Travel Advisor

Jenny Kager
She/Her
Expertise
- New York City,
- All-Inclusive Travel,
- Costa Rica,
- Couples’ Travel,
- Paris,
- London,
- City Travel
Based in
Milwaukee, WI
Languages spoken
French
Profile details
About
Lover of food, wine, travel and big city life. Currently live near Milwaukee and Chicago with my husband and Old English Bulldog, but spent many years soaking up the energy of NYC.
Travel style
I love exploring big cities, with all they have to offer in food, wine and culture. I also live for a good beach vacation, whether it be relaxing at an all-inclusive resort, or traveling around Costa Rica.
Jenny's travel guides & trip reports

Site Inspection: Crosby Hotel-NYC

The City Different: A Guide to Santa Fe, New Mexico

Fall in Love with New York City: The Perfect 7-Day Itinerary

Adventure Awaits in Costa Rica
Favorite hotels
Jenny's reviews
Jenny was beyond incredible. She worked with my family to plan the trip of a lifetime. She booked in three cities, two countries, various modes of transportations, hotels, tours, special birthday surprises, and more for 8 - 15 people depending on the day and city. She navigated all of the bookings with multiple family members who all had different needs, and she also did it with ease and great consideration. Also, during the trip she checked in on multiple occations to make sure everything was going smoothly. If I could give her 10 stars I would.
- Holly R.
Booked travel to Paris
- June 2025
Jenny was terrific, She handled everything very professionally and was quick to answer any of our questions.
- David L.
Booked travel to Mexico
- January 2024
Jenny took our family’s diverse needs into account and got us set up in the perfect place! She gave us tons of options and went the extra mile to get us set up in the place that met the needs of two adult couples and our elderly parents. It was our first time at an all-inclusive, and Jenny helped us navigate that AND set up our transportation for us, taking a huge chore off our to-do list. We will definitely have her book our next family vacation!
- Liza P.
Booked travel to Mexico
- January 2024

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