How to Pack Everything in A Carry-On

There’s nothing worse than missing a connection and realizing that your luggage is who-knows-where while you’re in a hotel halfway to your destination! Or arriving safe and sound in your intended destination while your bag has gone on holiday somewhere else! All that worry and focus on retrieving your carefully packed luggage takes up precious vacation time. The clear solution is to keep your luggage with you. Plus, packing it all in a carry-on prevents you from overpacking and having to cart and carry heavy luggage around on your trip!

But how on earth do you pack everything you need into one small carry-on? This question baffles so many travelers and often discourages them from even trying. Don’t worry! It can be done, even for very long trips. And we’re here to walk you through every step:

What to Bring

What you need to bring will be different for every trip, but there are some top tips and general rules to follow. It doesn’t matter if you’re heading out on a 4-day beach excursion or a 14-day European Adventure, always keep these tips in mind when packing:


three women ( Ann and Kristy) toast white wine in front of Villa Laura in Tuscany

Pick a color palette. You don’t have to wear only neutrals but sticking to a color palette will help you maximize the mix-and-match ability of your wardrobe. Think of it as a mini-capsule wardrobe.

Choose wrinkle-resistant clothing. Even in cold climates stick to breathable fabrics, that don’t wrinkle easily.

Layers layers layers. Rather than trying to pack a bunch of bulky sweaters, try to stick to layers. They give you versatility for sudden weather changes.

[Photo Credit: Ann via Shared Adventures. Packing layers and light accessories like scarves prepares you for all kinds of adventures! Read about Ann’s Tuscany adventure here!]

2 Pairs of shoes. You should have one pair of walking shoes ( which you will wear on the plane) and one pair of nicer dress shoes OR sandals if it’s a beachy holiday. Make sure your dress shoes are still comfortable to walk in and your walking shoes are nice enough to eat out in.

Do laundry. Depending on the length of your trip, pack for only 5 days and plan on doing laundry about halfway through.


Everything should be mini! Remember, there is no reason to bring a full bottle of anything. Aside from the airport security 3oz rule, you aren’t going to use a full bottle on your trip. Put all toiletries in mini bottles, use samples, and take half a bar. Or plan to pick up some new toiletries at a local store when you arrive.

Just the basics. Try to shrink down your cosmetics and skincare items to the basics.

Packing cubes/ Compression bags

We love using these for organization and for maximizing space. We’ve found a combination is best. Use compression bags (no vacuum required) for your bulkier items and anything that is truly wrinkle-resistant. Use packing cubes to organize the rest.

Pro-tip: If you’re traveling to several destinations with different climates– pack your cubes according to the destination rather than category. That way in each new destination you just need to unpack one cube!

Visualize Your Carry-On

5-7 Days Before Your Trip

This may seem early, but having more time to consider and think about your packing choices will help ensure you’re only packing what you really want to bring. Often your first ideas of what you should pack are not your best ideas.

1) Look up the weather. This is the biggest factor in your packing decisions.

2) Make a list. Use an app like PackPoint or old school pen and paper. To start, write down the essentials. Medication, toothbrush, underwear, etc. Then, fill in everything else you want to bring. Focus most on the activities you’ll be doing on your trip.

3) Check the airline’s bag requirements. Each airline has slightly different dimensions and weight requirements. So, double-check that you know what those are and that your bag fits within them.

three piles of folded clothing and a woman's hands as if packing them

4) Lay it out, try it on! Lay everything you want to bring out on your bed. Then start trying it all on! You want to plan out your outfits as much as possible. See how many can be mixed and matched, make sure you feel comfortable in your clothes, and that they all go together. Generally, we try to stick to the rule of 2-3 tops for every bottom. Pick clothes you can wear more than once.

[Photo Credit: Sarah Brown via Unsplash]

5) Pare it down. Get rid of anything that can only be worn once or only with one specific item and anything you’re not 100% comfortable in. Get rid of anything that cannot be worn for at least 2-3 of your planned activities. There’s no need to pack for “just in case we go to a ball” or “ just in case I decide to get up early and go for a 10-mile hike”. You’ll probably know if you’re doing something like that ahead of time.

