Dream Big, Travel Bigger: Planning the Trip of a Lifetime With Your 2024 PTO

Post originally Published January 20, 2024 || Last Updated January 20, 2024

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Dream Big, Travel Bigger: Planning the Trip of a Lifetime With Your 2024 PTO - Pick a Place That's Been Calling Your Name


Dream Big, Travel Bigger: Planning the Trip of a Lifetime With Your 2024 PTO

When planning the trip of a lifetime, the first step is choosing a destination that speaks to your soul. This should be a place that has been on your bucket list for years, whispering its siren song, beckoning you to explore its wonders. Follow your heart and pick the locale that ignites your inner wanderlust.

Maybe it’s the tropical beaches of Bora Bora that have been calling your name, with visions of overwater bungalows dancing in your head. Or perhaps it’s the medieval history and rolling green hills of Ireland that are tempting you to book that flight. For some, it’s the mouthwatering pasta and wine in Tuscany or the epic safaris of Kenya. Listen to your travel dreams and let them guide you.
Do your research to uncover insider tips and hidden gems that travelers often miss. Study blogs, watch travel videos, pore over books and dive deep into your chosen destination. Identify the top sights you simply must see, but also learn about quiet treasures and local secrets. Develop a balanced itinerary that includes must-see attractions along with off-the-beaten-path finds.

Talk to friends who have visited this place and get their personal recommendations. Check travel forums and Reddit threads to gather intel from other travelers who have made the journey. Locals can provide priceless advice, so connect with expats and natives online to get their guidance. The more prepared you are, the more fully you’ll experience your destination’s magic.

What else is in this post?

  1. Dream Big, Travel Bigger: Planning the Trip of a Lifetime With Your 2024 PTO - Pick a Place That's Been Calling Your Name
  2. Dream Big, Travel Bigger: Planning the Trip of a Lifetime With Your 2024 PTO - Do Your Research to Find Hidden Gems
  3. Dream Big, Travel Bigger: Planning the Trip of a Lifetime With Your 2024 PTO - Get Clear on Your Budget Before You Book
  4. Dream Big, Travel Bigger: Planning the Trip of a Lifetime With Your 2024 PTO - Use Miles and Points to Fly for Less
  5. Dream Big, Travel Bigger: Planning the Trip of a Lifetime With Your 2024 PTO - Find Unique Lodging Options to Enhance Your Experience
  6. Dream Big, Travel Bigger: Planning the Trip of a Lifetime With Your 2024 PTO - Build in Plenty of Time for Wandering
  7. Dream Big, Travel Bigger: Planning the Trip of a Lifetime With Your 2024 PTO - Plan Some Activities But Leave Room for Spontaneity
  8. Dream Big, Travel Bigger: Planning the Trip of a Lifetime With Your 2024 PTO - Capture Moments That Will Last a Lifetime

Dream Big, Travel Bigger: Planning the Trip of a Lifetime With Your 2024 PTO - Do Your Research to Find Hidden Gems


Doing your homework before a big trip is key to having the most memorable experience possible. You want to dig deep and uncover hidden gems that most tourists never find. This takes time and effort, but it’s so worth it.

Read travel blogs and watch YouTube videos from people who have recently visited your destination. Get tips on beautiful, quiet spots away from the crowds. For example, when visiting Paris, wander down Rue Crémieux for its charming rainbow-colored houses. Or stroll through Cour du Commerce Saint-André, a hidden pedestrian square with cafes and fountains.

Another fantastic resource is Reddit. Search the travel subreddits related to your destination and read recent threads. Travelers often share advice on their favorite local restaurants, bars, parks and museums. You’ll discover places not listed in any guidebook. In Tokyo, Redditors suggest stopping by punk rock club El Puente in Shibuya. Or exploring the 300-year-old Daimyo Oak tree in Setagaya Park.

Don’t be afraid to connect with expats who live in the area through Facebook groups or Meetup. They can provide personalized recommendations from a local perspective. Maybe they’ll tell you about an indie bookshop run by a British couple in Mexico City's Roma Norte neighborhood. Or a speakeasy cocktail bar in Edinburgh that you need a password to enter.
Scour Instagram hashtags related to your destination and make a list of cool spots that capture your eye. Those colorful colonial houses in Valparaiso, Chile. That secluded swimming hole in Oregon surrounded by old-growth trees. That street art alleyway in Penang, Malaysia. Then try to hunt down the locations.
Pore over blogs like Atlas Obscura that specialize in unique, overlooked places. Peruse their archives for your target destination and bookmark intriguing spots. Maybe you’ll read about a restaurant in Tokyo with lifelike robot staff. Or a 600-year-old library carved into stone caves under a Moroccan mosque.

