Planning the Philippines Adventure

Eight months into dating Jen, we crossed a big relationship milestone—we decided to move in together. Not long after that came another milestone, one rooted not in logistics but in legacy: a trip to the Philippines to meet my Dad and step-mom. It wasn’t something I had to talk her into—Jen was immediately in.

It wasn’t just going to be the two of us, though. My sister, Charrina, and our close friend Marc Marx were quickly added to the roster. Anyone who’s traveled with us knows: when the four of us get together, it’s bound to be epic.

Marc has visited the Philippines 27 times (yes, twenty-seven). Charrina and I have each been seven times. Jen? Never. That number was about to change.

In the planning stages, she mostly just listened. We’d be talking about street food and sari-sari stores, karaoke parties and white sand beaches, family gatherings and ferry boat transfers—and she’d take it all in, wide-eyed, curious, patient. It’s a lot to absorb when you’re stepping into a culture for the first time, especially as the guest of a family like mine—Filipino, American, loud, loving, and full of quirks.

But this trip isn’t just about places on a map. It’s about people, heritage, connection. It’s about the stories we carry and the ones we’re about to create together.

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Passport Stamps and Promises

Jen isn’t the type to wing it.

As a school principal with a Master’s in Education, she’s the kind of person who’s always learning, always seeking context. A student of life, and for a lifetime. The moment we locked in our tickets, she dove into research. First stop? Her sister-in-law, Heather, who is part Filipino. Then it was anyone and everyone she could find who had set foot on one of the 7,607 islands that make up the Philippines.

She started compiling questions, bookmarking TikToks and travel blogs, even brushing up on basic Tagalog phrases. (“Mabuhay!” became her new greeting for a solid week.)

What’s the etiquette at a Filipino dinner table? What’s the difference between pancit and palabok? How do I avoid offending a lola? She wanted to know it all. Not because she had to—but because she wanted to. That’s just who she is.

And then there was me—her boyfriend, her partner, her new live-in travel resource. I love teaching and coaching anyone willing to learn, and Jen was hungry for it. I found myself fielding questions over breakfast, sharing cultural do’s and don’ts while folding laundry (yes, I help!), and laughing through karaoke stories in the car. Her curiosity brought out the best in me—reminded me just how deep my connection is to the culture I was born into, even while growing up in the U.S.

Naturally, I took point on the itinerary. I saw it as my role—part host, part guide, full-time ambassador. On one side, I had my Filipino family: my dad, stepmom, and stepsisters. On the other, my American team: Jen, my sister Charrina, and my brother-from-another-mother, Marc. The pressure to bridge those two worlds was real. But also, it felt… right.

Planning the itinerary wasn’t just logistics—it was diplomacy, strategy, and vibes management.

With three return travelers and one total newbie, the trip had to be equal parts nostalgic, bucket list-worthy, and culturally immersive. Everyone had their “musts.” Marc wanted his classic return-to-roots moments—certain beaches, restaurants, and family-owned spots that held personal meaning. Charrina asked for balance: “I just don’t want to be on the go every day. Can we build in some poolside chill time?” Jen wanted to see everything… and eat everything. No pressure.

Me? I wanted all of it to go smoothly. Which meant I built out a day-by-day itinerary: dates, locations, contacts, even backup plans for the inevitable “plan goes out the window” moments. (Because, you know… Philippine time.)

Here’s what we landed on:

Day 1–2: Bohol Beginnings – Tagbilaran City

We were to touch down straight in Bohol, landing in Tagbilaran City. The meet-and-greet would be at the house.

Day 3: OceanJet to Cebu

The fast ferry would zip us across the Visayan Sea to Cebu — a larger island with a different pace. We will recharge, regroup, and prep for the biggest adventure of the trip.

Day 4: Whale Sharks & Waterfalls

Off to see the Whale Sharks, and Kawasan Falls.

Day 5–6: Palawan — Paradise Found

Next? We would fly to Palawan, the island known for postcard-level perfection. The crown jewel? The Underground River, a UNESCO World Heritage Site. Stalactites, bats, and cave chambers large enough to swallow cathedrals.

The rustic charm of no Wi-Fi and star-filled nights was gonna be our new comfort zones. Jen was calling it “a spiritual reboot.”

