Pinpointing the Perfect Destination

Sometimes you just need a vacation! But deciding where to go isn’t always crystal clear.

I was super excited when my friend Tarah invited me to lunch so she could pick my brain about where to go for a long weekend with her husband.

I love sharing my travel ideas, and this was a great opportunity to fine tune my process for pinpointing the perfect destination.

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Where should we go?

Since most of us have precious little vacation time and limited funds to travel the world, we want to make the most out of each trip we take. And that starts with selecting the right destination.

I have identified 13 important questions to ask yourself to determine the type of trip you desire and help you select the ideal location.

Walk through the process with Tarah as she determines where to go for a weekend getaway!

1. Who will be going on this trip?

You might want to get away with your significant other, go on a solo trip, take the kids, travel with extended family, or plan a vacation with several other families. Your answer will play a significant role in where you decide to go.

Tarah’s Trip: For this trip it will just be Tarah and her husband, Tim. With a blended family of 6 kids, they are looking forward to some time with just each other!

2. Where have you traveled together before?

Now that you know who will be going, it is important to think about past trips taken together. This will serve as a reminder off the kind of destinations you enjoy, or reveal a location you want to return to.

Tarah’s Trip: Married just over 2 years, Tarah and Tim have taken some day trips and love getting out on their motorcycle. They also took an extended vacation to Punta Cana in the Dominican Republic and a weekend trip to Louisville, Kentucky.

3. What past trips were most enjoyable and why?

Begin to identify which previous trips stand out in your mind and what made them so enjoyable.

Tarah’s Trip: In the Dominican Republic, Tarah liked doing nothing! She appreciated not having all the responsibilities she has back at home. She admits she liked the down time, but also enjoys doing some sightseeing. She especially likes going to local places that aren’t so touristy. They both love eating and drinking and like being in social places. Not necessarily meeting other people, but being around the energy of others.

4. When would you like to go on your trip?

Your availability to travel and the timing of your trip can impact which destinations are practical and affordable. The time of year determines the anticipated weather for many destinations, and less than ideal weather can diminish your travel experience. At the same time, hitting a popular destination during the height of their peak season can mean higher costs and longer lines. All things to keep in mind!

Tarah’s Trip: They would like to travel this Spring, possibly around their April birthdays. Scheduling their trip for after the kid’s Spring Break and before school is out for the summer would be ideal. They are kid free every other weekend, so that gives a few possible options in April or May.

5. Are your dates flexible?

As a follow up to the last question, it is good to know if your travel dates are set in stone or if you have some flexibility. With a bit of flexibility you may be able to select the timing that will get you the best price at your desired location. If vacation days are set, then you may want a few destinations on your radar in case lodging or flights are all booked for those dates.

Tarah’s Trip: Luckily, Tarah and Tim have a bit of flexibility within their window of vacation time, as long as it falls on a weekend when they don’t have the kids.

6. How many days/nights will you be gone?

Of course, the length of your trip will help determine how long you are willing to spend getting there. You will also want to ensure that the destination you select has enough of the activities you like to do for the time you will be there.

Tarah’s Trip: They would like to get away for 3 nights and 4 days for a long weekend. Ideally taking their trip from Friday thru Monday.

7. Do you prefer to fly or drive?

Obviously, some destinations are reachable by car, but others necessitate flying. Choosing one travel method over the other will really help you narrow down your destination options.

Tarah’s Trip: Tarah and Tim are open to flying or driving for this trip, but did identify some stipulations for each. If driving, they don’t want to spend the whole time in the car, so they prefer not to drive longer than 4 hours. If flying, they also don’t want to waste too much time in the airport so they only want to consider direct flights.

Extra Tip: Either method you choose, consider the journey to your destination part of your vacation rather than simply transportation. Create a special playlist or find a podcast that peaks your interest for a roadtrip. Or splurge on an overpriced, inflight cocktail and toast to the start of an amazing adventure!

8. Are you looking for rest and relaxation or lots of activities?

It is important to have an idea of how active you want to be on this trip. Some destinations are perfect for relaxation, while others are full of options for sight seeing and other activities.

Tarah’s Trip: Tarah said they enjoy a mix of relaxation and activities, but rest and relaxation is most important on this trip.

9. What activities does everyone enjoy?

It’s important to select a destination that offers plenty of the kinds of activities you enjoy. Wine tasting, sunbathing, museums, fine dining, nightlife, shopping, live theater, outdoor activities? Think about how you want to spend your days during your trip.

Tarah’s Trip: They enjoy eating and drinking, museums, culturally or historically significant places. They are not particularly outdoorsy, but they do like shopping and seeing live shows and concerts.

10. What is your budget for this trip?

For most of us, how much we can spend on a particular trip is crucial to deciding where we can go. It is possible to have a fabulous vacation on a small budget, but it will narrow down your destination options.

Tarah’s Trip: Tarah did not have a specific budget in mind, but had looked into flights to Cancun. The cheapest flights she found were $2,800, and she knew she didn’t want to spend that much! She is thinking around $1,000 would be a good budget for this trip.

11. What kind of accommodations do you prefer?

Decide if a high-end or budget-friendly hotel would best fit your needs. Or you may want to consider renting a place through AirBnB or VRBO or maybe even staying in a hostel.

