I live in an almost constant daydream state when it comes to travel.  I window shop on AirBnB, saving favorites from Bali to South Africa, with a dream trip to Portugal in pre-planning stages.  I’ve been known to send random texts from the check-out line in Trader Joe’s asking if anyone is down for a quick trip to Hawaii.  I have wish lists, multiple Pinterest boards dedicated to destinations.  I’m serious about this travel thing.  I’m also the planner in my group.  I dream it, then I go about planning the logistics.  If you’re looking to plan your perfect vacation and you aren’t sure where to start, this post is for you!

Whatcha’ Workin’ With?

If trying to plan your perfect vacation leaves you feeling a bit overwhelmed, start with answering a few basic questions:

• What kind of time do you have? (a long weekend? a week? a month?)
• What is your total budget? (this should include accommodations, transportation, and food/spending money)
• Who will you be traveling with?
• What type of vacation do you have in mind? (i.e., beach, adventure/active, food-centric, festival/holiday)

Grab a copy of this vacation planning worksheet and let’s start shopping for a destination!

Find Your (P)inspiration

Create a Pinterest board to collect ideas, itineraries and tips about possible destinations.  This will become your go-to for where to stay, what to eat and great tips about your destination from other travelers.   Lay on the beach for a week with umbrella drinks; wander through Central Park with a slice of pizza; wine taste in Napa Valley; visit museums and shop your way through Italy.  Take some time to see what’s out there.  Use your Pinterest finds to browse itineraries and learn about destinations from other travelers.  If you don’t feel like creating your own, feel free to browse mine!

Location, Location, Location

With your budget, vacation time and departure location in mind, take a look at your Pinterest board and narrow down the viable options.   You’ve got a long weekend and you’re on the East Coast, the Caribbean is a possibility.  If you’re on the West Coast and it will take you 12+ hours to get to the Caribbean- you’re better off looking at Mexico.  You’d love to jet off to Paris for a week but you only have 16 vacation hours.  You may have to put that dream on the shelf for a while.  Look for an amazing weekend getaway instead.  Choose two destinations that fit your criteria to research further.

Planes, Trains or Automobiles?

Do a quick search for roundtrip flights to each destination.  Look at price, duration of the flight, number of stops and which airport is closest to your destination.  In some places, there may be three airports within 100 miles.  In other cases, there may only be one realistic option, with the next closest airport several hours away.

Weigh your transportation options, if you are traveling within the state, or between places in a region with a high speed train system.  Planes, trains or automobiles?  Balance cost with the amount of time that you are willing to sacrifice. Don’t plan to drive eight hours to a destination, if you only plan to stay for the weekend.   Researching transportation should be helpful as you look to narrow down your options.   Once you find the best transportation option, price it out with your travel dates.

Finding Your Dream (Vacation) Home

One of the decisions people struggle with the most is where to stay on vacation.  Understandably so, as this decision can make or break your trip.

When I think of the difference between our beautiful rental in Costa Rica and the hot mess in Positano, I’ve definitely learned that lesson.  Where you lay your head on vacation matters.  You don’t have to break the bank, but you want to be comfortable and able to relax.  Spend the time reading up on your options and be as clear as you can about what is most important to you.  For our travel group of four ladies, I look for 3-4 bedrooms, 2+ bathrooms, a pool, outdoor grill and jacuzzi.   That generally hits all the marks for us.

Home Sweet Home

Use a map to identify the nearest airport and proximity of the attractions you are interested in.  If you are looking to lay on the beach all day, book a hotel on the beach.  It will probably be cheaper to stay inland, but the time and money you will spend getting to the beach every day will eat that savings (plus some).  If you want to explore a new city, book in a walkable neighborhood, centrally located and close to public transportation.  Your vacation time is valuable, you don’t want to waste it in commuter traffic.