6) Ruminate. Set everything aside to think about it.


2-3 Days before your trip

It’s time to start packing in earnest! You’ve had time to mull over your outfit choices and make sure you’re truly happy with them. Now let’s get them to fit into your carry-on!

1) Look up the weather just to make sure there aren’t any major changes.

2) Get your checklist and lay everything back out on the bed.

3) Go over everything you want to bring one more time and make sure there are no “ just in case” items.

4) Set aside essentials. Anything you’ll need on the plane: your flight essentials kit, medication, kindle, phone charger, important documents, wallet, liquids bag, etc. Also set aside your travel outfit, bulkiest jacket, and bulkiest shoes.

First Layer

5) Start with your bulkier items like jeans, jackets, and sweaters. Roll them as tightly as possible (consider using a compression bag) and layer them in the bottom of your suitcase.

6) Next take your most wrinkle-resistant items and roll them up in a compression bag for the bottom layer. ( If you’re not using a compression bag, roll them tightly and place them in the bottom layer.)

7) Add your shoes. Just one pair of nice shoes OR sandals. Arrange them so that the soles are facing the side of the bag and the soft side is inside. If possible, stuff the toe with socks.

8) Fill in any gaps or spaces on the bottom layer with socks, cables, chargers, belts, hats, scarves, medications, spare batteries, or any other small items.

9) Put all your non-liquid toiletries and makeup in their pouches and layer on top of your bottom layer to maximize cushioning and prevent breakage.

Pro tip: Place a cotton round in between your pressed powders and the lid to help prevent breakage.

Second Layer

10) Fold and/or roll ( depending on wrinkle resistance) the remaining tops, dresses, and pants into packing cubes. Place bras, underwear, and remaining socks in a cube of their own. Layer these cubes on top of toiletries.

11) Fill in the gaps with any remaining extras ( belts, hats, scarves, chargers, socks, etc)

12) Throw in an extra compression bag for your laundry.

13) Look at how it is all fitting together. Re-arrange as needed. You may find that your sweaters or jeans take up less space when folded. Or that you have an extra gap in the bottom layer that can be filled. This is a game of Tetris and you may need to shuffle things around to optimize it.

14) Close your suitcase!

Final Checks

15) Pack your personal bag. This should be bigger than your usual purse – think a large tote or small backpack. Include your flight essentials kit, important documents and wallet, liquids bag, phone charger, and fragile electronics (camera, computer, etc).

people walking down the cobblestone streets of Bologna

16) Take it all for a test drive! Even with door-to-door services, you’ll have to do some walking with all your luggage. And probably on an uneven surface. So, roll it around, take it upstairs, lift it, take it down the street. Check out how the wheels are rolling on uneven surfaces. (if it’s a soft bag you may have to check weight distribution).

If you find yourself getting overheated, frustrated, and exhausted then you have packed too much! Go back to the beginning and consider what you can do without.

[Photo Credit: Ann via Shared Adventures]

With the right attitude, a minimalist approach, and careful planning you’ll find it’s quite easy to pack it all in a carry-on! Try to leave some space for souvenirs. And remember, if you can’t picture an exact moment on your trip when you’ll need or wear something — you can leave it at home!

If you’re feeling confident in your new packing skills and are ready to plan an adventure to go with them, let us know!

How to Approach Your Honeymoon Budget

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A honeymoon is a once-in-a-lifetime vacation! So it should be unique to you as a couple and should create special memories that you’ll be talking about for years to come. Whether you’re dreaming of an overwater bungalow, a fairytale town, or a cabin in mountains, you’re also planning for a wedding, and you probably don’t want to break the bank along the way. So, how do you even begin to put a price on your trip of a lifetime and plan your honeymoon budget? 

Where you want to go, what you want to do, and what level of luxury you want to experience will all factor into the overall cost. And there are a few simple steps to figure out what is realistic and what you can afford. We’ve created a fun worksheet to get you started with the steps outlined below. Download our free Honeymoon Budget Worksheet here!


