Plan Ahead and Vacation Like a Boss
One of our vision board goals was to travel more. When we say travel more, we don’t mean just within the United States.
While we indeed love our home county, we wanted to do more international traveling.
After an incredible honeymoon to Moorea, French Polynesia, we were absolutely stunned by its scenery and the crystal clear surrounding South Pacific Ocean.
On that list was Jamaica. Planning our trip to Jamaica started in April of 2023. The trip date was scheduled for the first week November 2023.
Plan Ahead for a Great Vacation Like a Boss
Travel Time
We literally plan how long its going to take from the moment we pull out of our driveway to the time it takes to get to the airport.
Planning your travel time is vital and of significant importance. We once missed our flight to Los Angeles and had to catch another flight.
Not fun but it was a learning experience nonetheless. Luckily we were able to get placed on the next flight out.
Parking
Remember when you were younger and family dropped you off and picked you up from the airport. Well that time is long gone.
To be able to have your car at or near the airport is a total game changer. You don’t have to wait on anyone and you most certainly don’t have to pay for an Uber nor tip.
Having your car with you provides you a safety net.
Flights
Planning your flight ahead of time is definitely worthwhile, and here’s why. When I start my vacation planning, the first thing I do is scout for flights well in advance.
This strategy not only helps me snag the best deals but also gives me a wide range of options to choose from.
By booking early, I avoid the last-minute rush and exorbitant prices that come with it.
Additionally, I find that early planning allows me to pick the most convenient flight times, ensuring a smoother travel experience.
I also use tools like Google Flights and fare alerts to track price changes and jump on the best offers as soon as they appear.
Trust me, taking the time to plan your flights early can make a huge difference in both your budget and your peace of mind.
Hotels/Resorts
Choose the right hotel or resort ahead of time, here’s why. Whenever I plan a vacation, I make it a priority to book my accommodations early.
This approach allows me to secure the best rates and ensures that I have a wide array of options to fit my preferences and budget.
By planning ahead, I can research and read reviews thoroughly, ensuring that the place I choose meets all my needs, from location to amenities.
Additionally, booking early often comes with perks like free cancellations and special deals that are not available last minute.
I also take advantage of loyalty programs and comparison websites to find hidden gems and exclusive offers.
Trust me, investing time in selecting your hotel or resort early can elevate your entire vacation experience, providing comfort and convenience from start to finish.
Food
Planning where to eat ahead of time is also worthwhile.
Whenever I plan a vacation, unless the resort is all-inclusive, I make sure to research the best dining spots well before I leave.
This strategy not only helps me find the most delicious and unique local cuisine but also allows me to make reservations at popular restaurants that often book up quickly.
By mapping out my dining options in advance, I can ensure that I won’t miss out on must-try dishes and can avoid the disappointment of long waits or fully booked establishments.
I also look for food tours and culinary experiences that can give me a deeper insight into the local culture.
Trust me, taking the time to plan your meals ahead can turn your vacation into a gastronomic adventure, making every meal a memorable highlight.
Excursions
When I plan my vacation, I make it a point to research and book my excursions in advance.
This not only helps me secure spots for popular activities and tours that often fill up quickly but also allows me to create a well-organized itinerary.
By planning ahead, I can prioritize the must-see attractions and unique experiences I don’t want to miss.
Plus, booking early often comes with discounts and the assurance that I won’t be left scrambling for last-minute options.
I also take the time to read reviews and compare different tour providers to ensure I’m getting the best value and experience.
Trust me, investing time in planning your excursions ahead can enhance your trip significantly, making sure each day is packed with exciting and memorable activities.
Tips
I’ve learned from experience that tipping can quickly become an annoying and unexpected expense, especially after shelling out a significant amount of money for the trip itself.
By researching and planning for tips in advance, I can budget more accurately and avoid those awkward moments of scrambling for cash.
Knowing the tipping customs of my destination helps me set aside the right amounts for various services, from hotel staff to tour guides and restaurant servers.
This forethought allows me to enjoy my vacation without the constant worry of whether I’m tipping appropriately or if I have enough local currency on hand.
Trust me, planning your tips ahead can save you a lot of stress and ensure you show appreciation without feeling financially drained.
Travel Recommendations
Save Like A Boss for a Great Vacation
Put up or shut up, that should be my motto, lol.
Seriously, if you don’t save well, how can you take trips? Planning ahead is crucial when it comes to saving for a vacation.
Not saving for the things you want or the activities you dream of doing simply does not make sense.
One of the best ways to ensure you have enough funds for your travels is to open a dedicated savings account.
If you don’t yet have a savings account, I highly recommend Marcus By Goldman Sachs.
By setting up automatic transfers into this account, you can effortlessly build your travel fund over time.
Planning ahead and saving diligently means you won’t have to worry about finances when the time comes to book flights, hotels, or excursions.
It also allows you to take advantage of early bird deals and special offers, reducing your overall expenses.
Trust me, having a solid savings plan in place can make a world of difference, turning your vacation dreams into reality without financial stress.
So, start saving now, plan ahead, and watch your vacation fund grow, enabling you to travel like a boss!
What We Would Do Differently
For the first time in eight years, we planned ahead and decided to book with Southwest. My wife wanted to figure out what why so many people like Southwest.
She quickly knew Southwest wasn’t her airline of choice.
Flying Southwest is similar to taking public transit. You pay your fare and you sit wherever you see an open seat. Horrible!
To be displaced from your family or group on a flight is totally unsatisfactory.
We’ve most flown on Spirit within the past four or five years. I’ve even spoke and left reviews online about Spirit about things that pissed me off.
However, for the most part, Spirit airline has some of the best fares you will ever find. You’ve seen the post, “Fly Spirit and you might become a one,” etc., etc.
Yet, each time we’ve flown Spirit, we felt very safe. The two things I hate about Spirit is that they are sticklers on their baggage fees and policy and they don’t serve free snack nor soft beverages.
Bringing it Back Home
Not literally, yet concluding this post, be sure to check all of these things off when you plan ahead for your vacation.
With proper planning, we often tend to spend less and within budget. This also helps greatly if we decide to purchase souvenirs.
Let me know in the comments what you think and if you have any other vacation savings tips to share.





