inflatable slider on this great yacht

I had no idea what I was doing!


Step by Step on Vacation! I’ve planned countless trips and vacations for myself, friends, family, and even group tours. In the beginning, it was trial by fire and I learned a lot of lessons the hard way. However, that helped me develop an efficient checklist that ensures I don’t miss anything important during the trip planning process.

After all, I don’t want to get to my next destination and then realize I forgot something. And neither do you!


The Wonders of the Andaman Sea
Exploring the Blue Desert with Charter Dock A

How do I put this all together? How do I plan a trip?”

Step by Step on Vacation! In a continuing effort to help you get out the door and into the world, I’ve created this step-by-step guide on how to plan a trip. It works for any kind of trip and no matter how long you’re going for! Just follow this checklist and you’ll be off in no time!

Table of Contents: Step by Step on Vacation!

Step 1: Decide Where You Want To Go
Step 2: Decide the Length of Your Trip
Step 3: Will you Travel Solo?
Step 4: Research Your Costs
Step 5: Start Saving Money
Step 6: Get a Travels Rewards Credit Card
Step 7: Switch to No-Fee ATM Cards
Step 8: Stay Focused and Inspired
Step 9: Check for Last-Minute Deals
Step 10: Book Your Flight
Step 11: Book Your Accommodation
Step 12: Plan Your Activities
Step 13: Sell Your Stuff
Step 14: Automate Your Bills
Step 15: Tell Your Card Companies You’re Traveling
Step 16: Pack!
Step 17: Buy Travel Insurance
Step 18: Enjoy Your Trip

How to Plan Your Next Trip

Step 1: Decide Where You Want To Go

Travel the world
It’s a lot easier to mentally get behind “I am going to Paris in the summer” than “I’m going to Europe” or “I’m going somewhere.” Not only will your trip become more concrete for you and easier to commit to, but it will make planning easier as well…because you know what to work towards. Get specific with your plans. Get detailed. The more focused and concrete your goal, the easier it will be to actually reach it.

Step 2: Decide the Length of Your Trip

How much does it cost to travel? That depends!

Without knowing how long you’re going away for, I can’t answer that question. And it’s a question you need to answer so you can start planning!

In order to figure out how much you need to save you’ll need to know how long your trip will be.

Are you going away for a week? A month? A year?

The length of your trip is a huge factor in determining how much money you need. Spend some time mulling that over until you have your answer.

For example, after you say “I’m going to Paris this summer,” add “for X days.” That way you can start to narrow down just how much money you’re going to need to save. “I am going to Paris for 10 days” is a trip that you can plan for. It’s an attainable goal.

Rent a Boat in Phuket Thailand?

Step 3: Will You Travel Solo or Go With Someone?

One of the biggest decisions you’ll need to make is whether you’re going to go alone or travel with someone. Both are great options — but they are decidedly different choices too.

Traveling solo will give you the freedom to go anywhere you want. No compromising. You just go wherever the wind takes you! However, it means you have to do all the planning yourself — which can seem daunting if you’re new to trip planning.

Traveling with someone means you have someone to help plan the trip with you. It will make researching your itinerary faster and you’ll have someone to spend time with on the road. However, it also means you’ll need to compromise sometimes. Perhaps on meals or activities or accommodation. It will just depend on you and the person you travel with.

At the end of the day, there is no wrong answer.

Step 4: Research Your Costs

So you know where you’re going and how long you’ll be there, but to really nail down how much money you need, your next task is to research the costs in your destination at the style of travel you want.

Do you want to backpack, or would you rather stay in luxury hotels?

How much are hostels, hotels, restaurants, and attractions?

Knowing will allow you to estimate how much money you’ll need for your trip. Here is how to research costs:

  1. Buy a guidebook.
  2. You can begin with a guide.
  3. Ask on community websites like Lonely Planet.
  4. Google prices for specific things you want to do.

You don’t need to do more than that. There’s so much information on the web that if you go down the rabbit hole of over planning, you’ll get lost and confused by the firehose of information. Stick to those four things and you’ll be set!

Step 5: Start Saving Money

saving money for travel in your piggy bank
Before you can start saving money, you need to know how much you have and how much you’re spending. Start to write down all your current expenses so you can determine where you are spending money — and how you can cut back.

People bleed a lot of money every day through small purchases: a coffee here, a snack there. It all of that adds up. In order to make changes to your spending habits, you first need to understand them. Making a list will do just that. It will also put your financial needs into a better perspective.

For example, if you need $2,000 USD for the trip you’re taking in eight months, that means you only have to save $8.33 USD per day. Couldn’t you find a way to save $8 USD per day? Heck, your daily coffee is most of that!

