What a Caribbean Cruise Taught Me About Small Business, Leadership, and Taking Time Off
I just returned from a 7-day Caribbean cruise, and it was exactly what I needed to refresh, recharge, and spark new inspiration for my business ventures—including this blog. Amidst the beautiful beaches, warm weather, and nonstop fun, I was reminded of something important:
Small businesses are everywhere—and they’re essential.
My fiancée, a group of 30 friends, and I boarded Royal Caribbean’s Icon of the Seas for a week on the world’s largest cruise ship. And let me tell you—there was never a dull moment. From exhilarating onboard activities to world-class shows, theme nights (70s Night was epic—strangers took more pictures with me than my own friends!), and incredible dining, it truly felt like a floating resort.
Our dining experience alone felt like a five-star restaurant every night. Our server, Bulent, was phenomenal—attentive, kind, and incredibly knowledgeable. We learned he has been with Royal Caribbean for over 30 years, and it was clear he loves what he does. Crew members like him—and the thousands who work onboard—are the heartbeat of the cruise experience.
But once we reached each destination, I noticed something else.
Cruising Depends on Small Businesses More Than You Think
Behind every memorable excursion—whether it’s a snorkeling tour, sightseeing shuttle, or local adventure—is a local small business.
Cruise lines like Royal Caribbean, Norwegian, Carnival, and MSC rely heavily on independent tour operators, local guides, family-owned restaurants, transportation companies, and small vendors at each port. These businesses know their islands better than anyone and help create the unforgettable experiences travelers rave about.
From markets and souvenir shops to beachfront bars and jewelry stores, each island showcased dozens of entrepreneurs supporting both their communities and the tourism economy.
It was a powerful reminder of what entrepreneurship looks like around the world.
My Key Takeaways for Entrepreneurs
1. Take the Vacation—You Earned It
Entrepreneurs work HARD. One of the best pieces of advice I ever received (even if it came later in life) is this:
Always have your next vacation planned.
This cruise forced me to disconnect, breathe, and enjoy life. I spent quality time with my fiancée and friends, and I returned home refreshed and refocused.
2. Use a Travel Agent—They’re Small Business Owners Too
For big trips like this, I always recommend using a travel agent—just like I tell my wedding clients to do for their honeymoons.
Rates are competitive, and you’re supporting another small business owner.
My agent, Luke Smith of Totally Booked Dude Travel, handled everything—from our bookings and show reservations to seating all 30 of us together near each other for dinner. If you need a pro… LUKE IS YOUR GUY.
👉 www.totallybookeddude.com
(Tell him “Marco” sent you—he’ll know it’s me!)
3. Plan Ahead for Your Business
Whether you close during a slow season or have a team running operations, planning ahead prevents chaos.
Here’s what helped me:
Letting clients know in advance
Setting expectations with staff
Using an email auto-reply
Adding a temporary website pop-up for online orders
Delegating key duties to your team
Giving team members additional responsibility can also reveal who you can rely on—and who may need more training. (There’s more about empowering employees in my book “The Small Business CEO’s Playbook.”)
4. Expect to Be Unreachable—and Be Okay With It
Cruise ships aren’t exactly known for perfect Wi-Fi. If something happens back home, there may not be anything you can do from the middle of the Caribbean.
And that's okay.
5. Enjoy Yourself
You’re paying for the trip—don’t spend it glued to your phone worrying about emails.
Be present. Take in the experience. Make memories.
And if inspiration hits (trust me, it will), jot it down and develop the idea when you return.
Final Thoughts
This cruise wasn’t just a vacation—it was a reminder of the power of small business, the importance of stepping away, and how valuable it is to reconnect with the people who matter.
Whether you’re an entrepreneur, team leader, or side-hustler, remember this:
Your business will still be there when you get back. You deserve the break.
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