Winter Travel Tips for Snowbirds: How to Plan the Perfect Seasonal Escape
Every winter, millions of snowbirds, or savvy retirees and seasonal travelers, migrate to warmer climates, escaping the winter’s chill for sunshine and palm trees. Perhaps you’re familiar with this migration and make the trip every year to escape the brisk chill of winter mornings for sun-drenched landscapes or salty air. But are you traveling as safely as you can?
Whether heading to Florida, Arizona, or the California coast, planning a long-term winter escape takes more than just booking a one-way flight or loading up the RV or the truck for a road trip. Taking a few extra moments to consider everything from health coverage to packing tips can help ensure a stress-free, sun-soaked escape.
How? Well, check out our guide to winter travel tips for snowbirds and why having travel insurance is key for your packing list.
Winter Travel Tip No. 1 for Snowbirds: Plan Your Escape Early
Winter is the peak season for warm-weather destinations, meaning flights and rentals can fill up fast, and get expensive, so lock in accommodations and transportation early for the best prices and availability. If you’re renting for several months, consider negotiating long-term rental discounts.
Choose the Right Destination
If you’re still exploring destinations or want to try a new spot this year think about what you’re hoping to experience. For example, if you’re looking for sunshine, beaches, and the perk of no state income tax, Florida could be your spot. But, you just want to gold, and want instead dry, warm weather, Arizona might make the most sense. Texas, California and South or North Carolina are other popular snowbird escapes.
Consider Your Budget and Lifestyle
Since every destination has a different cost of living, healthcare access, and recreational activities, it’s important to consider your financial lifestyle, too. Research the average cost of essentials such as rent, groceries, utilities, and transportation in your chosen destination. Consider tax implications, as some states offer tax advantages for retirees, while others may have higher sales or property taxes that impact your budget.
Beyond financial considerations, consider your lifestyle. Do you prefer an active community with golf courses, hiking trails, and social clubs or a quiet, laid-back environment with beautiful scenic views? Check out local amenities, entertainment options, and healthcare facilities to ensure they align with your needs. If you can, we also always recommend visiting the area beforehand to get a feel for the community and assess whether it suits your long-term winter living plans.
Winter Travel Tip No. 2 for Snowbirds: Get the Right Insurance Coverage
Even if you’re traveling within the U.S., having domestic travel insurance can protect you from unexpected costs such as trip cancellations, medical emergencies, and lost luggage. Also, for added stress, some Medicare plans don’t cover healthcare in certain states, making additional coverage crucial.
What Benefits to Look for in a Travel Insurance Plan
When selecting a travel insurance plan, ensure it includes the following benefits:
- Trip Cancellation and Interruption—These benefits protect your prepaid, nonrefundable travel expenses if you need to cancel or shorten your trip due to unforeseen circumstances, such as illness or severe weather.
- Emergency Medical Coverage – Essential for unexpected illnesses or injuries while away from home, especially if your regular health insurance lacks nationwide coverage, but most domestic plans will protect you anywhere you go within the country.
- Primary Plans vs. Secondary Plans: Primary travel insurance pays claims first, simplifying the process and avoiding the need to coordinate with other insurers. Secondary insurance covers costs after any other applicable coverage has been paid, which may require more paperwork but can still be just as effective. Both options help reduce out-of-pocket expenses and ensure access to care while traveling.
- Pre-Existing Condition Waiver – If you have an existing medical condition, look for plans with a waiver, which can cover unexpected flare-ups as long as you purchase insurance within a specific timeframe, usually 14 to 21 days of your initial trip deposit. Without this waiver, insurers may apply a look-back period (typically 60-180 days) to exclude coverage for recent treatments or diagnoses.
- Rental Car Coverage—Many snowbirds drive to their destination city, and this can protect them against damage and theft.
- Lost or Delayed Luggage—If you’re flying, this benefit reimburses you if your baggage is lost or delayed, ensuring you have essentials when you arrive.
- 24/7 Travel Assistance Services – Offers support for medical emergencies, lost documents, or unexpected travel disruptions.
