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  • Writer's pictureALEXANDRA


After my last post about how to travel more, a ton of you guys have been asking how we choose where we want to go when we do get the opportunity to travel. Obviously, one of my favorite things to do is travel! I am very passionate about it and put A LOT of research into each trip we take. I always get asked by a ton of you how we pick whether we are heading to an island, a metropolitan city, the mountains, or somewhere else magical! And, since this isn’t the first time, I thought I’d share my tips for how we choose where to go and how I plan our itinerary! A lot of these tips cross over with how we travel more in the first place, so they are tried and true!


This is probably the hardest tip for us to follow ourselves, since Ryan's schedule is ALWAYS changing! Luckily, we usually know tour dates pretty far in advance. I try to squeeze in trips here and there when we have time off, whether we go somewhere local for a "staycation" (like our trip to The Essex Resort & Spa this winter!) or we get on a plane to an exotic location (like our trip to Aruba at the end of last summer!). To get the best deals, we plan as far in advance as we can. The major reason for this is... it's a game changer financially. It’s amazing how many deals you can find if you give yourself ample time to plan. I usually start my planning by researching the best spots to go during a certain time of year. If you know your vacation will be in October, try researching the best destinations for October in terms of what you are looking for (weather, less tourists, cheaper airfare, etc.). Then, I usually set up alerts for the destination we choose. A website we frequently use for deals is We take advantage of's stay 10 nights, get one free reward regularly, and since we travel so much we end up getting a few free hotels per year. We also get secret sales through them for our high reward status. Planning ahead makes for a way less stressful experience. Once you have the travel plans locked down I love researching what I want to see and do in our destination.


If you look back at the Travel section of my blog, you'll see that a lot of the trips Ryan and I take are over long weekends. While we don't have conventional 9-5, Monday through Friday jobs, I know that many of you do! Long weekends are the perfect chance to get in a quick getaway that doesn't feel rushed. You can take the opportunity to visit somewhere a short car ride away (like our getaway to Kennebunkport, Maine for Valentine's Day!) or take a flight to a different part of the country (like our trip to Big Sur in California!). There are so many travel guides for 48 hours in a city, plus you can always take flights early in the morning or late at night to take advantage of every minute! Or use your Summer Fridays if you are so lucky! Fun Fact: Ryan hates when I book red eyes because he can't sleep on planes... but I still do it anyway!


If you've known me for a while you know that I am the master of credit card rewards (feel free to contact me any time if you have any questions!). Ryan and I spend a lot of money traveling, which is why we opted for the Chase Sapphire Preferred card. While this isn't the only travel credit card we have (we also have the American Express Delta Skymiles card - amazing if you fly Delta exclusively, or a lot!), it is the one that I think will be the most rewarding for you guys. The reason being - you can use the points you receive to purchase airfare on any airline. I would be happy to refer you to the card if you are interested - which will give us both added perks! Reward programs have made a huge difference for us. This year alone I used airline points for my trip to the northwest for Twiddle tour, my trip to Red Rocks, and our trip to the Virgin Islands. Traveling will always be expensive, so signing up for a good rewards program can make your dreams become more of a reality.



I definitely know how amazing it is to aimlessly roam the streets of a foreign city, dipping in and out of boutiques, cafés and museums, not knowing what you will find! I definitely try to keep a few "roaming days" on our itinerary, especially when we are abroad. Being tied to an itinerary can be pretty stressful, and something is bound to happen (like getting stung by a sea urchin and having to go to the emergency room!). BUT, when there is limited time, I definitely want to do as much research as I can to make sure we see everything (or as much as we can!) on my bucket list for each destination. I usually start by doing an online or Pinterest search of "things to do in XYZ," "where to stay in XYZ," or "best restaurants in XYZ." From there I make a list of all of the stand-outs and, I know this sounds nerdy, but I usually crosscheck with Instagram. A lot of locals in an area, as well as travel bloggers who visit an area, will post personal photos and stories about a place, and you can usually find really cool off the beaten path places! Another good idea is to check the city or country's Tourism Board website. That is where we got all of our ideas for excursions when we visited Aruba, US Virgin Islands, and British Virgin Islands. The Tourism Board will always have the best of the best!


One of the major tips I have for bringing your trip to life and getting the most out of it is to divide your destination into different sections. That way you can focus on a specific area for a day or two and hit up all of the sights, restaurants, etc that you might be interested in. Go back to that master list of all of your stand-outs and move each item into the corresponding section of its location and VOILA! Now you know how many days to spend in each area... or if there are only one or two things to do, you can re-evaluate if you want to skip them! **TIP: You can even create a Google Map with pins in all of the locations you want to visit for the day if you are super nerdy like me!


Once I have completed all of my research and divided up our trip into sections, I create a calendar for each day to list out what we will actually be doing. Of course, leaving extra time for us to get lost, wander around, or just go off track! The calendar is especially helpful when you are going to major sight seeing attractions that can only be visited on specific days, with limited hours, or with a reservation. And trust me, MAKE THOSE RESERVATIONS IN ADVANCE! After adding all of your excursions and their times you can fill in the blanks with breakfast, lunch, dinner, and any other fun activities you are hoping to do! Definitely leave room for fun opportunities and BE REALISTIC! You never know what amazing opportunity lies around each corner, so don't be upset if you don't check everything off your list. You may end up seeing something even more incredible!


Add your flight numbers, hotel addresses, maps, inspiration photos, prices of excursions you've paid for, etc. to your itinerary! I do this literary EVERY SINGLE TIME! Not only does it make it so much easier for me to stay on track with where we are supposed to be and when, but it also allows us to stay on our budget and see if we can splurge in certain places. And the inspiration photos, well DUH, I need to know all of the greatest places to get those Instagram photos you guys like to see so much! ;)


Like I said, the reason I decided to write this post is because you guys have been asking me how we travel so much and, when we do, how we decide where to go. I know that everyone's situation is different, but my biggest tip is DON'T MAKE EXCUSES! If you want to travel, you can! Planning ahead, saving up your money towards your vacation goal, taking advantage of your time wisely, and getting travel rewards from your everyday purchases is possible for EVERYONE to do! Plus, when you spend the added time to create an itinerary you can get WAY more bang for your buck! Making excuses for why you can’t go somewhere will only result in you not going! Caution: There may be times where you truly can not or should not go on a trip. Be honest with yourself and do not make compromises!

I hope these tips help. Now, start planning that trip!

xoxo. Alexandra



Hey guys! My name is

Alexandra Dempsey, I am 31 years old and live in Stowe, Vermont.

I recently decided to start this blog to give you all a look into the life of a tour wife - the highs, the lows, and EVERYTHING in between!

My rock star husband, Ryan Dempsey

of Twiddle, stands by me every step

of the way as we journey on this whirlwind we like to call the "tour life."

Follow along on my travels, hear

stories from fellow tour wives, and

earn about some of my favorite things. Hope you enjoy and

thanks so much for reading!!

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