Start Preparing For Your Winter Vacations Now

Contributing Editor: Derek Cullen

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Want to escape the cold? Or the heat? Maybe just looking for somewhere off the grid? Itā€™s not too early to plan where to spend some of the winter months this season. There are places here in the U.S. for men 50 and over that rank well in travel this time of year, and many exciting winter vacations to be explored. Most importantly, you can get great deals by booking early and securing those travel packages now.

Our Top 5 Winter Destinations in 2018

Key West, Florida

Key West is one of the most well-known travel destinations on the east coast. Located in the Straits of Florida at the southernmost point of the US, the region receives a healthy dose of sunshine year-round and temperatures above 70 degrees during the winter months. But thereā€™s much more to Key West than the favorable weather and shimmering water.

Key West Florida Buoy sign
Key West, Florida.

If you like to venture out after dark, Duval Street has the reputation for lively bars and fine restaurants. Sloppy Joeā€™s is a good example where a down-to-earth vibe never fails to impress locals and tourists equally. Meanwhile, Hogfish Grill serves up the finest seafood on the coast and ā€œBetter than Sexā€ is possibly the most unique dessert experience you can hope to enjoy with a partner.

Aside from Duval Street, Mallory Square is a bustling plaza with even more eateries and shops. If you crave history, Fort Zachary Taylor provides an insight into life before the Civil War and you can visit the home of Ernest Hemingway, classified as a walk-in museum.

Even with the waterā€™s coolest temperature at about 69 degrees, Smathers Beach or Higgs Beach are both ideal spots to spend the afternoon. Afterward, you can pay a visit to the Key West Aquarium and take a stroll amidst the endless stores on Caroline Street. Either way, Key West is a nonstop destination with enough fine food, interesting museums and energetic bars to keep you entertained!

Key West is a recommended destination for couples or groups of friends who seek fine weather. Keep in mind the winter months here are the busiest and priciest.

Magic Mountain Ski Resort, Vermont
Smugglers' Notch Mountain, Vermont
Smugglers’ Notch Mountain, Vermont

Quite a few Americans travel south in the winter months and who can blame them? After all, northern areas are subject to brutal weather and sometimes enough is enough. But, for those willing to brace the chill and want skiing or snowboarding adventures, the Magic Mountain Ski Resort in Vermont is a real gem.

Originally built in the 1960s, the ski resort has a small but loyal following and has undergone major refurbishments to its infrastructure, snowmaking, lifts and lodging as of 2017. Surrounded by dense forest and endless snow-covered canopies, the resort keeps to its old-fashioned impression. That is to say; modern ski resorts tend to demolish their immediate surroundings to create more space for more people. Yet Magic Mountain has remained true to the original construction and can feel more personal to the visitor.


no one deals like we do!
When you visit the ski resorts in most winter vacations, you can expect lengthy lineups for the ski lifts or other attractions. At Magic Mountain, the small crowds ensure this is never the case and makes the skiing less intimidating for beginners.

As for the accommodations, youā€™ll find everything you need for a memorable winter vacation. Magic Mountain is home to many excellent restaurants. Red Slate and the New American Grill are ideal for full-menu casual dining while SoLo keeps things classy with a much more upscale interior and variety of food.

The resort is best known for keeping things familiar and the tavern at the ski resort means you never need to leave this idyllic spot in the mountains. For adventure, mountains and a local atmosphere; Magic Mountain in Vermont is a favorite winter destination without the crowds.

Magic Mountain is recommended for ski enthusiasts and anyone that doesnā€™t mind the cold.

Memphis, Tennessee
Tram in Memphis
Memphis, Tennessee

Memphis, the location Elvis Presleyā€™s Graceland Mansion and a pilgrimage for admirers of the great Martin Luther King. But did you know itā€™s an incredibly fun for winter vacations with worthwhile attractions? Sure, it might not be the first place that crosses you mind for a seasonal vacation, but the food, bars and nightlife is unrivaled. The winter months are mild and itā€™s the quietest time in Memphis to avoid the crowds and long lines at popular restaurants.

Downtown Memphis has a remarkable venue for food, whether you opt for a straightforward barbecue from the renowned Charlie Vergosā€™ Rendezvous or something with a little more panache in the Flight Restaurant and Wine Bar, the flavors stand out on every occasion. But make sure and hit the unforgettable eateries like Central Barbecue, the Soul Fish CafĆ© to the legendary wings at Gusā€™ World Famous Fried Chicken.

