Jennifer Gregg · Advisor, Travel with Jennifer
Travel with Jennifer
You can search for the trip. Jennifer knows what to look for inside it.
Cruises, resorts, groups and custom trips — planned around the people actually taking them.
Personal travel planningNo additional planning fee
MCC · Cruise & group travel · Planning since 2019
At sea · cruise planning is where she's strongest
UNIVERSAL ULTIMATE EXPERIENCES
EXPERTISE
Now a Universal Specialist.
Jennifer can now help plan Universal vacation packages and Universal group travel—with one point of contact from the first idea through departure.
Start at sea
Cruising gives you more options than anyone wants to compare.
Hundreds of ships. Thousands of cabins. Jennifer already knows the questions that narrow the list — and the first one is rarely about the ship.
Who are you traveling with?
Some ships are a better fit for children and families than others.
Cabin layout, evening schedules, and how far the pool is from your room can shape the entire trip.
Jennifer brings expert knowledge to plan your perfect vacation.
Booked most often
Royal Caribbean
A frequent fit for families and groups — from first cruises to multi-generation sailings.
Choose your view
There are thousands of ways to travel. You only need the one that fits you.
Open water · sea day
The person planning it
The trip may be yours. The details are Jennifer's.
Years of cruise training, group experience and personal planning help Jennifer notice the details most travelers don't know to look for yet.
Jennifer Gregg · Est. March 2019
Credentials · MCC · CLIA · ASTA · IATAN · S&B
Straight answers
What people ask before they book with Jennifer
A travel advisor, not a booking engine: cruises, all-inclusive resorts, family and group trips, honeymoons and international travel, planned by one person who answers you directly.
Jennifer Gregg is the travel advisor behind Travel with Jennifer, an independent travel-planning practice she started in March 2019. She was a traveler long before she planned travel professionally, and she still plans every trip personally.
Ocean and river cruises, all-inclusive resort stays, family vacations, couples and honeymoon trips, anniversaries and celebrations, group departures for friends and families, solo travel, and international itineraries.
Cruises are her strongest category — ocean and river sailings, first cruises, Alaska and the Caribbean. She compares ships and cabins across cruise lines as an independent advisor; she isn't employed by any cruise line.
Yes. Jennifer is a Universal Specialist and plans Universal vacation packages for families and Universal group trips, helping choose hotels, packages and timing. Universal is a separate company; Jennifer plans and books on your behalf.
Yes. She has organized an Alaska trip with more than 100 travelers, and she handles cabins, rooms, payment schedules and communication for each party in a group.
No. Jennifer does not charge travelers a planning or consultation fee. Cruise lines, resorts, airlines and tour operators still set their own prices, deposits and cancellation terms.
Yes — that is one of the most common way trips start. Tell her who is traveling, roughly when, and the kind of week you're picturing, and she comes back with places and ships that fit.
Use Plan My Trip to tell her who's traveling, the type of trip and your rough timing, or contact her directly. She replies personally and the conversation starts from there.
Not sure yet? Good.
Start with what you want. Jennifer handles the rest.
Est. March 2019 · Tropical weather. Always.