Steps to Planning a Multi-City Vacation

Do you want to plan a vacation, but are unsure where to start? Here’s a plan to help you tackle the “who, what, when, where, how” logistics of multi-city travel. We’ll make sure the itinerary has something for everyone no matter where you decide to travel. And as a solo female traveler, I will also share some tried and true safety tips.

The Golden Gate Bridge in San Francisco, California \ July 2022

Step 1: When Am I Leaving?

Figure out the departure date for your trip and the estimated return date. Maybe it’s a two-week vacation in December or a three-day weekend in July. Determining the season will help you decide where to travel, especially if you want to factor in climate/severe weather, smaller crowd sizes, or a seasonal festivity in the region.

Specific Examples: Australian beaches are warmest from November to February. Venitian gondolas and Parisian streets are less packed in the winter months. I learned the hard way that New York City requires a very different wardrobe a few months apart.

Step 2: Who’s Down To Go With Me?

Is this a solo adventure? Romantic get-away? Girls’ trip? Family vacation? Stay-cation? There’s no need to ponder this question too intensely, but defining the number of those in your party, their age range, mobility levels, and dietary preferences are key factors in considering every other aspect of the trip.

Step 3: Where Are We Going?

Trip Inspiration Ideas: Spin a globe and see where your finger lands. Visit the setting or filming location of your favorite movie or TV series. Watch your favorite sports team play an away game in a different city. Experience the power of music as your favorite band plays a show in their hometown. Visit family or friends living out of state/country.

Step 4: What Are We Doing?

Once you’ve determined a region, country, and state, there’s a particular process I use to narrow down specific cities and make the decision-making a little smoother. In short: Make a list of sights and activities in different cities that interest you, then rank top choices. The longer version of this process looks like this:

  1. Start by Googling or searching on social media for “What to do in X county/state” and visit travel websites, local blogs, and video reels for detailed descriptions, suggested time allotments, and honest reviews.
  2. Focus on one specific city, and curate a long list of attractions, sights, experiences, restaurants, etc. that catch your eye — without factoring in price, time, or availability. Just write it all down or start a spreadsheet.
  3. Establish categories that make sense to you and your travel party. These are mine:
    • “When In Rome” – Iconic, must-see attractions for their cultural significance.
    • “This Sparks Joy” – Experiences special to you, but probably not for all.
    • “For The ‘Gram” – Recognizable photo-op moments that are free and fast.
    • “Treat Yo Self” – Pleasurable splurges that cost more money or time.
    • “Family-Friendly / Adult-Only” – If traveling with children or elderly adults.
  4. Categorize the items on your list, now adding relevant notes about prices, suggested time allotments, which days/times it’s open, and neighboring attractions.
  5. Don’t delete anything from your original list, but strike any items that don’t align with your budget or timeframe.
  6. Rank the top items you would like to experience regardless of their category.
  7. Repeat this list-creating process for other major cities or smaller towns to help you narrow down where to visit and how many days to spend in each city.
    • Ask other travel companions to compile similar lists and rank their top to-do items. This way, you can prioritize cities with the most exciting to-do items, coordinate overlapping “When in Rome” and “For The Gram” experiences, create a schedule that allows each person to do at least one thing from their respective “Sparks Joy” lists, and establish a budget range for “Treat Yo Self” items independently or together with the rest of the group.
This is an example of how I would categorize some itinerary items for a few days in Rome, Italy.

Now that you have a few specific cities and activities in mind, it’s time to put the puzzle pieces together:

  • Fly into the largest city to avoid additional connecting flights; depart from a large city as well.
  • Planning 2-3 activities per day is most realistic, maybe a few more quick items if they are close in proximity.
  • Look at a map when scheduling activities to ensure directional efficiency and to avoid unnecessary traffic when venturing throughout the town.
  • Don’t plan much on travel days in case there are delays or you’re feeling tired.
  • Schedule intentional rest days, especially on travel days in between cities. (On my first multi-city trip, I falsely believed I was the Energizer Bunny and was grumpily exhausted by the last leg.)
  • Make time to smell the roses, not just to snap a quick picture of the garden. Leave breathing room for being captivated by the sights, spontaneous side adventures, and getting lost on your way to the next activity.