The foundation of every good relationship is communication. And budgeting for the perfect honeymoon requires a lot of it! You want to ensure that you’re both on the same page in terms of expectations. 

honeymoon couple sitting on a log in a rainbow in hawaii

Start with the big picture. You don’t have to decide where you’re going or what exactly you’ll do when you get there, yet. Instead, talk about what kinds of things you imagine doing and in what kinds of environments.

Are you walking hand-in-hand along a white sandy beach with ocean waves as your soundtrack? Wandering the cobblestone streets of Europe and feeling like you’ve stepped into a fairytale? Spending your days lounging in your luxury honeymoon suite with an awe-inspiring view? Did you travel far to get there or was it a quick flight to paradise?

[Photo Credit: Molly & Matt via Shared Adventures. Read about their Hawaiian Honeymoon here!]

Try starting the conversation by telling the story of your honeymoon. “I imagine we spend our honeymoon… sipping cocktails in lounge chairs on the beach…”

Once you agree on the general big picture, take some time to write down things you love to do together to give the trip a focus on who you are as a couple. Then write out your non-negotiables. Do you want to leave right after the wedding? Does the accommodation need to have a pool? Do you want to have an immersive local experience? Make sure you’re both clear on what your partner expects from this amazing vacation.



Once you have the big picture, you can get into the details and the budget. First, consider how much time you have for the honeymoon. Most people have a certain amount of PTO and you will probably take some of that for the wedding. So, consider how many days you can realistically be away. 

If your dates are flexible and the destination is more important than the timing, you can skip the following step. 

honeymoon couple in the Dolomites Italy

Now, it’s time to consider the all-important seasonality. Many couples still travel right after the wedding, meaning a fixed time frame for their honeymoon. Consider which destinations are best at different times of the year, and look at whether your specific travel dates exclude any destinations because of poor weather conditions or too-high prices.

[Photo Credit: Shannon & Lou via Shared Adventures. Read about their winter honeymoon to Northern Italy here!]


If you have a specific destination in mind then you can skip this step. However, if you’re still not sure exactly where you want to go, the next step is to figure out a general region. Ask yourself the following:

Do you want to stay close to home or travel farther abroad?
Are you looking for warm or cool weather?
Do you want somewhere on the coast with a beach? Or a big city?

Take a look at a map and talk about the different areas these questions bring to mind in connection with your dates. For example: if you’re looking to stay close to home, with warm weather, on a beach in early June, then you’ll stay in the northern hemisphere and might head to places like Mexico, the Caribbean, or the Bahamas. 



Airfare costs are generally fixed with very little wiggle room and can take up a good chunk of your budget. This makes them the best starting place. Even if you’re not set on a particular destination yet, look back at your time frame, and potential regions. Then start looking at average flight prices for those options. Finding the average flight cost will give you a good starting point for your budget. 

Remember to be realistic when you’re looking at flights. You’ll only want one connection and not the super-restrictive basic economy fares that involve all sorts of added fees for seats and bags. Looking at the average economy class fare will give you a better idea of what to build into your budget. And if you’re thinking about splurging on Business or First class for this trip of a lifetime, take a look at those prices too.

The Rest 

Once the estimated airfare is taken into account, it’s time to work out the details. The rest of your budget can fall into roughly three categories: Activities, Accommodations, and Meals. Put these in order of priority (for you) to figure out where you want to splurge and where you can save a little. Are you set on being awe-struck during a hot-air balloon ride? Does your mouth water at the thought of eating at a Michelin star restaurant? Do you want only the finest luxury resort? Whatever is most important, allocate more of your budget towards that key thing. You can make compromises on the pieces that aren’t as important to you. 

Sunset beach Costa Rica Honeymoons

Pro Tip: If accommodations are important but the full trip in a high-end hotel is stretching your budget, try splitting the accommodations. Stay in a slightly cheaper hotel first and end the last few days on a high note at the luxury property!

[Photo Credit: Katey & Oliver via Shared Adventures. Read about their split-accommodation Costa Rican honeymoon here!]

After deciding which is most important, you can do a little research as to average costs. It doesn’t have to be exact, just a quick search to get a general idea. 

