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  • Writer's pictureChristine

Ready for Vacation? Tips and Tricks to Help You Figure Out Your Trip

Picture of our vacation to Porto, Portugal from across the Douro River. The picture shows all of the beautiful buildings.

Who’s ready for vacation? I love exploring new places. We visited Porto, Portugal earlier this year.

So, you’ve decided to go on a vacation! That’s the easy part. The next step is to answer all of the questions that will help you firm up your plans.

Where do I want to go? Do I need a travel agent or can I plan my vacation myself? Should I do a cruise or an all-inclusive?  Do I stay in a hotel or rent a house?

I am not a travel agent and I’m not here to give you professional advice. However, I’ve traveled a lot and done my travel a lot of different ways. I’ve done all-inclusives, ocean cruises, river cruises, and tours. I’ve also used a travel agent on some vacations, and planned other vacations on my own.

My hope is that this article gives you some things to think about as you are planning your next vacation. I am also going to share with you some of my tips, as you decide what type of vacation is best for you!

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The first question you need to ask is where do you want to go on vacation? The answer to that question is going to drive a lot of decisions. For example, if you want to go somewhere that is landlocked, doing a cruise is automatically off the table.

Additionally, whether you are traveling inside or outside of the country may determine how comfortable you are planning things yourself. If you are visiting a country you’ve never been, you will probably need help planning the trip.


Sometimes, I want to just go lay on a chair on the beach every day, read a book, and not move. If that’s my intent, an all-inclusive vacation is probably the way to go. Sometimes, I want to see as much as I can in as short a period of time as possible. That might lend itself to a tour group or a cruise.

Another thing to consider, is how tied down you want to be to a schedule? Are you the type of person that likes to know what is going to happen every minute of every day of your vacation? You probably want a tour that is planned out for you. Do you like to fly by the seat of your pants? You may be better off traveling on your own.


While it might sound like an adventure, if you are not an experienced traveler, I would not recommend getting on a plane and heading out to a destination on your own with no plan. This is particularly true if you are visiting another country.


I have used a travel agent on some vacations, and I’ve booked other vacations directly myself. A travel agent can be extremely valuable – not just when you are planning the vacation, but helping if things go wrong once you leave.

In my opinion, whether or not I use a travel agent comes down to how I answer a few questions.

Question 1: How much time do I want to spend planning? For me, I really enjoy doing all of the planning and I am lucky enough to have the time to do it. If you don’t enjoy the planning or don’t have the time, a travel agent is the way to go.

Question 2: How comfortable are you with the place you are going? We go to the same all-inclusive resort in Jamaica every year. I have gotten to know most of the staff personally. I also know exactly what room I want and when I want to go. In that case, there is no point in using a travel agent. I just book directly with the resort. However, if you are going to a new place, a travel agent can be very helpful in helping you pick locations and mapping the trip out for you.

Question 3: Can you handle travel blips on your own during the vacation? If you show up at your hotel and it’s overbooked, can you figure out what to do on your own? What about if your flight is delayed or cancelled, and you miss getting on your cruise ship, do you know what to do? If the answer to these questions is no, I recommend a travel agent. When there are issues that come up, you can give them a call and they will take care of fixing it for you.

Now that you’ve figured out where you want to go, the next step is to narrow down the type of vacation you want to take. I’ve grouped the next part into two sections – travel to the Caribbean and travel to Europe.


Most people travel to the Caribbean to enjoy the beautiful weather and have a relaxing vacation. There are different ways to visit, so make sure you consider your options.

Picture of the view from our room during our vacation to Jamaica. The picture shows the blue water of the Caribbean with sailboats in the distance.

My favorite place to go in the Caribbean is Jamaica. This is the view from our room at The Jewel Dunn’s River in Ocho Rios.

All-Inclusive Resort

Probably the most popular way to vacation in the Caribbean is going to an all-inclusive resort. This is the ultimate “hands-off” vacation. You can arrive at the airport, and not think about another thing until you fly back home.

Picture of a table set up with wine, cheese, crackers and fruit for a cocktail party.

You can definitely get the royal treatment at an all-inclusive resort. During our last trip, we had a butler suite. Our butlers set up this amazing cocktail party in our room for our group of friends. It didn’t cost us a penny!

The big advantage of an all-inclusive, is that everything is taken care of for you. In fact, you don’t even need to leave the resort.

Tip #1: Not every all-inclusive is created equal. Make sure you understand what is included at the resort you are booking. Some resorts have different levels of service you can buy. Depending on the level of service, you may be limited to eating at certain restaurants and have access to only certain activities.  Do you want to wear a wristband during your whole vacation?  If not, make sure you go to an all-inclusive that has one level of service for everyone.

A picture of the bed at our resort. There is a towel folded into a little character with sunglasses on. There are rose petals on the bed.

In my opinion, the level of service you get at an all-inclusive should be very high. At The Jewel Dunn’s River, we get turn down service every night, including some great towel art!

