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The crew behind every great trip

Real people in Portage, Michigan who plan every vacation as if it were their own.

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We treat every part of your vacation as if it were our own.

Our Story

Trips Ahoy Travel is a small team of advisors based in Portage, Michigan, near Kalamazoo. We plan honeymoons, destination weddings, family vacations, group trips, cruises, and European getaways.

Every trip starts with a conversation. We get to know your style, your budget, and what you want to feel when you get there. We’re here for you before, during, and after the trip, so you’re never on your own.

Meet the Crew

Your advisors are ready for boarding

Pick the advisor whose travel style matches yours, or just reach out and we’ll pair you up.

✈  Trips Ahoy · Boarding Pass
TA-01
Passenger

Hilary Olney

Travel Advisor
Specialties
Destination Weddings · Honeymoons · Family & Group Travel
Destinations
Caribbean · Mexico · Hawaii · European River Cruises

Hilary plans destination weddings, honeymoons, family vacations, and group trips to the Caribbean, Mexico, and Hawaii. For travelers who want more adventure, she also books European river cruises. Her goal is simple: help you relax and recharge with stress-free vacation planning.

Departing From
Michigan
✈  Trips Ahoy · Boarding Pass
TA-02
Passenger

Leslie Kepplinger

Award-Winning Top Specialist
Specialties
Sandals Luxury Included Resorts
Destinations
Caribbean Islands · All-Inclusive Resorts

Leslie is an award-winning top specialist agent for several resort chains and island destinations, with Sandals Luxury Included Resorts as her specialty. She always puts her clients first, making sure every detail fits the way you love to travel.

Departing From
Michigan
✈  Trips Ahoy · Boarding Pass
TA-03
Passenger

Terry Cheng

Travel Advisor
Specialties
Island Vacations · Cruises · Family Trips
Destinations
Islands · Open Seas

Terry is a mom of three in a family that loves to travel, so she knows what makes a trip work for everyone. She specializes in island vacations, cruises, and family trips, and would love to help you find the perfect spot for your next family vacation.

Departing From
Michigan
✈  Trips Ahoy · Boarding Pass
TA-04
Passenger

Stacy Logan

Travel Advisor
Specialties
Your Next Adventure
Destinations
Wherever Opportunity Knocks

Stacy lives by a simple motto: when opportunity knocks, don’t let fear hold you back. She brings that spirit to every trip she plans, and she’s ready to help you find your next adventure.

Departing From
Michigan
How We Work

From daydream to departure

01

Dream

Tell us where you’d love to go, who’s coming, and what you want to feel when you get there.

02

Plan

We match you with the right resort, ship, or tour, then handle the details, perks, and paperwork.

03

Go

Pack and enjoy. We’re still a call away before, during, and after your trip.

Let's plan your next trip

Call (269) 324-2430 or toll-free 888-862-AHOY, or send us a note.

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