I’ve talked before about how important it is to be flexible and open to new ideas when planning a trip. Travel has a funny way of throwing you lemons, and life is much easier if you can roll with punches. In this post, I’m sharing how I finally came up with a plan for one week’s holiday in the Northern Hemisphere. In the end, our trip looks very different to how we envisaged, but I’m so excited for it! Hopefully sharing this process will help give you some ideas of how you can overcome your own travel obstacles when planning your own adventures!

My boyfriend & I are going to New York in late August till early October, because he has a training program to attend for work. After his training finishes, we have a week off together!

Planning a trip from scratch, with zero criteria can be overwhelming. We had a few criteria which we were trying to meet, but in the end we had to really think hard about what was most important to us and be flexible.

CRITERIA

Not too far from NYC

We had to fly out of NYC, so we didn’t want to waste unnecessary time or money on longer flights.

Sunshine & Beaches
This was the dream. Spoiler Alert: This is difficult in October in the Northern Hemisphere

Affordable
We have a budget of less than $100-200 per night. Ideally, way closer to $100, but we found we were going to have to be pretty flexible if we wanted to be comfortable and conveniently located on an island. Such is life.

Developed enough for creature comforts 
The purpose of this week was to recharge after a draining year, not to be doing adventure travels, so our digs mattered!

…without being over-developed
While my boyfriend was planning to spend every day relaxing by a pool or beach, I wanted to visit somewhere that wasn’t too over-developed. I wanted to explore somewhere that was different to places I’ve experienced before, with a local culture that is alive & kicking, not masked by tacky, touristy developments.

Plan A: Maui

Our first idea was Hawaii. We’d heard the Waikiki area could be super touristy so we set our sights on Maui.

Unfortunately, the accommodation we found was ridiculously over-priced, even for very daggy accommodation. Since this week is about relaxing, not frantic sightseeing, we wanted a room we’d feel happy and relaxed spending time in. I was quite disappointed to find that the rooms in our price range ($100-$200 per night) looked like they’d been plucked out of 1980s middle America and not a beautiful Hawaiian island.

If that was the only issue, maybe we’d have gone to Maui. But since it’s also a 10 hour flight to and from NYC, it would eat into our week off together, not to mention be quite an expensive flight. Also, we’d fly into Honolulu and then need to get extra transport to Maui. It wasn’t feeling right, so we decided to keep looking.

Plan B: Bermuda

I started finding out as much as I could about the Caribbean. I thought we’d found the perfect place when I saw Alex in Wanderland’s gorgeous photos and posts from her trip to Bermuda, barely 2 hours from New York! It ran the risk of being a little touristy, but it looked beautiful.

Unfortunately, Bermuda is very expensive! We couldn’t justify the price at this point in our lives, so kept looking. As it turns out, lots of Caribbean destinations are crazy-overpriced.

Plan C: Curaçao

Finally, a destination we could afford! Stunning beaches, a reasonable level of development and Willemstad has a gorgeous old town. I read about Curaçao on C’est Christine, and within 24 hours David & I had decided this was it. This tiny island in the Dutch Antilles is near Colombia, but is “owned”  by the Netherlands.

Everything was perfect…except the flight schedule. The only direct flight we could get was 2 days after we arrived. There were no other direct flights which would get us back to NYC in time to make it on our big flight home. The indirect flights took a stupidly long time (around 7-10 hours from memory). Indirect flights mean more opportunities for delays and lost baggage and more time wasted at airports and in the air.

Plan D: Miami

We started to look for beaches within the US. I’d love to go to California, but the western USA will be another trip one day. This time, we were sticking to the east.

Miami is obviously very developed, but it has pretty art deco architecture, nightlife, beaches, and cultural influences from Latin America. Sounds cool!

So close, yet so far. This time, the wet season is working against us.

Hurricane season isn’t a major issue this year but October is one of the wettest months of the year. Beach destinations are rarely fun in the rain so we threw in the (beach) towel and went back to the drawing board.

NEW CRITERIA

Clearly, we needed to re-think our plans to find a balance between what we wanted and what we could have. What was important to us?

It came down to spending time together and enjoying a slower pace. At the end of the day, if we were together we’d have a good time. So we came up with some new, easier, criteria for a relaxing holiday in a new part of the world (to us).

Instead of beaches in October, we’re going to the Gold Coast after Christmas this year. Living in Australia, it seemed a bit silly desperately seek beautiful beaches when we have them on our doorstep.

Walkable, ambient cities 

We wanted to enjoy a slow place in places where it was enjoyable just to walk through the streets.

Decent food & bar scene

Eating and drinking is one of the things David & I do best. Lazy days spent wandering interspersed with delicious meals and drinks is the next best thing to relaxing on a beach.

Eastern half of the US

We still want to keep our flights on a budget, and not spend too much time in the air.

THE SOLUTION! New Orleans & Charleston

We decided if we were staying in the states, we’d go to two places for  3 nights each. We thought a week was a bit too long time to spend in a mid-sized city, particularly when the US is a long way from Australia and is full of diverse cities we really want to go to.

New Orleans

I’ve spoken to so many travellers who have said New Orleans was their favourite destination in the US. While there are some safety issues (I’ve heard really strict warnings on areas to avoid), it seems like a beautiful city full of history, culture and a lot of fun! We’re hoping to stay in the French Quarter, which is full of romantic boutique hotels.

New Orleans is famous for mouthwatering cuisine and insane nightlife. For more New Orleans nightlife inspiration, check out this post, which has great hotel bars that are firmly on my to-try list! This vibrancy was a big part of what attracted me to New Orleans.

Charleston

Another gorgeous Southern city, Charleston & Savannah have been in my sights for a while. David has wanted to go for to Charleston for a long time, so this one was a no brainer. I’ve heard the food scene is great, it looks like a really pretty place and there are even some beaches on the outskirts! It’s also much sunnier than Miami at this time of year, but if it does rain, I expect there will be more to do indoors.

Phew! Holiday = sorted. I’m really looking forward to the time off with David & experiencing these two cities. This process was very frustrating, but I kept reminded myself that travelling by choice is a privilege. Every day people are “travelling” to flee persecution, war zones or natural disasters. The frustrations that come with planning a holiday are just the flip side of a very fortunate coin.

Have you had to change your holiday plans? How did it work out?

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