Tip #2: Make sure you understand what is included in the price. Does it include transportation to and from the airport? Are tips included? How about excursions?

Tip #3: Make sure you understand the “culture” of the resort. Some resorts are party places that cater to singles. Other resorts are honeymoon destinations that cater to couples. Is the resort higher end and you have to dress up in the evenings? Or, can you wear shorts, t-shirts and flip flops to dinner.

Tip #4: Don’t be afraid to venture off the resort. We always try and have lunch and/or dinner at one of the local restaurants. However, make sure you don’t overdo it. If you prefer to eat locally and spend all of your time exploring, you are probably wasting money by staying at an all-inclusive.


Another popular way of seeing the Caribbean is going on a cruise. You can often find great deals on cruises, which makes it a cheap way to go on vacation. A cruise also lets you see a number of islands in one trip, while only unpacking once.

In addition, the large cruise ships today are destinations in and of themselves. Some people never even leave the ship.

A picture of the pool deck on a cruise ship.

The pool deck on our cruise ship during our Mediterranean cruise. This was a smaller ship. The larger ships have wave pools, slides, and all sorts of extras!

A picture of one of the greens on the putt putt course.

Our cruise ship also had a putt putt course. If you plan on spending time on the ship, make sure you understand the activities the ship has on board.

For me personally, the enormous size of these ships is a turn off. I personally want more privacy. I also want more flexibility and not be tied down to the cruise ship’s schedule.

Tip #5: Make sure you have a contingency plan (or are using a travel agent) in the event you don’t arrive at your departure port on time. When a ship is scheduled to leave, it’s going to leave, whether or not you are there. If you’re flight is delayed or canceled and you miss your ship, you will need to be able to adjust. Additionally, my in-laws went on a cruise once, and their luggage got lost on their flight. Be sure you have some basics in your carry-on bag, as it make take a few days for your luggage to catch up with you.

Tip #6: Determine how much time you want to spend in your room. The cabins on cruise ships are typically small, and feel a bit like being in a box. A resort, house, or hotel is going to give you a lot more room and feel more comfortable.

Tip #7: Are you a drinker? Make sure you understand what costs are included in the price of your cruise. Typically, alcoholic beverages are not included. I know of situations where people have run up more money on their bar bill than it cost for the cruise. Most ships have “beverage packages” you can buy. However, if you plan to eat and drink well during your trip, an all-inclusive may be the better choice.

Tip #8:  If you will be sailing out of the country, be sure to check with the cruise line to see what sort of electrical outlets are on board the ship.  You may need to bring an electrical converter with you.  They are typically less than $20 and easy to pack.  Check out this travel adaptor as a good option at a reasonable price. 

Renting a House/Condo or a Hotel

If you want the most freedom and privacy, look into renting a house or condo. Even staying at a regular hotel also offers you more freedom than you would have at a resort or on a cruise.

Tip #9: Understand your transportation options. It can be a challenge to rent a car and drive on many of these islands. Make sure you are up to the challenge. If not, make sure you know how to arrange for a driver if you plan on leaving the property. It’s not as easy as requesting an Uber on your phone on most of the islands!

Tip #10: Understand what amenities come with the property. This is especially true if you are renting a house. It’s not so easy as running to the Walmart when you need something. Do you plan on eating in? If so, where will you buy your food? Does the house include all of the linens you need? What about internet? Television? A pool?


To me, the two critical questions here are 1) how comfortable are you with where you are going, and 2) how experienced are you as a traveler? The answer to those questions determines the level of support that you need during your vacation. I classify travel options as “assisted” and “unassisted”.

Assisted Travel

This can take place in a couple of forms, and again, it depends on where you are going and what you are looking for.

One option to consider is a fully-guided ground tour. These trips are completely planned for you. We did one of these tours to Poland a few years ago. We had a daily schedule. A typical day consisted of waking up and taking a guided tour of the city we were in, getting on a bus and driving to a new city, and then checking into the hotel that night. We usually had to have our suitcases outside our hotel room door early the next morning, so they could be loaded back on the bus.

Tip #11: Strategic packing is the key. You will NEVER be able to unpack your suitcase on these types of trips, as you are going to a new city and a new hotel almost daily. I planned my outfits day by day before I left, and grouped things together that way in my suitcase. I also took a kitchen trash bag with me, and put my dirty clothes in the trash bag so they didn’t co-mingle with my clean clothes.

Tip #12: If you don’t like to be tied to a schedule, this is not the type of trip for you. You are at the mercy of the tour schedule, and the other people on the tour. For our Poland trip, the rest of the group was a bit older than us. Every time we drove somewhere new, we had to stop every couple of hours so EVERYONE on the bus could use the bathroom. We also had people that had to eat at certain times in order to take their medicine. Make sure you understand how much free time you will have on the trip, and determine if it works for you.

