top of page


#40 Bikes.jpeg



What the Group Asked For:

This group of 4 couples are seasoned travelers, and they wanted to experience a completely new area of the world that embraced the outdoors and filled them with awe. The gals were very focused on doing some serious horseback riding but the guys are not into riding at all. However, they are into some serious fishing and definitely wanted to partake on this adventure. In their spare time, they wanted to do a little hiking to get some incredible photos of the area. Lastly, they asked to learn about the culture and local customs through experiencing the wines of the region. Now that’s a challenge travel planners can really sink their teeth into – and we did!


What We Booked for Them: 

We searched the world over and determined Chile was exactly the right destination for them. Starting in the cosmopolitan city of Santiago with their Ritz Carlton lodging was the perfect way to rest and relax a bit after their flight. Excellent food and local wines combined with a beautiful and historic Old Town made for a picturesque couple of days. We then sent them just outside Santiago to do a day of wine tasting at several local vineyards to learn the history of the grapes and all the nuances of the different varieties of Chilean wines produced in the region. Then it was time to head further South to the awesome, wild beauty of Patagonia. We booked the group into a luxury lodge on a family-owned 5000 acre ranch situated on the Nirehuao river – arguably the best wild, resident brown-trout river in South America and perhaps the world. So the guys were very happy. However, the gals were also in heaven because this ranch has a herd of beautiful and sturdy Arabian/Chilean mix horses for the guests to ride across the vast and varied terrain of the ranch’s mountains and valleys any time they chose. When our group wasn’t riding or fishing, they experienced the breathtaking scenery on several amazing hikes.  The photo below was taken from a particularly great vantage point at the top of a mountain promontory overlooking the river. Add in lovely lodging and three gourmet Chilean meals per day, and our group never wanted to leave this outdoor paradise. Mission accomplished!



"This trip was a dream come true. Journeys That Fit did an amazing job of combining the guys love of fishing and the girls desire to ride horses til the cows came home. The accommodations, scenery, and especially the Chilean wines were perfect.  Simply amazing!"


What the Group Asked For:

This group of 12 people asked us to create an adventure that would give them a view of a new part of the world from the back of their bicycles and have the time of their lives doing it. They wanted to mesh with the locals and feel like they truly experienced all the area had to offer. To them, this meant embracing the local customs, food and drink and traveling the roads in a way that allowed them to stop and check out anything that looked interesting whenever the whim struck.  “Structured, but not restrictive” is how one member of this adventurous group put it. Fantastic! A perfect Journeys That Fit request.


What We Booked for Them: 

We came up with four different areas of the world for them to choose from, and they unanimously selected the Emerald Isle of Ireland. We worked closely with one of our favorite bike tour vendors to create a “structured, but not restrictive” biking itinerary that took this group all over Connemara in Northwest Ireland. All of Ireland is a picture postcard, but Connemara has a special something that we knew our biking adventurers would love. Sure, there was fantastic biking every day, but there was also unbelievable history to learn about, crescent-shaped beaches to explore, a little zen to be found at a spa overlooking Ireland’s only fjord, music, music and more music to enjoy and participate in, and of course a pint (or two!) of Guinness to be had sitting in a pub (sometimes more than 500 years old) at the end of each ride. Visiting villages in the tight knit communities around Connemara and staying in small, boutique hotels and inns gave this group a true feel for the amazing Irish people and their customs while allowing the structured freedom they wanted from each day of their journey.



"Thank you Journeys that Fit for such an awesome job planning and executing our cycling trip through Connemara, Ireland! The varied biking kept our interest peaked every day, and the countryside was simply captivating. Our local guide was fantastic and taught us so much about the customs, culture, landscape and ecology of this great country. And, of course, we learned everything we wanted to know about Guinness, craft beer and cider while sitting in the local pubs. The food and accommodations were top notch!


Thank you again for organizing this trip. Such a delight to have the perfect 'custom' trip to fit our active and adventurous life style!!"


What the Client Asked For:

This client is in the phase of life with teenage boys’ summer sport schedules and her husband’s quarter-end driven sales business. This meant that they had only one-time all summer for vacation. Given that tight parameter, we needed to design an inspired 12-day Italian adventure with a balance of active & relaxation for their family of five. The ‘where’ they suggested was mainly northern Italy, and perhaps the Amalfi Coast. For their three active boys, they shared their interests in cars/motor bikes, swimming, hiking, golf, and gelato, and the parents were interested in biking, boats, beach, and of course, great food and wine – it is Italy after all. 