Know Before You Go, Especially in the Pandemic Era: Certain places may only allow a limited number of daily visitors, so make online reservations early; print paper tickets ahead of your trip, if mobile ticket options are not available. Face coverings and proof of vaccination or a negative COVID-19 viral test may be required in order to gain entry. Security lines are quicker for those who only have a phone and wallet on them. For those carrying packs or purses, make sure the size aligns with the venue’s bag policy, and only carry what is absolutely necessary.

Financial Budgeting in Advance & Future Plans to Return: Compling your activity list is particularly useful well ahead of your trip to determine how much money to save in order to afford all the things you want to do. Any remaining items you didn’t get to check off your longer initial list can serve as a starting point for your next visit.

All in all, I hope this process of listing and categorizing items for your multi-city adventure will assist you in living the motto, “Veni, vidi, vici” / “We came, we saw, we conquered!”

The Julius Caesar Statue at the Imperial Forum in Rome, Italy \ May 2015

Step 5: How Are We Getting Around?

Traveling from Point A to B to C to D requires the most logistical attention to detail, but offers the most room for creativity. I use a combination of Expedia, TripAdvisor, and Google Maps to search for economical travel options and hotel/hostel deals relatively near the main attractions. Planes, trains, and automobiles are all on the table, as well as boats, buses, subways, and my own two feet.

Language Barriers: If you’re traveling to a country with a differing primary language, try learning the translated pronunciation of key survival phrases, numbers 1-10, right and left directions, and any allergies or health conditions you or your travel party may have. Knowing written translations for your favorite fruits, vegetables, and meats can help you recognize certain dishes on a menu. Install Google Translate or similar phone apps ahead of your trip to translate longer sentences if needed.

International Travel: Visit the U.S. Embassy website for the country you’re traveling to and note any safety warnings relevant to American travelers. Book long flights for evening departures so you can sleep on the plane and spend less on hotel costs. I recommend applying for the U.S. Passport Book and the U.S. Passport Card since the ID card fits in your wallet, and can be used for land border crossings into Canada and Mexico.

Packing Pro-Tips & Safety Suggestions

As an overly cautious traveler who always factors in worst-case scenarios, here are a few safety tips I’ve refined over the last five years:

  • Keep a picture on your phone’s Favorites album of your passport or ID as well as your vaccination card or proof of negative COVID-19 viral test and email these pictures to yourself ahead of the trip.
  • Invest in a portable phone charger.
  • It never hurts to pack band-aids, cough drops, allergy medicine, and chewing gum (in case your ears hurt after flying).
  • Leave the bulky camera at home (unless you’re a professional photographer); iPhone quality is impressive enough these days.
  • Don’t pack flashy jewelry that might make you a target for muggers.
  • Consider carrying a lunchbox instead of an expensive bag.
  • Pack a complete change of clothes in your personal item in case your checked-in luggage is temporarily lost. (I usually fly with only a carry-on size suitcase and a backpack as a personal item.)
  • Share your phone location with someone back home that you trust.
  • Don’t split cabs from the airport and don’t disclose that you’re traveling alone to strangers. (We’ve all seen the movie, “Taken.”) If anyone asks, you’re not new here; you’re meeting up with family who lives here.
  • Upon check-in, place a hotel business card in your wallet so you’ll have the name and address in case your phone dies or breaks.
  • Separate some emergency cash or a designated credit card in your suitcase in case you lose your wallet.
  • Look for emergency exits at every building you enter and notable landmarks near your hotel.
  • Plan most activities for daylight hours to better see your surroundings.
  • Trust your gut! If something feels off, deviate from the plan or path.

Mailing Postcards: Make loved ones’ day by sending them a postcard. Save home addresses on your phone’s Contacts app before you leave. To avoid extra costs, be sure to pack a good pen that doesn’t smudge and extra postage stamps from home.

My Travel Tradition: Instead of souvenirs, I buy a postcard for myself in each city and keep it with me. When I arrive home, I write a trip summary on the back for myself to reminisce upon. I note the date, itinerary, friends/family that I met up with, methods of transportation, and which activities I enjoyed most.

And with that, “bon voyage” and “safe travels!”

A Song I Listened To While Writing: “Who Says You Can’t Go Home” by Bon Jovi and Jennifer Nettles. Thank you for reading! Comment below where you think I should travel to next.

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