Day 7: Back to Cebu – A City Pause

We would return to Cebu for a more chill vibe. Magellan’s Cross, a quick visit to Ocean Park, and a proper hotel bed. After so many early mornings, we would need this.

Day 8–10: Home Base in Bohol – Family, Beach, Birthday Bash

Back in Bohol, Dad’s birthday would be a big Filipino bash — food, and family members who instantly made Jen feel at home. I promised a beach day, so on one of these days we would take a moment to breathe, and say our final goodbyes before flying out.

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A First-Timer’s Tour: Our Real-Life Philippines Itinerary

Planning a first-time trip to the Philippines with your partner is one thing. Living through it — heat, ferry rides, wildlife encounters, and Filipino family parties — is another.

But no amount of research could truly prepare her for the wonder — and chaos — of an island-hopping Filipino adventure.

This was no “let’s just see where the wind takes us” kind of vacation. As a Filipino-American son returning with my girlfriend Jen (a school principal and lifelong learner), my sister, and our travel-expert friend Marc Marx, I knew I was carrying the torch of family, culture, and logistics all at once.

The following is what really happened, just the alternate endings of the movie, Clue.

Day 1, Behold Bohol. July 8th, Tuesday

My dad and my brother-in-law, Awhong, met us at the airport to whisk us away. My stepmom (or just Mom — the word “step” doesn’t exist in Filipino households), and Jenna Mae were back at home cooking lunch for us … anticipating that we would be hungry. We checked into the Dayview Tourist Home just to get keys, toss our bags into the rooms, and go eat.

After introductions, and some fanfare, I withdrew so that conversations with Jen and the family can organically happen. And they did.

Eventually, the conversation steered its way to our intentions, to engage resources, and processes that take time. It was Jen’s first full immersion into tricycles, Pandesal, and tropical island vibes.

Day 2, Monkeying Around The Hills. July 9th, Wednesday

Mama Luz made breakfast before our full-day tour of the island of Bohol! Leo was our driver of the tour van. It was mostly a self-guided tour of sorts.

We made the rounds: the wide-eyed tarsiers, which only live in the Philippines, and in a specific area of the Philippines. The photos, and videos are posted to my social media platforms of Facebook, and Instagram.

Fun Fact About Tarsiers: They are the only entirely carnivorous primates, hunting insects, lizards, and small birds. 

Tarsiers are known for their ability to rotate their heads almost 180 degrees, a feature they share with owls. They are also exceptional leapers, capable of jumping over 40 times their body length. 

Leo stopped by Bohol Enchantment to offer us a bonus stop. In retrospect, kinda wish we bailed on it. Marc, Jen and I hopped out. Each of us are adventurers, so it was a vibe. That said, we were greeted with some unhinged artwork which should’ve been our sign to turn around.

We didn’t.

WCP (Charrina, my sister), Mama Luz, and Papa Charlie stayed in the air-conditioned van. We clamored into the van muttering to ourselves, and spouted “What the fawk” several times. We shook it off, and zipped off to Bohol’s Chocolate Hills!

The strange-yet-stunning Chocolate Hills has an EarthCache I’ve been wanting to complete, claim, actually 2 for a hot-minute. It was an easy sell to Jen and Marc. Once again, WCP, Mama and Dad posted up in the restaurant as they have done it already.

We were hungry, but quite far from home. Another fun unique experience is the Loboc River Cruise and Floating Restaurant! Floating attraction featuring a Filipino lunch buffet accompanied by traditional singing & dancing.

Dad requested our final stop should be Sikatuna’s Mirror of The World. See the beauty of the world in one place, with no visa and no passport. A grip of a tourist trap, but it made Papa Charlie happy so that makes the group happy.

Jetlag? What jetlag? It was time for dinner at a restaurant that was staff by the hearing impaired which Jen has some experience with American Sign Language (ASL)

Day 3, Bohol To Cebu. July 10th, Thursday

We decided to leave our main luggage with Inday (my youngest sister, Leonnie) while we took enough clothes, etc in carryon bags to use on our island-hopping trip within a trip. Quest Conference Center would be our home for the next couple of nights.

It was a short night because our pick up for our EPIC adventure was 04:00. NOT WAKING UP at 4 a.m. but be ready to rock at that time in the hotel lobby. This was a tour company, and not family, or family friends.

