Decisions, Decisions, Decisions, And The Evolution Of An Itinerary.

Decisions, Decisions, Decisions, And The Evolution Of An Itinerary.

I find wherever I go people are generally supportive of my endeavours and some even a bit envious.  But,  “I can’t (or wish I could) travel like you,” is what I hear over and over again.

I don’t believe that.  I believe if you want to travel, you can.  But it helps if you follow our formula.  SirOzzy’s aim is to help guide you on your perfect vacation.  We want to help you decide where to stay and eat, and where to relax and play.  We want SirOzzy to become a verb.  “Wow, where did you get all that great information for your trip?”  “I SirOzzy’d it!”

Yes, we have an amazing trip coming soon, but it wasn’t planned overnight.  As with most trips the SirOzzy clan takes, this one took two years in the making.  There is an infinitesimal amount of planning and organization that goes into a successful trip.  The details can be overwhelming.  Here we will begin to spell out and simplify the decision making process that goes into a vacation like this.

There are three key elements to the art of travel.  Each piece has it’s own importance in the puzzle and will affect the outcome of another piece and thus, the trip itself.  These pieces are Time, Location, and Money.

Let’s start first with the time frame.  The busy time at Mrs. SirOzzy’s job ends every year in early February.  The busy time in my career starts in March.  Now we know February is a good time to travel.  Lesson number one is plan ahead, there are way too many decisions to make in a short period of time.

Now begins the process of where do we go?  This is the fun part.  We could go virtually anywhere in the world, so before we decide where we’re going, let’s decide where we are not going.  Europe is out, it’s too cold in February for us.  Australia is out, we went just two years ago.  Hawaii?  No, too long a flight for what we want.  Africa? No.  Asia? Nope. The Caribbean?  The weather is perfect in February and it’s fairly easy to get to from New York. Yes, the Caribbean it is.

The Caribbean.  That’s kind of a big place, a little too big to conquer all at once.  Let’s narrow it down.  There are some amazing all-inclusive resorts and beautiful hotels in the islands.   But for this trip I don’t think I really want to fend for myself too much and I don’t want to sit in one place for too long either.  A cruise?  I love to cruise.  My favorite thing about cruising is that everyday you wake up you’re in an entirely new place, and you’ve done absolutely nothing to get there.  Yes, a cruise it will be.

Our favorite cruise line is Royal Caribbean, for reasons we’ll leave to another post.  Looking through the cruise book can be a bit overwhelming.  The first thing we decide is where do we leave from.  Bayonne, NJ and Baltimore, MD are both within driving distance and have cruises departing from there, but sailing the Atlantic during February can be unpleasant.  We looked to leave from further south and found The Jewel Of The Seas is in Puerto Rico.

The Jewel is the first ship Mrs. SirOzzy and I went on together and has been our favorite ever since.  On that ship was the first of many times I would ask her to marry me.  Yes, The Jewel Of The Seas.  Next, the itinerary.  The Jewel has two different sailings in the month of February, both are 7 nights and both go to the southern Caribbean.  One itinerary happened to also fall on our anniversary.

Simple, right?  No way.  Sure, you can just fly straight to Puerto Rico and jump on a ship, but why do that when you can go a few days in advance and acclimate and enjoy your trip even more?  Besides, we have 2 weeks of vacation time, let’s use it.

We began to look at different hotels and realized, shit, we’re already down there, do we necessarily have to stay in Puerto Rico?  No, we started looking at the surrounding US Virgin Islands.  St. Thomas is not part of the cruise itinerary, and since it is part of the US there is no international flight required.  Sounds good, but, hmmmm, there is one other option.

Key West is only a short flight to San Juan.  One item that has been on my bucket list for a very long time is driving a convertible to Key West.  We can get a direct flight from our local airport to Fort Lauderdale, we’ll rent a car from there.  We’ll use our top secret code to get a deal on a room at the Hyatt next to Mallory Square.

Now we have a cruise and Key West.  Coming off a cruise and going straight home is always a bit of a drag, so let’s stay one more night and take advantage of San Juan before leaving.

This didn’t happen over night.  We began our planning two years ago and solidified the itinerary about 6 months ago.  Here’s what it looks like now:

  • Day 1  Fly to Fort Lauderdale. Drive to Key West.
  • Day 2 Key West
  • Day 3 Key West
  • Day 4 Drive back to Fort Lauderdale
  • Day 5 Fly to San Juan, Puerto Rico.  Cruise
  • Day 6 Sailing on The Jewel Of The Seas
  • Day 7 Bridgetown, Barbados
  • Day 8 Castries, St Lucia
  • Day 9 St. John’s, Antigua
  • Day 10 Philipsburg, St. Maarten
  • Day 11 St Croix, US Virgin Islands
  • Day 12 San Juan, Puerto Rico. Intercontinental Hotel, Isla Verde
  • Day 13 San Juan. Fly home.

Now that is what a two week vacation looks like.

As far as the 3rd part to planning a successful trip, Money?  Shit, we’ll have to figure that out too, but we have two years to do it.

Enjoy The Journey.

 

 

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9 thoughts on “Decisions, Decisions, Decisions, And The Evolution Of An Itinerary.

  1. You have some beautiful pics. If I steal them and use them when I need them and someone ask where I got that beautiful picture can I “I SirOzzy’d it?” 😉 Totally kidding. Did you enjoy Key West? Living in FL, I’ve been quite a few times myself. It has a unique culture . . . as weird as the rest of FL, lol. I look forward to following you o the rest of your journey.

    Liked by 1 person

    1. Thank you for the follow Laura. I’ll be leaving for Key West in 3 weeks, not a day too soon. I also really like appreciate your blog and intentions. I have a personal attachment to it that you may want to hear about someday, when I’m ready.

      Liked by 1 person

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