Honeymoon budget worksheet filled out with examples


The final step, once you have a ballpark cost is to add 20%. This is your honeymoon and there are going to be many “treat-yourself-moments”! It’s best to build those into the budget early on. 

Finally, decide how you want to start saving! Consider a honeymoon registry to help fund all the extras. After establishing the basic framework for the trip, you can set up a wish list for guests to contribute to tours, activities, spa treatments, dinner on the beach, etc. Set aside a certain amount each month and start saving! 

Remember, this method only gives you an estimate, not a hard and fast exact cost. There is always some wiggle room.


If you’re finding it hard to get everything on your wish list AND stay within your ideal budget there are a few things you can do to save money:

  1. Consider cutting a night (or two) to make it work. No one ever remembers how many nights they spent at a destination. It’s better to have exactly the experience you’re dreaming about, but for one less night. If you cut back on the overall experience just to stay longer, you’ll regret it.
  2. Keeping your dates flexible lets you take advantage of low-season travel and lower prices. Or head to a less-expensive and popular but no-less-amazing destination. 
  3. Talk with a travel agent! Travel agents have years of experience and know-how. If your final budget is just a little more than you want to spend, a travel agent can help. We might know a unique destination that has everything you’re looking for with a slightly lower price tag. We might be able to get you special rates and perks on accommodations. We have connections with tour guides, private drivers, and hoteliers all over the world, giving us the inside scoop on the best destinations for every size budget.

Even in money matters, travel planning should be fun and inspiring. After you fill out the worksheet, let us know what you discover about your dream honeymoon and we can get started!

7 Travel Apps to Use On Vacation

Top 7 Apps to use During Your Vacation Pin
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It is such a magical moment when you step off the plane in a new destination and start your adventure! But even a perfectly planned, tailor-made adventure has some things you need to keep track of. And a few to figure out along the way (like where to grab a delicious gelato!) There are lots of tips, tricks, and apps out there about what to pack, how to plan, and where to go. But what about when you’re actually on the vacation? Whether you’re discovering a new destination or exploring an old favorite, here are our top 7 travel apps to take your vacation to the next level. 


Screenshot of the Wanderlog Travel App

This is the perfect all-in-one app to organize your travels. Wanderlog offers you a one-stop spot to keep track of your reservations, itinerary, and wishlists for each destination on your trip! You can input all of your flight, hotel, and transportation reservations automatically from your emails. The app will compile the most important information from the email into an easy-to-read summary and pinpoint it on their map. You can also attach files for any museum or tour reservations.

Screenshot of Wanderlog Travel Apps

Once the details of your itinerary are in, you can begin the exploration process. Wanderlog brings all the “top spots” from thousands of blogs across the web into one app and then- the best part- it will put them on a map for you! No more switching between blogs and google maps to try to figure out if the site you want to see is close to that café you want to try! Once you’ve saved your wish list of destinations, you can add personal notes. And finally, put them into a day-by-day itinerary with one simple click! It’s a great way to keep all your inspiration, planned adventures, and confirmation details in one spot. You can even add other travelers and track expenses so you’re all on the same page.


Although most of Europe uses WhatsApp as its main messaging app, it’s not as popular in the U.S. However, we cannot recommend it enough when you travel. The main reason is that it uses WiFi. So you don’t need a local SIM card to send messages and connect with your friends and family all around the world. You can send texts and make phone and video calls with any other WhatsApp user. Because it utilizes your Wifi you won’t have any of those pesky international charges. 


If you are visiting one of the 80+ cities this app covers, CityMapper is a perfect app for getting around. It combines thoughtful route planning and real-time data. It is especially helpful if you’ll be taking public transportation. It not only provides the best route but also information on arrivals, departures, delays, and costs. It has options to customize your route to help you stay out of the rain or use a particular type of transportation. And you can download routes to use offline. Right now Citymapper covers most of the major US and European cities and a handful in Asia and Canada. 


This is a route planner for the outdoorsy traveler. Whether you’re cycling, backpacking or hiking, Komoot is an incredibly useful trail tool. You can easily discover new trails nearby, plan out your route and use the app to navigate while on the trail. With a very advanced routing system, it’s extremely customizable. You can filter by elevation, surface type, and difficulty. Share the trails with your friends or on social media. The only drawback of so many features is that it takes some time to figure out how best to use them all.



