Puerto Rico isn’t just a destination for Howie D; it’s his roots. His mother was born and raised in Puerto Rico and brought much of the island’s flavors, traditions and culture to Howie and his siblings growing up in Florida. ¡Volviendo! is a return to Howie’s roots, his heritage and his family. Join Howie as he hosts a cultivated weekend of Puerto Rican traditions, cuisine, culture and, of course, music!
Hosted by
HOWIE D
Howie Dorough, best known as a founding member of the iconic pop group Backstreet Boys, has brought his passion for music, family, culture, and connection into experiences and events held around the world.
Inspired by his Puerto Rican roots, family traditions, and travels around the world, Howie is expanding this passion into a full-scale vacation to San Juan, Puerto Rico!
Join Howie as he celebrates his heritage in la isla that inspired his love for food, music and culture. From treasured family stories to hidden local gems, this will truly be the trip of a lifetime!
“Sharing culture with each other through art, food and music is a gift. Having the opportunity to share my Puerto Rican heritage with the people who have supported me for over 33 years is a privilege.”
- Howie D
You will have a chance to experience the places and flavors that shaped Howie and his family, enjoy incredible food, music and storytelling while connecting through unforgettable shared experiences.
Part culinary journey, part music experience, and part personal homecoming — this is your chance to experience Puerto Rico with Howie D!
Your chance to hang out
This is your chance to be part of Howie’s very special journey as he returns to his roots in beautiful San Juan, Puerto Rico.
This is your chance to be part of Howie’s very special journey as he returns to his roots in beautiful San Juan, Puerto Rico.
We are partnering with PRxPR -
We are partnering
with PRxPR -
THE ITINERARY
DAY 1 | FRIDAY, MARCH 19TH
BIENVENIDOS
A LA FAMILIA
Arrive in San Juan and make your way to the iconic Caribe Hilton — your home for an unforgettable weekend in Puerto Rico.
Once you’ve checked in and settled into your room, it’s time to kick things off with a vibrant Puerto Rican welcome inspired by the feeling of stepping into your Tía’s backyard — warm, lively, full of flavour and instantly familiar.
Join Howie and your fellow guests for a relaxed evening of authentic Puerto Rican food, generous shared plates and plenty of time to connect.
As the sun goes down, live salsa music fills the air, dominoes and cards come out, and the weekend officially comes to life.
Throughout the evening, Howie will mingle with guests, share stories and personally welcome everyone to the island, setting the scene for a weekend celebrating family, music, culture and his Puerto Rican roots.
Settle in, meet your new familia and soak up your first night in San Juan.
The music is playing, the energy is building, and the weekend has officially begun.Bienvenidos a la familia
Day 2 | Saturday, March 20th
CULTURE, TRADITION & MUSIC
Wake up in San Juan and start the day with breakfast, cafecito and one of the weekend’s most anticipated moments, your official Meet & Greet with Howie D including a fan photo.
Then it’s time to turn up the energy as we head to the beach for an unforgettable Bomba Cuarteto performance and dance experience. Discover the powerful history and cultural significance of Bomba before local musicians and dancers invite you to step into the rhythm and join the celebration by the sea.
After lunch, experience another true taste of Puerto Rico with a special Ron del Barrilito Rum Tasting at the Caribe Hilton. Explore the fascinating history, craftsmanship and traditions behind one of the island’s most iconic rums, with a guided tasting of beautifully aged expressions and the stories behind each blend.
The afternoon is yours to relax, recharge and enjoy the resort before everyone comes back together as the sun begins to set.
Gather around the table for a family-style dinner, sharing generous plates, great conversation and plenty of anticipation for what’s coming next.
Then, as night falls, the lights go down and Howie takes the stage for an exclusive private concert created especially for this weekend in Puerto Rico.
Expect favorite songs, personal stories, surprises and unforgettable moments in an intimate setting shared with Howie and your new familia.
From cafecito and Bomba to Puerto Rican rum and a private concert with Howie — this is a day you won’t forget.
DAY 3 | SUNDAY, MARCH 21ST
EXPLORE PUERTO RICO
Today, step beyond the hotel and experience the heart, rhythm and culture of Puerto Rico.
The group will split into two, with each group enjoying a different experience before swapping later in the day.
One group will head to Escuela Bomba Caridad Cepeda, where Howie will be joining guests for a special Puerto Rican music and cultural experience.
