jamaica in october, our third anniversary

We’ve wanted to visit Jamaica for a long time and thanks to some creative planning help from my parents who have been several times, we were able to get our October trip booked at the end of last year. We decided to catch flights out of Baltimore so that we could drop Ollie off on his own little vacation with my parents and took our time driving up on Saturday.

When we landed in Montego Bay Sunday afternoon, we were greeted by a Club MoBay representative (included with our resort package but the coolest international airport experience I’ve had). We were personally escorted through a VIP customs checkpoint and handheld through paperwork in a matter of minutes, before being led to a private lounge with complementary rum punch and snacks while we waited for our ground transportation to the resort. As two cheapos who fly frequently but still refuse to pay for TSA PreCheck, that was an unexpected experience that we were really grateful for!

The bus ride to Negril took about 90 minutes, but it flew by since there was so much to look at as we wound our way around the island. We arrived to our resort* in the late afternoon, where we were given more rum punch and checked in. Unlike the mega resort we chose for our honeymoon, this one was much smaller and had these amazing treehouse cabins instead of blocked rooms. A bellhop took us and our bags to our new home for the week, where we packed our phones away in the safe and went for a walk around.sunset at the palms resort room

We stopped at the pool bar for a drink before we went back to change for dinner, then over to the piano bar where the player took a lot of fun liberty with some of our favorite classic songs. We had our first dinner at the resort restaurant and left feeling very full and fancy, stopped by the pool and made a few friends, then went back to our treehouse to unpack and unwind for the night.

After breakfast Monday, we left our cameras in the room and took a quick trip to the beach. We ate jerk chicken and fries smothered in jerk sauce at the beachside grill for lunch, then headed back to the room for a quick shower. There was a quick detour back to the pool before we made our way to the spa for a couple’s massage. Our incredible masseuses found knots in places we didn’t know we could get knots, so we wobbled away an hour later promising to make another appointment before we left. It was Jamaican night at the buffet that evening and we loaded up plates with a little bit of everything to try. There was a live reggae band by the pool and some dancing along by the stage, but we spent most of the night talking to other couples from Canada, England, and around the US about traveling, why we were there, and where everyone wanted to go next.

7 mile beach negril jamaica

On Tuesday, we walked over to the beach again after breakfast and spent a long time splashing around in the ocean. We walked up 7 Mile Beach to check out the local artisan stands and decided to eat hamburgers at the grill again for lunch once we walked back. As soon as we sat down facing the ocean to eat, the skies opened up and it started to rain for the first time all week. We took our time eating but it didn’t look like it was going to let up anytime soon, so we threw our beach towels over our heads and made a run for it back to the room. Eric smoked a cigar out on the treehouse balcony while we listened to the rain pound the roof and plants around us for a while.

Jess and Eric Pendergrass in rain jackets

Since the weather had predicted rain all week, we packed thin rain jackets and threw those on to meet our new friend crew by the pool for a couple hours. The rain moved along and we walked over for dinner was at the fancy restaurant again. We were feeling pretty sluggish afterwards and decided to head to bed, only realizing it was just 10:00 as we were laying down. After a few minutes of listening to the faint live reggae music floating across the resort, we decided to get back up and rejoin the party for a little while longer.

Jess and Eric Pendergrass Jess and Eric Pendergrass

Our actual anniversary was on Wednesday, so we tried to make it a special day. The resort offers a yoga class on certain mornings, and I somehow rolled out of bed before Eric was awake, grabbed a quick snack at the buffet, and visited the gym first thing. Class was amazing and by the time I was back at the room, Eric was up and I was ready to revisit the breakfast I had rushed through earlier. Since the weather was nice, we went to the beach again to swim and listen to the walking musicians who slowly made their way down the shore every day. Our second couples massage was that afternoon, where our masseuses set up the tables under the curtained outdoor canopy area since it started to rain again. It was kind of like magic.

Jess and Eric Pendergrass

massage tables in an outdoor canopy room

Thoroughly relaxed and feeling like jello, we met up with other guests again before getting ready for our anniversary dinner. The resort offered a Chef’s Showcase dinner once per stay, where the head chef prepares a five course meal in front of you – too fancy. Our table was decorated with fresh flowers and a bottle of wine Eric had quietly ordered that morning while I was off at yoga, so the whole experience felt really special. The chefs even had special dessert plates for us with “happy” and “anniversary” written in icing. I left dinner feeling very giggly, which only got worse as our resort friends saw us walking back and called us over to toast us as the bar. It was the best anniversary yet.

