Your First Vacation: A Guide for Busy Professionals

Step 1: Start With a Dream—But Make It Manageable

Sure, the Amalfi Coast sounds fabulous, but if the idea of planning a complicated European getaway makes your eyes twitch, start smaller. Think long weekend getaway, domestic flights, or even a destination with direct flights (I live for fewer layovers and no chance for delays!). Some easy ideas are:

• Beach escapes: San Diego, Miami, or the Gulf Coast
• City adventures: New York, Chicago, or San Francisco
• Chill vibes: Sonoma Valley or a cozy mountain lodge
• Hometown Explorer: Don’t be afraid to start right in your backyard! 

Pro tip: Pick a destination with minimal connections so travel is smoother—this is a vacation, not an Amazing Race challenge.

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Step 2: Research Like a Pro Without Going Down the Rabbit Hole

You don’t have time to spend 17 hours in a TripAdvisor vortex or scroll TikTok until 2 a.m. Instead, streamline your research:

• Booking.com or Expedia: Great for tracking flights and pricing trends. Expedia has package deals that make it even easier. 
• Instagram Hashtags: Want to know what a place really looks like? Search travel hashtags (#MiamiVacation, #SantoriniSunsets) and enjoy your visual reconnaissance mission.

Pick three key things for each location: where to stay, what to do, and where to eat. Anything beyond that? Optional. You’ll be sipping cocktails soon enough, no need to overcomplicate it. You don’t need to pack your itinerary minute by minute on any trip. You always want to leave space for places or ideas that will be discovered along the way. Plan your stays, meals and 1-2 activities per day and the rest will be an adventure! This may sound scary for the first time, but trust me on this. Nothing hurts like buyers remorse when you are planned down to the minute and arrive at your destination only to find a super fun entertainment that you would have loved to go to but can’t because you have zero flexibility in your plans. So choose a loose timeline and you will always be happier!

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Step 3: How to Know When You’ve Found a Good Deal

Ah yes, the alluring “good deal.” What makes it good? Timing and value. Here’s how to know:

• Flights: If it’s within 10-15% of the “normal” rate for that route, it’s solid. Use Google Flight alerts to track prices over a few days. You can easily compare the exact same flight across 1 or 2 other websites to verify that the deal is actually good. Sometimes someone’s sale is not actually a sale. I always check at least 2 flight websites first before booking, including the direct airlines website. Then it’s a good deal-jump on it. Flight pricing changes often. 
• Hotels: Look for free cancellation policies (flexibility = luxury). Check for extra perks—free breakfast, Wi-Fi, or airport shuttles save both cash and headaches. Being able to cancel up to a few days before the travel date is king. If you find another hotel or something else pops up, being able to change your hotel is the best option. Same notes on hotels as airfare. Always pop over to one other website and the actual hotels website to double check rates. They are normally pretty stable across the board but every now and then you will find one $10-$20 less per night. 
• Packages: If bundling flight + hotel costs the same or less than booking separately, snag it. While this is easier you definitely need to to spend a little more time reading the details of the bundles. Some bundles don’t tell you the actual hotel or airline. They just say things like “ similar to ___”. When that is the case that means that they will choose your hotel for car rental for you. If you are fine with any of the options that you might get then these are good. I have had good luck here. But just don’t glaze over and book. Stay with it and read the details. Your first trip is not the time for surprises! 

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Step 4: Avoiding Scams Without Losing Your Mind

The internet can be a jungle of phishing emails and “too-good-to-be-true” deals. Here’s how to steer clear:

1. Stick to trusted booking platforms like Expedia, Priceline, and VRBO. If it’s a sketchy site from 2002 with Comic Sans font, exit immediately.
2. Never pay by wire transfer. Reputable bookings use credit cards, PayPal, or official apps.
3. Check reviews. No reviews? Red flag. Look for consistent themes—if five people mention roaches or bad customer service, believe them.

Step 5: Timeline Checklist – Because Procrastination Isn’t Cute

No one likes scrambling the night before a flight. Here’s a quick planning timeline for maximum smoothness:

3-4 Months Before

• Choose your destination and finalize your dates.
• Book flights and accommodations. If your schedule is flexible, mid-week flights tend to be cheaper. Most airlines and booking platforms allow you to look at the dates in a calendar view showing you at a glance the dates. This can really add up for some savings if you have options to travel on slower travel dates. Don’t get hung up on flying on specific days if you don’t have to be. When you look back at your vacations you won’t remember that you flew out on a Tuesday afternoon and came home on a Friday.  
• Set a vacation budget. Yes, you need one. Unless you plan to sell NFTs upon return, keep your spending in check. If you have a basic idea of what you are good with spending for your big 3 items: hotel, travel, transportation, then you can build a budget out for the other remaining items. The destination will determine your budget really quickly. Example: San Antonio for 4 days is NOT the same as New York City for 4 days. So be realistic here and choose something you budget to have a really great time. I would rather go to a place where I can do a lot of things than go somewhere where I can only walk down the streets and eat at the local fast food. It is not the same experience. Trust me on this one, I have done both!

