Travel with style: Tips for dressing, sight-seeing and more

Stylish men on vacation

Travelling in style seems like it should be easy, yet we’ve all had at least one “vacation” that was left decidedly unstylish (and uncomfortable) by a nightmare of extra luggage fees, last-minute shopping or truly bad restaurant experiences. To ensure your next vacation is both stylish and smoothly planned, consider these tips for streamlined packing, stress-free shopping, and enjoying the local atmosphere of your destination.

The Pros and Cons of Packing a Single Bag

Travel with style carrying a single bag may seem impossible, simply based on your itinerary and the variety of activities you have laid out: a semi-formal evening dinner one day, poolside activities another, and a hiking excursion on another day. If you have a wide variety of activities on your travel list, it’s better to be honest with yourself about your packing needs and take that extra bag, rather than find yourself missing something crucial while en route and be forced to pay extra for a replacement item that you probably won’t even need once you return home. You may also assume you can find an item while at your destination and come up empty-handed, which could cripple your plans.

That said, vacationing in style doesn’t necessarily mean packing two bags; there are probably quite a few items you can do without, even with a varied itinerary. At many destinations, you can rent the gear for adventure outings instead of packing it along, from swim gear to hiking boots and parkas and more. While gear rental charges can be high, you may be able to get a discount through your hotel, and they may be preferable to the expense and hassle of lugging heavy accessories on your trip, particularly if you plan on hitting multiple destinations in a short span of time and wish to minimize your airport hassle as much as possible. Call ahead and find out if this is an option so you’ll know just what you need to pack and what can be left at home.

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How to Travel with a Single Carry-on?

Taking the above into consideration, many fashionable travelers have found that vacationing in style with no more than a carry-on is a perfectly attainable goal. Your travel experience will be certainly be much more enjoyable without the hassle and expense of checked luggage. There are some things that can make packing a carry-on easier and maximize your room.

First, plan your outfits from the shoes up. It’s easy to vacation in style with some smart outfit planning; you may be able to get away with a single pair of stylish shoes (such as a smart pair of brogues or leather drivers) for the entire trip, and wearing them on the plane frees up a great deal of luggage room. If you do pack a second pair of shoes, such as a pair of fancier dress shoes for an evening meal, pack them in the bottom of the bag and fill them with accessories (ties, jewelry, a scarf) to make the most of that space.

Likewise, you may only need one sport coat for the trip, and can wear it on the plane. In cooler months, lightweight cashmere or wool scarves and cardigans can add warmth without taking up too much room in your bag. Try to color-coordinate your clothing items so they can easily be mixed and matched, and pack thin layers to adjust to fluctuations in temperature as opposed to taking bulky sweaters or coats.

Travel with Style and Comfort

Men stylish travel

Vacation days can tempt you to look just a little too casual, but vacationing in style and comfort is possible. Chinos, colored slacks and tailored shorts are all great; cargo shorts or baggy denim pants are not. In warmer months, polos, lightweight button-downs and fitted t-shirts are presentable; baggy t-shirts, tank tops and anything with a slogan should be left to the gym. In cooler months, look for chambray shirts, cardigans and scarves to add warmth without bulk.

As for shoes, a nice pair of drivers or brogues can take you through most events; a very stylish pair of luxury sneakers is a good alternative for sportier vacations, while fashionable boots are good for colder months. A linen blazer or one made of a colorful cotton/wool blend is casual enough for vacation that it won’t look like office wear, but it will still pull together an outfit and make it clear you’re not letting yourself go just because you’re on holiday. You can also use it to easily transition from daytime to nighttime: wear a tailored pair of shorts or slacks, a button-down, a fedora and drivers during the day for touring activities; slip on the blazer and lose the hat at night, and you’re ready for drinks and dancing. If your vacation leans more toward the sporty/adventure side, you might swap the sport coat for a smart-looking leather bomber.

Finally, don’t forget to pack extras like a nice belt, a good watch, and a stylish yet rugged shoulder bag for day trips. You’ll probably be using these on the plane, so they won’t even take up room in your carry-on.

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How to Deal with Souvenirs?

If you plan on shopping at your destination, you have a couple of options for taking your goods home. Some shoppers opt to have purchases shipped home, while other items can simply be packed in a carry-on. It’s wise to plan ahead and consider the type of items you’ll be purchasing; if they’re very bulky or too fragile to pack well in a duffel bag, you might be better off paying to have the item properly packed and shipped home. You’ll need to check with a local postal office for shipping policies and costs, and to be sure you have the proper packing materials needed to give your item a safe ride home.

If you choose to take your purchases home on the plane, you might want to pack a duffel in one of your main bags for holding holiday souvenirs, or purchase a bag at your destination. Remember that some items may not be permissible in a carry-on bag, so you’ll have to pay a checked baggage fee for your extra items. Small items of clothing and the like can probably be easily packed with your existing luggage, and as an added bonus, you can wear them at your destination, upping your vacation style quotient with a little local flair.

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Planning Your Itinerary

Some vacations are all about the thrill of discovery, and there’s no set plan for each day; you simply enjoy each morning as it arrives and plan your entertainments as you find them. While these vacations are often relaxing and enjoyable, you may find yourself missing out on fun and interesting events if you don’t plan ahead. Even if you aren’t keen on crafting a formal day-by-day plan for your trip, do check up on local entertainment listings and schedules to see what’s up for offer during your stay. Not only will you be clued in to can’t-miss events, you may also learn of closures that could affect your plans—not something you want to discover at the last minute.

With that being said, beware of over-planning. Many tourists make the mistake of zealously overstuffing their schedules, only to burn out before the end of the trip. Allot no more than one or two scheduled excursions per day, and allow yourself plenty of time in between them in case of traffic or in case you have to return to your hotel for something (a change of clothes, minor first aid, etc.). Try to leave at least one unscheduled day at the end of your trip to simply relax before you head home. This will allow you time to mentally and physically unwind before the trip home and will prevent you from feeling too harried when you return home and have to jump back into your daily routine.

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Hitting the Local Scene in Style

Vacationing in style doesn’t just mean dressing well; it also means you’re enjoying the best of what the local area has to offer. Your hotel is a great starting point for scoping out the best local hotspots for food and entertainment; it can also help provide the amenities of home that you need for a more comfortable stay. For example, many hotels offer on-site gym facilities for patrons, or they may be able to score you a deal on a day pass to a local gym; ask at the front desk. They can also point you to local deals for everything from restaurants to dry cleaning; a discreetly tipped concierge is a valuable source of information on where the locals prefer to do business, and may even be able to point you to some valuable discounts while in town.

Be sure to ask: where do the local residents dine, shop and play? Whether you’re traveling at home or abroad, well-worn tourist hotspots tend to be more expensive and don’t offer the same local flavor. Asking a local insider where they like to relax can lead you to hole-in-the-wall pubs and markets off the beaten path, where you’ll get to sample local fare and have a more immersive experience than if you simply stayed in the city center. You should also check online or in local publications for art shows, live music, restaurant reviews and more that might not be widely publicized through major tourist websites or brochures.

Hope you enjoyed these tips to travel with style!

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