Tarah’s Trip: Tarah has never used AirBnB, but said they are open to it or staying in a traditional Bed and Breakfast. They have used Groupon for a hotel in Louisville before, so finding a good deal on Groupon is a possible option. With 6 kids they opt for budget-friendly hotels when the whole family travels, but this time their focus is on finding accommodations that promote relaxation.

12. What amenities are you looking for?

Some travelers have very high standards and some are easier to please. Either way, have an idea of what amenities are essential to ensure your trip is everything you are hoping for and what is realistic given your budget.

You may insist on having access to a pool, hot tub, or fitness center. Or you may want a beachfront location, on-site restaurant/bar, a suite, adjoining rooms, free breakfast, Wi-Fi access, or free parking. It may be important that your lodging is within walking distance to attractions and dining or that it is private and secluded.

Tarah’s Trip: Having access to a bar would be nice, as well as someplace they will have privacy. Tarah felt they wouldn’t use a pool or hot tub, but of course that would be very different if they were traveling with all the kids!

13. How would you rank these 4 general types of destinations: City, Small Town, Beach, and Mountains?

If it isn’t already clear, ranking these basic kinds of locations should start to bring your ideal destination into focus.

Tarah’s Trip: Smalls towns ranked #1 for Tarah. She was torn between the Beach or Mountains for #2. And a vacation in a city came in fourth on the list.

Weighing the Options

Now that you have a really good idea as to the kind of trip you want to take, hopefully some possible destinations have already surfaced. If not, use your answers to the questions above to start searching for destinations that meet your needs.

Start googling, check Yelp and Trip Advisor, post an inquiry on social media, or ask a friend who is well traveled.

In Tarah’s case, she made a great decision to ask Traveling Tanya for advice!

I provided Tarah with several suggestions I thought might meet her wishes for a long weekend away with her husband. Tarah and Tim should now talk through these options and start crossing off the ones that are least appealing. Once they have narrowed the list down to 2 or 3 they can do a bit more research on those destinations, including whether or not accommodations are available on their preferred dates.

List of Drivable Destinations:

Galena, Illinois (about 5 ½ hours), small town vibe, long main street with lots of shops, restaurants, wineries, and several BnBs. I highly recommend Cloran Mansion. (Tell them Traveling Tanya referred you to get a 10% discount!)

Saugatuck, Michigan (about 3 ¾ hours), upscale beach town, along Kalamazoo Lake, very short drive to the beach, several blocks of quaint shops, bars and restaurants, short drive to other fun towns (Douglas and Holland).

Granville, Ohio (about 3 ¾ hours) listed as one of the 40 Charming Small Towns You Have Never Heard of (along with Galena), and referred to as a quaint new England style community.

Shipshewana, Indiana (3-hour drive) small town, Amish community, lots of cute shops and restaurants, Blue Gate Theater with concerts and plays/musicals.

St. Louis, Missouri (about 3 ¾ hours) It is a city, but it’s not too big and it’s manageable. Several fun districts outside of the downtown, including The Loop. Anheuser Busch Museum and Brewery offers a fun tour and of course beer! Downtown of course is the Arch, the riverfront, and the baseball stadium which has an adjacent building with several sports-themed restaurants and bars. And the St. Louis Zoo is fun even without kids, and it’s free!

Nashville, Tennessee (around 4 1/2 hours) a city, but very manageable and not too big. Downtown has several restaurants and honky tonks with live music. But also Blues and other kinds of music, shops, and the Country Music Hall of Fame. Don’t miss the Gaylord Opryland Hotel, about 15 minutes from downtown. It is huge and worth a stop even if you don’t spend the night there. You will find rivers and waterfalls inside the hotel and tons of fun-themed restaurants and cute shops. Next door is the Grand Ole Opry. Extra Tip: If you don’t stay at the hotel, park at the Opry Mills Mall and walk to the hotel…otherwise you will pay $29 just to park at the hotel!

List of Destinations Offering Direct Flights:

Austin, Texas
Charleston, South Carolina
Fort Lauderdale, Florida
Fort Myers, Florida
Jacksonville, Florida…..under an hour drive to St. Augustine with lots of historical sights, unique restaurants, and plenty of shops
Myrtle Beach, South Carolina…stay at North Myrtle Beach for a more relaxing setting
New Orleans, Louisiana
Salt Lake City, Utah
San Diego, California
Orlando, Florida…an hour drive to New Smyrna Beach, a fun beach town that’s perfect for a romantic weekend!

Where Will Tarah and Tim Travel?

They are still weighing all their options, but have decided they will likely drive. Galena, Illinois and Granville, Ohio are at the top of their list.

Stay tuned this spring to find out which destination they selected, and get a recap of their romantic weekend getaway!

Regardless of the destination they choose, I encouraged Tarah to keep her travel planning notes. Then next time they are ready to think about a weekend getaway, they will already have some great destinations in mind.

Join me in wishing Tarah and Tim a wonderful weekend away! Safe Travels!

Now, use these same questions and decide where your next vacation will be! Share your perfect destination in the comments below.

Wherever the road takes you, make it a joyous journey,
Traveling Tanya

Pinpointing the Perfect Destination