Top Winter Break destinations to explore

//Top Winter Break destinations to explore

DISCLAIMER: Hey reader! Please know Travel By Jennifer is a valued partner of theCityMoms. Because of this relationship, we are sharing sponsored content we feel could be valuable or interesting for your family, like this list of hot winter break destinations. Read on, reader!

Merry Christmas and Happy Holidays everyone!  Wait, it’s still Fall? Yeah, it’s not too early to say that, because it’s high time we planned our trips for winter break season, which is just around the corner.  

Here are a few of my favorite destinations for the winter break season:

Winter Break Destinations _ theCityMoms


Mele Kalikimaka is the thing to say on a bright Hawaiian Christmas Day.  My family was lucky enough to spend Christmas 2017 on the beautiful island of Oahu, and it sparked a new Christmas tradition for our family of vacationing at Christmastime.  We spent Christmas Eve visiting Diamond Head, blowholes, numerous beaches, eating poke, visiting the Dole Plantation, and stopping by Turtle (Laniakea) Beach.  We even ran into the real Santa Claus on Waikiki, resting before his long journey that night around the globe.  Christmas Day was spent on Waikiki at Hilton Hawaiian Village, building sandcastles accompanied by tropical drinks, and eating an amazing dinner at one of Honolulu’s top restaurants.  The Aloha Spirit was in festive overdrive, and our family fell in love with Hawaii in a profound way. Our 7 days in Honolulu was about 14 days too short, and we cannot wait to experience it again.  

Winter Break Destinations - theCityMoms

Bimini, Bahamas.  

We spent our summer vacation on this small yet easily accessible Bahamian island, and it springs to mind as somewhere that would fit the bill for an ideal tropical Christmas vacation destination.  Bimini, while only 700 yard across, has much on offer, from a developed resort area on the northern end, to the “real” Bahamas on the southern part of the island. Play in tidepools, lounge on gorgeous, untouristy beaches, swim with dolphin pods in the Atlantic, feed the stingrays at Honeymoon Harbor.  I can imagine a perfect Christmas Day spent eating conch salad from Stuart’s, driving the golf cart from beach to beach, napping in the sun after a rum punch, and having a lovely outdoor dinner at Luna Beach.  Bimini is only 50 miles due east of Miami, and is easily reached by a 2 ½ hour ferry ride. Alternatively, my recommendation is to take a sea plane with Tropic Ocean Airways.  It’s a 25 minute flight from either Miami or Fort Lauderdale, and you land in the water right in front of the Hilton Bimini.  It’s a fun, fast, and fabulous experience start to finish!

Winter Break Destinations - theCityMoms

Photo credits unknown but thanks to Jennifer for sharing!


Wait, what?  Iceland? In December?  Well, if spending Christmas in a legitimate Winter Wonderland, with the Northern Lights dancing overhead, then yes.  While there may be just around 4 hours of daylight in Iceland in December, that won’t stop you from spending the day in natural hot springs {check out The Blue Lagoon, just a short drive from Keflavik airport, and a great way to spend your arrival day before checking in to your Reykjavik hotel}, taking a tour of the Golden Circle, doing an Aurora Borealis tour with blankets and hot chocolate provided by your guide, and celebrating Christmas right by the Arctic Circle.  With Christmas-week flights from Chicago direct to Iceland in the neighborhood of $500 per person {on Iceland Air.  The budget carrier WOW Air out of Cincinnati is another option during other times of the year}, Iceland is well within reach!


Southern Indiana.  

If you prefer to stay a little closer to home for Christmas, I recommend you head south for a fun and festive family getaway.  The resorts at French Lick and West Baden Springs pack the Christmas season full of terrific family events, from story time with Mrs. Claus, to toymaking workshops, to of course twinkling lights galore.  Just under an hour from French Lick, you can visit the famous Santa Claus, IN, which hosts several busy Christmas weekends in the month leading up to the big day.  

MORE FUN TRAVEL-RELATED READING: 12 Great day trips for families in Indiana

Why would you want to book with a travel agent, when planning your own trip online is so easy?

  • A travel agent will help you think through all the small details, like logistics from point A to point B once you arrive in their destination.  
  • A Travel Agent can also answer your questions, no matter how small, based on their own first hand experiences or in depth research.  
  • Travel Agents often have access to deals that are better than you can find online.  
  • Most Travel Agents don’t charge you a fee for working for you?  Travel Agents are compensated after you travel, directly from the travel supplier.  
  • Perhaps the best benefit of having a Travel Agent becomes apparent in the unlikely event something goes wrong.  You have a partner on the ground back home who will advocate for you, and help solve problems that might pop up along the way.


If you’re the type that prefers to be heavily involved in your trip planning, then great!  Your agent will be happy to give you as much control and involvement in the process as you desire.  If you prefer to be more hands off, and leave it to the professionals, then your TA can provide you with a fully detailed itinerary, in which all you have to do is pay and show up!   

MORE INFO: Travel by Jennifer is happy to help you plan and book your family’s travel, be it a Christmas trip, or for some time in the future.  Feel free to contact us for a no obligation quote, or just to chat about trip ideas. Happy planning!



Jennifer Vail - theCityMomsJennifer Vail’s life long passion for travel began at age 3, while watching Sesame Street’s segments shot in New York.  She thought “there’s a world outside of corn fields and small towns?” and has wanted to explore the world ever since.  Her adventures have taken her to 14 countries on 4 continents.  When she’s not traveling, or helping others plan their travel, she loves watching Formula 1 racing, listening to The Beatles, or working on puzzles (both jigsaw and logic).  She lives in Fishers with her husband, Tommy, her 7-year old junior travel agent partner/daughter, Lizzy, and the doofiest English Bulldog around, Winston.

2018-10-02T18:45:10-05:00September 30th, 2018|