If you’re looking for a fun way to spend Presidents Day weekend, we’d love to have you join us!

This is a small group trip – meaning there won’t be more than 10 people participating.

No cliques, no feeling left out – just food, fun, and fair fabulous weather.

Our group trips feel like going on a trip with friends – so if you’re looking for a budget-friendly way to explore Puerto Rico and make friends with other educators, this is it!

Puerto Rico Group Trip for Teachers

Lush rainforests. White-sand beaches. Turquoise waters.

And a culture brimming with warmth and energy.

Welcome to Puerto Rico – a Caribbean paradise that offers the perfect blend of opportunities for relaxation and adventure.

And you’ll definitely experience both with us!

Once we touch down in San Juan, you’ll find that you won’t just be sightseeing; you’ll be immediately immersed into the island’s history, flavors, and natural beauty.

I’m sure you can already picture yourself wandering through the colorful streets of Old San Juan – savoring local dishes bursting with flavor, or dancing salsa under the stars.

But if you want even more inspiration, this short video will make you want to visit today.

Available Dates and Spots

When This Group Trip Takes Place

Our next Puerto Rico Group Trip starts Friday, February 13th, 2026 – and ends on Monday, February 16th, 2026.

If you’d like to arrive in Puerto Rico earlier, or if you’d like to stay after the group trip, let us know during checkout. We usually charge separately for travel planning and booking services, but we offer this as a complimentary service to our group trip travelers!

We don’t book flights for clients, but we’re very good at finding great flight deals.

So we’ll tell you where, when, and with whom to book if you want us to keep you updated on airfare deals!

As of January 10th, 2026, there are only 2 beds left.

Reservations for this trip are made by the bed.

If you have someone you’d like to bring with you, and they’ll be sharing a bed with you, you’ll see the option to add them on at checkout at a significant discount to them paying for a separate bed.

We find that this option works great for best friends, siblings, etc.

This trip is not suitable for couples who want to share a private room.

All guests will be sharing the same room and both bathrooms.

What’s Included?

Here’s everything that’s included in the price for our Puerto Rico Group Trip:

• On-the-ground support from a Trip Host
• Accommodations in a shared home
• Light, grab-and-go breakfast items on Saturday and Sunday mornings
• Breakfast outing on Monday morning at a highly-rated, local brunch spot
• All tours and activities mentioned on main itinerary
• All ticket admissions to points of interest mentioned on main itinerary
• Transportation to/from the tour starting point on included tours

What’s NOT Included?

Here’s a list of everything that is NOT included in the price for our Puerto Rico Group Trip:

• Flights to/from Puerto Rico
• Transportation to/from the airport
• Transportation around Old San Juan
• Lunches and dinners unless indicated as part of the included tours
• Personal travel insurance (required for the trip)

What to Expect

Accommodations

Our group trips feel more casual and intimate than tours.

It really is more like you’re traveling with friends!

On our trips, it’s very common to leave making a friend who you’ll travel with in the future.

You’ll be sharing a home (and possibly a room) with others on our trip.

For this booking, reservations are made by the bed, assuming single occupancy.

If you don’t bring anyone with you, you’ll have your own bed, though you might be sharing a room.

If you’d like to bring someone with you, add on the “Bring a Friend” option at checkout.

We’ll ask for their name and travel details before the registration cutoff date.

Food

Since we’re sharing a home together, you’ll have full-access to the onsite kitchen.

This is great for anyone with dietary restrictions, allergies, or particular food preferences – because you can prepare everything exactly to your liking.

Closer to departure, you’ll receive a form asking for more information and personal details.

This will dictate the food items available for light breakfast every day.

Certain tours provide snacks and drinks.

So if you have any questions about what will be available, just email us and we’ll get more information for you.

Activities & Day Trips

You’ll love these activities.

They’re tried and tested by our hosts, and we’ve only included the best of the best in this itinerary!

