Travel Destinations for Every Season

When clients start looking to fill their travel calendars, the question I'm asked most is: “Where should I go when?” Being in the right place at the right time is everything with travel. I've rounded up some of my favorite destinations for each time of year, so you can be sure you're always in season! Where do you plan to travel next?

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Winter: Snow, Sun, & Fireworks

Salt Lake City, Utah

What better way to soak up the beauty of winter than by swishing down a mountain covered in fresh powder? With 7 ski resorts within a half hour of Salt Lake City airport around the vibrant mountain town of Park City, you'll never get bored! I can create a "ski-inclusive" package combining Park City, Deer Valley, Alta, Solitude, Brighton, or Snowbird and include ski-in/ski-out lodging, lift tickets, ski rentals, and ski school! You can even try bobsledding at Utah Olympic Park. During the holidays, families can ride the North Pole Express in Heber Valley to meet Santa and have hot chocolate with Mrs. Claus.

Megève, France

Megève, France borders Switzerland and Italy and lies at the foot of the majestic Mont Blanc mountain range, with two mountain streams traversing the village. Upscale shopping, holiday charm, ice-skating, carriage rides, Michelin-starred restaurants, and views of Mont Blanc create the perfect alpine experience. When you need a break from downhill skiing, go hot-air ballooning (even in winter!) or skijoring (where skiers are towed behind a train of horses or dogs)!

Hawaii

Follow the humpback whales to Hawaii in winter where they breed, give birth, and nurse their babies in Hawaii's warm waters. The whales especially love Maui, and you can easily see them from shore! We were there in February 2023, and the whales were everywhere! Winter is peak season, so plan to book 9-12 months in advance. As a Certified Hawaii Destination Specialist and seven-time visitor myself, I have extensive knowledge and invaluable local partnerships that can help make your Hawaii dream vacation spectacular!

Find Hawaii Inspiration Here

Madeira, Portugal

Madeira, an island west of Morocco, is known for its mild, spring-like climate, even in the winter. From towering cliffs like Cabo Girão to lush forests like Laurisilva, hiking on Madeira is an unrivaled experience due to the island’s epic landscapes. Madeira's biggest claim to fame, though, is its impressive fireworks display over Funchal Bay on New Year's Eve. Since 2006, the fireworks display has been a Guinness World Record holder for "Greatest Fireworks Show in the World." We had clients celebrate their NYE anniversary here last year!

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Spring: Blooming Beauties

Washington, D.C.

In the spring, Washington DC comes alive with blooming cherry blossoms, mild weather, and cultural events. The National Cherry Blossom Festival takes place from the end of March through mid-April and offers many free events like the Opening Ceremony, Kite Festival, and a parade. Combine this with visits to the Smithsonian museums and historical landmarks. Check the National Park Service’s Cherry Blossom website for peak bloom predictions.

Learn more about planning a trip to DC

Sedona

If you crave adventure and the beauty of the outdoors, you came to the right place! Spring in Sedona brings blooming wildflowers and daytime temperatures in the 70s - ideal for hiking, mountain biking, or rock climbing. Splurge on a hot air balloon ride at sunrise!

Get my top 10 Sedona activities!

Costa Rica

Costa Rica is a perfect choice if you're seeking lush landscapes, diverse wildlife, and outdoor adventures. While the fall is rainy season, spring is a drier time of year. My family will be back in Costa Rica this spring!

Learn more about Costa Rica here!

Caribbean

Spring Break is the perfect time to visit the Caribbean. You escape the cold without worrying about hurricane season, which begins in June/July. The Caribbean offers more than 20 destinations to choose from. Looking for a romantic destination with dramatic scenery, lush rainforests, and luxury boutique accommodations? Check out St. Lucia. Looking for white sand beaches and clear turquoise water as far as the eye can see? You need Turks & Caicos!

The Best Places to Visit in the Caribbean

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Summer: Road trips and sunny mountaintops

California’s Pacific Coast Highway

What's better than an epic summer road trip? Stretching over 600 miles along the stunning California coastline, the Pacific Coast Highway (PCH) offers breathtaking views, charming towns, and countless attractions. If you're doing a romantic road trip, check out Alila Ventana, an adult-only all-inclusive resort perched on the cliffs above the Pacific. Their tagline is: Where awe meets ahhh.