After the hotel restaurant dinner, and our exhaustion levels high, we withdrew to our respective rooms, and slept.

Day 4, Sharks and Falls. July 11th, Friday.

This day will live in travel infamy: a 14-hour thrill ride that included an epic whale shark swim in Oslob, followed by the canyoneering experience of a lifetime at Kawasan Falls. We all climbed rocks, jumped off cliffs, floated downstream — all with a smile and a nervous laugh. We were somewhat sunburnt, totally sore, and completely alive.

Day 5 – The Travel Day That Wasn’t. July 12th, Saturday

We packed our bags in Cebu, checked out of the hotel, and made our way to the airport—ready for our next adventure to Palawan. But the universe had other plans. Just as we settled into the terminal, news broke: a sinkhole had opened on the main runway at Mactan-Cebu International Airport.

A sinkhole.

In all my 30 years of traveling, I’ve never run into this one before. Cebu Pacific kept announcing that repairs were underway and that flights would resume by 9 p.m.—but we weren’t buying it. We spent the day in a holding pattern, surrounded by stranded travelers, flickering updates, and mounting uncertainty.

No Palawan. No Underground River. Just a crater in the concrete and a massive pivot in the itinerary.

Cue collective disbelief.

Cebu Pacific, bless their ever-optimistic hearts, kept repeating to us in-person that the damage would be patched up and the runway reopened by 9 p.m. They sounded confident. We, however, were not. The hours ticked by. We clung to snacks, each other, and the hope that we’d be sipping coconut water beachside in no time.

Instead, we spiraled into a full day of airport limbo: delays, re-check-ins, gate changes, and progressively louder sighs. It was a lesson in patience, Filipino-style. Even Marc, our 27-times-veteran, hadn’t seen this one coming. Eventually, we had to call it. No Palawan. No Underground River. No remote beach hut with stars overhead.

Marc, Charrina, Jen, and I quickly huddled like a crisis team. The terminal was chaos, but we found our rhythm. Jen, who had booked the airline tickets, took point on negotiating with the Cebu Pacific desk—calm, persistent, and determined to get answers, rebookings, or refunds. She had the most skin in the game and handled it like a true principal handling a school-wide power outage.

Because what else can you do when the literal ground gives out under your vacation plans?

Charrina, my sister and fierce protector of our stuff (not calling her a dog, but she’s the kind of ride-or-die you want watching your gear), parked herself over the luggage like Cerberus guarding the gates of baggage claim.

Marc and I, clearly the self-appointed field agents of the group, went full detective mode. We scoured message boards, eavesdropped on other travelers, asked pointed questions to distracted airline staff—anything for a sliver of actual, reliable information. Because let’s be honest, no one was getting a straight answer from Cebu Pacific at that point.

In moments like this—under stress, in foreign countries, with plans crumbling—you see the true dynamic of a travel group. Families can snap. Friends can fracture. Couples can crumble.

But not us.

We had our moment of scramble, sure. But then we recalibrated like the freakin’ Avengers. I took the unspoken leadership role—Captain America style—and laid it out: We need shelter. We need Wi-Fi. We need a bathroom not shared with 200 other stranded people.

Time was ticking. Hotels in the area were vanishing fast, already booking out as other travelers made the same calls. At 7 p.m., with the airport shut down until at least 9 p.m., we pounced on the first hotel that made sense: Hamersons Hotel.

It wasn’t part of the plan. But it was safe, available, and we were a team in need of a base.

Day 6 – Stranded in Cebu. July 13th, Sunday

While at the “included breakfast”, we continued to strategize. My heart broke saying goodbye to UNESCO for now because that was MY must-do in the Philippines.

The falls was Jen, Tarsiers and Chocolate are a given for Bohol. I asked the group, “Aiight, with Palawan out of reach we either extend our time in Cebu, Bohol, or split the difference. Marc?”

Marc E Marx, “Split, one more 1 night in Cebu, then an extra night in Bohol.”

Charrina exhausted with no sleep, “Split.”

Principal Jen voted, “Split. We enjoy Cebu one more night, while we try to get another night at the hotel on Bohol. Los, your vote?”

