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Last year, I embarked on both my first and second cruise. (Pun intended.) While the first was a short, but sweet Ensenada Cruise on Carnival Inspiration, the second was a longer, wonderful Caribbean Cruise on Royal Caribbean’s Oasis of the Seas. The size difference between those two ships is mind-blowing. And so was the difference in accommodation, food, service, and overall entertainment. While I enjoyed both, our Caribbean Cruise on Oasis of the Seas was my favorite!

Reese and I flew to Orlando from LAX in first class with Virgin America. You can read more about that in the points and miles roundup at the end of this post. We spent two days exploring Orlando before the cruise. We went on an airboat ride and then explored Disney Springs. Unfortunately, we didn’t see any gators. I think they disliked the heat and humidity as much as we did. We did enjoy Disney Springs especially the Daily Poutine and Chef Art Smith’s Homecomin’. (Honestly, most of the things I love about any vacation are food based.) I am beyond thrilled to announce that we will be returning to Walt Disney World for a proper visit in 2018!

Day 1 – Embarkation at Port Canaveral, Florida

The morning of our cruise, we packed the rental car to brim with our luggage plus a few extra bags from our five friends who were joining us on the cruise. It’s hard to pack lightly for a cruise. Check out my list What to Pack: Cruise Essentials for some tips. It turns out that Port Canaveral is about an hour away from Orlando. We were going to try to squeeze in another Orlando activity the morning of our cruise, but decided to just head to port instead.

Gammie’s Cruise Tip #5: Drop your bags off at the port before you turn in your rental car.

Reese and I dropped our carload of bags at the port before we went to get gas and return the rental car. You just pull up to a designated area near the parking structure, drop off your bags, and drive away. We ran into the rest of our party at the gas station. They took their bags with them to return the rental car. They dropped them off after we all took the rental car shuttle back to port. It took nearly 5 hours longer for them to get their bags than it did for Reese and me! Read more of Gammie’s Cruise Tips here and here.

Once we got on board, we headed straight to our cabins to get settled in and to unpack. Well those of us who had our luggage, unpacked. We booked two Superior Ocean View Staterooms with balconies and one interior stateroom. We politely asked our room steward to remove the partition between our balconies so we could have one giant balcony. She was happy to oblige. We really enjoyed having a party balcony. I highly recommend it if you’re traveling with a group in more than one cabin. Each cruise line treats the request differently, but it never hurts to ask.

We decorated our doors to commemorate our cruise. My friends Anne and Catherine were celebrating their birthdays and Catherine and David were celebrating their wedding anniversary so we wanted to make it special. Mallory made awesome banners. (You can find more of her work on Etsy.) And I made little mermaid/mermen cutouts of everyone.

Caribbean Cruise on Oasis of the Seas

Door decorations for each cabin.

That night we had dinner in the main dining room. With such a big group, we ordered several appetizers and entrees for the table and shared. Again, we took Gammie’s advice and ordered at least one of everything. Our dining room attendants were awesome. By the second night, they had all of our preferred beverages waiting at the table for us when we arrived. They also knew what appetizers and desserts we were likely to order. I talked a lot about how fun the main dining room is in the Ensenada Trip report, but this was even better. Since we were such a large group, we had our own table which Reese loved.

Gammie’s Cruise Tip #6: See all of the shows.

After dinner, we saw the ice skating show “Frozen in Time.” If you think ice skating is impressive on land, you’ll be amazed at ice skating on the ocean! On a ship the size of Oasis of the Seas, make sure to book your shows in advance online in the Royal Caribbean Cruise Planner. The shows are free, but they fill up. Guests with reservations are the first to be let in. I booked seats for everyone at a different show each day. Not everyone went to every show, but at least they had the option. I saw them all and I loved them all. Except for Cats. But more on that later.

Day 2 – At Sea Day

Our first day at sea was a pool day. All seven of us posted up in the Solarium and stayed there most of the day. The Solarium is an adult’s only area on the bow of ship. It’s covered with windows so you have nearly unobstructed views of the ocean. The pool is small, but everyone was very friendly. The water in the pool rocks with the movement of the ship which is a little disconcerting at first. There are also hot tubs and tons of seating throughout the Solarium.

Caribbean Cruise on Oasis of the Seas

View of the pool in the reflection of the Solarium windows.

That night was our first formal night. For tips on what to wear for formal night, check out my guide What To Wear On A Cruise. Somewhere during the planning stages of this trip someone thought it would be a good idea for the ladies to dress in a theme for each formal night. The first theme was “Ocean Ombré”. Never have I ever been so stressed out about any aspect of trip planning. And I bought my dress first! Anyway, I loved formal night, but I hated the rigidity of a theme. To be honest, I’m sure someone will convince me to do it again.

