Introducing Guilt Trip 2022: Italy Awaits

I have been planning this trip in my head for a long time. Covid19 crushed my plans last year but I am delighted to announce the next Guilt Trip will be in Italy!  

Below I have shared the anticipated schedule. For a more detailed outline and to be put on the waiting list please click HERE.

Italy is one of my favorite places in the world. From the delicious foods, to the incredible culture and history, mouth watering gelato and unexpected delights around every corner, it is a destination I look forward to visiting time and time again. 

Join me next Spring as we explore Venice, Tuscany and Florence with a thoughtfully planned itinerary and custom experiences you won't find on any other tour.

I personally design every detail from beautiful accommodations, memorable restaurants, shopping experiences, food tours and wine tastings, plus unique activities you wouldn't experience on your own. Guilt Trips are simply extraordinary trips for extraordinary women. 

What should you expect?

  • Expect to participate in hands on experiences that you can only do in specific regions of the world.
  • Expect to walk the grounds where your food and wine have been carefully grown.
  • Expect to see the most stunning villages you've ever seen.
  • Expect to have relaxed, leisurely meals and flavorful wine tastings.
  • Expect comfortable lodging and delightful welcomes.  
  • Expect to visit UNESCO world heritage sites and cities filled with history.
  • Expect to eat lots (lots!) of gelato. Did I mention gelato? 
  • Expect to shop artisan products in the cutest local shops and browse the coziest bookstores. 
  • Expect new friendships, plenty of laughs and a ton of fun! 

"Guilt Trips" were designed for women who are interested in connecting with other female travelers and sharing memorable experiences while safely traveling with an educated travel advisor. 

"Guilt Trips" were created to empower women to explore the world and get out of their comfort zone guilt free while delighting in unexpected thoughtful gestures around the world. 

To purchase a spot on one of these exclusive trips, booking quickly is key. 

The trips are small groups, anywhere from 10-16 women and sell out quickly.

Pricing is based on double occupancy so grab your bestie, mom, sister and tell them to get their passport ready!

To get on the waiting list and be the first to book, sign up HERE. You can also check out our FAQ page or email for any questions. 

Values of each Guilt Trip 

  • Frequent and clear communication leading up to the tour and during travel. Private Facebook Group offers ease of communication as well as getting to know fellow women travelers prior to the tour. 
  • Well organized, detailed trip itineraries and packing lists. Access to custom google documents created specifically for your tour. 
  • No questions unanswered. We want to answer all of your questions prior to travel so you can fully relax and enjoy the tour.  
  • Each tour is focused on food, wine, Instagram worthy destinations and unforgettable experiences. 

Sample Schedule for Italy 

Day One 

  • Option for Early Arrival to Italy
  • Arrive in Venice
  • Relax + Explore Venice
  • Famous Bellinis at The Belmond Hotel Cipriani   

Day Two 

  • Gondola Ride
  • Explore Venice 
  • Unique Venetian Mask Experience + Dinner  

Day Three 

  • Private Transfer to Tuscany
  • Wine Tasting
  • Farm to Table Dinner

Day Four

  • Explore + Shopping in Sienna 
  • Farm to Table Dinner 

Day Five

  • Cooking Class with Tuscan Chef + Family Recipes 
  • Explore + Shopping in Medieval Town of San Gimignano
  • World Famous Gelato

Day Six 

  • Private Transfer to Florence
  • Explore + Shopping in Florence 
  • Florence Rooftop Experience 

Day Seven  

  • Departure Day
  • Option for Extended Stay in Florence 

Ready to explore some of the most iconic locations in Italy? Click HERE to be put on the waiting list. Ciao! 

Thoughtfully, Chelsey