The Ultimate Guide to Designing Your Dream Getaway

The best trips happen before you even start booking! Choose your adventure and identify your travel style in advance of your trip. You’ll save yourself lots of stress in the process. Check out this guide filled with step-by-step instructions on designing a dream getaway!

(This article is Part 1 of the Choose Your Adventure Series)

This article will cover the following:

  1. Finding Your Travel Style

  2. Charting Your Path

  3. Figuring Out Finances

Find Your Travel Style

What Kind of Trip Do You Want?

This is the daydreaming phase, when you start thinking, ‘Where in the world should I go next?’. Perhaps scrolling through Instagram and you see a friend eating pizza in Naples, or you’re watching the latest nature documentary show and remember that you’ve always wanted to see the Great Barrier Reef. Maybe you’re like me – always longing to see what the next frontier offers.

Use this time to reflect on what type of trip you’ll want, and think of places you want to go. Hoping to lounge on a white sandy beach with a drink in hand? Perhaps you’ll stick to resorts or frequently visited beach destinations that offer high-class amenities. If you’re looking to take in city views and nightlife, maybe start envisioning activities that you’d like to do or skylines you’d hope to see in real life. Alternatively, if a quieter trip is more your speed, start thinking of locales that might offer more R&R and solitude.

Once you decide on the type of vacation you hope to have, it’s time to hop online and start doing some research!

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Pinterest is an great place to find images and links for potential vacation options. You can start up a Pinterest board and save all of the links to it, so you can organize and save information before you go. Additionally, Pinterest offers links other sites for education on places around the globe.

I also use social media to help me find places I’d like to visit. There are so many creators that are sharing their adventures, and their posts and profiles help me to get a taste of what that area may be like. It doesn’t take long to get inspired!

Once you’ve identified a general idea of where you’d like to visit and the kinds of experiences that fit, you can start to define your travel style.

Define Your Travel Vibes

The key here is to know yourself. What travel style best suits you?

Are you a free-spirited solo adventurer that wants eco-friendly accommodations? Or maybe you’re trying to escape the pace of a tightly packed schedule and you’re looking forward to well earned luxurious free-time.

Keep in mind that most (but not all) trips can be oriented to accommodate for more than one type of experience or comfort level.

However, take care that whoever you’re traveling with has the same expectations about the type of trip this will be. No one wants to arrive in a location only to find that someone is destined to not enjoy their trip.

The list below offers some categories and examples of trips to help you narrow down your own goals.

Outdoor Adventure

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Looking to climb some volcanoes or venture into rainforests or glaciers? For thrill seekers and adventure junkies, a resort robe and a piña colada just aren’t going to cut it. You likely want to get off the beaten path and take some risks. Consider the following for your trip:

Experiences / Excursions

Start thinking about the physical experience you’d like to have and the sites you’d like to see.

Remember factors like your age, experience level and risk tolerance. What would it physically take to complete the goal, and what offerings already exist that can satisfy your urge for adventure?

For example, if you want to go on long-distance thru-hikes, you’ve got options all around the world, including Iceland’s Fire Ring Road (mild), the Spanish Camino de Santiago (medium), and the Pacific Crest Trail in California (spicy).

Once you’ve identified your options, scale the adventure level according to what you can handle.


Adventure accommodations vary wildly (pun intended) according to trip. However, it’s important that you identify a general type of accommodation with enough advance notice to make a booking. For example, non-traditional housing like treehouses, yurts, RV’s and campsites typically require at least a few months of advance notice to secure the reservation.

Inquire with as much time as possible, if you seek specialty experiences that include room and board (e.g. Safari Tours or camping in a National Park), since they often get fully booked in advance.