Screenshot of TravelSpend Travel App

If you have a specific budget, or just love keeping track of expenses this is a great lightweight app. It is easy to use with a simple, intuitive design. TravelSpend lets you input every purchase, spread expenses across multiple days, and even split costs between travelers. It allows you to track your overall budget and your daily budget, with automatic currency conversion. Use the statistics page to visualize which category you’re spending the most money on. It also works offline, so need to worry about using up data!


This is our favorite photo editing app. It’s easy to use with a lot of different features. WIth more than just filters, this app allows you to edit all the details of your photos. We like to think of it as a little lightweight Photoshop app. It’s perfect for really making your vacation photos pop and showing off sites with the detail and vibrance of how they looked in person. 


 Certainly the most well-known translation app. It’s Google’s seemingly unending features that have marked it as a top translation app for travelers. Our favorite travel feature is the camera scan, which allows you to instantly scan and translate text like menus, signs, or instructions. And the ability to download language packs for offline use is a huge bonus. The main drawback of GoogleTranslate is the quality of translations. They tend to be more literal and lose some of the intentions behind carefully chosen words. However, for quick questions, like asking directions or ordering a meal, GoogleTranslate will ensure communication. 

Deepl [honorable mention]

Deepl is a newer translation app that we’re giving an honorable mention. Like GoogleTranslate it also has a website, app, and voice-to-voice translations for conversations. But its high-quality translations are what really shine. If you want to communicate more accurately or send a message with the same intention you had when you wrote it in English, this is the best app. The reason it’s only getting an honorable mention is that, while the translations are better, it doesn’t work offline and the camera scanner is currently only available on iOS. It’s an app to keep an eye on as its list of features grows. 

4 Ways to Skip Security Lines at the Airport

There’s nothing worse than the stress of running late to catch a flight. These days you need to factor in an extra three hours to get to the airport, check in, and get through security. When you land back home, you stumble off an international flight and straight into an insufferably long customs line.

If only you could skip those lines….

Fortunately, you can! There are several programs that address these airport inconveniences. But which should you choose? TSA-precheck, Global Entry, CLEAR, Mobile Passport? It’s difficult to know where to start.

We’ve put together the pros and cons of each service to help you decide:

a busy airport terminal
Waiting in a crowded airport line is the worst! [Photo Credit: Hiurich Granja via Unsplash]

TSA Pre-Check

What is it?
TSA pre-check is a government-run skip-the-line option. When you arrive at the airport enter a special security line for both identity checks and scanning. It’s often significantly shorter than the regular line and will help you arrive at your gate stress-free!


  • Skip the long lines and fast-pass your way through security!
  • In over 200 U.S. airports and with 73 airlines
  • No need to unpack and de-shoe as you go through a separate scanning line
  • Children under 12 don’t need their own membership and can sail through with you


  • You need to make sure you have a pre-check logo on your boarding pass. Sometimes during the booking process, it will disappear, so it’s important to double-check that.
  • No guarantee. As more people sign up there is a risk the line will be as long or longer than the regular line.

How to get it: After applying online go for a 15min in-person interview, background check, and fingerprinting.
It’s a straight-forward process but needs to be completed before you book your flight.

Cost: The initial application fee is 85$ for 5 years. (17$ per year)
The application fee is non-refundable. 
Some credit cards will pay this fee for you. Be sure to see if you qualify.

Verdict: TSA pre-check is perfect if you’re a frequent flier. While there’s no guarantee of a shorter line, the odds are in your favor and it will cut down on the hassle of going through security.


What is it?
CLEAR is a privately owned company that uses your biometrics as identification instead of your driver’s license or passport. Simply go to the CLEAR kiosk, scan your boarding pass, and tap a finger or blink into an eye identifier. Then a CLEAR representative escorts you to the front of security where you’ll join the regular scanning line.


