Bright lights, big cities: How to prep for a city trip

March 14, 2023

There’s something about the energy of a big city: from the non-stop action to the all-hours lifestyle, it can be a vacation destination that packs maximum activity into minimal time. And for those who head to urban landscapes for their vacations, the ultimate thrill is city hopping, where multiple points on the map fill an itinerary. 

If you’ve been meaning to hit the major metropolises of the world, there’s no better time. Between a wide variety of accommodations, top-notch dining opportunities, easy transportation and a plethora of entertainment options, you can craft an experience you’ll remember your entire life. Here is a list of to-dos as you put together your city-by-city-by-city plan.

Itinerary

It may be tempting to cram every single landmark and hotspot into your city getaway, but that’s a recipe for not having room for spontaneous fun. As you plan your city trips, learn about the must-see attractions, but give yourself permission to only visit a couple a day. Prioritize and plan for rest, relaxation and aimless exploring, as well — some of the best travel surprises happen off the beaten path.

In addition to your per-city planning, think through your plan for getting from city to city. Will you train, drive or fly — or all three? Each offers a different experience, and can be part of the experience. Also, researching the cultural roots in each city you visit may open your eyes to neighborhoods and experiences you hadn’t considered and could add an all-new dimension to your trip. Immerse yourself in the local culture by visiting neighborhood markets, trying traditional foods, and attending cultural events and festivals.

If possible, inject an unplanned day or two into your schedule. This gives you the chance to adjust your plans and embrace unexpected experiences during your trip. City hopping can be a great opportunity to try new things, meet new people, and have unique experiences. It’s easier to be flexible and go with the flow if you’re not crunched for time.

Most-visited cities

If you’re prepping for city travel, you’re probably wondering about the best cities to visit around the world. Here are the most popular international city destinations, according to a recent CNN report:

1. Paris. The City of Lights never disappoints, drawing visitors from around the world
2. Dubai. Incredible Arabic architecture and one-of-a-kind adventures await.
3. Amsterdam. Enjoy world-class museums, charming canals, and a bike-oriented culture.
4. Madrid. Outdoor plazas, distinctive neighborhoods, and grand palaces fill this historic city.
5. Rome. A dream destination for those who love art, history, archeology… and pasta, of course 

Top cities for U.S. weekend getaways

Not headed overseas? Consider taking some short weekend trips within the U.S. borders.

1. New York. The mother of all American cities, with something for everyone in its museums, theaters, parks, musical venues… and the list goes on.
2. Miami. Enjoy amazing architecture, delicious cuisine and the beach during the day — then club all night.
3. Los Angeles. World-famous beaches and boardwalks, landmark museums and theme parks and Hollywood.
4. Orlando. For the young at heart, the combination of over-the-top amusement parks and sunshine is impossible to beat.
5. San Francisco. There’s something uniquely American about this Western city’s gold-rush history, plus amazing cultural institutions and beautiful outdoor destinations.

Budgeting

When traveling to new cities, it's important to budget your expenses carefully. City costs can be higher across the board, so make sure you have enough money to cover all your expenses, including food, transportation, activities, and any other necessary items. Consider using budgeting apps or creating a budget plan to help you keep track of your expenses and avoid overspending.

Transportation

Getting around a new city can be a challenge, so it's important to research transportation options in advance. Public transportation, such as buses, subways, and trains, can be a cost-effective and convenient way to travel, plus offers a front-row seat to the people and neighborhoods that define a city. Taxis and ride-sharing services are also convenient options, but they can also be more expensive. If you plan to do a lot of driving, consider renting a car—but be sure to factor in the expense including gas, parking, and insurance.

Accommodations

From budget hotels to high-end boutique stays to apartment rentals, there’s a wide range of ways to experience city life. Do research as you are prepping for city traveling to identify safe, convenient places to stay near the activities you will attend, keeping your spending limits in mind as you price out the different options. During your stay do not display large amounts of cash or expensive jewelry in public places, such as the hotel bar or lobby. While in your room, it is recommended that you make sure that the front door is locked. Furthermore, make sure that all windows, sliding glass doors and connecting room doors are locked as well. Different neighborhoods can offer equal safety and convenience, so pull out the map and be open to adding a little in-city travel along the way. Consider the commute yet another chance to experience a city like a local.

Safety and health

Safety should always be a top priority when traveling, especially in an unfamiliar city. Familiarize yourself with the local laws and customs, and take the precautions you’d take anywhere else, such as avoiding walking alone at night, being cautious at ATMs, and keeping your phone and other belongings tucked away at all times.

If your tour of cities takes you overseas, the U.S. Department of State offers per-country information that is extremely helpful in terms of necessary documents as well as safety tips and alerts. A quick check ahead of time may — at the very least — save you hassle at the border.

Whether you’re traveling within the United States or around the world, consider what to do if an illness forces you to cancel a trip, or if you possibly run into cancellations or other interruptions during your vacation. Consider trip protection to cover the costs of luggage loss or unforeseen complications. For those traveling overseas, consider a plan that includes both trip protection and medical insurance for health care needs you may have.

For instance, SafeTrip from UnitedHealthcare Global protects your travel plans with both medical and trip coverage. The U.S. domestic Travel Protection plan covers you in case of flight cancellations or delays, hotel snafus and more, and you can even add on rental car damage protection just in case. If you’re headed overseas, be aware that many health insurers won’t cover health care needs outside the U.S. International Travel Medical is a good solution for many headed to foreign countries, while many travelers choose International Travel Medical Plus for its combination of medical insurance and trip protection in one plan.

*Policy availability varies.

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