Take part in an interactive music and culture class, enjoy a hands-on maker’s workshop, create a take-home souvenir and share lunch together.
At the same time, the other group will set out on an Old San Juan Walking Tour, exploring the colorful streets, rich history and local flavours of one of Puerto Rico’s most iconic neighborhoods, with lunch included along the way.
The groups will then swap, ensuring everyone has the chance to experience both sides of the day, before meeting in Old Town for a group dinner and further festivities.
After dinner everyone will return to the Caribe Hilton for the grand finale of the weekend — the One World Farewell Party.
For the evening, guests are invited to dress to represent a country that means something to them — whether it reflects where you’re from, your heritage, somewhere you love or a place that holds a special connection.
Come together for one final night of music, dancing, celebration and unforgettable memories with Howie and your new familia.
One world. One weekend. One incredible celebration to finish it all.
Daily Experience
DAY 1 | FRIDAY, MARCH 19TH
Afternoon | Caribe Hilton Hotel
Evening | Caribe Hilton Hotel
Evening – Late | Beach bar
Day 2 | Saturday, March 20th
Morning | Caribe Hilton Hotel
Morning | Hotel Beachside
Afternoon | Hotel Beachside
Afternoon | Caribe Hilton Hotel
Evening | Caribe Hilton Hotel
Evening | Caribe Hilton Hotel
Evening - Late | Caribe Hilton Hotel
DAY 3 | SUNDAY, MARCH 21ST
Morning | Caribe Hilton Hotel
Midday | Escuela Bomba Caridad Cepeda and Old San Juan Walking Tour
Evening | Old San Juan Town Dinner
Evening | La Placita de Santurce
Late Evening | Caribe Hilton Hotel
Late Evening | Caribe Hilton Hotel
DAY 4 | MONDAY, MARCH 22ND
Morning | Caribe Hilton Hotel
Morning | Caribe Hilton Hotel
Accommodation
Discover paradise at the Caribe Hilton Puerto Rico, the iconic beachfront resort where history meets luxury.
Nestled on a lush 17-acre peninsula between Old San Juan and Condado, this legendary escape offers sparkling pools, tropical gardens, world-class dining, and the birthplace of the original Piña Colada.
Whether you’re seeking sun-soaked relaxation, vibrant nightlife, or unforgettable cultural adventures, Caribe Hilton is your gateway to the best of Puerto Rico — all with stunning ocean views and timeless Caribbean charm.
PACKAGES
Quad Share Room
$2,999.00 USD
PER PERSON
Triple Share Room
This room can be booked by 3 people or purchased as a single and you will be randomly assigned two roommates of the same gender.
$3,499.00 USD
PER PERSON
Double Share Room
$4,499.00 USD
PER PERSON
A special Opportunity for Puerto Rico Residents 🇵🇷
A limited number of special local tickets will also be made available exclusively to Puerto Rico residents for Saturday, March 20, including the official meet and greet and Howie’s intimate private concert.
If you’re a Puerto Rico resident and would like to be considered for a local ticket, please keep an eye on our website and socials; a special option just for you will be live soon!
INCLUSIONS
- Three nights at the stunning Hilton Caribe
- Personal formal meet and greet with Howie D
- All meals included in the itinerary (three breakfasts, two lunches, three dinners)
- Intimate weekend with 200 Howie D super fans
- Bomba Cuarteto Performance & Dance Class
- Old San Juan Walking Tour
- Group Photo with Howie D
- Ron del Barrilito Rum Tasting and mixology experience
- Dinner in San Juan Old Town in the heart of the action
- Exclusive Private beachside concert with Howie including free flowing alcoholic (and non) drinks (Alcoholic beverages include house beer, house wine, and house spirits only)
- Free flowing alcoholic and non alcoholic beverages across three dinners, two lunches and during Howie's private concert
- Puerto Rican Music and Culture class with maker's workshop and a take home souvenir
- Puerto Rican Backyard Welcome Party
- One World Farewell Party
EXCLUSIONS
- International and domestic flights
- Additional meals, excursions, or transfers outside of the listed inclusions
- Beverages beyond those specified in the inclusions
- Personal expenses including laundry, room service, spa treatments, and retail purchases
- Airport transfers in Puerto Rico
Frequently Asked Questions
When and where is the Howie D Puerto Rico experience?
The experience takes place over four days and three nights in San Juan, Puerto Rico, with guests staying at the iconic Caribe Hilton.