Salsa Dancing Lesson & Night Out

Salsa dancing is something done all throughout the Caribbean and Latin America.

Once you’ve settled into your accommodations, it’s time to get ready and go out!

You can choose to just attend the class, or you can explore the nightlife of Old San Juan after the class.

We’ll be busy the rest of the weekend – so this might be your only chance to see San Juan at night!

This experience includes a complimentary cocktail.

*Note that the group trip taking place in February, 2026 occurs during Carnaval de Ponce.

El Yunque Rainforest Tour

This is when the real adventure starts!

Our group will join others as we head into El Yunque National Forest – a proper tropical rainforest.

We’ll do 15-20 minute, moderately-rated hike into the jungle – where we’ll find a natural rock waterslide and the river where you can swim!

You’ll have a couple of hours there – so you can explore natural pools, caves, and waterfalls… or you can sit and chat with other travelers by the river. Totally up to you!

On our way back towards San Juan, we’ll visit the famous Loquillo Beach – which is where we’ll have lunch at Kioskos de Luquillo nearby.

You’ll have some time to eat, chill on the beach, and rest before we take the trip back to San Juan.

Some snacks and samples will be provided by the tour operator.

You will get wet and you will be active on this tour, so definitely plan accordingly.

And don’t worry! We’ll tell you exactly what to pack with our personalized packing list – just for this trip.

This short video gives you an idea of what to expect:

Optional Add-On Tours & Experiences

Kayak on a Magical Bioluminescent Bay

Close your trip out with a bang.

There are many bioluminescent bays in Puerto Rico, but Mosquito Bay is one of the brightest in the entire world.

The only catch is, you have to fly over, or take a ferry to the island, then tour from there.

For this reason, this is a trip add on starting Monday, February 16th, ending Tuesday, February 17th.

We’ll travel together to and from the island, enjoy this magical experience together, then return to stay in mainland Puerto Rico on the night of the 16th.

This trip will take place during the New Moon phase, which is the best time to view bioluminescence.

To join this tour, you must be able to swim.

To see an idea of what to expect, watch this quick video:

Authentic Food Tour By a Local

Have a flexible schedule?

If you can stay for an extra day or two, you have plenty of choices for other tours and activities!

Here’s a quick description of what you can expect from each one.

You’ll see options for each of these tours and activities at checkout.

Roast Pork Highway Road Trip With a Local

This will be an entire day of full immersion.

This tour will be between 6-8 hours long, so it’s ideal for travelers who have a bit more flexibility in their schedule (or, a later flight out that night).

You’ll walk away from this experience knowing you did something that was more than a food tour; it’s a rite of passage.

You’ll leave truly understanding Boriken flavor and culture.

This 20-minute video gives you an idea of what to expect:

Taste of San Juan Food Tour

This will be the perfect choice for a traveler who needs to leave earlier in the day on Monday.

It’s just 3 hours long, and you’ll leave full!!

If you enjoy chatting with other travelers, and if you want to see Old San Juan during the day, then this would be the better choice for you.

Here’s a short video showing you what to expect:

The Vibe

We offer four travel experiences for Traveling Teachers:

1. Tours
2. Meetups
3. Retreats
4. Group trips

This is a group trip.

Though we do have some day tours and certain activities booked, you won’t be on a schedule that requires a breakneck pace!

As much as I LOVE multi-day tours, they can be really exhausting sometimes.

You’re up early, out late, and you come home needing a vacation from your vacation.

Worse than that – when you’re on a huge bus with 50 other people you don’t know, it’s hard to make friends!

This is why I love group trips.

It feels like you’re on a weekend vacation with friends, but this just happens to be the first time you’re meeting.

Cost & Payment Plans

You can pay for your trip in full using this booking page.

The total cost per person is $1,200.

Through Friday, November 21st, you can lock in a price of just $1,000 with a 50% deposit ($500).

Prices for our Group Trips go up as time goes on, so early bookers ALWAYS get the best deal.