Dream Big, Travel Bigger: Planning the Trip of a Lifetime With Your 2024 PTO - Get Clear on Your Budget Before You Book


The thrill of planning a once-in-a-lifetime trip can quickly turn to regret if you don’t take the time to clarify your budget beforehand. Getting clear on how much you can realistically spend before booking anything is crucial. Otherwise, you may end up in debt and filled with resentment over a journey meant to be magical.

Start by reviewing your current finances and savings. Be brutally honest about where you stand. If your rainy day fund is lacking or you have lingering credit card debt, consider delaying this epic adventure until you’re on more solid ground. Rushing into it could negatively impact your finances for years.

Next, research all the costs associated with your chosen destination during your travel window. Accommodations, food, transportation, activities - it adds up quickly. And don’t just look at lower-end options. Treat yourself a little by including some splurges in your budget for unique experiences. Just balance them with more affordable basics.

Building your budget in a spreadsheet is extremely helpful. You can play with numbers and projections. And easily see where you may need to scale back or compromise. Be flexible - maybe choose a less expensive destination like Portugal over Switzerland. Or visit during the off-season rather than peak summer. Small tweaks can yield big savings.
Pad your budget with at least 10% more as a buffer. Unexpected expenses inevitably pop up when traveling. And exchange rate fluctuations or price increases can surprise you. Having this cushion brings peace of mind knowing you can handle bumps in the road financially.
Once your budget is set, stick with it. When booking, avoid going over those carefully calculated amounts for each expense category. It’s easy to get swept up in choosing higher end options, but hold the line. Being disciplined now means no regret or financial hangover after your journey.

Dream Big, Travel Bigger: Planning the Trip of a Lifetime With Your 2024 PTO - Use Miles and Points to Fly for Less


One of the best ways to make your dream trip more affordable is to use airline miles, credit card points, and loyalty programs to help cut down on costs. Flying can be the biggest line item in any travel budget, so free or reduced price tickets can make a huge impact. With some strategic planning and smart point maximizing, you can cross the globe in style without breaking the bank.
Signing up for travel rewards credit cards and collecting miles through everyday spending is a great place to start. Cards like the Chase Sapphire Reserve and Amex Platinum offer 50,000+ point bonuses just for meeting minimum spend requirements when you open the account. Put your regular household expenses on the card, pay it off each month, and watch those points add up quickly.

Before you know it, you’ll have enough for a free domestic flight or to heavily discount an international ticket. Just be sure to avoid cards with high annual fees unless you can reap enough perks and points to offset the cost. Check out The Points Guy for the latest credit card offers and insider tips on maximizing point earnings.
Don’t forget to link all your loyalty programs accounts to your new travel rewards card. From airlines to hotels to ride shares, connecting them allows you to earn extra points on top of the credit card rewards. Log into your United, Marriott, Hertz and Uber accounts and add your new card as the form of payment. The points will accumulate across all platforms with every purchase you make.
When it comes time to redeem your points and miles for flights, flexibility is key for finding the best deals. Consider flying on off-peak days or choosing indirect routing if it allows you to cover more ground on an award ticket. Use sites like AwardHacker to determine the optimal programs and point transfers for a specific route. And set up alerts for reward availability on your ideal dates and destinations.
If you’re still short on miles, there are ways to top up your account through points transfers from credit cards, shopping portals like the AA eStore, or even buying miles when promotions are offered. Every mile helps bring you closer to a free trip.

Dream Big, Travel Bigger: Planning the Trip of a Lifetime With Your 2024 PTO - Find Unique Lodging Options to Enhance Your Experience


Selecting a hotel is one of the most exciting parts of trip planning. But defaulting to a big chain hotel, no matter how nice, means you’ll miss out on the local charm and personalized hospitality of a boutique property or family-run inn. Seeking out these unique stays can transform a standard vacation into a truly memorable cultural immersion.