The weekend begins with arrivals and our welcome celebration on Friday and concludes after breakfast and farewells on Monday.
Is Howie D actually attending the weekend?
Yes! This is a hosted experience with Howie D, and he will be joining guests throughout the weekend.
There will be a number of opportunities to spend time with Howie, including breakfast, cultural experiences, dinners, the official meet & greet, Casa Bacardí experience and, of course, his exclusive private concert.
Is there an official meet & greet with Howie?
Yes. Every guest will have the opportunity to take part in the official meet & greet with Howie, including a professional photo opportunity.
Further details regarding the meet & greet will be provided to registered guests closer to the event.
Will there be a private concert?
How much time will we actually spend with Howie?
Where will we be staying?
What accommodation packages are available?
Quad Share Room – $2,999 USD per person
This room must be booked by 4 people at a time. This room only includes 2 beds, so must be booked as a complete room.
This room can be booked by 3 people or purchased as a single and you will be randomly assigned two roommates of the same gender.
This room can be booked by 2 people or purchased as a single and you will be randomly assigned a roommate of the same gender.
Private room for one guest.
All prices are per person.
Can I attend by myself?
Can I book a shared room if I am travelling with a friend?
What's included in my package?
Your package includes three nights at the Caribe Hilton together with the official Howie D weekend programme.
This includes scheduled meals and drinks, the welcome celebration, cultural experiences, official meet & greet, professional photo opportunity, private concert, Ron del Barrilito Rum Tasting and mixology experience, local dining experiences, closing ceremony and an event merchandise pack.
A detailed final itinerary will be provided to registered guests before travel.
Are flights included?
Are airport transfers included?
Which airport should I fly into?
What time should I arrive on Friday?
What time can I depart on Monday?
Are meals included?
Are drinks included?
Can you accommodate dietary requirements or food allergies?
Do I have to drink alcohol to take part?
Not at all. Although the itinerary includes a Ron del Barrilito Rum Tasting, you do not need to drink alcohol to enjoy the weekend. Non-alcoholic options can be made available.
What should I wear?
Puerto Rico is warm and tropical, so comfortable, lightweight clothing is recommended during the day.
There will also be evening celebrations and special events where you may want to dress up.
For your Sunday evening One World Farewell Party, guests are encouraged to wear something that represents your country — whether through colours, clothing, accessories or something meaningful from home.
More detailed packing and dress information will be sent to guests before the event.
Do I need to participate in every activity?
Is the Bomba dance class suitable for beginners?
Absolutely. No dance experience is required. The class is designed to be fun, welcoming and interactive, giving everyone the chance to experience this important part of Puerto Rican music and culture.
What is the mask-making experience?
How many guests will be attending?
Can children attend?
Is Puerto Rico part of the United States?
Do I need a passport?
Is travel insurance required?
What isn't included in the package?
Unless specifically listed as part of the programme, the package does not include:
- Flights to and from Puerto Rico
- Airport transfers
- Personal purchases
- Room service
- Spa treatments
- Laundry
- Additional meals or drinks outside the programme
- Optional excursions or activities you arrange independently
Will the itinerary change?
Will we receive a detailed itinerary before travelling?
Can I extend my stay in Puerto Rico?
Who is Insider Expeditions?
Who can I contact if I have a question before booking?
Is this just another fan event?
Is the event and rooms wheelchair accessible?
BE PART OF THE JOURNEY
19+ Years of Delivering the Trips of a Lifetime
Luxury. Impact. Unforgettable Journeys.
Insider Expeditions blends luxury and purpose to create extraordinary travel. With 500+ journeys across the globe, we offer exclusive group expeditions and bespoke private trips tailored just for you.
From wellness retreats to immersive adventures, our expert team perfects every detail, seamless logistics, deep cultural connections, and lasting impact.
As leaders in sustainable, carbon-neutral travel, we’ve raised $1M+ for global causes and lead iconic trips like our Antarctica expeditions.
Solo, group, or bespoke, Insider Expeditions delivers experiences that inspire and connect.
Ready for your next unforgettable journey? Travel with purpose.
Have questions?
A weekend designed for connection, culture & celebration
Whether you’re ready to book, curious about package options, or simply want to know more about the experience, we’d love to hear from you.
From beachfront sunsets and unforgettable live performances to incredible food, culture, and connection – this is more than just a getaway.
It’s a curated experience designed to bring people together in one of the Caribbean’s most iconic destinations.
