Tips and Trends for your Winter Vacation! | Greenwich Moms

As the leaves change and we welcome brisk air, and all things Fall it’s hard not to think about shorter days and frigid temps right around the corner! So, what does one do when they begin to dread those long and at times dreary winter months? You plan a vacation of course! The world has reopened and while we may still have concerns about Covid in the cooler months, most of us have already gotten back to traveling.

Mandarin Oriental, Canouan

Cheval Blanc Courchevel

Here are some tips and overall things to consider as you plan a Winter vacation:


Plan ahead!

We are still experiencing revenge travel and demand for the best hotels and things like connecting rooms or family suites will be gone first!  If you haven’t booked your Christmas or New Year travel yet you will want to do so ASAP.  Be mindful of minimum stay requirements which is typically anywhere from 7nts and sometimes 10nts!
*Jolie’s Tip:  book festive travel 6 months out and February break/Presidents Week travel at least 4 months out*

Why is everything so darn expensive??

High demand leads to what we call Dynamic Pricing.  Dynamic pricing, in a nutshell, is a strategy the hotels use to price their rates based on factors such as demand and seasonality.  Hotels don’t have to offer “fixed” rates, instead they have algorithms that cause nightly rates to fluctuate.  So the same room rate you saw online yesterday could be $100 more tomorrow; unless you booked and confirmed the rate you could be out of luck so please have an experienced travel professional on your side to assist!

Haven’t the airlines messed up enough?

We are fed up with the airline and airport excuses as they bumbled summer travel yet still raised prices. Ground crew and airline staff shortages which led to cancelations plus the rise in fuel costs are all to blame. I predict airfares to key resort and city destinations will still go up!  Avoid connections when possible.  Jolie’s Tip: while there is ZERO way to know which flights will be cancelled, I always urge my clients to avoid connecting via large airports that are affected by winter weather such as O’Hare and Denver and to leave plenty of time.

Scenes from the Medina in Marrakech

Jolie’s Travel Trends


  • Short international getaways that pack a big punch culturally! Marrakesh, Barcelona, Cartagena, Lisbon and Mexico City to name a few that you can do in 4/5 night
  • Europe for skiing! Courchevel, St Moritz and the Dolomites have been popular destinations for the Holidays and winter break!
  • The Grenadine Islands with 5-star resorts like the Mandarin Oriental Canouan the Cotton House Mustique, Spice Island Beach House and the Silversands Grenada are all super buzzy right now and continue to be on the top of my recommended list for couples and families alike seeking beach!
  • Driving distance! There are some incredible resorts offering loads of family activities and perhaps a chance for Mom & Dad to relax! Look out for the Preserve Sporting Club in Rhode Island (sister hotel to The Ocean House) and bound-to-be-hot newcomer Wildflower Farms from Auberge Resorts.
  • As always please reach out to Journeys by Jolie to book and get special amenities and perks like upgrades, complimentary breakfast, resort credits and overall VIP treatment

Content provided by contributor, Jolie Goldring of Journey by Jolie, Contact Jolie at [email protected]| (917) 693-8814
Instagram: @journeysbyjolie

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