How I Plan a Year of Travel: Tips, Tools, and Strategies to Maximize Time and Money

Travel is one of my greatest joys. My husband, Josh, and I spend much of our time exploring the world, whether that means cruising in the Caribbean, road-tripping through national parks, or spending a few days in a city we have never visited before. Over the years, I have developed an annual travel planning system that allows us to take multiple trips each year without overspending.

If you have ever wondered how to plan a year of travel in a way that feels exciting and realistic, this guide walks you through my exact process. I will share how I choose destinations, find deals, make the most of loyalty programs, and balance big adventures with smaller getaways. These year-round travel tips are what help us see more of the world without draining our budget.

Step 1: Start with the Big Picture Calendar

The first step in my annual travel planning process is to look at the full year ahead. I open both my personal calendar and Josh’s to see what is already scheduled. Weddings, family gatherings, and other personal commitments all go on first.

With those in place, I can see my open travel windows. From there, I match potential trips with the right season:

• Caribbean cruises are more affordable during hurricane season, though there is more weather risk.

• European trips are ideal in April-May and September-October for lighter crowds and better prices.

• National parks are less crowded and cooler in late spring or early fall.
  

I also look for opportunities to link travel to holidays or special events, which naturally spread out our trips over the year.

Step 2: How I Prioritize Destinations

I keep a running list in Trello of places I want to visit. This “travel wish list” includes everything from bucket-list trips like a cruise from Sydney to Auckland to short, budget-friendly weekend getaways.

When deciding which to plan first, I ask three questions:

1. Interest level – Is this a must-do trip or something we can push to next year?

2. Budget – Is this a high-cost adventure or an inexpensive getaway?

3. Seasonality – When is the ideal time to visit?
   

By evaluating each option this way, I can create a year-round travel plan that feels balanced.

Step 3: Research Travel Deals and Packages Early

Once I have a draft list of trips, I start looking for deals. My go-to resources include:

• Point.me for airfare deals

• Chase Travel Portal for hotel deals

• DailyDrop for available points transfer bonus opportunities
  

For cruises, I check both the cruise line’s website and trusted travel agencies that sometimes offer group rates or perks like onboard credit. When creating a budget-friendly annual travel plan, I decide early whether a trip should be booked far in advance for better selection or held for a last-minute bargain.

Step 4: Using Loyalty Programs to Plan a Year of Travel

Loyalty programs are essential in my travel planning strategies. They stretch our budget and sometimes make trips possible that would otherwise be too expensive.

Airline Loyalty

We focus most domestic flights on one airline, Southwest. They tend to have the most direct options from our home airport, so it makes it easier to travel with them. We’ve also had their Companion Pass for over a year, so all of my flights have been free and we only pay for Josh to fly when we’re together. Internationally, we don’t focus on a single carrier, but have flown internationally on Delta, American, and United, as well as other non-US carriers. Concentrating miles with a single carrier or with programs that allow for miles transfers makes it easier to earn free flights. I also watch for promotions like double points or reduced award fares.

Hotel Loyalty

I belong to all the major hotel loyalty programs and have several of their credit cards. The cards can give you hotel loyalty status so you can get free anniversary rooms and upgrades when you check in. Even without top-tier status, free nights, upgrades, and perks like late checkout add value.

Credit Card Rewards

We use cards like the Chase Sapphire Reserve, CapitalOne Venture X, and American Express Platinum that earn transferable travel points. I save these for high-value redemptions, such as international flights where the cash cost is high but the points cost is reasonable.

Step 5: Book Anchor Trips First

Anchor trips are the backbone of my year-round travel plan. These are the largest, most fixed trips, such as a two-week international cruise, a guided tour, or a trip that involves long-haul flights.

Once these are set, I fill in smaller trips around them. For example, when we booked our Norwegian Joy Alaska cruise for July, we planned short, Vegas trips in the months before to keep costs balanced.

Step 6: Add Short Getaways to Keep the Year Exciting

Between anchor trips, I schedule shorter, flexible getaways. These can be road trips or long weekends in big cities. They keep the excitement of travel going year-round without requiring big budgets or heavy planning.

