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The anatomy of a great trip – Top 10

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oesn’t matter if you put a giant boulder or a hundred beer bottles in a river, give it enough time and all will end as small pebbles; rounded and smooth with all the hard edges worn off.

This holds with travel. Whenever you can smooth off the rough edges you end up with a better trip. Throwing money at it can help to a large degree, but doesn’t totally solve the situation.

Here’s my list of 10 things that help create a smoother trip.

1. A great destination

This might seem self-evident – but, If you end up in the middle of no-where, with nothing to see, it’s almost impossible to make it a good visit of it. Some places just don’t lend themselves to a great vacation due to poor infrastructure and lack of things that most travelers might want to see. Somaliland and Djibouti spring to mind. If you end up with a top-end hotel you can have a good resort stay, but the destination is everything. I’d much rather have a dirt-cheap hotel in Fiji than a beautiful resort in Mombasa. Sometimes cheap fares can lead you to places you never wanted to go like Brunei when spending a little more at the outset would get you someplace memorable – like Bali.

2. A posh hotel

The best hotel is a comfortable one, a large room, soft bed, extra pillows, minibar, pool, blackout curtains, hot water, and a deep tub to take a bubble bath in and cold air condition to hide from under the covers. A little style never hurts either, design hotels have an edge, especially when they offer branded amenities instead of the single push-button soap/shampoo dispenser on the shower wall. Doh!

Hotels with either unusual locations (on stilts over the ocean, up a mountain, in a tree, made of ice, Petra bubble hotels or Japanese capsules) or in the heart of the nightlife action also are great. A staff that understands how to deal with their guests efficiently and politely and go the extra mile to make things right.

A great bathroom that’s completely separate from the bedroom space is a must for me. Nothing is worse than an open window to the bedroom. Or your travel partner hearing every noise you make in the facilities.

3. Money to spend on the smaller niceties

Sometimes a good trip can go bad through death by a thousand cuts. If you can smooth out the smaller stressors the trip will be less taxing and more enjoyable.

Things like:

  • Having a limo waiting at the airport rather than trying to fight the system to find a train or bus into town or negotiate with the local taxi mafia.
  • Upgrading to a better seat class on the plane, not something I normally do, but what a huge difference it makes on long flights
  • A good travel kit for the plane, quality luggage, all the gadgets, and accessories to make a flight easier – movies on your iPad, games, and audio-books on your phone, etc.
  • I bring my fave pillow on long flights, and always book the window seat, so I can lean against the window and pretend I’m home in bed
  • A prescription for sleeping meds to make the long flights disappear if you’re so inclined.

4. Activities for the body

  • Private tours or small group tours that can take you out of the city center and let you see more of the countryside or a special place.
  • Outdoor activities; winter sports like skiing, tobogganing, ice-skating, or summer ones like swimming, hiking, or just bumming around in the beach life
  • Pick-up and drop-off tours that don’t require you wearing yourself out just to get to them. Trying to desperately find your way to a meeting point for a tour at 7 am in a strange city is never fun.

5. A few luxuries

  • Usually the better class of hotel the more luxuries you’ll have surrounding you. Places in the hotel or nearby that offer upscale dining, drinking, and entertainment
  • Eye candy and design for the soul – Infinity pools, well-designed gardens, hotels that overlook the ocean or have private pools per room.
  • Authentic or artisanal experiences that get you off the bus-tour trail and into the reality of the city you’re visiting
  • Curated itineraries with personal tour guides to make the most of your time and see exactly what you’re interested in. Be it museums or shopping.
  • A large enough hotel room so you and your partner can have room to relax without being in each other’s eyesight all the time. If I can afford a 1br I always get it.

6. Activities for the senses

  • Food walking tours are a great way to flood your senses with new tastes and combinations
  • Massages, especially good (and affordable) in Asia
  • Spas and spa treatments. From mud baths to hot stones to facials.
  • Art, museums, galleries and hunting down street art. If you end up in Paris and see 6 museums in two days they’ll probably end up a blur. Same goes if you try to see too much of a large museum. If you go from Egyptian art to Post Impressionism – you know your brain is bleeding.

7. Find a home bar

Nothing beats a great bar to chill out in, good bartenders with innovative drinks or just a good beer menu always help. Microbrews are fun, but just finding the best local brews that everyone else is drinking is perfect. I tend to go back to the same bar repeatedly during a trip – after a long day of sight-seeing having a few drinks in a place I recognize is relaxing.

8. Time

A very short trip is rarely a good one. A single day in a country is never going to allow you to see everything. Or if you can somehow fit it in, it’s sure to add stress.

For me, three days is a minimum to get in, see, and relax into a city, four even better. More than a week and I get antsy to move on in most places.

Sometimes a luxury is just laying in bed for a full day, either recovering from the night before – or just to decompress from the pressures of long trips.

9. A relaxed itinerary

  • When I travel I try not to book any flights or trains before noon. This allows plenty of time to sleep in and not have any 5 am wake-up calls to race get to the airport
  • Close connections, if you can avoid flying and take trains to your next destination it makes an easier trip as your hotel will often be close to the station.
  • Staying close to things you want to see or nightlife activities
  • Not over planning your trip. I tend to use Google Maps and go Pin crazy with restaurants, sights, bars and then once I’m on the ground I just open the map and look for what’s nearby. Traveling across town to get some food is rarely worthwhile.

10. A good travel partner

When you’re having a bad day your partner should either know how to cheer you up, or give you some space and let you relax. Sharing similar interests and likes also helps – if they like adventure parks and you’re terrified of rides, or you like museum art and they want to sit in a bar all day – you’ve got a problem.

  • Ability to compromise on things like dinner. You’re both in a foreign place and maybe one of you feels more comfortable trying out new food while the other has had a long day and just wants known comfort food. This is a time to compromise.
  • Having a partner with similar energy levels. I like to photograph so tend to go out in the morning with the best light, come back to the hotel in the heat of the day and then go back out in the evening.
  • Lastly, a good drinking partner. Nothing is worse than traveling with someone who isn’t into a few beers or cocktails during a night out. A drinking buddy can last a lifetime.

There are plenty of other items to add to the list, this is just a short primer of how I like to travel towards the end of long trips when I already am starting to get stressed. It’s the small, nice, simple pleasures that reduce friction and transport you effortlessly into the next destination.

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