No matter how well you know someone, you usually learn a lot more once you’ve traveled with them. We are all different in this activity, from people who prefer aisle seats over window seats, to Airbnb renters or hotel enthusiasts, to the outdoorsy versus museum aficionados.

Friendship compatibility does not always translate to travel compatibility. Therefore, before you load up the car or board public transportation, it will help to communicate preferences, establish a few ground rules, and, perhaps most importantly, decide how to share expenses.

There are plenty of advantages to traveling with another person or a group of people, even if you tend to be a loner. For example, sharing expenses for accommodations, a car rental, or even a bottle of wine over dinner can cut your vacation budget substantially. However, if you don’t have a plan for what expenses to share and how to track them, you may return home short-changed, resentful, and with one less person in your life.

Ground Rules

It’s important to gauge upfront if everyone is on the same page as to how much money they want to spend on the trip, and even establish a maximum budget so no one gets trapped into paying more than they can afford. This means determining the level of accommodations (e.g., luxury versus budget-friendly) to shop for, whether or not you want the option to cook meals as opposed to eating out all the time, and the main activities the group plans to engage in (e.g., free hiking versus expensive snow skiing). Establish what types of expenses will be shared, such as group meals, housing and car rental, and what will be paid for individually, such as airfare, solo outings and souvenirs.

Choose Your Tracking Method

There are two approaches for sharing the expenses of travel: Wing it or track it. Winging implies a more casual tactic. For example, one person picks up the hotel room tab, another pays for the rental car, another pays for meals. Perhaps you rotate or take turns picking up comparable bills. The goal is to generally spread expenses evenly across all payers, but winging it may lead to one (or more) travelers paying more while the other(s) pay less. If everyone agrees their outlays may differ, then this tactic will probably work just fine.

Tracking Tools

The second approach is to track all shared expenses with some degree of accuracy. This is easier if all expenses are shared evenly, but more complex if expenses need to be broken down into who ordered a salad and who ordered the filet mignon.

Fortunately, there is a plethora of electronic technologies and digital tools designed to make it easier to track travel expenses and ensure no one overpays – right down to the penny.

PayPal, Venmo, Zelle – These services make it easy to send or request money using apps. They may require travelers to keep receipts and calculate individual tabs, then settle up at the end of the day or the end of the trip. This tactic can be a little unwieldy, and may require manual tracking to ensure no one is paying too much or too little along the way. All travelers should sign up for at least one compatible money transfer app; they are generally free to use.

Splitwise – This app enables participants in a travel group to enter the expenses they paid by adding the names of the participants and breaking down the individual amounts each person contributed to each bill. The app tracks expenses by person, then tallies up who owes money at the end. Splitwise calculates who owes whom. Travelers can then settle balances using their preferred payment method, such as PayPal, Venmo, Zelle, bank transfer, cash, or another supported payment service. Splitwise is just one brand name of many apps that work similarly, including Tricount and Revolut.

Cino – This app works a bit differently in that each traveler links it to their personal credit or debit card, and the group Cino card is loaded into Apple Pay or Google Pay. Then all participants share a virtual card to pay for expenses, which divides each payment at the point of purchase among the participants for that expense. When one person pays for an expense, everyone’s share is automatically charged to each member’s connected credit or debit account. Note that Cino does not break down invoices by line item to track exactly who ate what; it follows a split ratio (e.g., 50%-50%) as determined up front by the group.

Artificial Intelligence – Travelers may want to give AI a try, where as they start with a prompt asking the service to track and split group expenses, then enter the names of participants and related expenses to the prompt on an ongoing basis. AI tools can organize, categorize, and calculate shared expenses that users enter manually. Some AI assistants may also summarize spending trends or generate settlement calculations, but they generally do not automatically track purchases unless integrated with financial apps.

Given today’s higher prices, group travel is becoming more prevalent as a way to share the cost of vacation. According to a 2025 Zeta Global survey, 40 percent of travelers are going on trips with family while 21 percent opt to vacation with friends. Today’s new digital tools make it easy to track and share expenses so that you don’t strain relationships with travel companions.