- Cancel For Any Reason (CFAR) – Provides the most flexibility by allowing you to cancel your trip for reasons not typically covered, such as a change of plans or concerns about safety. While it usually reimburses up to 75% of non-refundable trip costs, you must purchase it within a specific timeframe after your initial trip deposit.
Squaremouth Recommended Travel Insurance Plans for Snowbirds
- Tin Leg Gold – High medical coverage with pre-existing condition waivers.
- iTravelInsured Travel Lite – Affordable for long-term domestic trips.
- Arch RoamRight Pro – Excellent for rental car coverage and trip delays.
- Travelex Travel Ultimate – Great for comprehensive benefits, including coverage for activities.
- AXA Assistance USA Silver Plan – Strong emergency medical coverage and flexible options.
Pro Tip: Look for a plan that includes Trip Interruption coverage in case you need to return home early for emergencies.
Winter Travel Tip No. 3 for Snowbirds: Prepare and Secure Your Home
Leaving your home unattended for months requires careful preparation or a trustworthy house-sitter. Consider reviewing the following before heading out:
- Secure Your Home – Install timers on lights, set up security cameras, and have a neighbor check in periodically — if only to check on the pipes.
- Forward Your Mail – Use USPS mail forwarding or a digital mailbox service to stay updated.
- Winterize Your Home – Drain pipes, set the thermostat to at least 55°F, and unplug unnecessary appliances.
- Arrange for Snow Removal – If you live in a snowy area, hire someone to maintain your property to prevent buildup and potential fines.
Tip No. 4: Pack Smart for a Long-Term Stay
Versatile Wardrobe
Even in warmer climates, nighttime temperatures can dip. So stay prepared by packing a versatile wardrobe with a mix of lightweight clothing, comfortable layers, and cozy options for chilly evenings. Don’t forget to pack pool or beach gear, too, including sunscreen.
Pack your Documents
Once you have your closet figured out, don’t forget to consider essential documents, like your driver’s license and passport (it can help if you don’t have Real ID yet, or plan to also venture internationally), your health insurance (health, auto, and domestic travel insurance policy), prescriptions and medical records, emergency contact information, and of course, any receipts that are necessary in the event of a claim
Creature Comforts Like Technology
Sometimes a vacation means a break from technology, but if you’re heading for a winter escape for more than a week, consider your “creature comforts” including a strong WiFi signal. You can get a decent deal on a portable Wi-Fi hotspot for reliable internet, or even for chargers and backup power banks. If falling asleep to the television is part of your routine, consider packing your Roku or Fire Stick for entertainment on the go and if reading is more your speed, don’t forget your e-reader or books.
Winter Travel Tip No. 5 for Snowbirds: Stay Healthy on the Road
Find a Local Doctor and Pharmacy
Check if your health insurance covers doctors in your winter destination. If not, consider using online or local community forums to find recommended doctors and pharmacies. Transfer prescriptions to a national chain like Walgreens or CVS to ensure easy refills. And be sure to have your documents ready if you need to make a travel insurance claim for medical reasons.
Stay Active
Many snowbird communities offer group fitness classes, pickleball, and outdoor excursions. Walking on the beach or hitting the golf course is a great way to stay active.
Eat Smart
It’s tempting to indulge on an extended vacation, but maintaining a balanced diet will keep you feeling your best. Stock up on fresh produce and cook at home when possible.
Winter Travel Tip No. 6 for Snowbirds: Maximize Savings on Your Snowbird Stay
Leverage Senior Discounts
Snowbirds can take advantage of senior discounts on airfare and dining at many places. AARP membership can also offer exclusive deals.
Consider a Travel Rewards Credit Card
Use a credit card that offers travel perks, like rental car insurance and travel reimbursements.
Join a Local Community
Many snowbird destinations have clubs or meetups for seasonal residents. These are great ways to meet people, find discounts, and get local recommendations. Clubs often organize social events and group activities and provide information about local services and amenities, making your stay more enjoyable and convenient.
Bottom Line
Being a snowbird is about enjoying the best of both worlds, escaping winter while maintaining a comfortable lifestyle. Planning, securing domestic travel insurance, and following these winter travel tips can make your seasonal migration seamless and stress-free. So pack up, head south, and enjoy your well-earned winter retreat.