7 Tips for Planning a Big Trip

Planning a long trip can be daunting. With flights, activities, accommodations and meals to plan, there is a lot that can get in the way of your dream vacay. Here are my tips and tricks for organizing the perfect trip this year.

Step 1 – Pick a theme

Is this going to be a lazy lay-on-the-beach type of trip or a lets-see-all-the-sights trip? Either way, start the planning process by coming to a consensus with your travel companions. Everyone should be on the same page from the get go.

Step 2 – Flights

Once you know what the goal of the trip is, decide where to go! Whether, you want to stroll the streets of Paris searching for the perfect croissant or see a show in London’s West End, usually the earlier you book flights the better. My go to site is Skyscanner, you can search specific dates, but with an open-ended location, which is perfect when you need some inspiration on where to visit. Also, you can set price alerts on specific routes that will alert you if the price goes up or down.

Step 3 – Hotels

Major views: View from our balcony at the Palace Lucerne

After you have your flights booked, the next step is choosing your hotels. The main consideration to take here is location. Pick a neighborhood you want to explore and find a hotel within your budget there. My typical requirements are: recently updated furnishings, a great view and a reputation for attention to detail. And if you are traveling to multiple cities on one trip, maybe go out of your comfort zone in one or two of the cities–pick a funky new boutique spot rather than your go-to chain for instance or if you will have a car, maybe try a spot out in the countryside rather than in downtown.

Step 4 – Activities

Planning a trip is like life, if you focus on the big things the little things will take care of themselves. So unless you have a must must must activity on your list, don’t plan any activities or meals until you have your hotel and flights booked because what if you find a great deal on the Intercontinental but you planned all your dinners across town near the W?

Don’t discount hotel restaurants either. Many hotels in Europe have Michelin starred chefs.

All that back and forth is really going to harsh the vibe of the trip. The best lesson I have learned from my frequent travels over the past few years is that if you have a great hotel in a great neighborhood, whatever meals you end up eating and whatever activities you end up doing will be a lot of fun. Don’t get paralysis by analysis, narrow down your choices after you have the big decisions made.

Step 5 – Packing

Now that you have your trip planned, it’s time to start packing. Again, start with the big things and end with the little things. Do you need a killer evening gown or a chic tux for that big gala you are attending abroad? Find those items first, so you don’t run out of time and have to stress about over night shipping the day before you are set to leave. Pro tip for all the guys in your life: need a custom tux quickly? Order a made to measure tux or suit from Snap Suits and in 14 days one that fits like a glove will arrive on your doorstep.

Tux by Snap Suits

Also, for any special outfits you are bringing, don’t forget to keep in mind how you will pack them. For example, I brought this absolutely gorgeous 2-piece outfit from Graciela Rivas’ “Waves” collection with me on our recent European tour not only because it was made for Europe in the spring, but also because it is made out of the very wrinkle proof neoprene. And as you can see, I was wrinkle free (seriously no ironing required).

Step 6 – Pre-Trip Appointments

If you are going on an extended trip (anything over a week), really think about any appointments you may need to make in order to prep for the trip. Think about: doctors appointments, hair cuts, mani/pedis and if you are going somewhere warm perhaps a sunless tan!

For all my Bostonians out there I am obsessed with G2o for all my mani/pedi needs, in fact you can now get OPI Gel for a look that will last 2 weeks!

A gel mani is a vacation must!

And I recently tried Skin Spa New York’s organic sunless tan, and I was absolutely Lake Como ready last week!

Loving my sun kissed look at Casta Diva Resort and Spa on Lake Como last week!

Step 7 – Be Flexible

This is probably the most important tip of all. Use planning to take the stress out of the trip, not to add to it. For example, do not plan every minute of every day. Plan the big things like splurge worthy meals and excursions and buy tickets to museums in advance. But do not map out the exact route you are going to walk to lunch. Allow yourself to be spontaneous. I plan  so I do not have to worry, I do not worry about the plan.

10 thoughts on “7 Tips for Planning a Big Trip

  1. Awesome tips babe!! Wish we read your tips earlier ~ now my hubs is still planning for our big trip (we’re flying off in 2 days’ time) 😂 hope everything goes well and if not, your Step 7 will come in super handy *fingers crossed*

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  3. Amazing tips! I agree on the first one, it is indispensable to agree on the type of vacation with your travel mate. My hubby is all for “lay down, do nothing, another mojito please” type of trip, and I am like “we only walked 20 miles through the city today, tomorrow shall do more” LOL
    So we usually book two big trips per year with those different scopes!

  4. If I’m in a good mood, I’m the best at planning trips. But right now I’m going through a little bit of a rough patch and I forget things! I’m trying to plan a trip right now and I can’t even get past your first tip!

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  6. I love planning trips and the most I love checking tips on restaurants:) Its such a big part of a good time so I spend definitely few hours to check where and what to try, so you dont fall into a tourist trap:)
    xoxo Sharka

  7. I like what you mention about the big activities being the priority when planning for a trip. It makes sense that planning out every little thing might be stressful and overkill. I’ve been wanting to take my wife on a trip and although the main focus of it would be to take pictures for her new found photo passions, I think letting the little things play out when we get there could make it much more stress free.

  8. I didn’t realize that being flexible on your vacation can help you relax and not worry so much about a set schedule. My wife and I are going on a trip to New Zealand in a few months. Hopefully, we can use these tips to make our trip a very special one. Thanks!

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