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How to Plan a 2–3 Day Weekend Getaway That Feels Like a Real Vacation
  • MM|
  • Tips
  • April 10, 2025

How to Plan a 2–3 Day Weekend Getaway That Feels Like a Real Vacation

As a working millennial, I’ve learned to treat long weekends and public holidays like rare currency opportunities to pause, reset, and slip away just long enough to feel renewed. These brief escapes require a delicate balance of planning and spontaneity, practicality and indulgence. When done well, two or three days can feel like a world away.

Here are my favorite tips for curating an effective 2–3 day trip because sometimes, 48 hours is all you need for a total reset.

Start With the Calendar

Your best friend? The public holiday schedule. Mark those long weekends months in advance and consider adding a strategic PTO day here and there to stretch your time. Booking early often means better flight prices and hotel availability, so plan ahead especially for peak holiday weekends.

Plan Smart, Not Rigid

You don’t need an hour-by-hour itinerary, but having a loose structure ensures you make the most of your time. I always suggest:

  • Early morning sightseeing: You’ll beat the crowds and the heat.
  • Mindless afternoon strolls: Perfect for getting lost in a city’s soul.
  • Evenings to unwind: A chic hotel bar, sunset by the water, or just a plush robe and a view.

Location Is Everything

Pick a hotel that’s centrally located—not just for aesthetics, but for logistics. Being able to walk to restaurants, markets, or sights saves time (and money) on transport. It also means you can pop back for a quick change, nap, or swim without a long commute.

My personal non-negotiables? A room with a view, a good pool, and if I’m beachside, easy access to the ocean.

Use the Tools at Your Fingertips

Technology makes short trips smoother:

  • Book transport ahead—shuttles, trains, even car rentals, so you’re not figuring it out last minute. The Rome 2 Rio app is your bestie in figuring out the best way to get around
  • Apps like Viator are good for booking excursions that have been reviewed and some companies in tourist cities even offer hotel pick up offer hotel pickups and can save serious planning time.
  • Google Maps lets you pin your must-visits—restaurants, shops, sites—so you’re not zigzagging across town.
  • Google Translate is your best friend when traveling to countries where you don’t speak the language. 

Eat Like You Live There

Skip the hotel concierge’s recommendations and dig into local food blogs or TikTok roundups. Look for that no-frills neighborhood spot with a line out the door and the chef who’s been making the same recipe for decades. I always mix it up, one must-try fine dining spot and one beloved local gem.

Know Your Travel Style

Tailor your trip to what you love:

  • I like a mix of culture and thrill with historical sights and adrenaline activities like a boat ride, cenote diving, or swimming with whale sharks (yes, I really did that).
  • I live for a golden hour moment. Sunset drinks with a view? Always.
  • Nightlife isn’t optional—I need to feel a city’s pulse.
  • And no trip is complete without a visit to a local market. There’s something about seeing how a place lives and breathes.

Short trips can be just as enriching as long vacations, especially when they’re done with intention. You don’t need two weeks to feel transported—you just need a plan, a sense of curiosity, and maybe a rooftop pool.

Also Read:

A Quick Getaway to Ajijic: My Weekend Escape to Mexico’s Lakeside Gem

Itinerary: 48 Hours in Washington D. C.

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Categories: Tips, Travel Tags: travel, Weekend Getaway, weekend travel

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