Let me guess what’s running through your head:

This sounds amazing, but… what is it actually like?

Is it awkward?

Is it forced?

Do I have to be “on” the whole time?

What if I don’t click with anyone?

What if everyone’s coupled up by Day 2 and I’m left out?

I get it. The idea of traveling with 39 strangers—even carefully curated strangers—can feel intimidating.

So let me walk you through exactly what a Passport to Love trip looks like. Not the glossy version. The real version.

What happens from the moment you land to the moment you leave. The nervous anticipation of Day 1. The organic connections of Day 3. The bittersweet goodbyes of Day 7.

Because the more you know, the less scary it feels.

And honestly? It’s not scary at all. It’s one of the most authentic, hopeful, and memorable experiences you’ll ever have. 

Before You Even Arrive: The Application Process

Step 1: You Apply

The application is thorough. I’m talking 30-45 minutes of thoughtful questions about:

• Your relationship history and patterns
• What you’re genuinely looking for
• Your emotional availability and readiness
• Your travel style and preferences
• Your values, lifestyle, and long-term goals

This isn’t a formality. I personally review every single application.

Step 2: We Talk

If you seem like a potential fit, we hop on a 20-30 minute call. This is where I get a sense of:

• Are you actually ready, or still healing?
• Are your expectations realistic?
• Will you vibe with the group we’re building?

I’m not trying to fill spots. I’m curating a group of people who will genuinely get along and potentially match with each other.

Step 3: You’re In (Or You’re Not)

If it’s a fit, welcome aboard! You’ll get all the trip details, logistics, and a “getting to know you” questionnaire.

If it’s not a fit, I’ll tell you honestly and kindly. Maybe it’s timing (you’re not quite ready). Maybe it’s alignment (this trip’s group doesn’t match what you’re looking for). No hard feelings. This only works if everyone is genuinely compatible.

What This Means for You:

By the time you land in Malta, Portugal, Barcelona, or Sicily, you already know:

• Everyone here is emotionally available
• Everyone has been vetted for compatibility
• Everyone wants the same thing: real connection
• No one is “just traveling” or “seeing what happens”

This isn’t speed dating. This is intentional, curated matchmaking.

Day 1: Arrivals and First Impressions

Morning/Afternoon: You Arrive

Most people land throughout the day. Private transfers pick you up from the airport and bring you to the hotel.

(Yes, private transfers. You’re not navigating a foreign city with luggage after a long flight. We handle the logistics so you can just… arrive.)

3:00 PM: Check-In

The hotel is beautiful. Not stuffy-fancy, but elevated-beautiful. The kind of place that makes you feel special without making you feel like you have to perform.

You check in, go to your room (private room or share with a friend. Yes, if your friend is single and a good fit for our group, we take that into account), and have a few hours to:

• Unpack
• Shower
• Decompress
• Maybe take a nap
• Text your friends “OMG I’M HERE”

5:30 PM: Welcome Reception

This is it. The moment you’ve been nervous about.

You walk into the rooftop bar (or terrace, or garden—somewhere beautiful with a view). And there they are: 39 other people who are exactly as nervous as you are.

Here’s what actually happens:

I welcome everyone. Brief intro to the week. Ground rules (be kind, be open, be yourself). Then:

“Alright, go mingle. Your people are in this room.”

And you know what? They are.

Within 10 minutes, you’re talking to someone about travel, work, why you’re here. Someone else joins.

You laugh. The wine helps. The sunset helps. The fact that everyone is in the same boat helps.

Is it a little awkward at first? Sure. Does it warm up quickly? Absolutely.

7:30 PM: Welcome Dinner

We move to dinner—usually a long table (or a few tables) at a beautiful restaurant. You sit next to new people. You talk, you laugh, you share stories.

Someone asks, “So what’s everyone’s biggest dating app disaster?” The table erupts. Everyone has a story. The ice? Officially broken.

10:00 PM: The Night is Yours

Dinner ends, but the night doesn’t have to. Some people head back to the hotel. Others grab drinks at a nearby bar. A few night owls stay up talking on the hotel terrace until 2 AM.

No pressure. No FOMO. Just options.

What You’re Thinking by the End of Day 1:

“Okay, these people are actually cool.”

