My Favorite Winter Travel Traditions (and Why I Always Start the Year Away)

Winter is my favorite season to travel, and over the years it’s become a personal tradition to start every new year somewhere else—somewhere calm, beautiful, and inspiring. While most people see winter as a time to stay home and recover from the holidays, I see it as the best moment to hit reset. January and February are two of the most underrated months for travel, with lower crowds, better prices, and destinations that feel completely transformed by the season.

As a travel advisor, I’ve also learned that winter is when many places truly shine. From cozy New England towns blanketed in snow to warm Caribbean beaches where the days feel endless, winter getaways offer the perfect mix of rejuvenation, inspiration, and adventure. Over time, I’ve built a series of winter travel traditions that help me start the year with clarity, energy, and excitement—and I want to share them with you.

Why I Always Start the Year With a Winter Getaway

There is something grounding about leaving town right after the holiday rush. December can be loud, busy, and overwhelming; January feels like a breath of fresh air. Traveling at the start of the year gives me space to reflect, reset, and map out the months ahead without the noise of everyday life.

Another reason I love winter travel? The off-season advantage. Cities like New York, Chicago, Boston, and Seattle feel completely different in January—calmer, more authentic, and often more affordable. Boutique hotels run winter specials, flights drop in price, and even popular restaurants are easier to book.

And for anyone who loves warm weather, winter is the perfect time to escape somewhere tropical. The Caribbean, Mexico, and parts of Central America enjoy their best weather of the year from December to March, making it the ideal moment for sunshine, beaches, and all-inclusive resorts.

For me, starting the year away is as much a mental reset as it is a travel tradition. It’s how I reconnect with myself, find new ideas for content, and return home feeling grounded rather than burnt out.

My Personal Winter Travel Traditions

1. A Cozy New England Escape to Start the Year

Every January, I find myself returning to the Northeast—specifically the Berkshires, Catskills, or Vermont. These destinations are made for winter weekends: fireplaces, snow-covered trails, charming downtowns, farm-to-table restaurants, and a level of stillness that feels restorative.

Lenox, Stockbridge, Stowe, Woodstock, and Lake Placid are some of my favorite towns for a winter getaway. This is when small inns and boutique hotels feel their coziest, with hot cider, fireside lounges, and snowy walks through historic streets.

2. My January “Wellness & Reset” Trip

The start of the year is when I intentionally slow down. A wellness trip—whether it’s to Canyon Ranch in the Berkshires, a spa hotel in the Catskills, or a quiet coastal retreat—helps me reset physically and mentally.

I use these trips to disconnect, sleep in, enjoy healthy meals, join fitness classes, journal, and set goals for the year ahead. It has become one of my most meaningful traditions, and I truly believe winter is the best time for a reset trip.

3. A Warm-Weather Escape (Usually in February)

If you know me, you know I love a warm winter getaway—especially after weeks of freezing temps. February is my go-to month for sunshine destinations like:

• Punta Cana

• Cancun & Riviera Maya

• Cabo San Lucas

• Jamaica

• Turks & Caicos

• The Bahamas

These destinations offer perfect winter weather, beautiful beaches, adults-only all-inclusives, and boutique resorts that cater to everything from relaxation to adventure.

4. A Winter City Break (My Underrated Tradition)

Winter is also one of my favorite seasons for city travel. Fewer crowds mean lower hotel rates, easier dining reservations, and a more enjoyable way to experience local neighborhoods.

Some of my favorite winter city breaks include:

• New York City in January

• Chicago for museums, food, and skyline views

• Seattle for coffee shops and waterfront walks

• Boston’s Beacon Hill during snowfalls

• Austin for food, nightlife, and warm-ish weather

Winter transforms cities. You experience them the way locals do—cozy, quiet, and charming.

5. My Annual “Planning Weekend” Trip

This is a tradition I built for myself and one I look forward to each year. I take a 2–3 day trip in January or February solely to plan the year ahead—content, travel goals, business plans, personal goals, everything.

I usually choose a peaceful boutique hotel, bring a notebook, unplug, and map out the year in a way I can never do at home. Traveling removes distractions and gives me the clarity I need to create.

Where I Love Sending Clients Each Winter

Because I start every year traveling, I always discover places that become incredible recommendations for clients looking for winter travel ideas. Here are a few categories I love suggesting:

Best Cozy Winter Destinations

• Berkshires, MA

• Catskills, NY

• Stowe & Woodstock, VT

• Lake Placid, NY

• Jackson Hole, WY

Perfect for fireplaces, winter hiking, snowshoeing, breweries, and romantic inns.

Warm Places to Travel in Winter

• Punta Cana (especially all-inclusive resorts)

• Cancún & Riviera Maya

• Cabo San Lucas

• Puerto Vallarta

• Aruba

Ideal for sunshine seekers and couples looking for a tropical escape.

Best Cities for Winter Travel

• New York City

• Chicago

• Seattle

• San Diego

• Austin

Great for food, culture, museums, and off-season hotel pricing.

Underrated Winter Destinations

• Asheville, North Carolina

• Charleston, South Carolina

• Savannah, Georgia

• Sedona, Arizona

• Scottsdale, Arizona

These offer mild weather, great food scenes, and plenty to explore.

How These Traditions Help Me Plan Better Trips for Clients

Traveling consistently in winter allows me to give clients real advice based on firsthand experience—like where to stay, how pricing changes, what weather to expect, and how to avoid crowds. It also keeps me updated on boutique hotels, new all-inclusive options, seasonal events, and the destinations that truly shine in winter.

Whether someone wants a winter wellness retreat, a cozy cabin escape, a long weekend in New York City, or a tropical getaway in Mexico or the Caribbean, these traditions help me recommend the best options for every travel style.

Ready to Start Your Own Winter Travel Tradition?

If you’re thinking about a winter trip—whether it’s a January reset weekend, a cozy getaway, or a warm tropical vacation—I’d love to help you plan it.

My planning service is completely free, and I can pull multiple options that fit your dates, budget, and ideal travel experience. Winter is one of the best times to travel, and with the right plan, it can become a yearly tradition that you look forward to as much as I do.

If you want help choosing the perfect winter destination, reach out anytime or send me your dates—I’d love to help you kick off the year with something unforgettable.