Tip #13: As I’ve mentioned before, be sure you understand what is included in the tour. Are meals included? If you want to take any extra side trips, will that be an extra cost? Are tips included for the bus driver, the overall tour guide, or the local tour guides?

Another assisted travel option is to take a cruise. This could be in the form of a large ship on the ocean, or a river cruise. River cruising has become very popular in Europe particularly.

A picture of our river cruise boat in port in Portugal during our river cruise vacation.

River cruising is very popular. We recently did a cruise along the Douro River in Portugal. We cruised on AmaWaterways.

To me, the biggest advantage of a cruise is that you unpack once, but still get to see multiple ports. Of course, you are limited to see cities that are located on the water and with accessible ports.

If you want to learn more about river cruising, check out my article about the river cruise we did of the Douro River Valley.

Tip #14: Really think about the size of the cruise you are comfortable with. While I have no interest in being on one of those giant cruise ships, I have done an ocean cruise on a smaller ship (800 people) and I’ve just booked my second cruise on the same cruise line. While the smaller cruises are usually more expensive, they have definite perks. The crew to passenger ratio is usually much higher, resulting in more personalized service. The cabins are usually larger as well.

A picture of the Marina cruise ship that we were on during our Mediterranean cruise.

We did a Mediterranean cruise on Oceania cruise lines. Their ships are smaller than some of the large cruise lines.

Tip #15: I can’t say it enough….make sure you understand what is included. Are excursions included? If not, how much are they? How about alcohol? Can you bring your own alcohol on the ship? If so, how much can you bring? Do you have to pay extra to eat in certain restaurants on the ship?

A picture of me with two of our bartenders on our river cruise of the Douro River.

We have always gotten great service on a river cruise. Our bartenders were a lot of fun, and took great care of us. Just be careful. Your bar bill can go up quickly!

Tip #16: Pack your patience. You are going to be living on a small vessel with a lot of people for several days. Even the process of getting everyone on and off the ship when you are in port can be frustrating.

Tip #17: Look for an itinerary that fits you. Both of our river cruises have been on AmaWaterways. While we like that cruise line, I have also heard good things about several others. To me, the thing that counts is the itinerary and the timing. There are lots of options out there, so look around (or have a travel agent help you figure it out), and book the trip that works for you. Many cruise lines also offer special themed cruises. We’ve done two river cruises, and they have both been wine themed.

Unassisted Travel

For the ultimate amount of freedom and flexibility, travel on your own. This doesn’t have to mean that you are backpacking through Europe with no plans at all. I’ve done a couple of vacations to Europe that have been completely planned out by me. I’ve figured out where we are going, made arrangements for transportation, and booked all of our hotels directly.

The big thing to remember here, is that this takes some time and effort on your part. While you don’t have to plan every detail, you need to plan enough in advance to know where you are going and what you want to do.

Tip #18: Even for unassisted travel, you may want to look into booking some tours during your trip. Private tour guides are often more cost effective than you think, and can be a great way to learn about a city. Many cities also offer “free walking tours”. You just show up at a certain time, and pay the guide what you think is a reasonable amount. I also love tours that combine sightseeing with food or drinks. These tours are a great way to meet like-minded travelers.

Tip #19: If you are booking everything on your own, be sure to confirm your hotel reservations before you leave. Booking hotels anywhere in the world is easy with today’s technology. However, nothing beats a phone call to the hotel to confirm that your reservation is in their system.

Tip #20: If your “unassisted trip” includes visiting some popular tourist attractions, make sure you book your visits in advance if possible. One of the big advantages of going with a tour group or on a guided excursion from a ship, is that you can skip the line and get right into the attractions. If you are on your own, you won’t have that advantage.

Tip #21: Don’t be afraid to ride the train. Train travel in Europe is a great way to get around. Trains are cheap, clean, fast, and almost always on time. Within a city, utilize the public transportation system for getting around.

My husband and I riding a train in Germany.

We love traveling through Europe by train. The trains are comfortable, fast, and run on time. They are also very cheap and easy to figure out.

The Hybrid Model

The happy medium to all this might be a combination of “assisted” and “unassisted” travel.  For the last trip to Europe we did, we started in Lisbon.  I booked the hotel for Lisbon myself, figured out the transfers from the airport, and planned all of our sight seeing.  I also booked the train from Lisbon to Porto on my own.  Once we arrived in Porto, we boarded our river cruise.  During the cruise, we did a combination of the planned cruise excursions, as well as spending some days just wandering on our own.  On the back end of the cruise, we used the cruise line’s planned transportation to Madrid as well as the hotel that they booked us in.  Once we were in Madrid, however, we went out on our own and found our own way back to the airport at the end of the trip.

There are a lot of options out there for you when it comes to vacations.  Take some time and think about what you need and what makes you comfortable.  Make sure you are making good memories on your vacation!  Happy traveling!

Have questions about figuring out your travel options?  Do you have some tips that you want to share?  Comment below or e-mail me at 

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