When traveling with three or more people, vacation rentals can be a comparable (or cheaper) option to hotels.  With more overall space, a full kitchen, private bedrooms and additional bathrooms (so important!), many vacation rentals also have access to amenities similar to hotels.  For your trip, price both a few hotels and a few vacation rentals.  I generally use Expedia for my hotel bookings.  I’ve had success with booking through several vacation rental options, including HomeAway and AirBnB.  To set your price, figure out the budget per night for your group.  I generally use $100/night per person as my baseline.  So if there are two of us, I’m looking for $200-$250/night; if there are four of us, I’ll look for options at $400 – $500/night.

Read reviews carefully.  Take note, if a hotel or rental has very few total reviews, or several negative reviews that highlight the same issues.  Also be wary of perfect five star reviews with no details.   It’s hard to tell if they are real or not.  For hotels, look at the most recent reviews and keep your eyes open for any mention of ongoing construction or closed amenities.  I like to book vacation rentals that:

• have 20+ reviews
• average at least 4.5 stars out of 5
• have all my ideal amenities
• are centrally located for the activities I’m excited about
• reference the property manager or owner as very responsive.

Book It!

You’ve chosen your ideal ‘home away from home’.  You’ve found your ideal transportation.  Now it’s time to book!  A few things to keep in mind:

• Many hotels require a credit card to hold your reservation, but won’t charge you until your stay.  Vacation rentals are different- you will usually pay a deposit at booking (roughly half the cost), and then make the final payment the month before you arrive.  There is also often a security deposit that will be held on your card, in case of any damages.
• If you book months in advance, you may want to take advantage of trip insurance.   Some rentals charge cancellation fees after a certain date.
• Keep an eye on airfare.  If you see a great deal, don’t wait.  Two days after I booked my flight to Costa Rica, the airfare nearly doubled!?!
• If you are going on a short trip to one destination, you should be able to keep your trip organized just with email confirmations on your phone.  However, if you’re headed on an epic three-week journey through Europe, you may need a tool to keep yourself organized.  If you use Google, create a spreadsheet and save it to your Drive.  Save yourself the hassle of printing and keeping up with travel confirmations.  Even better, download an app like TripIt to organize everything for you.

Brown Lady Travel Tips

When you travel in a big group, be prepared to go with the flow.  Know that you will not be together every second of the day.  Don’t turn your vacation into a class field trip.  You will inevitably end up irritated (or irritate others) trying to coordinate 20 people to eat breakfast together and move as a unit throughout the day.  Try to plan 1 or 2 group activities  (a nice dinner and maybe an excursion) and expect that the rest of the time people will move in smaller groups or on their own.

On my trip to Soul Beach Music Festival, our group was well over twenty people.  We stayed in a few different hotels and rentals only coming together as a full group twice- at a sunset dinner on the beach and when we watched the Warriors game (go dubs!).

If your travel plans coincide with a festival, holiday break or other special event- book several months in advance!  For popular annual festivals and holiday breaks, accommodations start booking up 6 months in advance (or earlier).  This year at Essence Festival, I heard stories of people staying all the way in Baton Rouge and driving to New Orleans.  That had to be miserable, as the ~80 mile drive would have been easily three hours or more with festival traffic.

What About Your Friends?

As you plan your perfect vacation, keep this in mind: you can’t travel with everybody.   Not every friendship was built to go on the road.  You may have a great friend who you love to hang out with at home.  You have epic day trips, wander through festivals together and love the same food and music.  That same friend may get up at 6am on vacation and plan every moment of every day.  Meanwhile, you roll out of bed at 10am and want to go wherever the wind blows.  Do yourself (and your friendships) a favor- take a short test trip with a friend to see if you’re compatible travel buddies- before you plan an epic 3 week adventure together.

Okay, now you’ve got what you need to plan your perfect vacation!  Don’t forget to download your vacation planning worksheet.  I’m sure some of you have already moved on to another often worrisome task.  Now that you have your trip planned, what and how should you pack??  Fortunately, I’ve got your covered on that as well, whether you’re headed to Europe or for a quick festival weekend.  Happy planning!

I’m off to day dream about Portugal…