I used to live in Portland, Oregon, and every Winter I would have to book a plane ticket and head for somewhere with some warmth and sun.  I wouldn’t care where I went for my winter holidays as long as there was sun. I would search the internet for the best winter vacation package and just go.  Are you in the same boat (or wishing you were on a boat) and trying to figure out where you should go?

Here are a few of my favorite destinations for spending Winter holidays in the sun:

Walking in Havana, Cuba

1.  Cuba

There is no place to fill your heart full of sunshine like Cuba.  The beaches are stunning and the people are some of the kindest, most beautiful people who I’ve ever met.  The icy mojitos are perfect, and you will find yourself salsa dancing in the colorful streets with thoughts of victory that you have cheated Winter out of its hold on you.  Cuba will change you.

Playa Las Galeras Beach on the Samana Peninsula in the Dominican Republic

2.  Dominican Republic

The Dominican Republic has some of the best beaches that I’ve ever seen.  These beaches are the technicolor, true paradise beaches that you usually dream about. Many of the beaches are deserted and you must reach them by boat or by hiring a motorcycle driver to take you there.  This is the perfect place to go to sink into the sand and forget about everything for a while.

Thailand Beach on Koh Phangan

3. Thailand

The beaches in Thailand are what I think of when I hear the song, “Bali Hai.”  The food in Thailand will warm you up from the inside.  You will be lulled to sleep by the breezes blowing through the palm trees, and the waves softly lapping on the shore. You just can’t go wrong by booking a trip to Thailand. There are so many great islands to choose from such as Koh Phi Phi, Koh Lipe, or Ko Phangan.

Limes and Sol Beer in Mexico

 4.  Mexico

What’s there not to love about Mexico?  The sun shines brightly, the colorful culture draws you in, as the people flood you with affection.  If you are looking for blissful winter holidays, then Mexico is your place.  But, be careful, it may pull at your heartstrings so much that you might wind up moving there just like I did!

Sunset on Santorini, Greece

5. Greece

I have never seen more stunning sunsets than in Greece.  I love everything about Greece.  The old history, the passion of the people, the food, the sapphire blue waters.  I dreamed of Greece long after I returned and am excited that I will soon go back to explore some of the other islands.  The islands in the Southern part of Greece are the warmest and driest during the Winter months.

What’s your favorite Winter holiday spot?  Let me know in the comments below!