Jess and Eric Pendergrass Jess and Eric Pendergrass

With the rain rolling in during the afternoons, we hadn’t had a chance to get off resort yet and planned on making that a priority Thursday. Over breakfast, we ran into one of the newlywed couples we had met and they suggested we all get a cab and go together that afternoon. After another visit to the beach, we changed for lunch and met up with them again to head out. While the resort offers a lot of great excursions, there were also reliable cab drivers right outside the gate. We had met them all earlier in the week and verified with other guests who had used their services, so we figured that would work better for us. Randy lives about 10 minutes away from the resort itself, making him the most authentic “local” tour guide we could have asked for.

rick's cafe negril jamaica

Randy drove us up to the iconic Rick’s Cafe on the cliffs of Negril, where guests can dive into the ocean from as high as 35 feet. (The lifeguards walk around with a tip bucket before they’re allowed to climb a giant mast overhanging the cliff at double that height.) We watched our friends nervously jump off the edge a couple times and ran into some other guests from the resort who had come there by boat for the afternoon. We ordered a bucket of Red Stripe and a handful of fruity shots in test tubes for cheap and sat out on the patio for an hour or two.

Jess and Eric Pendergrass at Rick's Cafe

Jess and Eric Pendergrass at Rick's Cafe

It started to sprinkle and there was a flood of tourists starting to crowd in, so we asked Randy if he could take us to somewhere more quiet to see the sunset. And oh man, Randy delivered. About 10 minutes away from Rick’s Cafe is a tiny place on the rocks called Fire Water Love Nest*. It only had a few tables and a small bar using bottled everything to mix drinks, and there were only two locals and the bartender there when we arrived. The view of the sun setting over the waves softly crashing into the cliff below us was almost too much for my heart to handle. Randy came in to sit with us and the bartender turned up American music, asking us all to get up and dance. When it finally got dark, we piled back up in Randy’s taxi and headed back to the resort while he told us stories of Jamaica and how they became the nation they are today. It was a perfect afternoon.

negril jamaica sunset Jess and Eric Pendergrass negril jamaica

After checking back in with security at our resort, we grabbed a table for four in the main dining room and talked about the day. We spent a little time in the room packing our bags before we walked back over to our trusty pool bar, met up up with the rest of our crew, and sat around talking well into the night. One of the coolest things happened when, even though it wasn’t raining, the electricity flickered and we were all plunged into total darkness for a few seconds. While it caught us all off guard for that quick moment, it made me realize how very far away from home we were in every good way. Time and space feels different there, like they’ve left room still for nature, and I’d love to go back when it’s less cloudy and see the stars. Sometime after midnight, we went to bed for one last sleep in our magical treehouse.

On our last day, we woke up early to get as much time at the beach as we could. We took our last swim, took a last long walk up the sand, and had one last drink at the beach bar. I checked one last time that our flight didn’t get cancelled (wishful thinking), before we met our same bellhop back at the room. Our bus back to the airport had a series of cancellations that morning (smarter people than us who were extending their stay), so we got the whole bus to ourselves. We decided to pay for Club MoBay for our departure from the airport, so we grabbed lunch and sat drinking complementary drinks in the lounge bar to ease the pain of leaving Jamaica. There was a little moment of extreme stress as I (and a handful of other passengers) were selected for a “random secondary security screening” at our gate while everyone else was boarding. Eric and I both travel very well, but being separated, at the gate, in a foreign country, while one if you is boarding the plane, was definitely a first and made us both very uncomfortable. My Kindle and stuffed turtle from the resort gift shop (a present for Ollie) we’re not deemed a threat though, so it wasn’t the end of the world… but it was jussst enough to get me over the sadness and ready to be home.

Jess Pendergrass in negril jamaica ocean with arms up

The sunset flight was beautiful and customs was moving quickly in Baltimore, so we were back at my parents house before 10:00 that evening. Ollie was almost as excited to see us as we were to see him, then we ordered a pizza and everything was right in the world again. We spent another day with my parents so we could get off island time before making the road trip back to Charlotte Sunday afternoon.

Our third anniversary trip was genuinely some of the happiest days of our marriage and one of the best weeks of my life. I cried at several points out of sheer happiness – which feels like a lot, even for me. Eric and I seem to be in a really sweet spot in our relationship with each other, something that this trip made me appreciate more than ever. I feel very grateful to get to experience life with my favorite person in the world, and so grateful we had this opportunity. And we can’t speak highly enough of the Jamaica, Jamaican people, their culture, and natural beauty of the island. We absolutely will be back again, mon. Respect.

anniversary sign hanging on door negril jamaica

Our second anniversary.

Out first anniversary.

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