Step 6: Get a Travels Rewards Credit Card

travel credit cards

While you’re working to save money get a travel credit card so you can earn sign-up bonuses to redeem miles and points for free flights and hotel stays. Collecting points and miles from travel credit cards is how I get tons of free flights, free hotel stays, and free travel perks every single year — and without any extra spending too!

These days, most cards have welcome offers of up to 50,000 points when you meet their minimum spending requirement. That’s enough miles for a free flight almost anywhere in the world!

If you want a free flight, sign up for the cards that help with that. If you want free hotel rooms, get a hotel card. Either way, sign up for a travel credit card and start earning points today. As long as you can pay off your monthly balance, you’ll get free travel credit.

You don’t need to sign up for very many cards either; pick one or two and focus on those. Do this the moment you decide you want to travel. Don’t wait — waiting equals lost miles, which means less free travel.

Collecting points and miles (which is called “travel hacking”) is what all the experts do to cut their costs and travel longer. It’s what has kept my costs down and me on the road for so many years.

Charter this Brand New Raptor with us …

Step 7: Switch to No-Fee ATM Cards

Once you’re abroad, you;re going to need money. While many countries will accept credit cards, in the majority of countries cash is still king. That means you’ll need to use ATMs to withdraw the local currency. And that also means you’re going to get dinged by ATM fees.

If you’re just away for a week or two, paying a few dollars in ATM fees isn’t the end of the world. But if you’re away for a longer period, those fees will add up and chew into your travel budget — a budget you’ve worked hard to grow. Don’t give banks any of your hard-earned money.

How? By using a no-fee ATM card.

I use Charles Schwab, but there are lots of other banks (don’t forget to check your local banks) that don’t charge ATM fees. Additionally, you can join a bank in the Global ATM Alliance.

By using a no-fee ATM card you can avoid those pesky ATM fees, leaving you more money for what it was intended for: TRAVEL

Step 8: Stay Focused and Inspired

While you get closer to your goal, make sure that you keep feeding your desire to travel. Travel planning can be exhausting and overwhelming — especially if you don’t have support from your friends and family. It can often get discouraging and feel out of reach at times.

Luckily, there are tons of ways to stay focused and keep your spirits high thanks to the amazing internet

Rossinavi 157 Aslec 4 Argentario Italy Superyacht
ASLEC 4 Superyacht ITALY now available for charter

Step 9: Check for Last-Minute Deals

Okay, you’re inspired, prepared, and on your way to saving money for your trip. But before you go buy that flight or book that hotel, check for deals you might have missed. You may dream of Paris but maybe there are great deals to Berlin right now. Or maybe you can get a seven-day cruise for 70% off, a package deal to Hawaii for the price of your flight to Paris, or 50% off sailing trips around Greece.

These days, there is always a deal to be found — especially if you’re flexible with your dates and/or destinations. Some deal websites worth checking out are:

SAMBUCA 59ft Motor Yacht - Phuket
Sambuca Private Yacht Charter in Phuket

Step 10: Book Your Flight

After you’ve used your travel credit card and received your sign-up bonus, use your miles to book your flight. It is harder to use miles these days due to less availability, so make sure to book early to ensure you get your desired flight.

Fortunately, there are still many ways to avoid being the person on the flight who paid the most for their ticket. My favorite sites for finding cheap airfare are:

  • Momondo – A great platform for finding flights.
  • Skyscanner – Skyscanner is one of the best websites for searching multiple destinations at the same time.
  • Google Flights – Like Skyscanner, Google Flights is great for open searches to multiple destinations.
  • Kiwi – Kiwi is great for finding lesser-known routes or smaller carriers.
  • AirTreks – AirTreks focuses exclusively on multi-destination RTW tickets.

Step 11: Book Your Accommodation

If you’re traveling for under two weeks and have a set schedule, feel free to book accommodation for the duration of your trip if it will give you peace of mind (or if you’re visiting during the high season).

Villa Sanyanga is a beautiful seven bedroom villa above Surin beach. We provide a free mini-bus with driver, private full time chef, and three maids. The villa is very spacious and can sleep up to 18 or more, with plenty of space and privacy for everyone.

Located in a private and exclusive residential development high in the hills above Surin Beach on the West coast, the villa has spectacular ocean views over the Andaman sea. Being so spacious, this is perfect for family reunions or large groups of friends, as there are many separate private areas. If children are included, the villa can sleep up to 20 guests in the seven bedrooms.

Villa Sanyanga is one of the most popular luxury rental villas on Phuket Island. It is a “home from home” family friendly villa, with five star service. Our chef Lily has been praised in more than 170 TripAdvisor reviews over eight years. She not only produces the most amazing delicious meals, but also manages the villa, and takes care of our guests, ensuring they have a holiday of a lifetime.