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Want to see the world in a sustainable way? Now more than ever, travelers are choosing to be mindful of the impact of their trips on the environment. There is a trend toward climate-responsible traveling, and along with it entire industry shifts to accommodate a smaller carbon footprint. Consider the following for your trip:

Experiences / Excursions

Eco-Tourism trips often overlap with outdoor adventures, as usually the most sustainable activities are when you just take advantage of the nature around you. Hiking, swimming, and beach-going are both zero impact and free! While you may need to figure out which parks and or nature preserves that you’d want to tour in advance, there is typically no need to make bookings ahead of time. Different national parks may require a nominal fee, but typically they are very economical.

The great part of eco-tourism is that the types of experiences are varied and scalable. For example, you can attend a deluxe and curated yoga retreat in Costa Rica, or volunteer to take care of Elephants in Thailand. Budget ranges also range from work exchanges to more elevated eco-lodges and resorts.


Accommodations have really improved in the eco-tourism industry. From eco-resorts that are upscale and built to integrate with the ecosystem to eco-hotels that offer environmentally friendly products, there are many options in locations around the world.

Pro Tip: If you’d like your bookings to reflect even more climate consciousness, consider using the google tracker “emissions” setting to assess the carbon deposits from your selected flight.

Cultural Connections

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Do the UNESCO World Heritage Sites call your name? If you’d prefer to spend your days roaming cobblestone streets while touring landmarks, museums and galleries, perhaps a cultural trip is more your style. Consider the following for your trip:

Experiences / Excursions

Due to their widespread acclaim, major cultural sites typically attract more tourists. Expect to pay a little more for your activities in these regions. For example, visiting vineyards and chateaux in France’s Bordeaux region will require more expensive arrangements for transportation, activities and lodging.

If you’re really hoping to get a feel for the local culture and experience, I recommend you spend some time outside of the tourist destinations as much as possible. For example, while in Oahu, Hawaii, I went to a luau and learned about Hawaiian and Pacific Island culture and history. I also went to the tourist landmarks and beaches in Honolulu. However, I set aside days to tour the North Shore and looked for locally reviewed small businesses and restaurants to support. By including iconic cultural activities with everyday life, I was able to get a better perspective of the culture on the island, away from the touristic scene.


There are so many accommodation options for travel now compared to the past. For starters, you can make sure to use maps and sites to ensure that your lodging is geographically close to the cultural attractions that you wish to see.

I often select the “Distance to City Center” feature on booking apps or websites, so that I can find the best lodging for my trip. For cultural trips, you’ll want to get as close to the city center as possible, since that is normally where are the activities are and/or the public transportation hub is most connected.

Pro Tip: To get a better feel on how the locals live, consider using AirBnB. Not only will you be better able to connect with residents, but you’ll also be able to practice living as they do. If you’re hoping to understand the culture, society or language of a place, choosing comfortable and safe lodging in line with the larger society is a good way to start.

Luxury Escape

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Is it time for a lavish vacation? If you’re celebrating a big milestone and you’d like to #treatyourself holiday, then an upscale trip is just the ticket. You want full amenities, spas, deluxe hotel rooms and yacht parties? Countless options abound for those who like to experience the finer things in life. Consider the following for your trip:

Experiences / Excursions

One great thing about luxury travel is that most places do have options that cater to those who want to spend top dollar. If you’re looking to travel in luxury, start thinking about they type of locale that you want to explore and then identify the hotel brands or franchises that operate there. Certain experiences might even be all-inclusive where food and board are included in the cost of your lodging! For example, if you’re looking to enjoy a private Balinese beach, consider renting a private ocean bungalow. In some of these places, you can even upgrade services to enjoy dinners by a private chef or a spa!


If you want opulence and originality, think outside the box. Lodging now comes in so many forms, including luxury cruises or private plane charters. If you’re hoping for first-class service, there are numerous hotel chains that offer the top-of line accommodations and experiences, including the Peninsula and the Ritz-Carlton hotels. Best of all, these brands are global. You can expect the same high-quality treatment and prized location no matter which destination you visit.

