La Via Cara | Fora Travel

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Boutique Travel

Food & Wine

Italy

Portugal

Spain

Our Story

I’m Cara Stewart, a Fora travel advisor who designs thoughtful, detail-driven journeys shaped by my Italian heritage and Boston roots—influences that inspire my love of great food, beautiful landscapes, and intentional travel.

For over a decade, I’ve been crafting trips not only for my family, but for friends as well, designing seamless stays complete with daily itineraries, transportation, tours, and dining reservations. Whether it’s a glass of Brunello in Tuscany, a sunset along Portugal’s coast, or a perfectly paced family escape, every journey is tailored to you.

La Via Cara—curated travel for those who wander with intention.

I’m Cara Stewart, a Fora travel advisor who designs thoughtful, detail-driven journeys shaped by my Italian heritage and Boston roots—influences that inspire my love of great food, beautiful landscapes, and intentional travel.

For over a decade, I’ve been crafting trips not only for my family, but for friends as well, designing seamless stays complete with daily itineraries, transportation, tours, and dining reservations. Whether it’s a glass of Brunello in Tuscany, a sunset along Portugal’s coast, or a perfectly paced family escape, every journey is tailored to you.

La Via Cara—curated travel for those who wander with intention.

Travel Style

You dream it. I’ll handle it.

No two travelers are the same, and neither are the journeys I design. Every itinerary is shaped around your preferences, pace, and priorities—from boutique hotels and smooth transportation to thoughtful experiences and unforgettable dining.

A sunrise coffee in Lisbon, a hidden enoteca in Piedmont, or a cooking class in Florence—I aim for moments that feel personal, effortless, and beautifully timed.

La Via Cara is travel planned around you: your style, your pace, your priorities, with expert guidance and attentive support every step of the way.

You dream it. I’ll handle it.

No two travelers are the same, and neither are the journeys I design. Every itinerary is shaped around your preferences, pace, and priorities—from boutique hotels and smooth transportation to thoughtful experiences and unforgettable dining.

A sunrise coffee in Lisbon, a hidden enoteca in Piedmont, or a cooking class in Florence—I aim for moments that feel personal, effortless, and beautifully timed.

La Via Cara is travel planned around you: your style, your pace, your priorities, with expert guidance and attentive support every step of the way.

Stay connected

Reviews (9)

J

Jennifer F.

travel to Zermatt

5 days ago

Fantastic choices. She did her homework. Europe is not the easiest place to accommodate 4 people, 2 adults and 2 kids. Cara chose skillfully. The places we stayed always had the best view of our destination for a fair price, accommodated our teens well and in general were super clean, comfy, and great places to stay. We beyond felt very lucky as we moved through Europe to have such perfect accommodations.

C

Chad S.

travel to South Carolina

6 days ago

Cara has planned many vacations for me, including car rentals, trains, planes, and restaurants. She is always on point. I would highly recommend her.

J

Julie H.

travel to Florence

29 days ago

Cara found options to sleep 5 people which was important to us and we couldn’t have found the place without her!

G

Gayle J.

travel to California

2 months ago

Cara was extremely attentive to all of our requests. She really listened to us and gave us great recommendations. Would highly recommend her!

M

Michael S.

travel to Mexico

4 months ago

I recently worked with Cara Stewart from La Via Cara to coordinate a complex group trip for six couples to celebrate my 50th birthday adventure in Tulum, Mexico, and I cannot recommend her services enough. Organizing travel for 12 people is usually a logistical nightmare, but Cara made it look effortless.

She curated a truly spectacular experience for us, starting with a stunning villa that actually featured seven master bedrooms—ensuring everyone in our group felt like a VIP. From securing seamless private transportation for the entire group to arranging elite private chefs and breathtaking beachfront dinners, every detail was handled with precision and style.

Cara’s expertise really shined in the activities she curated. She managed all our access and tickets to the cenotes, booked us into the most amazing clubs, and organized an unforgettable day out on the ocean. Because she is a Fora Advisor, her connections and 'VIP' touch were evident throughout the entire itinerary.

If you are looking for a travel advisor who can handle high-level logistics while maintaining a sense of beauty and intention, book with Cara. She took the stress out of the planning so we could simply enjoy the moments. We will definitely be using La Via Cara for our next escape!

J

Jennifer F.

travel to Zermatt

5 days ago

Fantastic choices. She did her homework. Europe is not the easiest place to accommodate 4 people, 2 adults and 2 kids. Cara chose skillfully. The places we stayed always had the best view of our destination for a fair price, accommodated our teens well and in general were super clean, comfy, and great places to stay. We beyond felt very lucky as we moved through Europe to have such perfect accommodations.

C