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Mountains with people hiking in the foreground

 Destinations Designed: Custom Travel & Itinerary Planning

Take the stress out of planning your next vacation, with custom itinerary planning services

Acropolis in Greece

Photographed above: At the Parthenon in Greece, on my most recent trip with my favorite travel MOM!!


My name is Ashley Tuggle and I'm the passionate travel enthusiast and researcher behind Destinations Designed. From a young age, my curiosity for locations across the globe was sparked by a simple elementary school report on Rhode Island, where I discovered the quirky fact that it takes just 45 minutes to drive across the entire state. This ignited a lifelong love affair with travel and exploration. I thrive on the thrill of discovering unique experiences, off-the-beaten-path opportunities, and hidden surprises in every destination. While I appreciate the allure of typical tourist hotspots, my heart belongs to the unexpected stops that add an extra layer of magic to any journey. A self-proclaimed foodie, my love for culinary delights also plays a crucial role in crafting unforgettable travel itineraries. Let's embark on a journey where every moment is tailor-made for discovery!

I currently live in downtown Chicago with my partner and our two furry companions.

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What's Included in a Custom Travel Itinerary?

Detailed travel itinerary provided via PDF and / or mobile app with all the necessary information

Interactive map with all destinations marked (as well

as links, distance between spots etc.)

Local restaurant, bar and interesting food stop recommendations tailored to the Client's tastes

*Note: Recommendations will not be made for every meal / every

day and some recommended restaurants may not take reservations,

or may not have availability to book in advance

Hotel recommendations based on the Client's preferences 

*Note: Hotel Recommendations will not be given until flights are

booked and itinerary is confirmed, as dates can change - thus altering availability

Travel Insurance Recommendations

*Note: The cost of travel insurance is not included in a custom travel itinerary, however recommendations and guidance based on your needs (as well as facilitating the booking) will be offered

Dietary restrictions, disabilities and pets factored into plans

*Note: Must be disclosed in client interview (after officially booking services)

*Booking of itinerary tours, excursions or activities, as well as coordination and booking of transportation and reserving of restaurants and / or hotels is all included, unless asked otherwise

If you would like more information about custom travel planning, get in touch today.

What to Expect / What Happens Next?

01Get your Questions Answered

Your journey with Destinations Designed begins by getting all your upfront questions answered. Feel free to reach out via email or phone, fill out the contact form or schedule a time to chat. 

Payment 02

To kickstart your custom travel planning journey, I kindly request upfront payment. This is essential to initiate the time it takes to craft a tailor-made itinerary that reflects your unique preferences. Destinations Designed charges $50 / day (regardless of the number of travelers) for custom itinerary planning services. For added convenience, arrangements for activities, hotels, transportation and / or restaurants will be facilitated unless asked otherwise. Customers credit card will be kept on file and used upon authorization, once the itinerary is finalized, to purchase and book all necessary arrangements.

*NOTE: There is an adjustment in the daily fee for 'last minute bookings' (i.e. 60 or less days out)  


Embarking on a seamless journey with Destinations Designed begins with a personalized interview tailored just for you. Together, we'll delve into your interests, hobbies, and travel goals, exploring not only where you want to go but also when and with whom. Don't have a specific destination or date in mind? No worries – I'm here to assist in choosing the perfect option. Our conversation will also extend to your prior vacations, dissecting what you enjoyed and what didn't quite hit the mark. At this time, please share any must-do activities or sights (if you have any), and your preferred travel style and pace.

*Note: Please allot 45-60 minutes


Armed with insights from our personalized interview, I'll create a custom travel plan, crafted to align precisely with your interests, needs, and desires. 

05Communication / Proposal

I believe in a collaborative travel planning journey, so you can count on me to keep you involved and informed throughout the process. Once your personalized itinerary is crafted, we'll schedule a proposal call. This dedicated time allows you to provide feedback, seek clarifications, and make any necessary adjustments, to ensure the final travel plan perfectly reflects your vision. 

*Note: Please allot 30 minutes

Get Excited and have FUN!06

Embark on your stress-free journey, confident that every detail is covered. Your only task? Enjoy the adventure! I'd love to see your pictures and hear all about your experience afterward. Safe travels! 🌍✈️

Once the travel bug bites there is no known antidote, and I know that I shall be happily infected until the end of my life.          – Michael Palin, Actor / Comedian and Travel Enthusiast

Destinations Designed Specialties

Luxury Experiences

Road Trips

Culinary & Wine

Solo or Group


Architectural and / or

Historical Focus

picture of a globe

Active and Adventure Travel

Cultural Immersion

Honeymoons and

Romantic Getaways

Budget Conscious Travel

International or Domestic Getaways

Jessica Chang

Chicago, IL

"Our trip was awesome and we really appreciate the wonderful planning that [Ashley] did. Our itinerary was perfectly tailored to our needs, all our tours were awesome and I wouldn't change a thing! My [10-year-old] daughter said it was her best vacation ever!"

Matt Brookings

Windham, CT

"Destinations Designed plans a
flawless trip!"

Debbie Mudd

Louisville, KY

"Ashley listened, asked the right questions and came up with a custom itinerary that really met our needs. She is dependable, pleasant and well-versed!"

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