Independent hotels and small lodges allow you to support local businesses rather than big corporations. The staff takes pride in sharing insider knowledge and hidden gems since the property feels like an extension of their own home. The design and amenities often reflect regional history, artisans, cuisine and nature in ways that chain hotels rarely do. It creates a sense of place that enhances every aspect of your visit.

For example, an eco-lodge nestled in Costa Rica’s rainforest allows you to fall asleep to the sounds of howler monkeys and parrots, then wake to hiking trails right off your doorstep. A 300-year-old ryokan in Kyoto treats you to lavish multi-course kaiseki dinners, soothing onsen soaks and rooms with rice paper walls, tatami mats and futons.

A vineyard inn in Tuscany pours glasses of its own crisp white wine before meals of handmade pastas, local olives and pecorino cheese. The owners share favorite hiking routes through the surrounding hills and arrange private tastings with nearby family-run wineries.
Seeking out these one-of-a-kind stays does take more research and planning. Travel review sites like TripAdvisor are invaluable resources, especially for parsing through smaller cities and remote destinations that lack big brand hotels. Don’t just read the ratings, but dig into the reviews. Travelers will highlight what gives the property its charm and character.

Booking sites like Tablet, Mr&Mrs Smith and Onefinestay specialize in curating unique high-end accommodations. These run the gamut from a luxury African safari camp to an avant-garde artist’s loft in Barcelona to a remote Alpine lodge reachable only by helicopter. For more affordable options, boutique rental platforms like Luna or Fleur offer apartment-style stays in reimagined older buildings, often with lots of historic details.
If your budget is tight, don’t rule out unique stays. Hostelworld and Airbnb open up possibilities like a jazz hostel in New Orleans where you sleep in retro Pullman train cars. Or a 300-year-old stone cottage on a sheep farm in the Irish countryside. Private rooms in smaller, locally owned guesthouses are also very reasonable in much of Asia and Latin America.

Dream Big, Travel Bigger: Planning the Trip of a Lifetime With Your 2024 PTO - Build in Plenty of Time for Wandering


The magic of traveling lies in possibility. You never know what delights each new day will unfold or where your whims and curiosities will lead you. Building in ample time to freely wander and get happily lost should be a priority when planning this trip of a lifetime. Otherwise, you risk an overly regimented experience where spontaneity is strangled.
Cheryl Strayed, author of Wild, writes, “I believe in walking, getting lost, taking my time. I believe in writing things down on pieces of paper...and following the pen scratchings wherever it may lead — these tiny trails of ink mapping out new paths.” When you leave room to follow your pen scratchings — or simply wander with no aim — you give yourself the gift of happening upon hidden wonders.

Meander down narrow cobblestone alleys that beckon with wafts of fresh pastries and bursts of flowerboxes. Squeeze into hole-in-the-wall joints with tantalizing aromas and neighborhood chatter tumbling through open doors. Sit awhile in shady parks to write postcards and watch locals go about their days. Traipsing without agenda leads to stumbling upon mom-and-pop shops, street musicians, pop-up markets, and impromptu conversations with the most interesting characters.
Wandering away from major tourist centers rewards you with glimpses into everyday life. Like noticing the elderly woman who carefully sweeps the steps outside her Paris apartment each morning while wearing curlers and a pink bathrobe. Or the dreadlocked surfers sipping mango lassis after catching waves near an old bombed-out church on Sri Lanka’s south coast. Or the giggling children who practice their English with you on a park bench in Seoul.
Unstructured exploration opens you up to moments of joy, awe and meaning. There's the gasp when you turn a corner and find yourself facing the Eiffel Tower in all its magnificence. The sense of smallness when confronted with thousands-year-old ruins being reclaimed by tropical jungle vines and clouds of hummingbirds. The surge of accomplishment upon reaching the breathtaking viewpoint you spotted from below on your spontaneous hike. Moments you’d miss by racing between scheduled activities with blinkers on.
Wandering without wifi or 4G keeps you present. You observe more closely. Attune to details. Notice shifts in light, sounds, and smells. Allow natural curiosity to take the lead rather than relying on an algorithmic map dictating your route. There is power in being fully in your body, senses alive, during this beautiful temporary freedom from real life’s demands. Drink in every detail so your memory holds the technicolor.

