Italy 2022

April 2, 2022 to April 8, 2022

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 trip. Chelsey custom designs every detail from beautiful accommodations, menus, to tastings, and unique activities. 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. This trip has room for only 16 women and will sell out quickly. There are only SIX rooms available so be prepared and ready to book.

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 trip is focused on food, wine, Instagram worthy destinations and unforgettable experiences. 

Sample Schedule for Italy

Day One 

  • Arrive in Venice
  • Relax + Explore Venice
Optional Activities:
    • Famous Bellinis at the Belmond Hotel Cipriani
    • Dinner at Cip Cips 

Day Two 

  • Relax + Explore Venice

Optional Activities:

  • Coffee in Italy's Oldest Cafe
  • Gondola Ride  
  • Unique Venetian Mask Experience   
  • Michelin Star Tasting Menu for Dinner 

    Day Three 

    • Private Transfer to Tuscany
    • Two Hour Stop for Lunch in Bologna
    • Tuscan Wine Tasting
    • Farm to Table Dinner
    Optional Activities:
      • Food Tour in Bologna 
    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
    • Farm to Table Dinner 

    Optional Activities:

    • Eat Award Winning World Famous Gelato
    • Climb the Torre Grossa
    • Try Wild Boar Salami, a Tuscan Delicacy
    • Taste Vernaccia di San Gimignano  
    Day Six  
    • Private Transfer to Florence
    • Explore + Shopping in Florence 

    Optional Activities:

    • View the David at Galleria dell'Accademi
    • Visit the Santa Maria del Fiore Cathedral   
    • Walk on the Ponte Vecchio Bridge  
    • Shop at one of Florence's oldest markets, Mercato di San Lorenzo
    • Eat at Mercado Centrale 

    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.

     What's Included: 

    Bonus! Professional photographer will be traveling with us! Take home memories and beautiful photos from our trip together! 


    • (2) Nights in a Historic 15th Century Palazzo in Venice 
    • Private Transfer to Tuscany with Stop in Bologna  


    • (3) Nights in an Authentic Agroturismo in Tuscany
    • (3) Farm to Table Meals (Breakfast) at Agroturismo
    • (3) Farm to Table 8 Course Meals (Dinner) + Unlimited Wine at Agroturismo
    • (1) Wine Tasting of Local Organic Wines + Charcuterie
    • (1) Pasta Cooking Class with Tuscan Chef + Family Recipes + Apron
    • (1) Agroturismo Tour including Chianina Open Air Stables + Olive Tree Groves  
    • Private Transfer to Sienna for Shopping + Sightseeing
    • Private Transfer to San Gimignano for Shopping + Sightseeing
    • Private Transfer to Florence 


    • (1) Nights in a Stylish Hotel in Florence 
    • Gucci + Gelato: Custom Guided Tour of Florence Created by Chelsey
    • (1) Meals (Breakfast) at Hotel in Florence  

    What's Not Included: 

    • Airfare
    • Meals (Except When Specifically Included Above) 
    • Additional Excursions, Activities or Shopping 
    • Transfer to / From Airports   
    • Gratuities 

    Monthly payment plans are available after initial non refundable deposit has been received.