From Dream to Departure: How Far in Advance to Book
—Why Timing Matters—
Photo Credit Casa Chablée, Sian Ka’an, Mexico
You’ve decided to book that dream vacation. It’s been on your mind forever, and now, after watching a show or seeing that CNT article that reignited your wanderlust, you’re ready to make it happen. And festive feels like the perfect time—just two months away. We can do this! Right?
Cue the reality check. You open your laptop, ready to book, and… everything is so expensive. Availability? Almost nonexistent. Your dream vacation is slipping out of reach, and you’re left with two options: either push it off to next year (swearing this time you’ll start planning earlier) or scramble to make it happen. The trip ends up being great—because you’re diligent and selective—but you know it could have been better. You spent so much time planning it that you could have used elsewhere, and it cost way more than it should have. Sound familiar?
This scenario plays out a lot. And it's not your fault. Planning times have become a moving target since 2020, with last-minute trips dominating in recent years. But lately, we’re seeing a shift back to long-term planning, catching experts off guard, too. If you want a one-of-a-kind experience, choice locations, and less stress while planning, knowing when—and how far in advance—to book is crucial.
Photo Credit Palm Heights, Grand Caymen
Why Advance Planning Has Shifted in Recent Years
Post-2020 travel brought us into a new world of flexibility—uncertainty about regulations, work-from-anywhere options, and fear of lockdowns made last-minute planning the norm. But demand has surged in the past year or two, and long-term planning is making a solid comeback.
Take destinations like Europe, Hawai'i, or parts of Asia: spots that were easier to plan in previous years now require booking much earlier. It’s not just about peak season (although that plays a part)—it’s about how demand has evolved. Whether it’s destination hotels, the best private guides, the best flights, or unique experiences, waiting too long could leave you with limited options (and exorbitant prices).
Surprising Availability Gaps
Even for travel advisors, availability and pricing can be surprising as we navigate the ever-changing trends. Planning summer 2024 trips to Europe this fall, I’ve noticed many of my go-to hotels filling up faster than ever. It’s not that they’re fully booked already, but the most exciting properties—especially if you need specific features like connecting rooms, a balcony with the best view, large family suites, or a combination of things—are harder to secure than this time last year.
If authentic, character-filled accommodations are a priority for you (I know there are or you wouldn't be here, yes?:)), waiting could mean missing out on your perfect spot.
Photo Credit Oasy Hotel, Tuscany
When to Plan: By Destination and Experience
Some destinations inherently require more planning than others. Here’s what to keep in mind:
Europe in Summer: Dreaming of Italy, Spain, Greece, or France? Book 6-9 months ahead. Waiting until spring will leave you with slim pickings, especially for the hotels that elevate your experience. Side note for 2025: Italy’s Jubilee Year will bring an extra 50 million visitors. Consider skipping it until 2026 unless you book now and are ok with crowds.
Hotlist Destinations: Destinations like Japan, Thailand, the Faroe Islands, and Kenya are trending or expected to see heavy tourism next year. Plan 9-12 months out—or consider visiting once they’re passe (we're beyond trends, right?).
Cultural Transit: For immersive experiences—like private cruises along the Nile, the Belmond Orient Express, or driver-guides in the UK and Ireland—plan 9-12 months out. These highly personalized experiences are in limited supply, and as demand for unique trips rises, they’re becoming harder to book with short notice.
Safaris: These life-changing trips are complex and costly. They require time (and a big budget) to plan well. Nine to 16 months is a good rule of thumb for securing top lodges and guides in places that won't be swimming with safari jeeps.
Destination Hotels: Properties with small room counts and big reputations can book out as early as 9 months ahead. The right accommodation can shape how you experience a destination, so it pays to secure these early. And like flights, prices only rise as the dates approach. Recently, I’ve seen rates jump significantly between a client inquiry and their decision to book. As advisors, we’ll always negotiate when we can—but sometimes, waiting means losing out.
When to Plan: By Season
Travel planning also depends on when you want to go. Here’s how to approach planning for each season (seasons differ by destination):
High Season (e.g., Summer, Festive, Spring Break): Aim to book 9-12 months out. Popular destinations like the UK and Europe in summer, Japan during the cherry blossoms, and the Netherlands in Tulip season require long lead times to secure top-tier accommodations and experiences.
Shoulder Season (often in spring or fall): Book 6-9 months ahead. This is my favorite time to travel—it strikes a balance between peak and slow seasons. There are pros and cons: fewer crowds and lower costs are expected, but weather and other factors can be less than ideal (think hurricanes in Central America).
Low Season (e.g., July/August Near the Equator, January/February/post festive): 3-6 months ahead is often enough. Flexibility helps, but this is the best time for good value for your wallet and meaningful local connections. We frequently go to the beaches in the low season in Mexico—it’s hot but perfect after the year in the Netherlands. The key is to find your quirk—odd for others—even if it’s offbeat.
Last-Minute (Under 3 Months): While possible, this often means higher costs, fewer options, and and more urgency in the planning process. If you’re flexible with dates, destinations, and priorities, you can still make it work—but it’s a gamble.
Photo Credit Habitas AlUla, Saudi Arabia
Planning with Purpose
Travel’s Impact on Communities
Timing your trip is largely about logistics—and equally about creating a meaningful experience for you and the places you visit. Mass tourism peaks can overwhelm travelers and locals, leading to underwhelming experiences and strained communities. Consider visiting during quieter months or exploring lesser-known regions. It’s better for everyone involved and often leads to a more authentic connection to the destination.
Working with an Advisor
Partnering with a travel advisor well doesn’t just simplify the process—it creates opportunities to elevate your trip. With more time, we are more likely to:
Secure intimate, unique, and high-quality stays that fit your style.
Arrange personalized experiences, from private tours to hands-on workshops.
Time your visit to avoid the crowds and make the most of your destination.
Advance planning also ensures a smoother, less hectic process. While we’re always organized, rushed timelines force us to condense months of planning into weeks, which can feel overwhelming. A more intentional timeline means a more enjoyable experience for you.
Packing it up
Planning your dream vacation takes more than a few clicks. The earlier you start, the more options you’ll have—and the better your experience will be. Whether it’s a year out or just a few months ahead, understanding the right timing can mean the difference between “good enough” and beyond what you imagined.
Our retainer clients experience this firsthand. By dynamically planning a year as a whole (with flexibility), we can secure dream destinations and sprinkle in spontaneous weekend getaways with minimal stress. If this is your style, learn more about our retainer services HERE.
If you’re ready to plan something incredible, let’s talk. Together, we’ll make it happen—stress-free and unforgettable.
Katy HOogerwerf
Katy is a New Orleans native who grew up shaped by the art, design, music, and famously good food her hometown is known for. Her passion and expertise lie in finding design-led conscious businesses around the globe and sharing them with you.
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