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Compass Roam
  • Destination
    • North America
      • Canada
        • Cape Breton, Nova Scotia
        • Whistler, British Columbia
      • U.S.A.
        • Big Sur, Pebble Beach, Carmel
        • Cape Cod, MA
        • Cape May, NJ
        • Jackson Hole, WY
        • Kauai, HI
        • Lake George, NY
        • Lake Placid, NY
        • Orlando, FL
        • Santa Barbara, CA
        • Sedona & Scottsdale, AZ
        • Twin Farms, VT
        • Watch Hill, RI
        • Woodstock, VT
      • Mexico
        • Riviera Maya
    • Europe
      • Florence & Tuscany
      • Munich
      • Puglia
      • Rome
      • Sicily: Syracuse & Taormina
    • Africa
      • Tanzania
    • Middle East
      • Turkey: Istanbul & Cappadocia
  • Hotels
  • Guides
  • Services
  • Shop
  • Subscribe

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Some skiing, some playing, some winter adventuring Some skiing, some playing, some winter adventuring…mostly eating. ❄️🍽️

Our family winter trip to Jackson Hole was skiing and so much more. Don’t get me wrong—I do enjoy a good day on the slopes (team green forever), but what I really love about a ski trip is the vibe. The cozy. The fireside chats.  The warm drinks.  The hot tub!  And can’t forget the “we-worked-so-hard-for this” lunch. Yes, I am absolutely the person who skis a few runs and then has a great lunch spot reserved at the top of the mountain.

Here are my recommendations for a family winter trip to Jackson Hole 

✨ Where to stay (luxury + family-friendly):
• @fsjacksonhole - luxe hotel right next to the slopes
• @hoteljackson - downtown boutique hotel
• @amangani- perfect for luxury lovers who also value quiet + nature

❄️ Winter things to do with kids in Jackson Hole:
• Skiing (the ski school here is incredibly well run)
• Elk sleigh ride (our favorite activity) with @natioanlelkrefugesleighrides
• Shopping + wandering the town square
• Backcountry snowmobiling 
• Winter “safari” 
• Yellowstone tours 

🍴 Kid-friendly restaurants with fantastic food 
• Snake River Grill
• Persephone Bakery 
• The Kitchen
• Steadfire Chophouse
• Corsa

𝐅𝐨𝐥𝐥𝐨𝐰 𝐟𝐨𝐫 𝐦𝐨𝐫𝐞 𝐟𝐚𝐦𝐢𝐥𝐲 𝐭𝐫𝐚𝐯𝐞𝐥 𝐝𝐞𝐬𝐭𝐢𝐧𝐚𝐭𝐢𝐨𝐧 𝐢𝐝𝐞𝐚𝐬

#jacksonholewinter #jacksonholewithkids #skiingwithkids
RANKING TOP 5 OF THE BEST FAMILY HOTELS WE VISITED RANKING TOP 5 OF THE BEST FAMILY HOTELS WE VISITED IN 2025 

Our favorite stays of 2025 — sharing the vibe of each, who it’s a good fit for, and why my kids loved each one.

As a travel advisor, I can book these hotels for you with preferred rates and complimentary perks that can save you hundreds (sometimes thousands) of dollars.
𝐂𝐨𝐦𝐦𝐞𝐧𝐭 “𝐥𝐮𝐱𝐮𝐫𝐲 𝐡𝐨𝐭𝐞𝐥” 𝐢𝐟 𝐲𝐨𝐮’𝐝 𝐥𝐢𝐤𝐞 𝐭𝐨 𝐠𝐞𝐭 𝐬𝐭𝐚𝐫𝐭𝐞𝐝 (FB friends - reach out on IG please) 

5️⃣@jwmarcoisland – This hotel is a great luxury option that doesn’t break the bank. The wide white-sand beach, family pools with waterslides, off-site excursions (dolphins!), and especially the arcade made this unbelievably fun for kids. Room choice really matters, so reach out if you want a travel advisor’s take.

4️⃣@seaisland – We’ve visited three times and it continues to deliver. For parents: world-class spa and truly jaw-dropping golf facilities. For families, you could stay a week and never get bored. The multigenerational activities are endless and unique — turtle dawn patrols, falcon walks, and beach horseback riding.