Dream Big, Travel Bigger: Planning the Trip of a Lifetime With Your 2024 PTO - Plan Some Activities But Leave Room for Spontaneity


While a bit of pre-planning is wise on a special trip, overscheduling destroys the joy of discovery. Finding balance between structure and spontaneity ensures you see top sights but also encounter wonderful surprises.

Pick two or three major bucket list items you refuse to miss – the Colosseum in Rome, the Taj Mahal, hiking Machu Picchu. Plot these must-do highlights first. Then pepper in activities like food tours, cooking classes or bike rentals that let you easily mingle with locals. Read up on festival and cultural event dates, choosing a travel window that lets you experience celebrations like Mardi Gras in New Orleans or Dia de los Muertos in Oaxaca. Having these tentpoles gives peace of mind that you’ll see the destination’s iconic sights while keeping most days flexible.
Many travelers cram in back-to-back activities from dawn till dusk, exhaustedly checking off their list until the joy is stripped away. But racing means you experience each place only superficially, barely scratching the surface. Trading breadth for depth brings far more rewards. Lingering in fewer places with an unhurried attitude lets you sink into the rhythms of daily life. You bond more strongly with locals who become friends, not transactional service providers. Each city’s vibe reveals itself when given time and attention.
Planning just one special event for mornings and another for late afternoons prevents burnout while still gently guiding your days. Start with a cooking class learning regional specialties, then spend afternoons wandering bustling markets and winding side streets, choosing dinner spots based on what looks best in the moment. Another day, begin with a bike tour around iconic landmarks, then meander wherever your whims lead afterwards. Scheduling too much risks missing those unplanned gems, like stumbling upon musicians jamming under a century oak tree in a neighborhood park. If you’re overbooked, you’ll miss the street festival erupting just steps from your B&B or the impromptu invitation from a local to visit their relative’s beachside café.

Dream Big, Travel Bigger: Planning the Trip of a Lifetime With Your 2024 PTO - Capture Moments That Will Last a Lifetime


This epic journey will be filled with incredible sights, exotic tastes, and thrilling adventures. But what you’ll cherish most are the quiet, simple moments that etch themselves into your memory. Capturing these through photos, journaling, and intentional presence cements the trip in your heart forever.
Fellow wanderlusters understand the power of presence. For Courtney M., slowing down to take it all in was crucial in Tanzania. “Watching the sunrise over hot air balloons floating above the Serengeti is etched in my mind. The memory is so vivid I can still hear the sound of wild animals calling to each other.”

Ryan S. echoed this while recounting his time in Patagonia. “Sitting alongside the icy Perito Moreno glacier, listening to ancient cracks and groans as it carved its path, I felt so small yet so connected to the earth. I put away my camera and just breathed it in.”

Mindfulness matters. When your senses are flooded, soak it up fully. Pause frequently to imprint magical moments - the neon glow washing Tokyo’s streets at night, the swell of hymnals within Notre Dame’s cavernous nave, your first taste of real Neapolitan pizza warm from a wood-fired oven.

Don’t view experiences through your phone’s screen, watching life on replay mode. Be present. Let moments imprint naturally. The mind preserves what the heart feels. Fumbling to capture that YouTube-worthy shot means missing the mindfulness of here and now.
Journaling further cements memories. Jotting thoughts, smells, sounds, feelings in the moment revives them later with full emotional potency. Dedicated travelers like Cynthia H. journal morning pages daily. “My HDD memory drive gets overloaded quickly. Putting thoughts on paper downloads them permanently. Reading journals brings it all back as if I’m there again.”

Jot down overheard conversations that reveal local character, like the hilarious grandmother-granddaughter duo debating gelato flavors in Rome. Note the cries of gulls swooping over Portuguese beaches, reminding you of carefree childhood days at the shore. Scribble impressions of incense smoke swirling around golden Buddhas in Burmese temples. Describe the friendly nods from fellow hikers along the Inca Trail recognizing the shared gratitude and exhaustion of accomplishing this epic trek together.

Photos certainly have a place for fixing memories too. But strive for connection, not perfection, when clicking the shutter. Posed poses feel stale years later compared to candids that transport you back to the scene’s mood and moment. Forget worrying about crooked horizons or rule of thirds. Let images capture emotions to make them last.
At trip’s end, print favorites to frame or create photo books rather than leaving images stranded on SD cards and online clouds. This elevates them into tangible treasures that immerse you in nostalgia whenever engaged.

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