Step 1: Research Potential Destinations

The hardest part of planning a trip? Deciding where to go! The key is to start with the basics:

• When are you going?
• How long are you planning on being gone?
• What activities do you want to do?
• What's your budget?

Answer these questions first, and the destination options start to narrow down. Google Flights is my go-to tool. You can read how to use it here. It provides the ability to search for flights by departure airport and explore destinations that are within your budget. This is an awesome tool if you’re flexible with your travel dates and open to exploring new places you hadn’t thought of before.

Step 2: Choose 2-3 Destinations & Do a Deep Dive

Once you have a few options, dive into the details. Let’s say you’re deciding between Maui, Puerto Rico, and Spain. Now it’s time to research things like:

• Flight and accommodation options
• Top activities and attractions
• What's trending (or hidden gens) on TikTok

When I’m researching, I look at blogs, personal recommendations, and social media to get the real scoop. If I see something mentioned more than once, I add it to my list.

I also create a comparison document (because who doesn’t love a good spreadsheet?) to weigh the pros and cons of each destination. Keep in mind, off-season travel can be cheaper, but it might come with some unpredictable weather.

Step 3: Pick your Top Destination

The decision-making process can be tough, but remember: if the destination doesn’t work for this trip, it’s not the end of the world! There will always be future vacations. Sometimes it’s better to visit a destination after it’s no longer the latest “hotspot,” which can mean better deals and fewer crowds. For instance, when we booked Bali, we jumped on it 10 months ahead—best decision ever!

Step 4: Book your Flights Early for the Best Deals

Now that your destination is locked, it’s time to secure those flights. The earlier, the better! I usually book 8 months ahead for international trips and 2-4 months ahead for domestic ones. Pro tip: Use the “watch price” feature on Google Flights to get alerts when fares drop.

Flying out of major international airports like Boston or Washington DC can often save you money on your flight. And don’t forget to build in some wiggle room to account for any delays or hiccups on travel day. Trust me, it’s worth the peace of mind.

Step 5: Secure your Accommodations

Once your flights are set, it’s time to find your home away from home. For longer trips, I like to split my time between a couple of different areas so I get the full experience of the region. Think: a few nights in a bustling city and a few more in a tranquil coastal town.

Whether you choose a luxury hotel or an Airbnb depends on your travel style. For more tips on choosing the right place to stay, check out my blog post on when to choose Airbnb vs. Hotels.

Step 6: Craft your Itinerary (but keep it flexible!)

I love to have a rough outline of what we want to do each day—activities, restaurant reservations, tours, etc., but the key is balance! I leave plenty of free time for spontaneous adventures or relaxation. After all, it’s a vacation, not a race.

I use a digital planner to organize everything, ensuring that no two activities overlap and that there’s enough breathing room between each. Trust me, leaving some unscheduled hours is the key to staying relaxed and enjoying the moment!

While some things can be done on the fly, certain experiences—like popular tours or reservations at highly sought-after restaurants—should be booked well in advance. Whether it’s a sunset cruise, a cooking class, or a day at a world-renowned spa, you’ll want to secure your spot early.

Step 7: Travel Insurance: It's a Must for International Trips

I know, I know—no one wants to think about the “what ifs” on vacation. But travel insurance is a lifesaver, especially for international trips. From flight delays to lost baggage and unexpected medical expenses, it’s always worth the small extra cost.

I’ve used InsureMyTrip for several of our trips and it gives me peace of mind knowing we’re covered in case anything goes wrong.

Step 8: Arrange Local Transportation

For domestic trips, Uber and Lyft are usually my go-to for getting around, but for international destinations, I always pre-arrange transportation. When we went to Rome, our Airbnb host set up a private car to pick us up directly from the airport—no stress, no confusion, just smooth sailing.

For our Bali trip, we pre-arranged transfers between resorts to ensure a seamless experience between each location. It’s all about comfort and reliability!

Step 9: Pack Smart and Prepare for the Unexpected

Finally, it’s time to pack! But remember: travel is unpredictable. So, while you should definitely pack for your planned activities, it’s also a good idea to be prepared for changes in weather or unexpected detours. A flexible mindset is your best friend while traveling!

Step 10: Jetset into the Adventure of a Lifetime!

The hard work is done, and now it's time for the most exciting part: your vacation is officially here! As you board that plane, you’re not just starting a trip; you’re embarking on a thrilling journey full of unforgettable moments. Let go, relax, and savor every second of this epic adventure. From new sights to incredible stories, you’ll create memories that will last forever and stories to tell for years to come! So go ahead, let the fun begin!

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