What We Booked for Them: 

Get ready to want to jump into their suitcases as their trip had it all! They toured Florence with invaluable skip-the-line tickets at their selected venues. The Lakes district called their names and they enjoyed a guided tour and lovely lunch in Bellagio and a relaxing and informative ferry tour while looking at all the ‘eye candy’ on Lake Como. The octane was added to their adventure with museum tours of Ferrari, Lamborghini and more, plus self-driving Fiat 500 tours in the Tuscan countryside. Keeping the boys active, they enjoyed e-bike tours near Florence, and lots of swimming during their boat tour around the gorgeous Island of Capri. We didn’t forget the great food and wine as the boys were able to make their own pizza and gelato, and the parents enjoyed amazing culinary experiences, especially when visiting winery restaurants in the Chianti region and overlooking the slopes of Mt. Vesuvius! They were excited to spend some decadent time on the Amalfi coast enjoying the beauty and sunshine from their pool overlooking the Mediterranean Sea.   



"Journeys that Fit planned a fabulous Italian vacation for us!! We were definitely active, we saw wonderful parts of Italy, we ate delicious food and drank delightful wine! We walked all around Milan and Lake Como plus we took a ferry ride across the lake. We rode electric bikes through the Tuscan countryside. Our apartment in Florence was within walking distance to several yummy restaurants, museums, shopping and farmers markets. All of which we enjoyed!! Our final stop was in the town of Amalfi where we swam at the beach, and had a private boat take us to various grottos around Capri. Everything about our trip was impeccable: from the hotels/apartment to the restaurant reservations, train tickets, to the drivers and tour guides. We couldn’t have asked for a better family vacation. Thank you Journeys that Fit!! Ciao!"



What the Client Asked For:

Cancer and wellness aren’t usually in the same sentence, but that’s exactly what was on the mind of our client. She wanted to treat her sister to a wellness weekend at the conclusion of her chemotherapy treatments, but before the start of other treatments, in a place that gave her space to relax and focus on her own healing. The timing was the most important aspect, so she left the location and other details up to us to plan.    


What We Booked for Her: 

We selected a wellness spa resort in the Texas hill country with a comforting vibe. It was on a lake with lovely views, but also had a state-of-the-art spa, plus many other options for fitness, mediation, and cooking classes. This all-in-one venue was important as they needed to arrive and then just ‘be’. They selected many wellness-specific spa-treatments and took advantage of the cooking and mediation classes. The resort had its own garden, and they enjoyed many wonderful and nutritious farm-to-table meals.  



"Journeys That Fit planned an amazing wellness experience for my sister and me. It was just what the doctor ordered. They customized the perfect trip with all the wellness components to strengthen the body and rejuvenate the soul. The experience was designed with relaxing spa treatments, restorative yoga, singing Chakra bowls, and delicious wellness meals all in a beautiful setting. My sister returned ready for her next round of treatment with new found strength. She shared about the impact of the trip with her doctor who said she would be prescribing similar wellness experiences for all of her patients to benefit from. Now that’s a wonderful ‘wellness’ testimonial, right from a doctor’s mouth!"


What the Client Asked For:

This family wanted a great US ski resort location where they could take their three kids (ages 14, 13 & 8) to learn to ski/snowboard. They had six days and wanted to be on the mountain for half of it. The remainder of the trip was open for us to design something special for the whole family. 


What We Booked For Them: 

They were speaking our language as our Colorado based agency loves designing ski trips around the world. We selected a spacious villa in a Steamboat Springs ski-in/ski-out resort with the rental shop right in the resort. No lugging their gear around for this family! After seamlessly booking all the lift tickets, rental equipment and lessons, we moved on to all the other aspects to enhance their trip. Envision three more days that included driving their own dogsleds, tubing down groomed designated runs, and soaking away their sore muscles in a gorgeous hot springs venue tucked into the mountains. This foodie family also enjoyed being taken to dinner on a sleigh ride and in a gondola, and then enjoyed top-notch food and wine. Bonus – the kids were skiing ‘blue’/intermediate runs by the end of the three days!



Our Chicago family has never traveled out west for a ski adventure. So, when we decided to take our family to Colorado, we immediately contacted Journeys That Fit! They took care of everything from beginning to end! From transportation to and from the airport, to lift tickets, ski lessons, and equipment rentals, plus extra non-skiing excursions and even dinner. They made the trip turn-key for us! They even provided us with an app on our phone with our interactive itinerary for each day and easy links to all our important travel documents and confirmations! Our trip was truly outstanding, and we not only already started working with them on our next ski adventure but this time we’re bringing others along with us!

bottom of page