Memphis is the origin of rockā€™nā€™roll and you will find almost every bar has a musical tribute in kind. Wild Bills, Tin Roof and the Rum Boogie CafĆ© are just a few of the names but the truth is, anywhere in Memphis is a good place to be after dark.

Youā€™ll find a range of attractions in town outside the music scene such as the National Rights Museum, Memphis Zoo and even the City Tasting Tours. However, thereā€™s no denying the main draw are the music-related landmarks such as Graceland, Sun City Studios and B.B Kings Bar on Beale Street. Memphis-a winter journey that will make a difference.

Memphis is recommended for culture, foodies and music lovers.

Hawaii
Palm trees on the sandy beach in Hawaii
Poipu beach in Hawaii, Kauai

When most people think of winter vacations, Hawaii is at the forefront of their mind, so we would be remiss to not mention it here. While itā€™s proximity to the west coast provides easier access for those who live there, with planning and willingness to endure the jet lag crossing five time zones, Hawaii is an option even for east coasters.
Save on Hawaii Resort Hotels!

Featuring five stunning islands and continuous tropical weather, Hawaii is a reliable winter destination which offers the perfect mix of sightseeing, food, accommodation and warm weather. The choice becomes; which island do you visit?

Kauai Island ā€“ Kauai is blessed with rugged landscapes and luscious natural surroundings. If you want to get out and explore the outdoors, this might be the island for you. Koke State Park has many hiking trails, Wailua Falls is stunning, and Poipu Beach is one of the finest stretches of sand you will ever encounter.

Maui Island ā€“ The most famous of all the islands, Maui is known to have the best beaches in the world. You can also visit the ancient town of Lahaina for culture and travel the Road to Hana for an unforgettable road trip.

Big Island ā€“ Big Island is indeed the largest island and known for sheer diversity. You will find rugged cliffs, snow capped peaks, rainforests and even beaches all within easy reach of each other.

Oahu Island ā€“ Oahu is where you will find Honolulu and two-thirds of the population of the state. Waikiki Beach is world famous but in truth, if time is limited, the other islands may be better for a relaxing winter break.

Hawaii is recommended for people who like to combine outdoor adventures with relaxation.

Astoria, Oregon
Canon Beach, Oregon
Canon Beach, Oregon

Few travel experiences can compare to a road trip and this is certainly true on the western coastline of America. In Oregon, using Highway 101 will give you access to 360 miles of rugged and scenic coast (along with a certain amount of infamy) to explore hidden coves, quaint towns and winding roads through stunning countryside. We know what youā€™re thinking; ā€œOregon? Winter vacations?ā€ The truth is the area is in the Mediterranean climate zone and enjoys mild and consistent weather year-round.

The three coastal regions (South, Central and North) each has exclusive landscapes and history and at the northern top at the mouth of the Columbia river is the antique port city of Astoria. With the distinction of being the first U.S. settlement on the Pacific coast, the city boasts many cultural attractions and points of interest. The Museum de Whimsy and the Oscar de Masi Art Studio offers insight into the town while a ride on the Astoria Riverfront Trolley is a great way to take in the local sights.

Parks and playgrounds are commonplace or you can enjoy a leisurely river walk and soak in the scenery at your own pace. Just 30 minutes away lies Cannon Beach and Haystack Rock, which movie buffs can tell you was one of the settings in the 1980s movie, The Goonies. The beach and surrounding area are true Pacific beauties and well worth the extra trip.

For foodies, the Bowpicker offers up fresh seafood entrees and the Bridgewater Bistro combines scenic dining, live music and upscale menus along with a wine selection of over 300 bottles. More of a beer connoisseur? Stop in at the Buoy Beer Company for handcrafted beer and made-from-scratch meals.

So while the crowds may be heading to Cancun, consider a stress free drive up the Oregon coastline and spend a few days in Astoria and relax!

Astoria is recommended for adventure seekers and anyone yearning for a road trip.

We hope you can use this information in planning your future winter vacations. (Check our blog on Trusted Traveler’s Program for easier airport security planning.) If there is a destination weā€™ve missed, or youā€™d like us to follow through on, let us know in the comments. Weā€™d like to hear about any of your favorite winter destinations, so we can share with our readers. Thanks!



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