3️⃣@altagraciaauberge – A bucket list hotel that delivered 100%. You fly directly into the property, which feels very James Bond (kid-friendly version). Tucked into the Talamanca Mountains, kids love the farm visits, horseback riding, and butterfly gardens, while parents get butler service, incredible food, a true remote escape, and a spa that’s an absolute must.

2️⃣@susurrosauberge – Every corner of this resort is stunning. Jaw-dropping pools, a pristine swimmable beach, beautiful villas for larger groups, and a kids club my children did not want to leave.

1️⃣@fscostarica – A perfect 10/10. A splurge that’s worth every penny. Nestled between two gorgeous beaches and surrounded by lush fauna, it feels like you’ve landed on the other side of the world. The on-site adventure is unmatched — ziplining, surfing, hiking, biking, kayaking, and more. Plus, the new Papagayo Park with waterslides just opened in December.

𝐅𝐨𝐥𝐥𝐨𝐰 𝐟𝐨𝐫 𝐦𝐨𝐫𝐞 𝐥𝐮𝐱𝐮𝐫𝐲 𝐟𝐚𝐦𝐢𝐥𝐲 𝐡𝐨𝐭𝐞𝐥 𝐫𝐞𝐜𝐨𝐦𝐦𝐞𝐧𝐝𝐚𝐭𝐢𝐨𝐧𝐬.

#bestfamilyhotels #luxuryfamilytravel #luxuryhotels
Sharing some favorite shots from 2025 to help insp Sharing some favorite shots from 2025 to help inspire  2026 family travel plans 

2025 was an incredible year for travel 💕 Costa Rica and Mexico  were top favorites — but we also enjoyed a baby moon with the kids in Florida, a mom and dad escape to @twinfarms, as well as trips to Disney, Jackson Hole and Georgia. Of course, our most exciting news of 2025 was that we welcomed a new member to the Compass Roam crew.  To date, at 8 months, he has been on 13 flights! 

It was also an incredible of travel for YOU- my wonderful clients. In 2025 I planned family vacations to 13 different countries, across 78 total trips! If you love luxury travel, would like to learn more about traveling with kids, or need some help planning your own trips — please follow along and reach out. This is what I love to do!

Cheers to a wonderful 2026 — I can’t wait to show you where we’re headed next. 

What’s your first trip planned for the new year?  Let me know in the comments below 

#familytravel #luxuryfamilytravel #travelwithkids
And this is why we have to budget for ski school, And this is why we have to budget for ski school, folks! 🤪

Couldn’t help myself - had to hop on this first vs secondborn trend after our recent ski trip to Jackson Hole. Always a fun time seeing how birth order translates to the ski slopes. 

#firstvssecondchild #skitrip #familytravel #skiingwithkids
WHERE DID YOU GO IN 2025 THAT WILL STAY WITH YOU F WHERE DID YOU GO IN 2025 THAT WILL STAY WITH YOU FOREVER? 

What was your favorite destination? Or was it a hotel that you keep dreaming about — one that was a destination itself? Who did you go with? 

I want to know everything so let me know in the comments below - I will compile your favorite spots into a list and share as future post 

But it’s only fair if I go first…

My favorite destination of 2025 was Costa Rica! 

I truly don’t understand why people “save” this destination for when kids are older.  It’s the type of place where you could go back 10x and each trip would be so drastically different — there’s just so much to see and do across age groups. 
We did 4 days at the incredible @fscostarica followed by 4 days @altagraciaauberge and WOW. Both hotels are magical, perfect for families with little kids, and are great to pair together. You’ll get to experience the beach and coastline, as well as temperate rainforest up in the mountains. 
It was a perfect 10/10. 

Not sure how to get started booking a trip here? Well ⬇️
___________

Hi - I’m Jillian - a luxury family travel advisor with 3 little kids. I share content about our favorite family destinations and hotels.  Kid approved. As an advisor, I can also book hotels for you with free perks as well as help plan your own family vacations. I specialize in luxury travel and 4 and 5 star properties.  Please reach out if you’d like to learn more! 

#favoritedestinations #favoritehotels #Traveladvisor #luxuryfamilytravel
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