Chart Your Path

Once you’ve gotten an idea of the type of trip you’d like to take, you can begin your planning. In my experience, there are two ways to go about this. One way to plan this is to choose a specific location and start to save and budget accordingly for the associated expenses. Another approach (the one I prefer) is to start out with your budget and find locations that fit it.

The pros and cons of each approach are below:

Location Based Travel

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  • Pros:
    Visit specific dream locales
    Plan your itinerary early
    Make deposits and reservations in advance
    Research excursions and specific activities
    Know how much to save upfront
    Can choose prime season to visit
    Invite others to travel with you
  • Cons:
    Not as flexible
    Risk losing deposits if plans change
    Requires budgeting a lot in advance (longer timelines)

Even though planning according to the location is more rigid due to making airfare/lodging reservations in advance, if you’re looking to do something specific, then it’s much more economical. Location based travel also gives you more time to define your timeline and budget for you to save up.

Location based traveling is also great when you know where you want to go and what you want to do. For example, if you really want to see the Northern Lights in Iceland, then you’ll need to be there between September and April for best viewing. By planning out your trip in advance, you’ll have enough time to save money to be there within that timeframe.

Finance-first Travel

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  • Pros:
    Highly flexible
    Can plan a trip with shorter timelines
    Wallet friendly
    Allows you to be more traveler than tourist
    Creative experiences that cost less (or no) money
  • Cons:
    Dates depend on the airline ticket
    May be harder to plan with a group
    Often “Off” Season or random dates
    Reservations for excursions may be unavailable
    Shorter timeline to save money

Finance-first travel is great for people who have high flexibility. If you’re a WFH employee or a digital nomad, chances are you’ll have more opportunities for travel. As long as you can bring your laptop with you and there is decent wi-fi, then you can pretty much work out of other locations.

Bottom line: With finance first travel you start with your budget and then find a location, experiences and lodging that works within that framework.

Finance-first travel is actually a decent way for everyone to plan trips. Thanks to websites like Scott’s Cheap Flights and SkyScanner, it’s easy to scour the web for good deals. As long as you’re open to the dates that the tickets offer, the rest of the trip planning experience is pretty much the same.

The nice part about finance-first travel is that it’s more economical. You decide the amount that you’re wiling to spend and then you start finding locations and designing your trip. The saving process is less worrisome, since you’re only booking what lines up immediately with your budget.

Additionally, finance-first travel often pushes you to be creative with the experiences that you will enjoy. The most touristic experiences are often big-ticket items that eat up a budget, however finance-first travel may mean that you shift the kinds of excursions you include in your itinerary. They say the best things in life are free, and walking, hiking, and sight-seeing certainly are.

Wander With Wren Approach: 

It’s much more spontaneous and fun to buy cheap airline tickets and then design the trip. For example, I recently purchased really affordable plane tickets to go to Guatemala. Although visiting that country wasn’t on my immediate destination list, I saw that the price of the tickets were in-budget, and that the rest of the activities in the country were affordable. After I purchased the tickets, I decided the kind of trip I wanted to have (hint: it’s always an outdoor adventure and/or a cultural one). I then researched that there are plenty of affordable cultural and outdoor activities to do that are free (or close to it). Once I had a shortlist, I began budgeting to save for the upcoming adventure.

Figure Out Finances

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Now comes the fun part – kidding! Figuring out finances can be a bit daunting, especially when it comes to planning a dream trip. It’s hard to see the cost breakdown for travel expenses: Lodging, food, transportation – all of it adds up fast. The easiest way to assess is to figure out what type of trip you’re going on. Are you ballin’ or are you ballin’ on a budget? It’s also good to try and get a commitment from any travel friends at this stage. If they are serious about joining you, get them to put their money where there mouth is and pool money for deposits so you don’t have the charges all on one card. Unless you want points for your travel card…more on that later.

The nice thing about budgeting is that it provides a rough outline for what you will spend. Most of the time, budgets can give you a rough idea of your upcoming expenses, however, there are always more unexpected expenses that you incur while traveling, so be sure to add a cushion to your budget.