2 Months Before

• Request time off and add your OOO (Out of Office) email message to your calendar. Get ready to decline any meetings that pop up! Notify any large client accounts that would need to be aware of you being gone so that you can get your work ready for them. I find clients are typically supportive of me being gone as long as I am caught up on my work to them before I leave. If your trip will line up close to a big project or event you may want to start preparing your client or team earlier rather than later. Tip: don’t allow anyone to make you feel BAD for leaving. You deserve to have a personal life. Teaching those around that this is a priority for you will benefit you in the future.I have had coworkers and clients make catty remarks but my reply is always “this is much needed time for me and hopefully, it will be your turn soon”
• Research things to do (but don’t over-plan—leave room for spontaneity). Get tickets to places that offer a lesser price when booking online. Some places only sell tickets online and not at the door so if you want to do something for sure make sure to check that. I like to have 1 or 2 activities for each day planned out. Then I know the general area I will be in that day. There will be plenty of time when you get there to find other things to do along the way. 
• Check your passport’s expiration if you’re leaving the country. Fun fact: Some countries won’t let you in if your passport expires within six months. (Ask me how I know…) Some countries also require travel visas. Most airlines will be vigilant in notifying you of any travel restrictions or conditions. They don’t want to have to fly you home early if you mess this up! This also goes for the real ID. Some states are really getting serious about requiring a real ID to board any domestic flights. TSA will not allow you to fly without it unless you have your passport. You can check your state here. 

2-3 Weeks Before

• Make restaurant reservations for those bucket-list meals. This would apply to fancier restaurants that require reservations. However, if it is super hard to get into a restaurant you may want to do this as soon as you have your airfare and hotel booked. 
• Pre-book any tours or special activities. You don’t want to find out the day that the yacht excursion is full. These often also either offer discounts on tickets for pre-booking or only sell online. So be sure to check before so you get the best price. 
• Plan your outfits and start mentally preparing for carry-on only packing (you can do it!). You will want to also start getting any travel accessories that you don’t own yet. You can see my overpacker anonymous detailed list here if you don’t know where to start. Don’t let your nervousness of your first trip cause you to overpack. Nothing is worse than dragging around large bags when you don’t need to! 

1 Week Before

• Confirm reservations and print hard copies (or at least download them). Wi-Fi isn’t always reliable. I use the TripIt app. It reads my emails and puts all my reservations in one easy to read timeline. Then I go through and make sure all my tickets are saved as files. You do not want to be searching all the other websites or apps when you are looking for details. Trust me…. Tears have been shed. You planned this far, take the extra time to make sure every detail that has been preplanned is logged into the app or saved on your phone or worst case, printed for your reference. There are many times that wifi is not working, even in the US. 
• Check the weather at your destination. Will you need a light jacket or SPF 1000? Be aware of low temperatures as well as the highs. If you are going somewhere that the weather has big temperature swings you will want to be prepared. Even the dessert gets cold at night! 
• Set up travel alerts on your credit card to avoid awkward “fraud alert” shutdowns mid-trip. These are the worst. Most apps allow you to put travel notices in your app. If that is not the case be SURE to do this. I have had many experiences where I thought “I am only going to X, I don’t need to do this” and then it backfired. 
• Order currency. If you are going out of the country you may want a few dollars in the local currency. I don’t recommend having a lot of money. But running into Canada you might want just a little bit if you need a quick tip or you run into a store and their card machine is down. Depending on your length of time I would say $50-$200 max. 

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Step 6: Pack Light, Pack Smart

Don’t be the person lugging a 50-pound suitcase for a 3-day trip. Stick to basics and versatile pieces. Think:

• Neutral colors (mix-and-match magic)
• A foldable day bag or backpack for excursions
• Power banks, chargers, and noise-canceling headphones (lifesavers)

And please, for the love of travel gods, don’t forget your chargers. Nothing says “rookie traveler” like scouring the airport for a $60 replacement.

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Step 7: Commit to Relaxing (Yes, This Is an Actual Step)

Once everything is booked and ready, your job is to mentally clock out. Leave work behind—set up your Out of Office message like the boss you are. Having good boundaries in your work life is just as important in your personal life. We all know that work becomes personal, especially for our career babes! It is very important for you to be able to shut work off and focus on yourself from time to time. It will actually make you better at your job when you return rested and relaxed. But if you try to balance work while you are out of town you will just end up sucking at both. You can’t attend a meeting and enjoy the museum. Be present. It is a great gift to yourself and those you are traveling with!

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In Conclusion: You Got This!

Planning a vacation for the first time is a bit like assembling Ikea furniture—you’ll feel overwhelmed at first, but the end result will be totally worth it. Just keep it simple, pace yourself, and remember: No one has ever looked back on their vacation and thought, I really wish I answered more emails. Click here to read How to Escape Work( Guilt-Free!)

So go on, book that trip, pack that bag, and treat yourself to a well-deserved break. Because life’s too short for “someday,” and frankly, you’ve earned it. You will not look back on your life and wish you took LESS vacations! 

Safe travels—and may your flights be on time and your drinks extra strong! 🍹✈️

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