“I can do this.”

“Wait, is that guy interested in me or just being friendly?”

“This might actually be really fun.”

Day 2: Getting to Know Each Other

Morning: Cultural Exploration

We do something immersive—a walking tour of Valletta’s history, a visit to Sagrada Familia, a wine tasting in the Portuguese countryside.

This is where the magic starts.

You’re walking next to someone. You’re both looking at the same incredible view. Someone makes a joke. You both laugh. Conversation flows naturally because you’re experiencing something together, not sitting across from each other in an interview.

You start to notice things:

• Who’s curious and asks questions
• Who’s present vs. glued to their phone
• Who’s kind to the tour guide
• Who makes the group laugh

Context is building.

Afternoon: Free Time

After the morning activity, the afternoon is yours. Some options:

• Pool/beach time with whoever wants to join
• Explore the city on your own or with a few people
• Spa, nap, read a book
• Grab lunch with the group (or a few people you’ve clicked with)

No forced activities. No pressure to be “on” all day.

Evening: Group Dinner

We gather for dinner—sometimes at a traditional local spot, sometimes somewhere elevated and beautiful.

By now, you’re not sitting with strangers. You’re sitting with people you’re getting to know. Inside jokes are forming. Someone references something from last night and everyone laughs.

You notice who you’re drawn to. Maybe it’s the person who asked thoughtful questions this morning.Maybe it’s the one who made you laugh at lunch. Maybe it’s the quiet one who opened up at dinner.

Attraction is clarifying. Not forced, just… emerging.

What You’re Thinking by the End of Day 2:

“I’m actually having a great time.”

“I definitely want to get to know [that person] better.”

“Even if nothing romantic happens, I’m making real friends here.”

Day 3: Where Things Get Real

Morning: Adventure Activity

This is usually the day we do something more adventurous—catamarans to the Blue Lagoon, boat trips along the coast, sailing, snorkeling.

Why? Because adventure accelerates bonding.

Someone’s nervous about jumping in the water. Someone else encourages them. You’re all on a boat together, sun on your faces, music playing, wine flowing, laughter everywhere.

This is where people let their guards down.

You see:

• Who’s adventurous and who’s cautious
• Who’s encouraging and who’s judgmental
• Who’s present and who’s performing

And you feel closer to the group—and to specific people—than you did 24 hours ago.

Afternoon: The Shift

By Day 3, something shifts.

People aren’t just being polite anymore. They’re being real.

Someone admits they’re nervous they won’t meet anyone. Someone else admits they’re scared they’re getting too attached. Real conversations are happening—on the boat, at lunch, in quiet moments.

Vulnerability is contagious. And vulnerability creates intimacy.

Evening: Smaller Group Dynamics

Dinner is still a group affair, but afterwards, people naturally break into smaller groups.

Some people go dancing. Some grab drinks at a beach club. Some stay at the hotel and talk until late.

And this is when romantic interest starts to become clear.

You find yourself gravitating toward certain people. Staying in conversations longer. Looking for them in group settings. Wondering if they feel it too.

It’s not forced. It’s organic.

What You’re Thinking by the End of Day 3:

“I’m definitely interested in [them].”

“I think they might be interested in me too.”

“But what if I’m reading this wrong?”

“Should I just… say something?”

Day 4-5: Deepening Connection

The Group is Now a Community

By mid-week, the group doesn’t feel like strangers anymore. It feels like a friend group.

Inside jokes. Shared memories. People looking out for each other.

Someone’s not feeling well? Three people check on them.

Someone’s birthday? The group surprises them at dinner.

Someone’s homesick? Others sit with them and listen.

This is what happens when you put good people together.

Romantic Connections Emerge

By Day 4 or 5, it’s usually pretty clear who’s interested in whom.

Not everyone is coupled up (this isn’t a reality show). But people are spending more time with specific people.

Long walks through the city. Staying up late talking. Sitting next to each other at every meal. The signals are there.

And here’s the beautiful part: There’s no pressure to define it.

You’re not texting “so what are we?” after three days. You’re just… enjoying getting to know someone in a natural, organic way.

You’ll have time to figure out what this is when you’re back home.

