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First thing on our New Year’s resolution list: making time for new experiences. The long weekend trip is ideal for when you can’t take time off work or you’re trying to save some cash.  But practically, we know that trying to fit everything in three days or less is tough. As avid-fans of the weekend getaway, we’ve put together the best tips we’ve learned after more than our fair share of quick trips. We’re here to help make sure you have time to do all of the sight-seeing and touristy things on your list, and most of all, maximize your time and money while getting in much needed time away.

Chicago, IL

1. Location is Key

When you’re going for a long weekend trip, time is valuable. Don’t spend too much of it traveling to your destination. Pick a place that is either a few hours drive or a short flight away (watch out for layovers and connecting flights) so that you can spend most of your time relaxing and enjoying the trip. Rumor has it the best time to buy airfare is 1.5 months in advance of your travel date.

But sometimes it’s fun to be spontaneous and hop in the car for a quick road trip. That’s what a long weekend is all about, right?

Make sure you also take the different areas of the city you’re visiting into account. If it’s a big city like New York that covers a lot of ground with different boroughs, plan to stick to one neighborhood a day to maximize your time.

High Line Park in Manhattan, New York

2. Prioritize Activities

If you’re visiting a new city, prioritizing what you want to do and see is a must. In a big city where you need transit from point A to B, you don’t always have time to see everything the city has to offer, but you can make sure you check off everything that’s at the top of your list.

Speaking of prioritizing, breakfast is said to be the most important meal of the day. Save time in your itinerary and have breakfast delivered to your hotel room. I mean, when else can you get away with drinking a mimosa in bed?

Quincy Market at Faneuil Square in Boston, Massachusetts

3. Have a Rough Schedule for Each Day

Loosely planning out each day will ensure you get everything you want out of the trip. Pick a few options for places to eat in the area you’re exploring, and choose what you’re in the mood for once you’re there. Everything doesn’t have to be planned down to the last detail—leave some time for going off the beaten path and being spontaneous!

Another tip: if you have any restaurants or destinations that are must-sees on your list, check into them ahead of time and make a reservation or purchase admission. Don’t miss out on that new restaurant you’re dying to try or that show you’ve been waiting ages to see.

Metro station – Washington National Airport, Washington, DC

4. Work Transit into Your Itinerary

When planning a quick trip, it’s easy to book activities back to back and forget to factor in travel time. Make sure to account for train and subway rides, Ubers, taxis, and other transit delays that might occur. We recommend you do as the locals do! Hop on the subway, hail a cab, or travel by foot if you’re looking to really take it all in. If where you’re headed is close, you might spend more time trying to catch ride than if you just set out on a walk.

Bonus tip: Most popular places have a recommended route and optimum form of travel for different areas to help you get where you’re going the quickest and most convenient way.

Omni Nashville Hotel in Tennessee

5. Use Where You’re Staying as Home Base

Wherever you stay will be your starting and ending point, so plan your day around this and use it to help you come up with an itinerary so that you won’t have to spend time doubling back.

When looking for accommodations, make sure you evaluate walkability, transportation options, and on-site amenities. Full-service hotels make for a great long-weekend choice so that you have everything you need in one place and can just focus on enjoying yourself.

Reunion Tower – Downtown Dallas, TX

6. Do Your Research!

Arguably the most essential part of planning the perfect long-weekend trip is the research you do ahead of time. Looking up hours of operation, purchasing admission to attractions in advance, and knowing which apps to download to help you around the city can go a long way in planning and prioritizing parts of the day.

San Francisco, CA

7. Take Recommendations from City Natives

No one knows a city better than a local. They have insider knowledge on the best way to get around the city, lesser-known local hot spots, and more. Most inhabitants will be happy to share their city with you! Quick tip: be brief with your questions. Instead of explaining “I’m from out of town and it’s my first time here…” Say “What’s your favorite place to eat at in the city for a quick bite?” Hotel concierges can also be a great resource.

Locals are more likely to give you the best recommendations that you can’t find on Google. Skip the chain restaurants and enjoy the local flair of the city!


8. Pack Light

Capsule wardrobe, anyone? This tip is especially important if you decide to fly. Skip the baggage claim wait and carry on. One of our favorites is recommended here. Only bring what you need for the planned activities, and don’t forget comfy shoes! Depending on your plans, exploring the city is probably on the list and hitting that 10,000 step goal is basically a given.

Pro tip: Use a clothing rental site like Rent the Runway and have your outfits delivered to your destination. No carry-on necessary. Just drop them in the mail on your way out of town, or your hotel can take care of shipping them back!

Now what are you waiting for? Get that trip on the calendar. As they say, “Any time is the best time for a weekend getaway.” And by they, we mean us. If you aren’t into all the details, we’ve done the work for you and crafted 48-hour city itineraries with the help of our local concierges. Happy planning!