Essential Tips for Planning an Extended Vacation

Essential Tips for Planning Your Long Vacation

By Laura Petrecca

Published 24 February 2024

If you’ve been dreaming of a month-long beachside retreat or a six-week bike tour through Europe, start planning your itinerary. It’s easier — and more affordable — than ever to take a long vacation.

Extended travel is no longer the domain of the rich and famous or recent college grads. Thanks to the ease of international communications, flexible work arrangements, and sophisticated trip-planning tools, long-duration getaways are becoming more accessible. By taking a month or more to travel, you may enjoy a host of benefits, such as broadening your perspective, enhancing your language skills, and deepening your knowledge of different cultures.

“It’s one of the few opportunities to unplug, reflect, and see how others live,” says Elliott Appel, a certified financial planner, who recently returned from seven weeks exploring Australia and New Zealand.

Focus on Your Vacation Goals

Envision your first night back home after an extended vacation. What would have made the trip ideal? Consider the climate, food, culture, activities, and cost. Would it be adventurous or relaxing? Luxurious or rugged? Would you have traveled to a mountain or a beach? Both? Neither?

If traveling with others, it’s beneficial for each person to list their ideal trip elements. For extended travels through various destinations, Patrick and his wife made wish lists of their desired places and adventures. “Luckily, the lists were pretty similar,” he notes.

Once you have a clear idea of what appeals to you, create a shortlist of potential destinations. Include both dream locations and more economical options. For instance, if relaxing in the Maldives is your ultimate desire, you could also consider visiting a less-expensive destination such as Costa Rica.

Crunch Some Numbers for Your Trip

Research the costs associated with each of your choices to see which best fits your budget. Factor in transportation, lodging, meals, activities, and shopping. Also, if you’re traveling to a country that doesn’t use U.S. dollars, consider the exchange rate.

Add 10% to 20% to your total as a buffer, suggests Derek DiManno, a certified financial planner. He recommends using a spreadsheet to track estimated expenses.

“A short trip can be easy to budget for,” DiManno explains. “However, a longer trip can lead to higher varying costs. Be exhaustive. It’s better to overestimate costs and have a surplus than to underestimate.”

Check Your Destination’s Entry Requirements

If traveling internationally, it’s important to check passport expiration rules for your destination, as many countries require that your passport is valid for several months beyond your date of entry. You may also need to apply for a visa.

Be thorough; government sites, airlines, and travel forums can provide helpful information. The U.S. embassy’s website is a great starting point to find information about various countries. Additionally, familiarize yourself with the etiquette and social practices to avoid misunderstandings.

How to Control Your Vacation Costs

Planning your travel well in advance can yield significant savings. Being flexible with your travel dates can help dramatically cut costs. “You can save money by traveling on less-popular days,” Appel advises. Traveling during off-peak periods can also save you money and provide a more authentic experience.

Capitalize on Rewards

Utilize perks offered by airlines, hotels, and credit card issuers, including cash back and lounge access. Some credit cards also cover fees for expedited services like Global Entry or TSA PreCheck.

Get Creative with Your Accommodations

When traveling, consider both traditional hotels and alternative lodging options, such as home swaps or vacation rentals. These options often provide unique experiences and can be more budget-friendly. Websites like Airbnb and VRBO can facilitate these arrangements.

Understand Your Travel Insurance Options

Travel insurance typically falls into policies that cover trip cancellations and health-related emergencies. Understanding your insurance needs and coverage limits is vital, especially for extended trips.

Finally, Create a Predeparture Checklist

A well-crafted trip may require months of planning, so start writing down tasks as early as possible. Proactive management will reduce stress before your departure.

If Traveling Overseas:

  • Contact your bank and credit card companies about your travel plans.
  • Exchange currency at a local bank ahead of time.
  • Research SIM card options to stay connected.
  • Download free communication apps like WhatsApp.
  • Check if you need an international driving permit.

Additional Checklist Items:

  • Put bills on autopay.
  • Refill any necessary prescriptions.
  • Put a hold on mail deliveries.
  • Create a detailed packing list.
  • Arrange pet and plant care.
  • Leave a copy of your itinerary with a trusted friend or family member.

It’s a big world out there. Get out there and see it.


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