5 Winter Getaways To Plan This Year

by | Jul 26, 2016 | Asia, California, Central America, Jamaica, Oregon | 13 comments

(Last Updated On: May 29, 2017)

For some people, their favorite time of the year includes cold, wet, snowy weather. For others, like us, we’d rather travel to warm, tropical destinations while its cold and rainy at home. The dreaded winter time: cold, rain, hail, sleet, snow, all words that can be devastating to our psyche.  That’s why we usually plan vacations to tropical places to escape the dreary weather.  We are definitely guilty of this in the fall and winter as the Pacific Northwest can be long and gloomy.  But not all vacations need to be planned around tropical destinations and fruity cocktails.  Some of the best vacations can involve the cold, in particular the snow! As we are making our travel plans for this upcoming winter, we have compiled a list of our 5 favorite winter getaways to plan for this year.

Ski Lodge

We are fortunate enough to have an amazing Ski lodge within 90 minutes of our house.  We live less than 100 miles away from Mt. Hood, which is home to some world class slopes.  Located on the Mountain is Timberline Lodge. There is nothing like being on the mountain after some fresh snowfall.  We will have to admit for being so close to an amazing ski and snowboard resort we do not take advantage of it enough.  If we are only able to make it out to the mountain once a season, we make the most out of it by making it an extended vacation.

* Fun fact: Timberline lodge was featured in the 1980 film starring Jack Nicholson titled “The Shining”. Aerial shots and exterior footage of Timberline lodge were used to portray the fictional “Overlook Hotel” throughout the movie.

This season we are excited to try a ski resort outside of Oregon. We have started to make our plans for this upcoming winter and we will be using Iglu Ski to book vacation. They are the largest independent retailer of ski holidays in the UK, with over 200 different ski resorts in 16 different countries. There are so many different options available when you book with them.  If you can’t find the perfect ski/snowboarding holiday with them then we don’t know where you would.

If you insist on getting out of the cold and into warmer weather continue reading because we will list our favorite tropical destinations…


During our winter months (November-February), the days can be quite dark and depressing.  But fortunately it’s not like that in Jamaica!  This might seem a little biased as we were married and honeymooned in Jamaica but by far it is our favorite tropical island that we have visited.  If you have never had the pleasure of dipping your feet into the warm Caribbean Sea, it’s something you must put on your cliché “bucket list’.  And if amazing beaches and warm weather is not enough for you, the Jamaican people and their culture are so friendly and inviting.  Not to mention the food! You haven’t had jerk chicken unless you’ve had it in Jamaica! Hands down the best jerk chicken we have ever had.  There is so much to do in Jamaica, from amazing waterfalls, to swimming in crocodile-infested waters, to enjoying food and drinks while watching people jump off cliffs into the ocean.  In the month of December while we were there it was 85 degrees, perfect weather if you ask us.  We will make plans to return to Jamaica sooner than later…


Central America

If you haven’t been to Central America, we suggest getting down there ASAP!!! We had the pleasure of traveling through Costa Rica and Nicaragua during the month of January.  And the weather was amazing, 90 degrees and not a drop of rain. We stayed on the Pacific side, and even though the Pacific Ocean is not typically as warm as the Caribbean is, it matches in its beauty and sunsets.  We witnessed some of the most amazing sunsets we have every seen while staying in Playa Flamingo, a lovely beach town just north of the more popular beach town of Tamarindo.  When in Costa Rica, you must indulge in the local eatery, specifically the dish so well known as “Casado’.  Which usually consists of a protein such as chicken doused in some special sauce, served with rice and beans.  So delicious words and pictures cannot describe, you must taste it for yourself.

Costa Rica can be on the expensive side, as it is a popular tourist town, that’s why were we happy to be able to travel to Nicaragua on the same trip. We went a few hours north to the hidden gem beach town of San Juan Del Sur.  In our opinion, the beaches and food were up to par with Costa Rica.  We especially enjoyed our time in Nicaragua because everything was rather inexpensive. We enjoyed fresh lobster tail dinners on the beach for around $12.  Nicaragua has so much to offer, you can go zip lining, or if you are into surfing, the surf is some of the best in Central America.  If you are ever in San Juan Del Sur on a Sunday, and you are looking for a good party, check out the Sunday Funday Pool Crawl.  If you are curious as to what it is check out our experience with the pool crawl here in this video…



