Why November Is the Best Time for a Caribbean Trip: Teacher-Friendly, Budget-Friendly Travel Guide

Discover why November is the perfect month for a Caribbean vacation — fewer crowds, better prices, and a much-needed break for teachers and introverts alike.

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My husband says my blog articles need to be shorter.
I tried to warn him — quiet people have a lot to say when we finally sit down to write. I will try to keep this one short and sweet.

Starting this blog has been a gift. Thank you to everyone that has taken time to read it! I’ve spent hours poring over old photos, feeling immense gratitude for the wild, meaningful, sometimes hilarious experiences we’ve had. And I realized something: so many of our favorite memories happened over Thanksgiving. We’ve spent several holiday weeks in the Caribbean, and I’m convinced November is the perfect time to travel from Maine to the Caribbean.

So… why is November a dream month for a Caribbean getaway?

Teachers, You’ve Earned This

My teacher friends — you already know:

• First-trimester grades are in.

• Parent-teacher conferences are complete.

• The time change has sent our routine-loving students into a tailspin.

• Everyone in New England is sick.

• It hardly snows anymore in November.

• And it’s freaking dark. All. The. Time.

Do I really need to convince you to trade that for warm turquoise water?

Probably not.

But here’s the thing: November is also a budget-friendly time to travel.

November = Shoulder Season

While I have discussed June as marking the affordable off-season for Caribbean Island travel, November is the shoulder season — that sweet spot with:

• Smaller crowds

• Better prices

• A slight chance of rain (which, honestly, most often happens at night)

Still a chance to escape the New England cold! Thanksgiving may be one of the busiest travel weeks in the U.S., but our American ego forgets something important:

Thanksgiving is an American holiday.

Other countries aren’t roasting turkeys or glued to football games. That means international flights can be cheaper and international terminals less congested.

A Note for Teachers About Time Off

If you’ve been in the classroom long enough, you probably remember being told not to be seen in public if you dared to use a sick day. And you definitely remember the era of “only two personal days” that could not be used around vacation times.

Thankfully, many districts have changed towards a more professional stance in their leave policies. I’m forever grateful for ours — we can use comp time before or after scheduled vacations, which means we can fly on Mondays or Tuesdays when prices are lowest.

But if your district still clings to outdated rules?

It might be time to join the negotiation committee. 😉

But What About Thanksgiving Traditions?

Of course, Thanksgiving is special. Some of my most cherished childhood memories include:

• Watching the parade on TV (I grew up in NY!)

• Incredible kitchen smells

• Silly family games

• Walks after dinner

• My mom and grandmother cooking and cleaning like superheroes

When my son was born, I took on that role — and I’m grateful I gave him those same cozy memories.

But does it really need to happen… Every. Single. Year?

Let’s compare:

🍗 Option A: The same turkey dinner, where kids eat mostly dinner rolls
vs.
🏝️ Option B:

• Warm turquoise water, snorkeling, sandcastles, waterparks, monkeys, and lazy rivers.

• An all-you-can-eat resort buffet with a turkey carving station (which our 11-year-old completely ignored for the pasta station and dessert bar)!

• Squeezing into a restaurant in Grenada under an assumed name to beat the 3 hour wait time — island time at its finest! Definitely an island to eat locally!

• A Mount Gay Rum tour in Barbados with incredible food and sugarcane plantation history lessons. It’s not a pub crawl; it’s a cultural experience!

• Eating hotdogs on a catamaran in the BVIs because we ended up at the world-famous Foxy’s on Thanksgiving night (amazing drink and beach bar vibes but not well equipped for a full turkey dinner).

• The commotion, local entertainment and delicious meals of an island fish market.

• Walking the beach at night, island sunsets, warm tropical breezes.

Oistins Fish Market, Barbados

I’ll let you decide which one is more memorable.

Our Thanksgiving Travels (So Far)

Over the years, we’ve celebrated Thanksgiving in:

• Jamaica

• Barbados

• Costa Rica

• Grenada

• Dominican Republic

• The British Virgin Islands

Each place gave us its own version of gratitude — the kind you can’t create at home, even with the best stuffing recipe. Unique memories of family time in unusual situations and beautiful destinations.

This year, maybe you stay home and soak in the warmth of your own traditions — the smells, the laughter, the familiar routines.
Feel that gratitude deeply.

And then… hop on Expedia and make next year look a little different.
Quiet tropical adventures are calling.

Travel doesn’t replace tradition — it expands it.
If there’s one thing these Thanksgiving trips have taught me, it’s this: gratitude grows when you give yourself permission to live differently every once in a while.
So savor this year’s holiday…
Then start dreaming about next year’s warm salty embrace.

Or maybe, why wait—A Caribbean Christmas is calling your name!