Frequently Asked Questions
Everything you know need to know about our Italy tours.
GROUP EXPERIENCES
How many people are in a tour group?
By design, all of Jason’s Journeys are intentionally kept small for more personal experiences. On average, we host 16-18 guests, with a maximum of 20. Plus, of course, Kelly and Jason, your two dedicated hosts, who are present 24/7 the entire journey.
What type of travelers typically join your trips?
Our guests are often couples, families with adult children, friends and small groups of friends traveling together, as well as solo travelers.
What makes your small group tours different?
Our tours are personally hosted by Pittsburgh locals Jason and Kelly, who have thoughtfully curated each itinerary over the years. Through their time in Italy, they’ve built meaningful relationships with property hosts, local artisans, winemakers, chefs, and guides — many of whom have become dear friends. We welcome our travelers the same way: as friends. This personal connection allows us to go beyond the typical tourist experience and introduce you to authentic, off-the-beaten-path Italy.
Will we interact with local Italians?
Yes! Often on an hourly basis! These authentic connections are the heart of our tours. You’ll make more friends than you think, since they love to share their passion, stories and traditions with us.
PLANNING YOUR TRIP
How far in advance should I book?
Because our groups are small and space is limited, we recommend booking as early as possible to secure your spot. We typically publish new dates and destinations about a year out.
What happens if a tour sells out?
We often create a waitlist once a tour reaches capacity. If space becomes available, we contact waitlisted guests in the order inquiries were received.
How do I choose the right tour?
We know it can be hard to decide — every itinerary has its own personality and focus. Just know there is no wrong answer. If you’re unsure which journey aligns best with what you’re looking for, reach out to us. We’re happy to talk through your goals and guide you toward the tour that suits you best.
Can you help with travel before or after the tour?
Absolutely. If you’d like to arrive early or extend your trip, Kelly can assist with arranging hotels, transportation, and additional experiences to ensure your entire journey is smooth and hassle-free.
Can you assist with flight arrangements?
Yes. Kelly is a certified travel agent and can assist with booking flights, trains and private transport for an additional fee. This ensures your travel plans will align seamlessly with the tour schedule.
ARRIVAL & LOGISTICS
How do we get from the airport to the hotel?
If you arrive on the official start day of the tour, we include airport transfers to the first host property at no additional cost. If you arrive a day or more early, we will assist in arranging transportation, often with other travelers, whenever possible.
Should we arrive early?
We encourage guests to arrive a day or two before the tour begins. This helps protect against potential flight or baggage delays and gives you time to adjust to the new time zone. If you prefer to stay at the host property, we can reserve rooms for you.
How much should I pack?
We recommend bringing one checked bag and one personal item per person. While you won’t be handling your luggage often, it will be necessary at some point. We also send emails well in advance of departure with packing tips and recommendations on clothing, etc. Most of our experiences are casual, including meals, so comfort is king.
DAILY EXPERIENCES
Is there a lot of walking involved?
There is a moderate amount of walking, as many destinations are best explored on foot. We do our best to minimize unnecessary walking, our transport providers can access places not open to general traffic. If you choose, you can always opt out of an activity if you prefer.
Will we have free time during the trip?
Yes. We intentionally build free time into every schedule, so you have time to relax, freshen up and recharge, or explore, or shop, independently. We also try to include one meal when you can dine on your own, otherwise all other meals are included.
What are the accommodations like?
Our tours are boutique in style — thoughtfully curated, comfortable, and well-located — rather than ultra-luxury or white-glove. We select our hotels based on location, cleanliness, comfort, and the strong relationships we’ve built with each property.
We typically stay in 4 and 5-star hotels that offer charm, convenience, and an authentic sense of place. Our goal is to provide excellent overall value while prioritizing experiences, location, and comfort.
FOOD & CULTURE
Do I need to learn any Italian before the trip?
No, but a few basic phrases never hurt. Italians enjoy helping with pronunciation if you ask! Nearly everyone we interact with speaks English, and your hosts are always there to assist. Learning a few simple phrases like “hello” and “thank you” is always appreciated by locals.
Can restaurants accommodate dietary restrictions?
Yes. Italian restaurants take pride in accommodating allergies and dietary needs, including gluten and dairy-free diets. Please communicate any restrictions to us in advance so we can coordinate with restaurants.
Are drinks included?
Yes. All meals are served with wine, beer on occasion. Many times we have an “aperitif” that’s also included. Should you decide to have cocktails or additional beverages at the host property after dinner, they can be billed to your account.
PAYMENTS & INSURANCE
How do you accept payments?
We accept major credit cards, ACH bank transfers, and personal or business checks.
Is there a payment plan available?
Yes. Each tour is divided into three or four scheduled installments. Your payment schedule will be outlined in your registration materials.
Do you recommend travel insurance?
Yes — we strongly recommend travel insurance to protect your investment and provide peace of mind in case of delays, cancellations, medical emergencies, or lost luggage. Our preferred provider is Allianz. Kelly can assist with obtaining this if you need help.
How much does travel insurance cost?
The cost varies depending on the total trip cost, your age, and the coverage plan selected.
ADDITIONAL EXPERIENCES
Do you offer private or custom group tours?
Yes. If you have a group of 12 or more, we can create a customized Italian experience for you. Whether it’s a friends’ getaway, family trip, or celebration, we’ll design an itinerary tailored to your group’s interests and travel style.
GRATUITIES
Are gratuities included?
Yes — gratuities for hotels, included meals, and scheduled guides are covered. At the conclusion of the tour, guests may consider offering a nominal gratuity to drivers if they feel exceptional service was provided. While not required, it is always appreciated.