Activities Continue

We keep exploring—day trips to nearby towns, wine tastings, beach clubs, cultural experiences.

But by now, the activities almost feel secondary. You’re here for the people.

The sunset is beautiful, but what you remember is the conversation you had watching it.

The dinner is incredible, but what you remember is the laughter at your table.

The experiences are the backdrop. The connections are the story.

What You’re Thinking by the End of Day 5:

“I don’t want this to end.”

“I really like [them]. Like, really like them.”

“But we live in different cities. How would this even work?”

“I’ve made friends I actually want to stay in touch with.”

Day 6: Choose Your Own Adventure

The Itinerary Loosens

By Day 6, we give you more freedom. Some structured options, but also plenty of free time.

Why? Because by now, you know what you want.

Want to explore on your own? Do it.

Want to hang with the full group? Join the planned activity.

Want to spend the day with the person you’ve been getting close to? Go for it.

No judgment. No FOMO. Just autonomy.

Real Conversations Happen

This is when people start talking about the future.

“What happens when we go home?”

“Would you actually visit me?”

“How do we stay in touch with everyone?”

“Is this real or just a vacation feeling?”

These are good questions. And it’s okay not to have all the answers yet.

What You’re Thinking by the End of Day 6:

“This has been one of the best weeks of my life.”

“I’m sad it’s almost over.”

“I hope [they] feel the same way I do.”

“I’m already planning when I can see these people again.”

Day 7: Goodbyes and New Beginnings

The Farewell Event

The last night is always a mix of emotions.

We have a farewell dinner—usually somewhere stunning. Candles, great food, wine, maybe a toast.

People share what the week meant to them. Someone gets emotional. Someone makes everyone laugh. Someone thanks the group for being exactly what they needed.

There are hugs. There are phone numbers exchanged. There are promises to stay in touch.

The Goodbyes

The next morning, people leave at different times (depending on flights).

Some people exchange one last hug. Some people wake up early to say goodbye to someone specific. Some people sit at breakfast, not quite ready to leave.

And here’s what happens next:

You go home. But you don’t go back to how things were.

You have:

• 40 new people in your life (Instagram follows, group chats, actual friendships
• Clarity on what you want (and don’t want) in a partner
• Memories that make you smile for months
• Maybe, just maybe, the beginning of something real with someone

What Happens After the Trip?

Let’s talk about the “real world” part.

The Group Chat

There’s always a group chat. And it stays active. For weeks. Sometimes months.

People share photos. Make plans to meet up. Celebrate when two people from the trip start officially dating. Check in on each other.

This isn’t a transactional experience. It’s a community.

The Romantic Connections

For people who connected romantically, here’s what usually happens:

Option 1: You stay in touch and plan to visit each other.

If you live in different cities, you figure it out. Flights aren’t that expensive. Weekends exist. If it’s real, you make it work.

Option 2: You realize it was a vacation connection, and that’s okay.

Sometimes the chemistry was real but the logistics are impossible. That’s not failure. That’s clarity.

Option 3: You start dating for real.

If you live near each other (or one of you is willing to relocate eventually), you actually date. You see each other in real life, not just on vacation. And you figure out if this is your person.

Success Stories

Over time, I expect we’ll have:

• Couples who met on a trip and are now together
• People who didn’t meet their person but met lifelong friends
• People who went on multiple trips because they loved the experience
• People who found clarity, hope, and restored faith in love

All of those are wins.

Common Questions (Let’s Get Real)

“What if I’m the only one not connecting with anyone?”

Unlikely, because everyone is pre-screened for compatibility. But even if you don’t have a romantic connection, you’ll connect with people platonically. The week won’t feel wasted—I promise.

“What if someone I’m interested in is interested in someone else?”

It happens. And it’s okay. You’re adults. You handle it with grace. And honestly? There are 19 other potential matches in the group.

“Is it awkward if two people clearly like each other and the rest of us are third-wheeling?”

No, because there are 38 other people. You’re not third-wheeling—you’re part of a group. And we design activities so no one feels left out.

“What if I don’t drink alcohol?”

Totally fine! Not everyone drinks. We have non-alcoholic options everywhere. And connection doesn’t require alcohol.