Southeast Asia

For some of us, Asia seems a whole world away.  But if you don’t mind a full 1-2 days of travel, I promise it is worth it once you get over there.  We were blessed to experience a month long trip to Thailand and Laos.  Laos has so much rich culture and amazing food, and your money will go a long way.  Laos is a country that has yet to become popular and over flooded with tourists so get over there before it does if you like to avoid crowds.  Thailand on the other hand is very touristy and over crowded, spending 1 day in Bangkok was plenty for us.  We spent most of our time island hopping around the Phi Phi islands, Phuket, Koh Lanta and Railay Beach.  We have visited many beautiful beaches during our travels, and each one has a special and unique place in our hearts, but the beauty of Railay Beach might be one of our favorites.  The landscape surrounding the beach is something that every traveler should see for themselves.



San Diego – Coronado Island

Now if you don’t want to go to the complete cold and play in the snow, or sip Pina Coladas on a beach, we have a happy medium for you…  Southern California in the winter months is amazing.  We can specifically speak about the San Diego area as we recently took a trip there in the month of December.  We must say it was a perfect mixture of nice weather and the holiday feel.  What do we mean by that?! Well it was 70 degrees and sunny! Not too warm and not too cold.  If you can make it out to Coronado Island, the Hotel Del Coronado is an amazing place to spend the day and evening.  They have so many festivities that go on, one in particular is an ice skating rink on the beach! Yes you heard it right, an ice skating rink on the beach in Southern California.  It was quite a site to see.  You can also swing pass this giant Christmas poinsettia tree along the water in downtown San Diego. Even though the weather was sunny and warm, it still felt like Christmas in San Diego.

Even though we love the warm weather and never want the summer weather to disappear, it’s time to start planning for your winter trips! Here are 5 winter getaways we suggest you plan for this year! Its right around the corner and we are starting to plan ours, so we suggest you get on it if you haven’t already!


What are your favorite places to vacation for the winter months?! We would love to know what you think so we can add it to our list!


winter getaways pinterest






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Tip and Tarah of Fit Two Travel

Tip and Tarah of Fit Two Travel

Tip and Tarah are the founders of Fit Two Travel. Since getting married in 2013, they have traveled to 26 countries and 22 states together. They are true Oregonian natives, and love to explore the outdoors, enjoy the food and drink, and spend time with their 2 dogs. They help others plan their international and local trips.


  1. Shannon Off Duty

    Winter travel is the best! Great blog and great post
    Shannon Off Duty
    (your Skyscanner Elite buddy)

  2. Rob Taylor

    I too love San Diego in the winter. It’s not packed with vacationers at all… but it’s also not hot like you want it to be. Still fun though!

  3. melody pittman

    I haven’t even begun to think about winter travel yet. Schedule is crammed until this but I do have my daughters wedding in December so we will be limited. Love San Diego though I wouldn’t think about going there in the winter, and live part time in Panama so that will be our January monthlong destination

  4. Lara Dunning

    We’ve been talking about San Diego lately. I’d love to see the ice skating rink on the beach. How cool!

  5. Heather Cole

    Jamaica sounds like the perfect place for a winter getaway, although not sure I fancy swimming in croc infested waters 🙂

  6. Victoria

    I like a lot the part with the snow and especially Timberline Lodge – amazing place : )

  7. Juliette@Snorkels To Snow

    Queenstown is always a winner for a winter getaway! Being in Fiji at the moment we’ll be very much looking forward to finding a cold climate for a couple of weeks skiing over the northern hemisphere winter as it will be cyclone season here and insanely hot!

  8. Conor

    So much choice and variety. Although I’m quite certain I’d never stay i Timberline Lodge… thanks of course to the movie, just too creepy! Give me a fresh mango juice and Railay beach instead 😀

  9. Amy

    As a Canadian, I am a winter girl! Living so close to Banff and the rockies, and having hockey makes me love the cold months. ..ok. …most of the time! But we try get away to break break it up, we love Hawaii and the Mayan Riviera 🙂

  10. Kevin Wagar

    Great list of winter travel ideas! Love Central America, great weather and amazing beaches!

    • Fittwotravel

      Thank you ! Central America is amazing, and we have so many more countries we want to explore down there !

  11. Ami

    South East Asia is amazing alright. Have not been to the others. They do sound like fun. Nice ideas.

  12. Barrett Villandry

    Instead of freezing in the Northeast and Midwest, head to these enticing locales found everywhere from Costa Rica to Queensland, Australia. Travel smarter on your next getaway with tips, tricks and intel from En Route’s panel of expert travelers.


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