Chicago at Christmas!
Jenna Hill Jenna Hill

Chicago at Christmas!

Skyscrapers. City streets. Busy people. Lights, steam, food, and wind in your face. Chicago at Christmas is cold and alive in the best way. Every year I squeeze in a few days just to walk, window shop, warm up over pizza, and remember why this city always delivers when I need a real city fix.

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An All-Inclusive African Safari… on a River Cruise?!
Jenna Hill Jenna Hill

An All-Inclusive African Safari… on a River Cruise?!

How awesome is this? An all-inclusive African safari… on a river cruise. Instead of long drives between lodges, you glide along waterways where elephants, giraffes, hippos, and birds gather naturally. A river cruise safari offers an immersive, relaxed way to experience African wildlife — small-group, expertly guided, and thoughtfully planned from start to finish.

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Colchagua Valley: Come for the Wine, Stay for the Vibe
Jenna Hill Jenna Hill

Colchagua Valley: Come for the Wine, Stay for the Vibe

Just a couple of hours from Santiago, Colchagua Valley offers sunshine, open space, vineyards in every direction, and a wine-country vibe that feels welcoming and fun. Come for the wine, stay for the ease, the social energy, and the feeling that you’ve discovered somewhere truly special.

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Montenegro Is Having a Moment—and It Makes Sense!
Jenna Hill Jenna Hill

Montenegro Is Having a Moment—and It Makes Sense!

I turned on the TV this week and heard Montenegro named one of the top places to travel in 2026. I paused, looked up, and thought—wait… do I know this place? A little digging revealed a country quietly stunning travelers for years, tucked along the Adriatic, blending medieval towns, sailing routes, and dramatic mountain landscapes. Montenegro isn’t loud about its beauty—but once you notice it, it’s hard to look away.

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Sports Weekends, Winter Travel, and Making the Most of It
Jenna Hill Jenna Hill

Sports Weekends, Winter Travel, and Making the Most of It

Winter weekends are about to be filled with swim meets, hockey tournaments, and quick trips across the Midwest. Here’s how I plan, stay sane, and make sports travel work for our family—plus a few tricks I’ve learned along the way.

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A Beautiful Day on Orcas Island
Jenna Hill Jenna Hill

A Beautiful Day on Orcas Island

Before our big bike tour from Seattle to Yellowstone, my husband and I detoured to Orcas Island—and it ended up being one of the best parts of the entire adventure. Doe Bay Resort, the soaking tubs, the winding island roads, and the people we met there made it a place I still think about. A little quirky, a little magical… and absolutely worth the trip.

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A Summer Escape to Michigan’s Keweenaw Peninsula
Jenna Hill Jenna Hill

A Summer Escape to Michigan’s Keweenaw Peninsula

A summer guide to Michigan’s Keweenaw Peninsula — one of the most underrated family road trip destinations in the Midwest. Lake Superior, Copper Harbor, hidden beaches, rock collecting, and quiet adventures perfect for kids and families.

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Es Mercadal: Life on an Island Off the Coast of Spain
Jenna Hill Jenna Hill

Es Mercadal: Life on an Island Off the Coast of Spain

Es Mercadal is a quiet village on Menorca, an island off the coast of Spain. With views from Monte Toro, traditional markets, and access to the island’s wild northern beaches, it’s an ideal base for discovering the real Menorca.

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Norway & Finland: Saunas, Sisu, and Scandinavian Dreams
Jenna Hill Jenna Hill

Norway & Finland: Saunas, Sisu, and Scandinavian Dreams

Norway and Finland call with wild beauty, fjords, and the Finnish rhythm of hot saunas and icy plunges. Discover the spirit of sisu—perseverance, balance, and simple living—and how to bring it into your everyday life while dreaming of a Scandinavian adventure.

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Morocco Travel & Why Everyone’s Talking About It
Jenna Hill Jenna Hill

Morocco Travel & Why Everyone’s Talking About It

Morocco has become one of the most talked-about destinations in the world—especially for group trips and women’s travel. From Marrakech to the Sahara Desert, here’s why it’s trending and what a sample 11-day Morocco group itinerary looks like.

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Honduras Bay Islands: A Hidden Caribbean Escape
Jenna Hill Jenna Hill

Honduras Bay Islands: A Hidden Caribbean Escape

Discover the hidden beauty of Honduras’s Bay Islands—Roatán, Utila, and Guanaja. From snorkeling the world’s second-largest reef to exploring quiet beaches and vibrant island culture, this Caribbean escape is as adventurous as it is unforgettable.

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Water Island: The Best-Kept Secret of St. Thomas
Jenna Hill Jenna Hill

Water Island: The Best-Kept Secret of St. Thomas

Water Island, just off St. Thomas, is one of the Caribbean’s best-kept secrets. From ferry rides and barefoot beach bars to camping under the stars and snorkeling with turtles, this quiet escape is all about slowing down and savoring the beauty of the Virgin Islands.

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