Painless Planning: How To Create The Perfect Itinerary For A Weekend Trip

BY LILI SARAJIAN

While international travel is still a distant daydream, there are a few feasible ways to get away from it all like road-tripping and staying in rental homes to avoid crowds. Or, if you’re like me, you can get your fix by wistfully planning weekend trips that will, maybe, hopefully, happen down the road. After planning a three-day trip to Austin, TX, I realized there’s a real art to doing the weekend vacation well. Factoring in travel time, transportation, and, of course, sleep, you’re left with a lot less than 72 hours. But after taking many mini trips to cities like Portland, New York and Boston, I’ve come up with a rough formula for how to best explore any city in three days.

First, here are some general tips for making the most of any short vacation:

• Arrive early on day one and leave as late as possible on day three

• Try to prevent travel fatigue or jet lag by staying hydrated and sleeping during the flight (or taking turns with another driver during the car ride)

• If you’re staying in a hotel, contact them ahead of time to see if you can check your bags in early

• Pick out a few sites, activities and restaurants that you want to try before you arrive so that you don’t waste precious time deciding what to do when you get there

• Take pictures! While it might seem like you’re detracting from the journey by stopping to take pictures, finding the perfect spot for a photo shoot can often lead you to the best places in the city and you’ll appreciate looking back on the memories

• Consider renting an Airbnb or doing a house swap to get a more authentic feel for what it’s like to live there

With that in mind, let’s travel!

Day 1

The first day is crucial to setting the tone of your trip. It’s a fine balance between slowly adjusting after a morning of travel and making the most of your limited time.

After you reach your destination, I would recommend dropping off your luggage, freshening up, and then heading right back out the door for a casual, self-guided walking tour of the city.

Taking a stroll around the city right away will quickly immerse you in the hustle and bustle, the sights and smells, and the overall flow of life in the city. Walking can also help you brush off some of your travel fatigue while giving you an opportunity to get your bearings for easier navigation later on. Plus, traveling on foot can help you figure out which places are popular without Google’s help. You might even find a hole-in-the-wall that only locals know about!

After all that walking, you’ll undoubtedly be ready for some food. Here’s my top tip for first-day eating: start with what that city does best. If you’re in Philadelphia, eat Philly Cheesesteak; if you’re in Maine, you’d better try a lobster roll. I see no reason to save the best for last! You might as well set your standards high and keep them that way if you’re only there for three days. To cap off your first night, find a scenic location to enjoy the sunset and whatever irresistible dessert calls your name. Feel free to retire a bit early, because tomorrow will be a big day!

Day 2

For any three-day trip, set aside the second day as your “busy day” because it’s your only full day in the city. This is the day for crossing off as many of those mustsee places and must-do activities as your heart desires. To make the most of day two, get up early—and I’m talking like 8 a.m. Wake your body up with a steaming cup of coffee and a light, but energizing breakfast. Then, while the morning is still fresh, find something active to do like kayaking or yoga on a nearby beach. Refreshed from your morning activity, it’s time to take a break and grab a bite to eat! One of my favorite ways to feel out a city is to visit a local market and grab some fresh food for a picnic. Pack your bag full of warm bread, cheese, cured sausage, berries, olives, nuts and whatever kinds of vegetables you like. Not only is this a delicious way to take in the city’s parks, but it’s also a fantastic opportunity for a little people-watching!

Now that you’ve refueled, continue crossing things off that bucket list. There’s no need to overwhelm yourself with a daunting list that you likely won’t complete, but it’s good to come prepared with a few places in mind— museums, monuments, scenic spots, vintage shops, bookstores, bakeries, gardens and the like. If the city is bike-friendly, cycling can be a great way to make traveling between destinations an activity in itself, or consider taking public transportation to get a feel for what daily commuting in the city is like. When you’re satisfied with the day’s excursions, find a spot to sit back and chow down. This is the perfect time to splurge on one of the more upscale restaurants that the city has to offer—after all, you’re on vacation! If you’re not anxious to hit the hay, check out the local nightlife scene, catch a show, take a late-night boat ride, or just find a cozy place to lay out under the stars!

Day 3

After yesterday’s endless activity, day three is the perfect time to slow down and soak in the city before you head home. A lazy, late-morning brunch full of sweet pastries, fresh fruit, and any-way-you-want-them eggs sounds to me like the perfect way to start the day. And don’t forget to visit that cute cafe down the road— the one that makes you feel like a regular—one more time before you leave. Sated and caffeinated, you’ve got a few solid hours ahead of you to play catch-up with any attractions or activities you missed in the days before. Or, my favorite way to spend the last day is by strolling around the downtown area, buying clothes and souvenirs that I definitely don’t need, and then finding a park or beach where I can spend a little more time relaxing in the sun before the stuffy plane ride home.

And there you have it! Now it’s time for you to pick a city and get to work. Happy planning!

ILLUSTRATION BY TRACY FU