For these trips, I often use credit card or hotel points to cover the stay and keep costs low.

Step 7: Coordinate with Work and Personal Commitments

Even though we do not have traditional jobs, we still have client projects, community events, and personal obligations to work around. I avoid scheduling major trips during busy work periods or important events.

Some trips are also coordinated with friends or family. Planning travel together can influence where and when we go, but it adds a social element that makes the trip even more memorable.

Step 8: Keep Detailed Travel Trello Boards

One of my most important travel planning tools is my Trello account. It includes:

• Destinations

• Dates

• Flight details

• Hotel or cruise reservations

• Transportation arrangements

• Booked activities

• Estimated budget vs. actual spending
  

Having this in one place keeps me organized and helps maintain a realistic annual travel plan.

Step 9: Set Price Alerts for Flights

To make sure I am getting the best airfare, I set price alerts on Google Flights for every potential route. I also use Hopper to gauge whether I should book now or wait.

Step 10: Plan a Year of Travel Around Shoulder Seasons

Shoulder season travel is one of the easiest ways to save money and avoid crowds. This in-between period offers lower prices, fewer tourists, and pleasant weather.

Examples include:

• Visiting Europe in late April or early October

• Traveling to the Caribbean in May before the summer rush

• Exploring U.S. national parks in September, after school starts

Step 11: Mix Different Trip Types for Budget Balance

A smart year-round travel plan includes variety. My mix usually looks like this:

• One or two big trips (international travel or high-cost cruises)

• A couple of medium trips (domestic flights, moderate hotels)

• Several short getaways (road trips or regional visits)
  

This approach keeps travel frequent but manageable.

Step 12: Build in Recovery Time

After long trips, I try to schedule at least one day at home before resuming normal routines. This prevents burnout and makes the reentry smoother.

Step 13: Make Transit Days Count

I look for ways to make travel days part of the adventure. That might mean scheduling a longer layover to explore a new city, taking a scenic train instead of a short flight, or booking a cruise that starts and ends in different ports.

Step 14: Keep a Packing List Template

My packing list template lives in my phone so I can adapt it for any trip. It saves time and ensures I do not forget essentials.

Step 15: Stay Flexible and Open to Change

No matter how well you plan a year of travel, things will shift. Weather, cancellations, or last-minute opportunities can all change the itinerary. Staying flexible means less stress and more chances for spontaneous adventures.

Final Thoughts on My Year-Round Travel Tips

Planning a full year of travel is not about locking yourself into rigid schedules. It is about having a framework that allows you to balance big adventures with smaller, budget-friendly trips, use loyalty programs strategically, and make the most of every opportunity.

By combining careful planning with flexibility, Josh and I are able to explore the world consistently without overspending. You do not need unlimited resources to travel more often - just a smart annual travel plan and the willingness to adapt.

Recommendations

Are you planning your next trip and looking for services that make travel smoother? Here are a few of my go-to recommendations:

• Stay Connected Abroad: I use Airalo eSIMs to avoid the hassle of swapping SIM cards in every country.

• Protect Your Data: NordVPN keeps my internet connection safe when I’m on public Wi-Fi at airports, hotels, or cafés.

  
  

• Travel Europe by Train: I book through Trainline for easy tickets across Europe, including London, Italy, Spain, and France.

  
  

• Relax Before You Fly: Priority Pass gives you access to airport lounges around the world.

  
  

• Find the Right Stay: For vacation rentals, I like using VRBO.

  
  

• See the City with Ease: Hop-on, hop-off tours are a fun way to get oriented. Check out Big Bus Tours in Vienna, Rome, Berlin, Istanbul, and Dubai.

  
  

• Book Tours and Transfers: I often use Get Your Guide and Viator to arrange activities, tickets, and transfers in advance.

  
  

• Hotels, Cars, and Flights: Expedia is one of my go-to sites for comparing and booking travel.

  
  

Disclosure: Some of the links above are affiliate links. If you choose to make a purchase or booking through them, I may earn a small commission at no additional cost to you. These commissions help me keep creating and sharing travel content here on From Lawrence with Love. Thank you for supporting the blog!