10 Warm Weather Getaway Ideas


I was recently home for my first winter in almost 2 years and lucky me – it was the COLDEST Christmas on record in almost 52 years. Waking up to bone-chilling -20 days and freezing wind can get old super fast.

We all know winter is coming soon.

Which is why I’m already jumping on the winter beach vacation bandwagon! It’s never too early to start planning and booking early can save you a bit of cash. Especially if you’re booking your flight separately. 

If you’re feeling just blegh about the weather, here are a couple of my favourite warm weather getaway ideas that I would suggest to get your summer fix!


1) Miami, Florida

If you’re looking for a quick trip and want a weekend of fantastic dinners, dancing, drinking and sunning yourself on the beach then Miami is a great destination for you! I recently went for a bachelorette party and we had the time of our life. Read more from my Miami Travel Guide for more getaway ideas.


2) Los Angeles, California

I’m bias because I lived in LA for years, but LA is the perfect holiday with a mix of beach, sightseeing and city life all rolled into one. Yes, you will likely need a car to get around – but if you stick to one neighbourhood you could uber your way through. Here’s my Los Angeles Travel Guide on how-to do the city right.


3) Maui, Hawaii

Need a vacation with lots of beach time and adventure? With Maui you have the option of both. You can lie around the resort and do nothing or you can bike down a volcano or go on a hike in one of the State Parks.

I had an amazing stay at BOTH the Four Seasons Maui and the Fairmont Kea Lani Maui and created this Travel Guide to Maui.

hey-cupcake-austin getaway ideas

4) Austin, Texas

Looking for a trip with a fun culinary component? Austin, Texas is calling your name with top-notch BBQ, food trucks, breakfast tacos and lots of independent shops to check out. The weather is still quite warm in the winter without lots of crazy humidity.

Check out my Travel Guide to Austin, Texas.


5) Punta Mita, Mexico

My final suggestion for my warm weather getaway ideas is Punta Mita, Mexico! I was lucky to enjoy a stay at the Four Seasons Punta Mita and just lived resort life. Spa days, lying by the pool and eating some amazing food at their restaurants. Check out my stay at the Four Seasons Punta Mita for more ideas.


6) Costa Rica  

How does zip lining over waterfalls, soaking in a volcanic hot springs spa, while surfing and doing yoga everyday sound to you? If you’re looking for adventure and a beach vacation, Costa Rica is the place.

Book into a resort on the west coast like the very posh Four Seasons Hotel in Papagayo. Give Tabacon Spa a google, it’s located at the base of the active Arenal Volcano. We found food and tacos to be pretty cheap when eating out – $1 beers and $2 tacos!

dreams palm beach

7) Punta Cana, Dominican Republic 

If you want to turn your brain off and not have to think at all, an all-inclusive is probably more up your alley. I hit up Dreams Palm Beach Resort in Punta Cana a couple years ago and had a blast.

The food was actually quite good (which is usually my all-inclusive fear) and we drank A LOT. It was really easy to relax here and we went with a big group of friends, so no worries about splitting the bill or how to meet everyone’s budget. 

key west florida

8) Key West, Florida

Walking into the waters of Key West is like walking into a warm sunny bath. It’s the perfect mix of small American beach town, with easygoing nightlife and restaurants. We stayed at the Waldorf Astoria and it was awesome – because it gave us amenities of a fancy resort with the proximity to all the fun things in town..

Key West is also the place to take a break from your car. Park it for the week, rent a bike and explore the city on two wheels. It’s a very easy place to navigate and the cars usually stay under a 40 km/h speed limit.

Did I mention all the delicious seafood and pink Florida shrimp?  Oh PS – don’t miss the drag shows 🙂

windsong resort turks caicos

9) Providenciales, Turks & Caicos 

So maybe you’ve already been to Mexico, Cuba and the Domincan Republic. You’re ready to shake off that all-inclusive action and explore on your own.

Grace Bay Beach in Turks & Caicos is one of the most beautiful beaches in the world with white sand and crystal clear blue water – perfect for snorkeling right from your resort. Paul and I booked ourselves a little condo on the beach at Windsong Resort (above) and ate conch fritters to our heart’s delight!

Since eating out in Turks & Caicos can get expensive, our condo had a full kitchen so we could cook a few meals at home.

10) Nashville, Tennessee

Nashville is one of my favourite cities for a long weekend getaway. It’s only a 3.5 hour direct flight from Toronto and there are some fantastic bars, restaurants and live music all within walking distance of each other.

I love all the independent stores, the cheap and delicious southern food scene and BBQ joints. Don’t forget to check out Husk Nashville, Gus’ Fried Chicken and Hot Chicken too! Plan your trip with our Travel Guide to Nashville.


Are you heading anywhere this winter? Do you have any warm weather getaway ideas to share?