You will feel pampered and relaxed, enjoying the spectacular ocean views from the villa, while our chef prepares all your meals, our staff clean the villa, and your driver awaits your request to take you anywhere you would like to go.

Step 12: Plan Your Activities

plan the perfect adventure overseas

To make sure you have budgeted properly, outline the major activities you want to enjoy during your trip and how much they cost. Make any last-minute adjustments to your savings so you can ensure you have enough money. This will also help you figure out if you need any reservations for your chosen tours or activities.

Search online for discounts as well. While some countries offer cheaper prices in person, others give discounts to those who book early/online. Research which is which for your itinerary so you can save money.

For shorter trips, you can also book your activities in advance to ensure you get tickets. For longer trips, book as you go.

Additionally, before you leave home, have a rough idea of what activities are priorities for you. That way, if you run out of time or money, you can focus on your top activities so you don’t miss out. Also, make sure to double-check that there are no holidays or other obstacles that will prevent you from certain activities as well.

Step 13: Automate Your Bills

Get rid of your mail, go paperless, and set up online bill payment for your recurring bills to ensure you won’t miss any while overseas. If you are still going to get paper mail, use a service like Earth Class Mail, which will collect and scan your mail for you. (If you are going on a two-week trip, you don’t really need to worry about this, so you can skip this step, too.)

If you have the option (and don’t want to pay for a mail service), you can also have all your mail sent to a friend or family member.

Additionally, you’ll want to make sure you cancel any phone plans you have or switch your plan to one that is more travel-friendly. T-Mobile is great for travelers going on trips under 3 months. For any trips longer than that, you’ll want to cancel your plan and just buy SIM cards abroad. That will be much cheaper!

Step 14: Tell Your Card Companies You’re Traveling

No matter how long you’ll be gone, it’s a good idea to let your credit card companies know you will be overseas; that way any transactions that you make aren’t flagged as fraudulent and your card is less likely to be blocked. There’s nothing worse than having to sit on the phone with your credit card company instead of enjoying your vacation.

Also, make sure you have multiple credit card and debit cards with you. That way, should one card get flagged, lost, or stolen you won’t be left high and dry. I’ve lost cards, had them stolen, and had them flagged many times over the years. Without a backup, I would have been stranded — so plan ahead and bring some backup cards just in case!


pack your bags

Step by Step on Vacation! Time to pack for your trip! It can be tempting to want to bring everything with you “just in case” but when it comes to travel, less is more. You don’t need 5 sweaters or 8 pairs of shoes. You can get by with less, I promise. it’s actually quite liberating once you get used to it!

I travel with a 40L REI bag and then a smaller day bag.

Additionally, make sure you bring any prescriptions with you so you have enough for the duration of your trip. If that’s not feasible, bring a doctors note and prescription with you so you can fill it abroad.


While a lot of people think, “I’m healthy. I won’t get sick,” travel insurance is much more than just medical protection. It covers you when your camera breaks, your flight is canceled, a family member dies and you have to come home, or if something gets stolen.

Yes, it’s an added expense. But it’s always better to be safe than sorry. I never leave home without it because I’ve seen first-hand just what can happen on the road.

I never thought I would pop my eardrum while I was scuba diving in Thailand or break my camera in Italy.

My friend never thought he would break his leg hiking.

Another friend didn’t expect her father would die and she would have to fly back home.

Unfortunately, bad things can happen when you’re traveling. True, these events are few and far between. But they can cost tens of thousnds of dollars to handle on your own. If you’re not prepared to pay out of pocket, buy travel insurance.


have a great time on your trip

Step by Step on Vacation!

And now, everything comes together. It’s time to go on your trip and have fun! Head to the airport, board your plane (don’t forget your passport!), and enjoy the fruits of your labor. You’ve earned this!

If you’re feeling nervous, don’t worry — that’s perfectly normal. You’re about to embark on an amazing adventure — and that’s a huge change. Feeling anxious or nervous or unsure is something every traveler experiences. But you’ve made it this far. Trust your planning, follow your instincts, and you’ll have the trip of a lifetime. I guarantee it.***By using this post as a guideline for your trip planning, you can better organize and prepare for your trip. You’ll check all the boxes, not miss anything, and have plenty of money for your vacation. It can be as simple as booking a flight and packing or as complex as rearranging your entire life to go backpack the world forever.

But, no matter how long your trip may be, this list will help you stay organized and motivated as you plan your trip and to step onto that plane and out into the world.

P.S. – Step by Step on Vacation! Yes, I did leave out visas and vaccinations, because needing those isn’t as universal as the other stuff on this list, but don’t forget to check if you need those, too!


Step by Step on Vacation!

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