Let The Happy Hypochondriac help you plan your next vacation! People often feel overwhelmed with planning a trip and come to Kat for itinerary ideas. She will do the research for you. You provide a budget and a time frame and she will come up with the trip of your dreams.

Contact for:

  • Daily Itineraries to any location, domestic or international
  • Help with planning transportation, hotel and restaurants
  • Ideas for different types of vacations: romantic getaways, family trips, girlfriend getaways, single travel, and more

Each trip plan is customized for your interests!

Prices negotiable based on budget and duration of trip 

Contact: thehappyhypochondriac@gmail.com


Sample Itinerary:

NEW YORK CITY for Adults

Designed for a couple in the Mid—Atlantic region who wanted to spend one night in New York City. They planned to drive and asked to eat great food, see some key sights and take in a show or two. They are an active couple who don’t mind walking a bit, but also don’t mind hopping in a cab, if necessary.



9:30 am – Arrive at hotel, park car, and check in at New York Marriott East Side, conveniently located at Lexington and 49th .  The couple wanted to use some hotel points.

10:30 am – Visit MOMA (Museum of Modern Art). I recommend purchasing tickets online in advance to avoid taking up time to stand in line.

12:30 pm – Lunch at Ma Peche, a Momofuku restaurant (delicious Vietnamese restaurant with fantastic dumplings), with dessert purchased at the adjoining Milk Bar. Restaurant located only a couple of blocks away from MOMA.

2:30 pm – Matinee performance of Off Broadway performance of “Buyer and Cellar” (a highly reviewed comedy) in the Village.

4:30 pm – Free time to walk and browse shops.

5:30 pm – Dinner at renowned Gramercy Tavern (amazing prix fixe dinner with wine pairings). Pick up a cookbook while you are there as a perfect NYC souvenir!

8:30 pm – Stand Up Comedy show at The Comedy Cellar (place where all the top comedians play). Tonight's show will feature well-known comedians, many who have appeared on "Last Comic Standing," "HBO," and "The Tonight Show."

After the show, try some pizza next door at Ben’s (which is shown in the opening credits of “Louie” with Louis CK).

If you are not too tired, stop in at the world famous Bull and Bear bar at the Waldorf Astoria Hotel, next to your hotel and indulge in a Rob Roy.



After sleeping in a little, and eating the muffin given to you by Gramercy Tavern the night before, grab a cup of coffee and head downtown.

10:00 am – Visit the 9/11 Memorial and museum.

Stroll along the water at Battery Park, and catch a glimpse of the Statue of Liberty, before heading in a cab up to Central Park South to meander around Central Park for a bit before brunch. Watch the ice skaters and perhaps take a handsome cab in the park. You can walk to brunch from here.

1:00 pm – Brunch at Norma’s at Le Parker Meridien Hotel (delectable dishes and the best bottomless glass of fresh squeezed OJ north of Florida).

Depart NYC.

Let your imagination be the limit!

Kat has also planned a family trip for two adults and two young children to Hawaii for 10 days, a 5-day anniversary trip for a couple to Iceland, and a 4-day girls trip to Mexico, among many others!