Take a Quick Quiz to Find the Best Vacation for You

In today’s world of rising stress levels and increased focus on wellness, more people are choosing to invest in experiences over possessions. Travel offers a much-needed break, a chance to recharge, and meaningful moments that enrich your life far beyond what material goods can provide.

Whether you’re planning a solo retreat, a romantic getaway, a friends’ reunion, or a family vacation, following a few key steps can make the process smoother and more enjoyable. Let’s explore how to plan the best vacation based on your preferences, lifestyle, and the latest travel trends.

Or, skip right to the last step: Get Vacation Insurance Now

1. Choose Your Travel Companions

Before you dive into booking flights or accommodations, decide who will be joining you. Are you embarking on a solo adventure to relax and explore at your own pace? Planning a romantic escape with your partner? Organizing a multigenerational family trip or friends' getaway?

Your travel companions will influence the destination, pace, budget, and even the kind of accommodations you’ll book. Aligning expectations early can prevent potential conflicts later. Solo travel remains a strong trend in recent years, but group travel (especially curated trips for couples and families) is on the rise as people prioritize deeper connections.

2. Pick the Best Time to Travel Based on Seasons and Events

Timing is everything. For most people, vacation time hinges on work schedules, school breaks, or seasonal availability. But more travelers are also prioritizing specific experiences over dates—like chasing the Northern Lights, attending music or food festivals, or visiting destinations during shoulder season to avoid the crowds.

Consider the climate, major holidays, and events at your potential destination. If you're aiming for a ski trip, plan during winter months in the region—remember that ski season in the Southern Hemisphere happens mid-year. For beach escapes, keep in mind the hurricane season in tropical regions or intense summer heat in desert areas.

Pro tip: Use tools like climate calendars and event guides to match your travel window with ideal weather and experiences.

3. Set a Realistic Travel Budget Early

Budgeting early helps narrow down your choices and reduces financial stress. According to the 2025 Generali Global Assistance Barometer Survey, the average vacation cost per person is around $1,876 or $3,752 for a couple, but your trip can be tailored to suit your lifestyle and goals.

Start by identifying your spending priorities—are you allocating more to flights, accommodations, food, or experiences? Don’t forget to account for travel protection, tipping, transportation, souvenirs, and emergency expenses.

A popular budgeting method is the 50/30/20 rule applied to travel: 50% on necessities (like airfare and lodging), 30% on experiences and entertainment, and 20% saved for unexpected expenses.

4. Research Trending Travel Destinations

Now the fun begins: choosing where to go. Let your interests lead the way. Do you want adventure, cultural immersion, wellness, nature, or luxury?

In 2025, trending destinations include:

• Sustainable escapes in Costa Rica and Slovenia
• Cultural hubs like Kyoto, Istanbul, and Oaxaca
• Remote digital detox spots like the Faroe Islands or Patagonia
• Underrated U.S. gems like Asheville, North Carolina, and Sedona, Arizona

Also consider safety, visa requirements, political climate, and accessibility. If you're overwhelmed, use tools like travel quizzes, AI-powered itinerary generators, or speak with a travel advisor to help guide your decision.

5. Book Lodging and Activities in Advance

Where you stay can make or break your vacation. Are you looking for a luxury hotel with spa services, a family-friendly resort, or a local Airbnb in the heart of the city?

Booking accommodations early—especially during peak travel seasons—ensures better rates and availability. The same goes for activities, especially popular tours, excursions, and event tickets.

Today’s travelers often seek personalized experiences, from cooking classes with locals to hiking with expert guides. Sites like Airbnb Experiences, GetYourGuide, and Viator can help you find curated activities that match your travel style.

And always check reviews. User feedback on platforms like TripAdvisor and Google Maps can provide real insight into what to expect.

6. Communicate Your Travel Plans Clearly

Good communication is essential, especially if you’re part of a travel group or taking time off work. Make sure everyone involved knows the timeline, itinerary, and expectations.

If you work remotely or run a business, prepare colleagues and clients ahead of your departure. Set an out-of-office message and delegate responsibilities where possible.

Sharing your travel plans with friends and family—not just on social media but also via shared calendars or group chats—can help coordinate logistics, avoid overlaps, and gather helpful tips from others who have visited your destination.

7. Help Secure Your Trip with Travel Protection

One of the smartest moves modern travelers make? Buying travel protection.

Whether you’re worried about flight cancellations, medical emergencies abroad, or lost baggage, travel protection can help provide peace of mind and financial security. Travel disruptions are becoming more common due to extreme weather, geopolitical events, or airline labor issues.

Generali Global Assistance offers three travel protection plans for traveler needs. For example, purchasing a plan when you make your first trip deposit (like airfare) can give you access to maximum Trip Cancellation benefits. If you or a travel companion have a pre-existing medical condition, consider a Premium Plan—just remember it must be purchased before or within 24 hours of your final trip payment to ensure coverage.*

Travel protection doesn’t just help protect your money it can help protect your peace of mind, allowing you to fully enjoy the experiences you’ve planned for.

Plan Well, Travel Better

Following these seven essential steps can transform your trip from stressful to seamless. From choosing the right companions and destination to helping safeguard your plans with travel protection, a little forethought goes a long way.

With flexible work arrangements and global travel options expanding, there’s never been a better time to embrace the joy of travel. So mark your calendar, start dreaming—and get planning.

Ready to protect your vacation? Start by getting a free quote here