Iceland

In the summer, take advantage of Iceland's long hours of daylight and warmest weather of the year. Journeys along the Ring Road
– an 830-mile-long route encircling Iceland – promise snow-covered mountains, active volcanoes, icebergs, lava fields, black-sand beaches, and towering waterfalls. Two Icelandic must-sees: Landmannalaugar, a lunar landscape located in the country’s highlands, and the Blue Lagoon, a serene geothermal spa set amidst a rugged lava field. You can cruise or drive your way around Iceland, but consider a stay at Eleven Deplar Farm, a converted sheep farm set along the otherworldly Troll Peninsula, where all farm-to-table meals are included, as are two guided adventures each day. Go hiking, horseback riding, fly-fishing, and sea kayaking during summer’s midnight sun.

Alaska Cruise

Tourist season in Alaska runs all summer long. Don’t expect summer weather, but you’ll get the warmest weather Alaska has to offer. You’ll also get daylight until long past your bedtime, which allows you to make full use of your time there. If you missed the whales in Hawaii last winter, you can find them in Alaska this summer! My family and many of my clients spent last summer on a combo land/cruise tour of this gorgeous state. Plan ahead if you want to experience Alaska during high season. I can help!

Click here for our Alaska itinerary

Banff, Canada

Known for its breathtaking landscapes, turquoise lakes, and towering peaks, Banff is one of Canada's most sought-after destinations. Kayak the iconic Lake Louise, drive the mind-blowing panoramas of the 143-mile Icefields Parkway, then relax in the Hot Springs or with a cup of tea at Lake Agnes. My family will adventure here this summer, and we'll be checking out the oh so beautiful Fairmont Banff Springs, Rimrock Resort, and Chateau Lake Louise.

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Fall: Golden Escapes

New England

Fall foliage in New England and the neighboring Canadian Maritimes must be seen to be believed, as deciduous trees explode in every shade of gold, orange, yellow, and red. Focus on Vermont, New Hampshire, Massachusetts, or Maine. From apple picking to pumpkin festivals, New England is brimming with seasonal activities. If you're looking for a romantic fall getaway, try Twin Farms an adult-only, all-inclusive resort on 300 acres in Vermont's pristine countryside.

Zimbabwe

From the dramatic Victoria Falls to the picturesque Eastern Highlands, Zimbabwe has no shortage of natural beauty. Autumn is one of the best times to see wildlife, when animals congregate around diminishing water holes in the nation’s little-visited national parks. I can arrange private journeys where you seek out the "big five" (leopard, lion, rhino, elephant, and buffalo), sleep under the stars, and take a sunset cruise on the Zambezi River. My first visit to Africa is this spring, when I'll tour Kenya with Hills of Africa!

Paris and ...?

Beat the summer crowds and stroll through Paris's stunning gardens, visit the charming Montmartre district, and soak up the art and culture of world-renowned museums, like the Louvre and Musée d'Orsay. You can easily pair Paris with a city stay in London, or a relaxing countryside stay in Provence or the Loire Valley.

Top: Paris in the fall

Bottom: London, Provence, Loire Valley

London & Paris itinerary

Southern Italy

Beat the crowds and the heat and visit Italy in the Fall. In southern Italy, it's still warm enough to enjoy the Mediterranean. We paired a trip to Sorrento, the Amalfi Coast, and Capri with a short stay in Rome. I loved the month I spent in Italy when I backpacked the country 27 years ago, but this trip with my family was a bit more luxurious and is one we'll never forget!

Whatever the season, let's plan a spectacular vacation you'll never forget!

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Heather Vergara is a former PepsiCo marketing executive who left the corporate world to be a Mom and never found her way back. Instead, she focused on her passion for travel and adventure and created Show Them the World, a travel concierge service for busy families longing to reconnect and see the world together. In less than four years, she's helped more than 300 families experience Hawaii, Alaska, Costa Rica, France, England, Greece, Italy, Croatia, Portugal, Spain, Ireland, the Caribbean, National Parks, and more to come!

Heather has an MBA in marketing from Indiana University, a Digital Marketing Executive Education certificate from Columbia University, and a BA in Journalism from the University of North Carolina at Chapel Hill. She lives with her husband, two kids, and two furry dogs in Zionsville, Indiana.