“Do I have to participate in everything?”

Nope. Some things are group activities (welcome dinner, farewell dinner). Most things are optional. You can skip, rest, explore on your own. No judgment.

“What if it feels forced or cheesy?”

It won’t. Because we’re not doing trust falls or speed dating. We’re just traveling together. Eating together. Experiencing things together. It’s natural, not contrived.

“What if I’m introverted?”

Perfect! So are about half the people on the trip. You’ll have plenty of downtime. And introverts often make the deepest connections because they’re thoughtful and present.

Who This Is For (And Who It’s Not For)

This IS for you if:

• You’re emotionally available and genuinely ready
• You value experiences and personal growth
• You’re open to meeting people outside your usual “type”
• You’re okay with uncertainty (no guarantees)
• You believe good people exist and you’re willing to invest in finding them

This is NOT for you if:

• You’re still healing from a recent breakup
• You want a party trip or casual hookups
• You need a guarantee you’ll meet “the one”
• You’re not open to vulnerability
• You’re not willing to invest (time, money, emotional energy)

The Investment

Let’s talk about cost, because I know you’re wondering.

Passport to Love trips range pending on the destination and your travel preferences. So an estimated costs from $3500 to $9,800.

(Note: You’ll set actual pricing based on your costs + margins)

What’s Included:

• 7 nights luxury accommodation (private room or sharing with a single friend you want to have with you)
• All curated experiences (catamarans, dinners, cultural tours, excursions)
• Ground transportation (airport transfers, day trips)
• Most meals (breakfasts, group dinners, some lunches)
• The matchmaking process (application review, screening, curation)
• Access to 40 vetted, compatible singles

What’s NOT Included:

• Flights (you book your own, but I can help)
• Some lunches and casual meals (you choose where to eat)
• Alcohol (available everywhere, but not pre-paid)
• Spa treatments or personal activities

Is It Worth It?

Here’s how I think about it:

You could spend:

• $50/month on dating apps x 12 months = $600
• $100/date x 20 dates = $2,000
• Therapy to process dating burnout = $1,000+

Total: $3,600+ with no guarantee of results.

Or you could invest in:

• An unforgettable travel experience
• 40 pre-screened, compatible matches
• A week of genuine connection
• Lifelong friendships
• Hope restored

Even if you don’t meet your person (though many do), you get an incredible trip, personal growth, and clarity.

Low regret. High ROI.

How to Apply

If you’ve read this far, you’re probably thinking: “Okay, I’m interested. What now?”
Here’s what to do:

Step 1: Follow Along

Instagram: [@mypassporttolove]

Get a feel for the vibe, the philosophy, the community.

Step 2: Join the Early Access List

[Link to early access signup]

Applications open February 2026. Early access gets first dibs.

Step 3: Apply

When applications open, you’ll fill out the full application (30-45 min). Be honest. Be thorough. This is how I match you well.

Step 4: We Talk

If you’re a potential fit, we hop on a call. I’ll answer your questions. You’ll get a sense of whether this feels right.

Step 5: You’re In

If it’s a match, you’re on the trip! Then we handle logistics, payments, travel coordination. 

Final Thoughts: What This Really Is

Passport to Love isn’t a gimmick. It’s not a reality show. It’s not a party trip disguised as matchmaking.

It’s a genuinely intentional way to meet people who align with what you want.

Yes, it’s travel. Yes, it’s luxury. Yes, it’s beautiful.

But more than that, it’s context.

It’s seeing people in real life.

It’s shared experiences that create intimacy.

It’s removing the noise of dating apps and replacing it with presence.

And it works.

Not because I can guarantee you’ll meet “the one” (I can’t).

But because I can guarantee you’ll meet yourself in a new way. You’ll remember what it feels like to hope. To connect. To be seen.

And that alone changes everything.

Your Move

You can keep doing what you’ve been doing:

Swiping
Wondering
Hoping the next match will be different

Or you can try something new.

Less swiping. More boarding passes.

Applications open February 2026/2027 trips for & dates coming soon:

• Malta
• Portugal
• Barcelona
• Caribbean/Mexico

Apply here or DM me on Instagram @mypassporttolove.

Your person might be one flight away.

Let’s find out.