  • Skip the long security line where a TSA agent is checking boarding passes
  • You can sign up at a CLEAR kiosk in less than 10 minutes
  • Easy to combine with TSA pre-check or Global Entry
  • Children under 18 can jump the line with you
  • You can add family members (over 18) for an additional $50


  • You still have to go through the normal scanning line. This means taking off shoes, unpacking liquids etc.
  • Only in 34 airports
  • By far the most expensive option

How to get it: Go up to a CLEAR kiosk at the airport, sign-up, pay, and enter some basic biometric data.
Easy- peasy and no need to do it before booking your flight.

Cost: The most expensive option at $179 per year.

Verdict: CLEAR is good if you’re a frequent flier out of one of the airports they’re currently in. It lets you feel like a VIP being escorted to the front of the line. But if you don’t often fly out of one of their airports it’s not worth the cost.

honeymooners on a boat in italy
TSA pre-check or Clear will fast-track you to the relaxing part of your vacation

Global Entry

What is it?
Global Entry is run by U.S. Customs & Border Protection. It’s perfect for international travelers because its main function is to expedite the return process. Instead of waiting in the customs line after your long flight home, you head to a Global Entry kiosk. Scan your passport or green card then scan your fingerprint and fill out the customs questions. The kiosk will give you a receipt and direct you towards your baggage claim.


  • Skip the long customs line when you’ve emerged bleary-eyed from a long flight home
  • Includes TSA pre-check to make your departure as smooth as your return
  • Applicable for valid passport holders or green-card holders


  • Children require their own membership
  • Currently only in 75 airports

How to get it: Fill out the online application. Then schedule an appointment at one of their locations for an in-person interview, background check, and fingerprints.
It’s a straight forward process but must be completed before you book.

Cost: Application fee of $100 valid for 5 years ($20 per year).
Because it includes TSA-precheck, think of it as an extra $15 to make your return as smooth as your departure.
Some credit cards will pay this fee for you.

Verdict: If you travel internationally this is a great option. You get all the benefits of TSA pre-check plus the benefit of sailing through customs. Because all children need their own membership this is not ideal for families.

Mobile Passport

What is it?
Mobile Passport is a free app designed to speed up your customs process. You simply save some basic passport info to the app. When you land back in the U.S., answer the usual customs questions. Mobile Passport will give you a QR code. Look for the much shorter Mobile Passport line in the arrivals hall, show the CBP officer your QR code and you’re on your way!


  • Skip the long customs line
  • Often just as fast as Global Entry
  • Great for families: it allows you to include everyone’s profile in a single transaction.
  • It’s free!


  • Only available in 27 airports
  • You must still be manually processed by a CBP officer (unlike Global Entry)
  • Only available to U.S. citizens and Canadian visitors

How to get it: Download the app on Google Play or the Apple Store, enter your basic information, and you’re good to go! It’s simple, fast, and incredibly easy.

Cost: Free!

Verdict: Although it’s only available in a small number of airports, it’s worth the download if you’re an international traveler.
Because you can add the whole family to one transaction it’s perfect for families with tired children.

air tahiti plane

So which is best? What should you choose to fast-pass your way through airline security? It truly depends on what type of traveler you are and where you’re traveling from to find the right fit.

With any of these services, your next experience at the airport will be much faster and less stressful. Combine that with a customized vacation designed by Annie’s Escapes, and your travel worries are over!

You provided excellent guidance for us. I appreciated that you really had us think about what was most important to us when we were selecting the right cruise – and not to totally focus on what other people had to say. THANK YOU for helping to make this a memorable trip for our family! It really was a trip of a lifetime!

Clare and Mark (family cruise to Alaska)

The level of service we experienced was out of this world (and we did NOT make it easy on Ann). We weren’t quite sure where we wanted to go, when we would be able to go, or what “vibe” we were going for. After asking us some key questions (what we liked, didn’t like, why, etc.) Ann helped us narrow down our trip details and planned the honeymoon of our dreams. She helped book some of our excursions, answered some emergency questions while abroad and was always available/willing to help. I think it’s safe to say we won’t be using anyone else for future travel planning – Ann is a rockstar!

Carli (Italy and Spain)