tastings, walking tour of the city, etc.). We typically prefer to go through a company for a tour or activity. Although you have to stick to the plan created by the tour company, which some may not prefer, you do gain more information about the city you are visiting, gain access to areas that other tourists do not, and hopefully have a stress free day! Some companies we have had success with include Vallarta Adventures, and Cabo Adventures.
• MAKING reservations for restaurants is a task that does not need to occur until your trip is closer approaching. Now that your flights, hotels, car, and excursions are booked, you can start planning where you will eat. I mix up our food experiences with some local, more informal places, and some resort, more tourist friendly places. I make reservations anywhere from one week to 2-3 months in advance. Not all restaurants will require a reservation and I do let some meals up in the air for the family to pick once we get there. Something we have found to be very helpful is to ask the locals, either the guides on our excursions or the waiters at the resort, for restaurants with some great local eats that they would recommend. I steer away from asking the concierge where to eat because they usually give us recommendations that are “tourist” friendly rather than authentic local spots. Great places to eat is always a hot topic I research on Pinterest and keep a list in my planner of spots to choose from that have been recommended by other travelers. Another great tool we use is the Google Maps app. You can create lists for specific locations you are visiting that can include places to eat and things to see and do. It will give you information about and reviews of the places you add. You can share this list with anyone you are traveling with. Once you hit your destination, you can see what spots are close to you at that moment. It’s great for those days you just want to explore!

Travel Day:

TRAVEL DAY has finally arrived!! As a family, travel day is always filled with excitement mixed with apprehension! My boys are great travelers, but traveling with kids is always an added stressor. Here are some tips and tricks to help alleviate some of the stress:

• GIVE yourself enough TIME! I cannot stress this one enough. Have a specific departure time in mind for when you need to leave for the airport. Typically my husband and I like to get to the airport 1.5-2 hours early to give ourselves enough time for parking, ticketing/checking bags, security, going to the bathroom, and grabbing food. My family has Global Entry, which is the international equivalent of TSA Pre-Check, so 1.5-2 hours gives us plenty of time; however, if you will be going through general security checks and/or are unfamiliar with airport protocols and policies, you may need to build in another 20 minutes or so. If you have an early flight, set your alarm about 15 to 20 minutes earlier than you think you need to. This helps to account for any unexpected situations. Additionally, the airports can be busier during holidays and/or school breaks. Keep this in mind when planning your departure and arrival times.
• Make LISTS! I always have everything packed no later than the night before, including carry-ons. Same-day packing is NOT a good idea! I keep out our outfits and essentials we will need the morning of the trip (i.e., toiletries, chargers, etc.). I then make lists of all the things I have to pack before we leave and of all things I need to do before we leave (i.e., take out the trash, start the dishwasher, turn down the thermostat, etc.). These lists help to keep me organized during a rushed morning out the door.
• Prior to ARRIVING at airport, my husband and I have found that pre-paying for parking is helpful. We typically opt for the parking garage for its convenience, but it does cost a bit more. However, when you pre-pay, it is usually slightly discounted. If you opt for long term parking, you will want to plan this into your arrival time, giving yourself an additional 30 minutes or so to park and get on the tram/shuttle to the terminal. I always pack lots of snacks for the trip. You are allowed to bring food through security, just nothing that has liquid or water. I do bring empty water bottles (my family likes Thermaflasks) that we are able to refill at the filling stations. Majority of airports now have filling stations located by their bathrooms. Another thing to consider is grabbing lunch or dinner to-go taking it on the plane with you, especially for your longer flights or you want to plan to eat at the airport prior to boarding. Just be sure to plan extra time into your arrival for these activities.

Although this is not an exhaustive list of all of the things that you may encounter on your booking and/or travel day journey, I truly hope you find these tips and tricks helpful to make your next adventure a success!!

Comment below any tips and tricks you may have learned along the way or leave a question. Can’t wait to hear about your adventure!

with love and dreams,

Jessica