Caribbean Cruise on Oasis of the Seas

Reese, David, Michael, Brittany, Catherine, Anne, Mallory on the first formal night.

After dinner, we saw Oasis of Dreams. This is the water show that takes place in the aqua theater on the stern of the ship. It was incredible. If you only see one show on Oasis of the Seas, you should see this one. The theater is outdoors so you might want to change into comfy clothes first and take some water with you.

Day 3 – Labadee, Haiti

Our first port of call was in Labadee, Haiti. Labadee is a beach that is owned by Royal Caribbean. Your drink package works in Labadee and the food is free just like when you’re on the ship. We booked a beach bungalow which was the farthest from the dock. We loved it! If you’re looking for a splurge, I cannot recommend a beach bungalow enough. There was plenty of room for our entire party of 7. It was shady, comfortable, and super relaxing. Our cabana attendant “Mickey” was great and took excellent care of all of us.

Caribbean Cruise on Oasis of the Seas

View of the ocean and the ship from the beach bungalows in Labadee, Haiti.

Reese and I went on the one hour wave jet excursion before lunch. It’s one of those things I’ve always wanted to do, but traveling with a small child prohibits. That’s why I recommend traveling without your kids from time to time. I was pretty surprised at how fast those things move. More than once, I thought I would fly off. The excursion is a follow the leader tour so you can’t do your own thing. That was a bummer, but they want to make sure tourists don’t destroy important marine life in the area. After the wave jet excursion, we went back to the beach bungalow, relaxed, and drank a few too many Labadoozie’s. A Labadoozie is a frozen citrus and rum based cocktail. They are exclusive to Labadee, but you can probably get any friendly Royal Caribbean bartender to make one for you.

Caribbean Cruise on Oasis of the Seas

Reese and Brittany getting ready for the wave jet excursion in Labadee, Haiti.

Okay, here’s some real talk. This beach does not in any way reflect real life in Haiti. There’s literally a chain link fence to keep Haitians out who are not authorized to work or sell goods in Labadee. If you visit, you will probably feel guilty for doing so. But take cash to buy something in the market and tip your hosts and guides very well. It’s the least you can do.

That night, Reese and I had dinner at Chops Grill which is one of the many specialty dining restaurants on the ship. You have to make reservations in advance and there is a surcharge, but it is well worth it. We had some of the finest steaks ever. They also wrapped up all of the dessert options for me to take back to the room. Talk about impeccable service.

Day 4 – Falmouth, Jamaica

Our second port of call was in Falmouth, Jamaica. We really didn’t venture far from the ship in this port. We had lunch at Margaritaville then hung out by the pool for a little while. The music and entertainment were fun, but it was crowded and expensive. Instead, we decided to go back to the ship and drink for free with our drink packages.

That night we saw the Headliner Showtime featuring an awesome cover band. Afterwards, our group hit the nightclub to celebrate Anne’s birthday. But quickly realized, we were old and headed back to our cabins.

Day 5 – At Sea Day

For our second day at sea, I sought out the casino. Unlike the casino on Carnival Inspiration, the casino on Oasis of the Seas was well ventilated and pleasant. It was also the location of the strongest drinks on the ship. I’m sure that had something to do with how quickly I lost all of my money.

For the rest of the day, we did our best to eat and drink our way around the ship. With so many options, it’s hard to hit them all in one cruise. We also did a few rounds of trivia and hit the Solarium again.

That night we had our second formal night. The theme was “Black and White”. It was much easier to accomplish than that Ocean Ombré nonsense.

Caribbean Cruise on Oasis of the Seas

David, Catherine, Mallory, Michael, Anne, Brittany, and Reese on the second formal night.

After dinner, we watched the late night comedy show. Much like the comedy show on Carnival Inspiration, this adult’s only show was a riot. But it’s not for the easily offended.

Day 6 – Cozumel, Mexico

Our third, and final, port of call was in Cozumel, Mexico. Royal Caribbean has made significant improvements to the port area so now you just walk of the ship into an expansive mercado. It’s kind of like the Disney version of Mexico.

Our entire group did the 3 reef snorkel by boat excursion. We had a lot of fun and saw some amazing marine life including eels, cuddle fish, crabs, and tons of colorful fish. Our guides were great, but they send someone out to take photos of you snorkeling and feed the fish to improve the photos. It sure convinces suckers like me to buy them.

Caribbean Cruise on Oasis of the Seas

Reese and Brittany snorkeling in Cozumel, Mexico.

That night we saw the aerialist/acrobat show Come Fly with Me. This was probably my second favorite show on the ship. It’s pretty similar to what you would see in a traveling Cirque du Soleil show.

