Updated: May 24, 2020
Does planning produce overwhelming anxiety or overwhelming joy?
*Nervous laugh ensues*
What do you think of?...Spreadsheets? Agendas? Schedule books? Calendars?
*Nervous laugh continues*
Now, let's add the layer of planning for travel?
*Nervous laugh grows louder*
Fortunately for you, I LOVE to plan! Over the years as a student leader and school leader, I have been told that planning is one of my greatest strengths. I am so good at planning that I have been delegated to plan as a major aspect of my professional career as an Assistant Principal. However, that joy also translates into my travel life as well. Planning a trip itinerary is where I can get lost in a destination before even stepping foot. It is where I can indulge in travel when I am not actually traveling (well, except in my head)
Having planned the majority of my domestic trips as well as some of my international trips, I have a go-to plan to plan. As they say, if you fail to plan, you plan to fail! Check out my top ten tips for planning a trip.
For me, one of the best ways to learn about a new state or country is through a tour! You've landed in a new city and you want to explore it, right? Why not explore it through the lens of an expert on a tour? By tour, I mean a walking tour that lasts somewhere between 1.5 to 4 hours. Don't worry, there are several stops, so time flies! A huge benefit of a tour is that you gain a deeper knowledge of a location in a short period of time. I love walking tours because it also allows you to meet new people you otherwise may not have ever met while traveling. For me, when I travel solo, it is a great way to socialize and allows me to not feel lonely on a trip.
A. Free Walking Tours
Without fail, I always search for free walking tours. Many major cities have #FREEwalkingtours, which is the new wave to "pay as you like." Considering that it is FREE.99 (although, do not be that cheap person and not tip!), you really get a quality tour. They are offered in many major cities across the country and throughout the world. You will definitely find something of interest!
For example, during a work conference in Boston, I found some free time to squeeze in a free walking tour with my Snapchat Friend (who I met for the first time on this tour)! She, as a local, learned a lot of things that she did not know about Boston. On this tour, I also got recs for delicious food spots to check out as the guide also runs a food tour. Unfortunately, we did not have time to check it out.
TIP: Several companies offer walking tours with the two most popular being Free Tours by Foot (for domestic big cities) and Sandeman's (for international big cities), which have an array of tours that include street art, food, and historical.
B. Food Tours
Food tours...now this is my favorite type of tour! I try to go on a food tour whenever possible as there is no better way to get to know a city than through its food. Food tours often replace a dinner I would have otherwise eaten. The beauty of it is that instead of having dinner from one place, I have the chance to try food from 4-7 different restaurants already carefully selected. Unlike the free walking tours, you will most likely have to pay ahead of time so that they can have the food ready to serve when you make stops along the tour. There are a few tours where you can pay as you go.
I have been on food tours in many countries including the Bahamas, Norway, Cuba, Iceland and Denmark. I have also done food tours in many, many USA cities such as Baltimore, Minneapolis, Atlanta, and Seattle.
TIP: Just google "food tours in <<insert city>>. You will usually see at least 1-3 options come up if a city has a food tour. Check out Viator as well!
C. Street Art Mural Tours
Street art mural tours are harder to find. However, when I do find them, I hop on. Some are pay-what-you-want while others are paid. I find them super helpful because you usually have the opportunity to connect with a local artist of the visiting city and you get to learn the meaning and history behind art images on street murals. For example, in the Bahamas we got the opportunity to spend 3 hours with a local Bahamian artist who comes from a family of artists. I learned so much history and culture in a short period of time as she took us to a Bahamian art museum as well as through art neighborhoods.
TIP: If you cannot find a guided street mural tour, there are often self guided mural tours posted online. It can also help Google: street art neighborhoods in a given city or search "Top murals in <<insert city>>" and collect the addresses of the top murals that you want to see on your visit. Very often, major cities have particular neighborhoods with concentrated street murals that lend themselves to a fun way to wander.
Viator is clutch for finding tours and excursions. An excursion can be a tour. However, not all tours are excursions. In the lens of Viator, excursions often involve being taken around on some mode of transportation (van, bus, boat, etc). I find booking excursions through Viator super helpful when traveling to another country. However, you do not want to be on a non-stop guided tour for the entire time you are in a location!
For example, rather than booking a 5 Day, All Included tour to Iceland that would have included flight, hotel, meals, and an exact itinerary, I decided that I wanted the luxury of piecing together my own itinerary so that I can pick and choose what I wanted to do. This would allow me to embed some slower-paced days, but also incorporate things that are not typically on a full guided tour such as a food tour or museum excursion. Instead, I booked full day excursions for every other day of the trip. Furthermore, excursions are super helpful if you do not plan to rent a car in a specific country as they drive you around. You can even hire a driver and then plan with your driver the places that you want to go.
TIP: Look for excursions that are comprehensive. This means that it includes transportation, guide, and a meal for the price. Might as well get the most for your buck!
3. Top Things to Do (and underrated too!)
A. "Touristy things"
I know what you are thinking...I do not want to do touristy things! Don't worry, I got a solution to that in my next point. However, let's not downplay the "touristy!" They are popular for a reason.Think about it like this: did you really go to India if you did not check out the Taj Mahal? Did you really go to China if you did not check out the Great Wall? The majority of your itinerary may not be centered around the top things to do in a city, but I think there is merit to crossing off a couple of items as those are things that often unite travelers.