I smiled, “It’s unanimous, split.” Using Hamersons’s Hotel Wi-Fi, we booked the One Central Hotel was close by, an upgraded hotel, and close to the SM Seaside City Cebu, AND the fast ferry terminal we were gonna need tomorrow morning to travel back to Bohol. After paying our bill, we post-haste to the new hotel … again to establish yet another homebase. However, with the vote to change we needed to change our ferry reservations as they were based on the fact we were visiting Palawan Island, a fresh wound opened up all over again.

Marc met up a local friend of his so he had a translator at the ferry terminal. Charrina, Jen, and I needed a currency exchange, food, and souvenirs so we hit up the SM Seaside City Cebu. We would all muster up at the mall once Marc was done. We literally spent all day at the mall, which each of us are Gen X, therefore malls were our type of playground.

After pivoting, making the best of a bad situation, this was a great call, the vibe was awesome.

Day 7 – Back to Bohol! July 14th, Monday

We packed up once more so we can travel to the Mayana Resort located on the island of Panglao which is connected by bridge to Bohol. Most the day was monopolized by travel so the resort restuarant was the choice for dinner.

Day 8 – Passport Promises. July 15th, Tuesday

I promised, (I never promise anything unless I can deliver) Jen a white sand beach experience since she loves the beach, and NEVER been to one. Alona Beach called our names, Mama Luz, Papa Charlie, Marc, Charrina, Jen, and yours truly popped on down in taxi-van. We thoroughly enjoyed our time there. Dad, and Mom went home afterwards, leaving us to go to the resort to chillax.

Day 9 – Hinagdanan Cave. July 16th, Wednesday

We spent the early hours out at Hinagdanan Cave. The rest of the day chillaxing, and packing up for our departure in the witching hour of 4 a.m. on Day 10.

The highlight of the evening was Dad’s, and my brother-in-law’s (Awhong) birthday dinner at Bohol Tropic! Everyone was available, my 4 sisters of Leonnie nicknamed Inday, and her two children, Jea nicknamed Mouth, and her husband Awhong, and the twins: Wang-Wang and Jenna Mae. The obligatory photographs were post dinner. Dad’s request of course. And it was all the different combinations, dozens of photos taken by the restaurant staff. The right and proper see you later (we refuse to say goodbye as it has a finality about it)

Day 10 – Day of Departure. July 17th, Thursday

A brutal, meat grinder of a travel day. 90-minute flight from Bohol-Panglao Airport to Manila, only to be met by a 12-hour connection time between flights. THEN! It was another 11-hour flight to Vancouver British Columbia Canada. Meanwhile, at the Vancouver Airport, a miscommunication between us and airline staff, we missed the connecting flight to Seattle-Tacoma International while waiting for our bags, which we didn’t need to! UGH. We were booked on an Air Canada flight hours later, and our bags didn’t.

By the time we touched down in Seattle, we were zombies with carry-ons. No checked bags, no clean clothes, just a soul-deep fatigue only international travel (and bureaucratic airline mishaps) can create. But somehow, standing there with Jen, Marc, and Charrina, bleary-eyed and beyond exhausted, there was still laughter.

Still gratitude.

Still a sense that what we just experienced was rare—an adventure made possible by family, resilience, flexibility, and a whole lotta love.

The itinerary wasn’t perfect — it wrote its own. Plans shifted. Unforeseen events happened. Transportation got “creative.” But that’s part of the Filipino experience too—rolling with the punches, laughing through the curveballs, and realizing that the best memories often come from the things you don’t plan.

Final Thoughts

Jen handled it all with grace and curiosity. She asked questions, tried new things, and opened her heart to every moment. And I got to share a piece of my story with her — and with my family.

All in all, it was another fantastic visit to the Philippines, peppered with pivot situations, and making the best of it. Just. like. life.

Be good like you should, and if you can’t be good … be good at what you do!

✈️ Planning your own trip?

• Bring sunscreen. The sun will find you.
• Accept that the schedule is a suggestion, not a guarantee.
• Learn to say “Salamat” (thank you). You’ll use it a lot.
• And if you’re lucky enough to have a Filipino family waiting for you — show up hungry and ready to sing.

🇵🇭 Thanks for reading!

If this story made you laugh, nod, or dream of your own island adventure — consider subscribing to my blog for more tales, tips, and thoughtful reflections. More real-life travel misadventures coming soon.