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Best Deals for Your Next City Trip

City Trips: Find Your Perfect City Break

Ahoy pirates, are you already dreaming of your next vacation but don't want to travel too far, spend crazy amounts of money, or stay away for longer than a few nights? Luckily, we always have some cheap city trip deals for you!  You can even find domestic city trip hotels for less than $100​​​​​​​, especially if you are looking for a great value last-minute vacation. Whether, you're planning a trip to the 'Big Apple' or another big city on the East Coast, like Washington DC or Miami. Or if you're venturing over to the West Coast and exploring the hilly city of San Francisco, or want to live like the stars for a day or two in Los Angeles and Hollywood, we will find the best deals for your trip to bustling metropolises around the globe. Check out these other destination pages for inspiration for your next trip.

The Most Popular City Breaks in the world

City breaks are welcome breaks from the stress of everyday life and are not as time-consuming as traveling halfway around the world. Usually, 3-5 days are enough to fully absorb a city and get to know all its corners. If you want to explore domestically, for example to New York, San Francisco, or New Orleans. or if you are looking to travel further out to Singapore or London - then simply combine the city trip with a small road trip or a round trip.

You're also never alone in the city–there are few better opportunities to meet new people or plan activities with friends. There's always something going on! Since you only need about 3 days for the average city trip, city trips are ideal for long weekends through the 2023 bridge days - save vacation days and still get the most out of them!

City Break Packing List: What to Bring on Your Next City Trip

It's the night before your vacation, you're standing in front of an empty suitcase and you haven't a clue of what to put in it. How often have we gone on a trip and then noticed that we’ve forgotten something important? Or come back from vacation and realized that we packed 20 lbs of stuff we didn’t need? To make sure that this doesn’t happen on your next weekend away we've put together the ultimate packing list for your next city break.

1. Tickets, Money, and Documents (and, Of Course, More Documents)

The important stuff. You can’t board a plane without a proper ID card or take a trip out of the country without your passport, and you can’t buy a coffee in any city without a bit of money. Here’s a tip: always bring your IDs and documents with you. If you don’t feel comfortable bringing the originals with you, take a photo of them or have a PDF scan on your phone. Just make sure a stranger isn't able to unlock your phone.

  • Credit card/Debit card

  • Cash (foreign and domestic)

  • Phone number of your bank if you need to lock (or unlock) your card

  • Consider bringing a bum bag to keep all your things in (all the hipsters are doing it)

  • Student card (if you have one)

  • Health insurance card and, if necessary, proof of health insurance abroad

  • Any medical prescriptions (in case you need them)

  • Train ticket or plane ticket

  • Hotel confirmation (with the address on it)

  • Visa (if required)

  • Maps if you need one—I’d recommend downloading an offline map of whatever you’re visiting

2. Toiletries

For toiletries, of course, it's all about what you need and what you use—everyone has their own routine. We've listed a few basic things that most of you will want to carry in your luggage. But no matter what you bring with you, please remember that in your carry-on bag you can only carry bottles with a capacity of 100 ml and you must put them in a transparent zip bag. Don’t be that person in the security line.

  • A zippered toiletry bag

  • Shower (shampoo, conditioner, shower gel)

  • Razor (the disposable ones usually make it through security, but double check w/ your airline to make sure)

  • Deodorant

  • Toothbrush and paste

  • Moisturizer (hand, face, body)

  • Sun protection (We’re pirates against skin cancer. Check here for some tips)

  • Lip balm

  • Cotton swabs

  • Brush/comb

  • Hand sanitizer

  • A towel (best ones are microfibre towels - they dry quick)

3. Clothes

Most of us often take too much in your bags. Pack only the bare essentials and spare yourself the unnecessary weight. Most city breaks are for a weekend or a little more, but even if you are travelling for more than a week, you often do not need more than a few days worth of clothes. No matter where you are in the world, you'll almost always have the opportunity to wash - even if it's only in a hotel sink. Your wardrobe may vary depending on the season, but make sure you always wear comfortable, broken-in shoes!

  • Trousers, shorts/skirt (or a kilt if you’ve joined the tartan army)

  • Belt (if required)

  • 2x T-shirts and long sleeve tops

  • Pullover (worth having for a cold flight)

  • Rain jacket

  • Underwear

  • Socks

  • Pajamas

  • Sunglasses

  • Hat (For warmth in winter or to shade the sun in summer)

  • 2 pairs of comfortable (!) shoes

  • Flip-flops (for the shower or the beach)

4. Cosmetics & Utensils

  • A hair scrunchy

  • Make-up and make-up remover

  • Feminine hygiene products

  • Contact lenses + accessories

5. Travel Items

  • Sleep mask

  • Water bottle you can refill

  • Combination lock for your luggage (especially important if you are in the hostel)

  • Book or magazine (Here’s some inspiration)

  • Glasses (if you need them to read your new book)

6. Technology & Accessories

Technology make seem like a luxury but having Google Maps on hand is an essential part of any city tripper's itinerary for a weekend break. Avid amateur photographers will also want their camera on hand. Charging these devices is also of course necessary, so make sure to bring an adaptor if it's needed.

  • Mobile phone + charger

  • Powerbank + charging cable (Definitely recommend for longer trips)

  • Headphones

  • Adapter for the socket

  • Camera + battery, charging cable u. SD card

  • Possibly laptop or tablet + charging cable

7. A Travel First-Aid Kit

There's nothing is worse than being unwell while travelling, so pack a few medical essentials for your trip. What you need depends, of course, on your destination and the season (for example, if you need mosquito spray). But first think about your individual medications, especially those you need to take regularly.

  • Personal medication

  • Wound and blister plaster

  • Pain and fever remedies

  • Something to calm a gippy tummy

  • Allergy pills (possibly nasal spray and eye drops)

  • Ointment

  • Mosquito repellent

The Best City Breaks for a Romantic Weekend

Paris is arguably the most iconic destination for lovers looking for a romantic escape but have you ever considered a city break to Florence? The Galleria dell'Accademia houses Michelangelo's David, which is just the start of this city's artistic offerings. Stroll hand in hand through the piazzas as you enjoy some gelato and see the Arno River at sunset.

Buenos Aires is often said to have the most European feel of the South American capitals. Explore the trendy and colourful La Boca neighbourhood and admire the gorgeous buildings in Plaza de Mayo. Or head to the medinas of Marrakesh. The vibrant markets and splendid architecture, such as the 19th-century Bahia Palace, set the stage for a culturally rich and romantic city break.

Or how about a visit to Venice? Wander the eternally romantic canals or splash out on a private gondola ride, admiring this city's famous bridges as you soak up the views. Kyoto is another top choice; visit during March and April to see the world-renowned cherry blossoms before heading for a relaxing onsen (hot spring) session.

Even More Inspiration