Retirement planning starts with retirement spending. Ideally, retirees are mortgage-free and relatively debt-free before they leave the working life behind. In retirement, a key strategy is to maintain low monthly staple expenses.

Therefore, if you want to devise a financial plan that will allow you to retire early, consider cutting back your basic household expenses a year or more before your target retirement date. Some retirees choose to downsize their home, which also tends to reduce property taxes, homeowner’s insurance and maintenance costs.

Also, use that time to shop for cable, internet, or cell phone plans that may be cheaper and suit your needs in retirement. Be aware that seniors often get additional discounts they may not be aware of, so be sure to explore those options. By reducing your pre-retirement cost of living, you can reduce the amount of income you’ll need after you retire.

Build up Coffers

Another way to plan for retirement is to increase your savings while still earning income. You should have more than the typical emergency fund when you retire – so you won’t deplete it before you die. You also don’t want to have to take large, unscheduled withdrawals from retirement accounts because that would deplete your principal and potentially reduce the ongoing income you receive from those sources.

Social Security

Remember that if you start taking benefits before your official retirement age, you will lock into a lower payout level for the rest of your life. So even if you can afford to retire early, it’s generally a good idea to hold off tapping Social Security until full retirement age or even up until age 70, when you earn additional income credits. Factors to consider in making this decision include your health and life expectancy, needs for income, and other retirement assets. Remember, Social Security will last the rest of your life with cost-of-living increases and no investment market risk, so it is one income source you should wait to maximize as long as you can.

By establishing an account at the Social Security website, you can check your benefit amount at various ages based on current earnings; these projections are updated every year. If you are married, consider both spouses’ benefits as it might be better to start one early while allowing the other benefit to accrue.

Pension

If you expect a pension from your employer, you can request projected payouts to help devise your early retirement plan. If you have the option to receive either annuity payments or a lump-sum distribution, you might want to consult with a financial advisor to determine your best option within the context of your entire portfolio of assets.

Investment Accounts

If you have a 401(k), 403(b), or traditional IRA, remember that once you turn 73, you must begin required minimum distributions if you haven’t already. As a general rule, the common strategy for drawing down invested assets in retirement is to use taxable accounts first, tax-deferred accounts second, and tax-free accounts (e.g., Roth IRA) last. Roth IRAs do not require distributions at any age and can continue to grow throughout retirement.

Rule of 55

There is a legal strategy for tapping 401(k) or 403(b) retirement funds before the age of 59½ without incurring a penalty. The Rule of 55 enables you to make a series of substantially equal periodic payments from a former employer’s retirement plan (not a rollover account) between the ages of 55 (50 for a government defined-benefit plan) and 59½. While this strategy waives the 10 percent early withdrawal penalty, distributions are still subject to income taxes.

Health Insurance

If you wish to retire before age 65, consider your health insurance options.

• Employer-sponsored coverage through COBRA
• Health insurance marketplace plans at HealthCare.gov
• Joining your spouse’s health insurance plan
• Potential discounted coverage through membership organizations (e.g., AARP)

When you become eligible for Medicare, you must apply during the seven-month period that begins three months before you turn 65 and three months after your 65th birthday. If you do not apply during this enrollment period, you may face penalties.

Long-Term Care

If you’re thinking about early retirement, you may not be thinking much about nursing home expenses. However, long-term care can be quite expensive, so it’s important to plan for it early so you don’t run out of money when you need it most. Help from family can reduce the need for paid long-term care in your later years, so you may want to consider moving closer to them before or after you retire. Note that Medicare generally does not cover ongoing long-term care, although it may provide limited coverage for skilled nursing and rehabilitation services.  As a result, you’ll either need to self-fund, purchase some form of long-term care insurance, or spend down your assets in order to qualify for Medicaid long-term care assistance.

An early retirement plan usually involves a number of moving parts, so carefully consider withdrawal strategies and your specific tax situation in order to develop a plan that works best for your circumstances.