TIP: Top places to visit can often be crowded. Therefore, try to check them out early in the morning or later at night when less people typically venture out. You can also look on Google to see when the times that are less busy to visit a popular landmark, museum or restaurant.
B. "Underrated, Hidden gems"
See, I got you. You can easily just search "Top Underrated Things to do" or "Top Hidden Gems" in a specific city. Very often what will come up are blogs or websites with very obscure lists of things to do. I would take the time to pour through some of these blogs to compile your own list of things that interest you. A good website to check out (not sponsored!) is Atlas Obscura.
TIP: While you are traveling, ask locals for their top places to go! I love talking to workers at restaurants and Uber drivers to get insider tips of a location.
4. Social Media is a Valuable Source
This is probably as valuable (and dare I say more valuable) than Google since social media is truly coming from the people. It can feel overwhelming. However, trust me when I say that it is well worth it. Many of the best places that I have been to are a result of a social media recommendation. Comb through Facebook travel groups and Instagram (I take notes from friend's IG stories of restaurants and things to check out). See where your favorite influencers have been as you probably have similar interests if you are following them religiously.
TIP: Additionally, search location and top hashtags to get ideas of landmarks and restaurants. If you see someone post a good restaurant or experience with no location or tag, I would just slide in the DM and ask. Most people are willing to share that information with you!
5. Most Instagrammable Spots
Let's be real, did you really travel somewhere if you did not post? Jk, jk... but seriously, it is important for me to have good pictures not only as a content creator, but for the memories as well. From very young, I grew up in a household where LOTS of pictures were taken (*throwback to posing for pics in Sears and disposable cameras*). Great pictures may include having a colorful street mural or impressive skyline backdrop. Very often, the best photo spots are not in the most obvious places. As a result, searching specifically for the most "Instagrammable spots" really helps you to find these hidden gems.
TIP: I would recommend skimming through multiple lists rather than just looking at the first link that pops up in Google. The places that you repeatedly see in multiple spots indicate that you should check it out. It's also helpful to find links that include photos so you know what to expect when you get there.
6. Top Black Owned Lists
When I travel, I always look to support black-owned spots. PERIODT. Not going to lie, it is a lot harder to find in some places *cough, cough Vermont*. However, trust me, those places are out there. Black history is American history...and world history! As a result, I think it is important for ALL people to experience black culture even if it's for a snippet of the trip. Whether it is looking through a Black travel group or googling it, there are many lists out there!
TIP: Travel Noire is clutch for finding black-owned spots in the USA. They have many "50 in 50" lists ranging from "50 In 50: The Best Black-Owned Brunch Spots In All 50 States" to "50 in 50: The Best Chicken And Waffles In Each State!"
I know museums are not everyone's cup of tea. However, I recommend visiting at least the state museums in the USA and the national museum in another country as you will truly get to learn about the history and development of a location from the start of their development to present-day -- much more than you would ever learn in a book. I try to look for an African American museum as well. Not all locations have one. However, when I do come across them, it is a gem as you get to learn about African American history through the lens of that particular location. Two helpful links to find African Museums are "50 in 50: Museums That Capture Black History Across America" and "Celebrate Black History Month with Lyft."
TIP: Before visiting a museum, check their website to see the discounts offered. Hang on to your college ID (especially if it does not list an expiration date in the front of it) or get an alumni ID. Numerous museums offer #studentdiscounts as long as you present a Student ID. In fact, some museums give teacher discounts and almost all give military discounts. Be sure to look for free nights as sometimes museums offer free admission on a certain evening of the week or a certain day each month.
8. Local Events
I love finding where the locals hang out because it is how you get a taste of the culture and ambiance of a location. If I am searching before arriving in a location, I would look for "events in <insert city>> and see what pops up in the Events section of Google. Very often, this is how I come across concerts of major artists, a unique theater show, or local art exhibition at a library.
TIP: Once you have reached your destination, search on Google and Facebook "events near me" to see what comes up. I have found this most effective as it finds events in a close radius to you. For example, I discovered an open mic night that occurs every Sunday in Copenhagen, Denmark using this method.
9. Live Music
I am separating this from "local events" as you may not find live music by searching for local events. I love live music, so I try to attend a music function when possible. For example, I discovered a bar in Minneapolis, Minnesota that features the only band given permission to play Prince's music. They apparently perform sets at the bar one weekend a month, and I happened to be around that weekend!
TIP: I have found it most useful to search "best free live music in <insert city>" or "best spots for live music in <insert city>."
10. Top Food Spots
I don't know about you, but I travel for the food! Food is culture, and it is so different by country, state, and even neighborhood. It can become really difficult to find good food spots -- as I find it can be hit or miss unless you have a way of filtering for the bad. Yelp I find is the best quality control. However, how do you find places to begin with? As recommended above, use social media! Take notes from friend's IG stories or posts. For domestic spots, I often look up locations featured in the TV show Diners, Drive-Ins and Dives. For the most part, they have not let me down on finding some of the best lasagna ever in Colorado Springs or tasty Trinidadian food in Minneapolis.
TIP: Search on Google for the national dishes of another country or state dishes for another state, or just dishes unique or popular to a location. You can then search the top places that feature this unique dish. It is a great way to get to know a place!