While the goal of this article isn’t to teach you how to budget, there are certainly a few tips to keep in mind while figuring out finances for your trip. These tips can be used for planning all trips, but they work even better if you’re planning using the finance-first approach!

Budgeting Tips

Tip #1: Use a travel credit card! (Responsibly!)

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I’m newer to travel hacking but I am already a convert. The long short of travel hacking is this: Use credit cards to earn points and then cash out those points for travel. Then rinse and repeat with multiple cards. I’ve travel hacked a couple trips now, including scoring lodging in Honolulu and round trip tickets and hotel stays in Spain. That’s just the tip of the iceberg of travel hacking!

People can get REALLY into travel hacking, and there are tons of websites and apps that offer information on how to best game the system. I’ll link resources here, but for the sake of this guide, I’ll keep the introductory tips brief.

Pro Tip:

Open a card with a large credit card company to earn the maximum amount of points. Most large providers offer sign-on bonuses with 50,000+ points and a variety of perks. The most renowned travel cards are offered by Chase, American Express and Capital One. These three behemoths offer the most bang-for-buck in points, which can be used as currency for flights, hotels, and other travel expenses in travel portals.

Pro Tip:

To maximize the travel credit card, be sure to hit the minimum spend to get the bonus points. For example, a Chase card may offer 60,000 points if you hit the minimum spend of $4,000 in three months. Every purchase that you put on the card conveys to points per dollar spent. Once you’ve met that spend minimum you’re able to start cashing in the points for travel and related expenses.

Pro Tip:

Not using points for direct travel expenses? Depending on which card you choose, they offer a host of other perks. Travel insurance, hotel and rental car discounts, excursions and wine tastings – all of these are benefits to using your travel card.

Important: The key with travel hacking is to make the card work for you. Remember, you’re not getting the card and going into new debt on purchases that you were not going to make. Rather, you’re putting all of your normal purchasing and spending on the card, and then you pay it off on-schedule. Once you’ve done that, rake in the points.

Tip #2: Use a flight fare alert system to scour for cheap tickets!

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Nobody wants to spend more on flights if it can be helped. Thankfully, there are entire companies and applications that track cheap flights and can send you alerts. Using these tools are best if you’re open to a finance-first approach toward trip planning. Fare alert systems often mean that you have last-minute availability or sudden changes in price on tickets, so you have to be flexible and willing to move on them quickly. Some tools that I use are listed here:

Pro Tip:

Scott’s Cheap Flights:  My favorite resource for finding affordable flights around the world. Thanks to them, I’ve scored discounted flights to Hong Kong, Spain and Guatemala! SCF offers three subscription tiers: Free, Premium and Elite. While you can absolutely score great deals through their free subscription, I’ve recently converted to their premium package to take advantage of more frequent and better flight options. You can try their free trial and then upgrade to a membership using this link.

Pro Tip:

Google Flights Tracker: This tool is free through Google Flights. Simply put in your desired dates and destinations, and then click “Track Prices” above the listed itineraries. Give yourself a few months in advance if you can, so that you can receive email notifications. Once the flight reaches a price you’re comfortable with you can book!

Pro Tip:

SkyScanner: SkyScanner is one of my favorite sites because it compares flights across third-party vendors and has them conglomerated here. It also the option to find cheap fares and track them.

Tip #3: Keep Booking Dates Flexible!

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Pro Tip: Consider booking on shoulder seasons with flexible dates (just off-peak of prime tourist season), so that you can enjoy the locale at a discounted rate and stay free from hordes of tourists.

Typically, “off-season” dates result in cheaper fares and accommodations for you. However, do your due-diligence as some activities require particular seasons or dates to participate.


The magic of travel begins before you even get on the plane. Daydreaming and identifying which travel style suits you make it possible for you to lay the foundation of a stress-free trip. Once you’ve gotten your travel vibes and budget down, be sure to check out the next part of this series to narrow down your accommodations and bookings.

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