After Come Fly with Me, we participated in the Quest. I’m pretty sure the first rule of the Quest is that you don’t talk about the Quest. But I’m going to do it anyway. The best way to describe this show is as an adult scavenger hunt. If you’re not into audience participation, you should probably sit in the back. You also might want to have a drink or two beforehand to loosen up your inhibitions in case you need to remove your pants or your dentures. Finally, I recommend bringing a bunch of random stuff with you like an extra bra, extra pants, makeup, high-heeled shoes, a tie, a sock, etc.

Day 7- At Sea Day

Our final day at sea was all about soaking up those last few hours of relaxation. Anne and Mallory enjoyed a fancy lunch and over used the term “The Golden Age of Cruising”. Reese shot ice off our balcony with a slingshot. David did the zip line which is a pretty short ride. The ladies managed a “spa day” on the party balcony. And we saw the musical Cats.

The performers in Cats were just as talented as you’d see in a stage production on land. Everything was great, except the story. I had never seen Cats and I knew nothing about it other than a few bars of “Memories”. It’s weird. Super weird. Maybe I just didn’t get it.

That night we had our last dinner in the main dining room. The staff gave everyone a warm send-off with dancing and singing. Seriously, if you skip the main dining room, you’re missing out on the last remnants of the golden age of cruising.

Day 8 – Debarkation at Port Canaveral, Florida

The debarkation process was pretty smooth. We ate breakfast in one of the dining rooms and by the time we finished, we were allowed to debark. I forgot to book transportation back to Orlando in advance, but we were able to sign up for a bus right outside of the cruise terminal. Reese and I spent a few extra hours sitting in the Orlando airport before our flight, but luckily they had a sports bar so we could watch some football. Then we flew back to California once again in first class.



Points and Miles Roundup

We booked 2 first class tickets from Los Angeles, California to Orlando, Florida on Virgin America using 100,000 Alaska Airlines Mileage Plan Points. We scraped those points together from Alaska Airlines Mileage Plan, American Express Membership Rewards, and SPG Starpoints. This saved us $2600 and we got to fly first class for 5 hour flights (without our kid)! It was fantastic. Fees for our flights cost $22.40.

First, I earned 36,000 Alaska Airlines Mileage Plan Points from the Alaska Airlines Visa Card. This included my entire sign-up bonus, points earned from meeting the minimum spending requirement, and bonus points from having a Bank of America checking account. This worked out to a value of 2.6 cents per Alaska Airlines Mileage Plan point.

Second, Reese transferred 40,000 SPG Starpoints to his Alaska Airlines Mileage Plan account. With an additional 5,000 points per 20,000 transferred, he had 50,000 Alaska Airlines Mileage Plan Points after the transfer was complete. This was his entire sign-up bonus from the Starwood Preferred Guest Credit Card not including points earned from meeting the minimum spending requirement. He managed a value of 3.25 cents per Starpoint which is much better than I did with my bonus.

Finally, I transferred 22,000 American Express Membership Rewards to the Virgin America Elevate Program at a ratio of 1:0.5. This might seem crazy, but I then transferred the points from the Virgin America Elevate Program to my Alaska Airlines Mileage Plan Account at a ratio of 1:1.3. I earned those American Express Membership Rewards as part of my sign-up bonus from the American Express Platinum Card. This worked out to about 1.69 cents value per Membership Rewards point. Unfortunately, you can no longer transfer Membership Rewards to Virgin America Elevate as Alaska Airlines Mileage Plan is the sole rewards program for the two airlines.

We also booked 2 nights before the cruise at the Hyatt Place Orlando/Convention Center for $99 per night. I could have booked the room for 8,000 points per night or 1.2 cents per point. Since the room rate was so low for cash, I decided to save my World of Hyatt points for a better redemption.

I didn’t use points & miles for the cruise itself, but I made sure to earn as many bonus points as possible. I paid for everyone’s deposits and our cabin using my Chase Sapphire Reserve. As a travel purchase, I earned 3x the Chase Ultimate Rewards. My friends later reimbursed me for their deposits.

Final Thoughts on our Caribbean Cruise on Oasis of the Seas

When traveling with a large group, it’s hard to find destinations and activities that everyone can agree on. That’s why cruising is such a great option for groups. There’s is a never-ending amount of things to do, great food to eat, strong cocktails to drink, or quiet places to get away from each other on a ship the size of Oasis of the Seas.

If you’re interested in a shorter cruise, check out how much fun we had on our Ensenada Cruise on Carnival Inspiration. And before you start packing for your first cruise, check out my guides What To Wear On A CruiseWhat to Pack: Cruise Essentials, and 10 Tips For A Well Organized Suitcase.