Prices will be:

• $900 per person before Friday, January 16th
• $950 per person on Friday, January 23rd
• $1,000 per person on Friday, January 30th
• $1,200 per person on Friday, February 6th

To get a room to yourself, select the Solo Room Upgrade option at checkout.

You also have the option of making payments.

You can setup a payment plan through PayPal which will show on our side as paying in full.

And remember – this is the cost for the first person to secure their bed & space.

If you’re willing to bring a friend and share a bed with them, the price goes down significantly per person!

Refund and Trip Cancellation Policy

Here’s everything you need to know about payments and refunds with us.

Our Deposit Policy

As soon as your booking is made, we get to work reserving the elements of your spot on our group trip.

When we arrange tours and accommodations with local hosts, they take a huge financial hit when trips are cancelled, since they’re unable to sell that space to other customers.

For this reason, there are no refunds.

Our Cancellation Policy

We understand that things happen – and for this reason, we require every traveler to have personal travel insurance for the duration of their trip.

We recommend a policy that immediately gives travelers cash advances, should something happen during your trip.

Note that Traveling Teachers will not and can not be held responsible for travel to/from the starting point of our trip.

Your insurance policy needs to cover travel to, from, and within Puerto Rico, including your flight(s) – as well as the ability to receive a payout for cancellations, since we are unable to issue refunds.

You can read the full policy on trip booking terms, cancellations and refunds here at this link.

About Traveling Teachers

We host tours, retreats, meetups, and group trips for teachers!

We’ve hosted several trips in dreamy destinations across Europe, the Caribbean, and the United States.

Click here to learn more about us.

About Our Trips

Our trips are specifically designed with teachers in mind.

We’re often asked if people can come if they’re not teachers, and the answer is yes!!

Friends and loved ones of teachers are more than welcome to join us.

About Puerto Rico

Puerto Rico is an absolute gem in the Caribbean.

This island has it all – stunning beaches, a vibrant mix of cultures, amazing food, and enough history to keep you fascinated for days.

Plus, since Puerto Rico is a U.S. territory – you don’t even need a passport or to worry about currency exchanges.

And, even though they use U.S. dollars, there are certain things that make Puerto Rico really affordable.

One fun fact – Uber is easy to use and widely available, especially between the airport and San Juan (the capital city). However, the rates are more akin to what you’d find in other Caribbean nations – way cheaper!

Now, let’s talk highlights.

Have you heard of El Yunque? It’s the only tropical rainforest in the U.S. National Forest System, and it’s packed with lush trails, waterfalls, and some pretty incredible biodiversity.

Think of it as an outdoor classroom where science, conservation, and pure adventure come to life.

And for all you history buffs, Old San Juan is a dream!

It’s the oldest city in the U.S. and has these stunning forts, like El Morro and Castillo San Cristóbal – where you can actually feel the centuries of stories woven into the stone walls.

Wander around the colorful streets and discover the island’s Spanish, Caribbean, and even African heritage, all blended in one place.

About Your Host

Brittany is the founder of Traveling Teachers, and a very experienced traveler.

She’s traveled more than 20 countries, and she’s hosted trips in 5 of those countries.

She considers herself a professional travel enthusiast.

She prefers the term “enthusiast” over “expert” because the focus is on curiosity and discovery – over what somebody already knows.

As a teacher yourself, you know that we’re all lifelong learners!

This has always been her approach to travel, and with her trips.

She has an idea – a vision of what a trip or experience could be.

Then, she sets out to see if she can make it happen.

As soon as she visited Puerto Rico herself, she knew she wanted to bring other teachers to experience it.

The food, the music, the dancing, the beaches…

A winter weekend in Puerto Rico is exactly what a teacher needs.

If you’d like to connect with her on Instagram, you can find her at @brittanygoesabroad.

You can always learn more about our trips on Instagram at @teacherretreats.