Blog · Seasonal Destinations

Where to Go This Winter: 5 Seasonal Destinations That Are Worth the Trip

By Kevin Kimpel · Kevin's Travel · November 4, 2026

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Here in Norfolk, winter has a way of making you choose: lean into the cozy, or go find the sunshine. I tell my clients both answers are right — it just depends on what you need most from your time off. A warm beach in January can reset you in a way nothing else does. So can a mountain town with fresh snow, hot cocoa, and nowhere you have to be.

Here are the five seasonal trips I recommend most for winter, and who each one is really for.

1. Maui, Hawaii — for whale season you will never forget

Winter is not low season in Maui — it is whale season. From December through April, humpback whales migrate to Maui's warm, protected waters to mate and give birth, and you can watch them breach and tail-slap right from shore in places like Ka'anapali.

If you go, get out on the water at least once. This Ma'alaea Harbor whale watching tour aboard a power catamaran is a simple two-hour trip that is fully narrated and runs through whale season — perfect if you want the experience without giving up a whole day.

Best for: couples, anniversary trips, and anyone who wants warm weather plus a true bucket-list wildlife moment.

2. Key West, Florida — for sunshine without a passport

Key West in winter is 75 degrees, walkable, and wonderfully unhurried. You get great seafood, sunset sails, and that laid-back island feeling — and for most of my Nebraska clients, it is an easier flight day than Hawaii and needs no passport.

My favorite afternoon there is on the water. This Key West reef snorkeling sunset cruise takes you out to North America's only living coral reef for snorkeling, then sails you back into the sunset. Pack light for a trip like this, too — I live by packing cubes like these Amazon Essentials 4-piece packing cubes so a carry-on actually works for a long weekend.

Best for: first-time winter escapers, friend groups, and couples who want warm and easy.

3. A Caribbean cruise — for unpacking once and seeing more

If decision fatigue is the real problem, a winter Caribbean cruise solves it. You unpack once, meals and entertainment are handled, and you wake up somewhere new. January through March is prime sailing weather — warm ports, calmer seas, and lots of ship choices from the Bahamas and Cozumel to St. Thomas and St. Maarten.

A quick honest note: winter is peak season, so the best cabins at the best prices go to folks who book early. Waiting for a last-minute deal in February usually means taking what is left, not what you wanted.

Best for: families, multi-generational groups, and first-time cruisers who want variety without logistics.

4. Alaska — wait, really? Yes, but plan it now

You do not take an Alaska cruise in winter — you book it in winter. Late May through early September is Alaska season, and winter is when I help clients lock in the best cabins, especially balcony cabins for glacier viewing, before they sell out.

Use these cold months to decide: Inside Passage round-trip from Seattle for ease, or a one-way Gulf of Alaska sailing with a land extension to Denali if you want the full experience. Booking now also spreads your payments out, with final payment typically due 60 to 90 days before you sail.

Best for: bucket-list travelers who plan ahead and want first pick, not leftovers.

5. A cozy mountain or city break — for leaning into winter

Not everybody wants to flee the cold. A long weekend in a mountain town — think Colorado, South Dakota's Black Hills, or a festive city break for holiday lights and great food — can be exactly right, especially if you only have three or four days.

The trick is pacing: pick one home base, build in one big experience per day, and leave real downtime. Winter trips go sideways when we try to out-schedule the weather.

Best for: short getaways, families with limited school-break days, and anyone who loves the season as it is.

How I help clients choose

• Start with your why: rest, adventure, celebration, or reconnecting — the destination follows that.
• Be honest about travel time: a three-day weekend should not spend two of those days in airports.
• Book winter warmth early: flights and resorts for peak dates are a first-come market.
• Protect the trip: if you would hate to lose what you paid, ask me about travel insurance before you book, not after.

Winter does not have to be something you just get through. With a little planning, it can hold the best trip of your year.

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