Plan B-eautiful – Setting Sail to the Caribbean

Did you ever notice how “plan B” often ends up to be the better way to go? Join us this week as we unpack how our trip to Venice and northern Italy was transformed into plan b-eautiful – setting sail to the Caribbean.

Plan A

This year we marked our 15th wedding anniversary and as travel lovers, we wanted to do something epic. (Or more epic than we’ve done previously). We batted around going to Greece before mapping a trip to northern Italy that would include Venice, Milan and Florence. But before we could book even one hotel, fortune smiled on us instead.

On a cool April weekday, I got a call from my dear friend, Shannon. We’ve been trying to find a time to get together since she and her husband, Jerry moved to Nashville. But being the big deal for Southwest Airlines, that she is, it’s hard for her to get time away.

It turns out that both she and Jerry won free cruises with Princess the last time they sailed and asked if we would like to accompany them as their guests for free. It was a 10 day sail around the Eastern Caribbean. Though I would have to wait for Stephen to get home from the gym to formally accept their offer, in my heart I was already packing my bags and making a shopping list.

You NEVER Went on a Cruise Before?

A lot of people we’ve met who know how much we love to travel are astonished to know that we’ve never been on a cruise before. We have always been reluctant to book a cruise for two very important reasons:

• I get extremely motion sick and was afraid of being trapped on a boat with no way off.
• People. I mean, have you EVER seen the pics of like a million people around a pool on a cruise ship?? Ewww. *Shudder*

But this trip was different. Why? Because of Jerry and Shannon. We haven’t spent any time with them in more than a year and here is an invitation to visit for 10 entire days. I knew what I had to do…find a way to manage the motion sickness and all the rest would be golden.

What Do We Need?

Thanks to Travel and Leisure magazine, this very timely article arrived about the things you must have for your next cruise. At the top of the list were these herbal patches that you place behind your ear and on your naval.

Besides the patches, I stocked up on full strength Dramamine and meclazine, the medicine in the non-drowsy formula. Though we had to buy the drink package in order to have soft drinks and Wi-Fi, I figured I would stick to non-alcoholic bevies to give me the greatest hope of getting my sea legs. And if things got too bad, our “plan c” was flying out of one of the islands we visited.

What do you need to Cruise Like a BOSS?

Now that the basics were covered, Stephen went into full on planned mode. He got for us:

AirTags for our luggage (which came in handy when my tote was misplaced).

Luggage tags with plastic sleeves, made especially for the printed tags Princess provide.

Holders for our watches that would allow us to easily keep our Princess medallions with us. (More about these nifty gadgets in a later post.)

Waterproof holders for our phones. Besides just the snorkeling excursion we booked, with all the rest of the time spent on a boat at sea, these seemed like a good idea.

Magnetic hooks for the metal walls of your cabin. Because space is at a premium on the ship, you can use these to hang clothes, hats and towels.

What to Wear?

Stephen and I don’t actually buy clothes every often for two very good reasons,

• We prioritize having experiences over buying new things and
• We live in a smaller home with many other humans and pets, so space is at a premium.

Thinking about what we would want to pack, we tried to remember the last time Stephen bought any new clothes. And though we could remember what we got and the shopping experience, we couldn’t remember the actual year. Apparently it had been a while. (Cue fun shopping montage music now!)

Quality over Fast Delivery?

For a last minute trip to New Orleans last year, I bought a couple sun dresses from Amazon. Though they were cute and useful for the trip, one of the two faded and pilled within a month and ended up in the trash before summer came back around. The lesson…you pay for quality but it saves you from having to go back to the store over and over to replace the items that just couldn’t take the daily wear and washings!

With this in mind, we made our way to a mall near our home that has a good mix of upscale and regular stores. We figured we’d start regular and work our way up, if necessary.

Stephen’s Shopping Spree

Because we were heading to the tropics, light fabric and colors were a must. We tried Eddie Bauer, Express and Banana Republic before finding linen pants and a shirt at Abercrombie and Fitch.

Our last stop was Tommy Bahama, where I found so many fun “cruise” shirts. It took some arm twisting, but I got Stephen to the fitting room. I knew if the clothes looked good, we’d be good to go. They even gave him a discount just because he asked for one.

Jill’s Personal Shopper

Stephen picked up some fun skorts and halters for me. I’m far too picky to step into a store and walk out with 5 new outfits. Unless it’s a resale shop then…maybe!

I also got a new coverup for my bathing suits since the one I owned wrinkles like crazy in the suitcase and had a small hole in the back. The hazards of buying anything cotton resale.

Just One More Thing

The Sunday before the trip, we had one more item Stephen needed to get, a hat for hot weather. He has many Boston Scaly caps which are stylish and perfect for 3 seasons. However tropical heat isn’t really what these are designed for.

Since our plans canceled that day, we had time to shop around and ended up at the Men’s Wearhouse. They didn’t have the hats we were looking for but they DID have a smoking hot deal on this smoking hot tuxedo jacket. Included in the price of the jacket, was a pair of tuxedo pants, a shirt and a bow tie.

We wouldn’t have time to have the pants altered but I was sure I could hem them myself…if only I could find my sewing kit. The last time I saw them, they were packed in the garage to make room for our youngest to move home with his girlfriend and their dog.

On a Mission and Then…

A woman on a mission, I opened the garage, pulled out the lawn mover and made my way to the boxes in the back. Somehow, I managed to catch the lawn mower with my pinky toe – resulting in my very first broken bone. Too bad I bought a cute pair of heels just for the trip that were already packed. Plan B?? Flip flops and canvas slip ons for the days I just couldn’t bear to wear shoes.

What Else Do You Need for a Free Trip?

Purchases set, we only had to pay for port fees, the WiFi / drink package and the excursions. We also upgraded to a balcony room, thinking the view and fresh air might help me fight the motion sickness just a little but more.

All told our free vacation wasn’t really free but we could have done it far cheaper than we did. The way we thought about it was…it’s a big anniversary for us and we don’t know when we will get the chance to visit these islands. And more importantly, how often do you get invited to spend 10 whole days with your friends?? It felt like a once in a life time trip. A b-eautiful plan B and we can’t wait to tell you all about it!

Be sure to join our tribe so you can hear about the rest of the journey to the Bahamas, St. Thomas, Dominica, St. Lucia and Antigua! And, as always, you can follow is in real time on Instagram at The__Travel__Oracle!