5 Local Experiences You Can’t Miss in St. Thomas

When you think of St. Thomas, crystal-clear waters and soft sandy beaches probably come to mind—but there’s so much more to discover beyond the postcard views. From rich cultural history to flavors rooted in island tradition, St. Thomas offers travelers the chance to immerse themselves in experiences that can’t be found anywhere else.

Here are five authentic, local experiences you won’t want to miss on your next Caribbean getaway:

1. Savor a Private Chef Dinner with Island Flavors

The Virgin Islands are known for their bold, vibrant cuisine. Think fresh-caught snapper grilled with West Indian spices, sweet plantains, and refreshing tropical fruit cocktails. Hiring a local private chef allows you to taste the best of the islands without lifting a finger—and often with stories about the traditions behind each dish. Whether enjoyed al fresco on your villa terrace or around a candlelit table, this is more than a meal—it’s a cultural experience on a plate.

2. Set Sail On a Charter Boat

Sailing is woven into the identity of the Virgin Islands. From the marina in Red Hook, just minutes from Castle at Cabrita, you can hop on a private catamaran or day sail to explore hidden cays, swim with sea turtles, and snorkel reefs bursting with color. Locals will tell you there’s nothing like watching the sunset from the deck of a sailboat, cocktail in hand, as the islands glow gold on the horizon.

3. Beach-Hop Like a Local

Yes, Magens Bay is world-famous—but ask around and you’ll quickly learn that locals have their own favorite beaches. Sapphire, Secret Harbour, Brewers, Hull bay, and Lindquist each have their own unique charm. From calm snorkeling spots to stretches of sand where you might be one of only a few people. Pack a cooler, grab your snorkel gear, and spend the day discovering the island’s diverse shoreline the way residents do.

4. Walk Through History in Charlotte Amalie

Beyond its turquoise bays, St. Thomas holds centuries of history waiting to be explored. The capital city, Charlotte Amalie, still carries the imprint of its Danish colonial past, from cobblestone streets to colorful 17th-century buildings. Climb the famous 99 Steps, browse local artisan shops, and stop by historic sites like Fort Christian and Blackbeard’s Castle. It’s a fascinating glimpse into the island’s layered story.

5. Indulge in Island Wellness

The Caribbean lifestyle is all about living life a little more in the slow lane— go-with-the-flow adventures in the sun followed by deep relaxation. Book an in-villa massage from a local therapist using natural island oils, or visit a St. Thomas spa for treatments that draw on Caribbean botanicals. It’s the perfect way to restore your body after days of exploring and return home feeling renewed.

St. Thomas is more than just a destination—it’s an experience shaped by its people, culture, and traditions. Whether you’re here for food, culture, history, sailing, or simply slowing down, these local experiences will make your trip unforgettable.

And if you choose Castle at Cabrita as your home base, our team is here to connect you with the very best local chefs, captains, guides, and wellness professionals—so all you need to do is arrive and enjoy.

5 Reasons Castle at Cabrita Is the Most Unique Stay in St. Thomas

While there are plenty of beautiful places to stay in the Virgin Islands, few are as unforgettable as Castle at Cabrita. Perched on the eastern tip of the island, our oceanfront villa offers more than luxury—it offers a story, a setting, and an experience unlike anywhere else.

Here are 5 reasons Castle at Cabrita stands out from the rest:

1. Built Into the Island Itself

Our iconic Rock Room isn’t just a design choice—it’s part of the mountain itself. The villa was built with deep respect for the land, preserving the natural rock face and integrating it into the architecture. This creates a one-of-a-kind shower and bedroom experience that literally grounds you in the island.

2. A Legacy You Can Feel in the Walls

Castle at Cabrita isn’t just a vacation home—it’s a family story. My dad, Thomas, built the villa from the ground up in the late 1980s. I grew up here, watching my parents welcome guests with genuine island hospitality, learning what it meant to create unforgettable stays. Now, as the second-generation steward of the villa and the land it sits on, I carry forward that same warmth and attention to detail. Every stone, every corner, holds a piece of our history—something you’ll feel the moment you arrive.

3. Unmatched Views From Every Room

Whether you’re soaking in the pool, lounging on the balcony, or cooking in the kitchen, the Caribbean Sea surrounds you. Every room was designed to frame the island’s natural beauty—sunrises that paint the water in gold, endless blues by day, and starlit skies by night.

4. Concierge-Level Service, Villa-Style

We don’t just hand you the keys—we curate your stay. Whether it’s arranging a private chef dinner, a luxury boat day, or a ready-to-go beach picnic with chairs, coolers, and umbrellas, our team takes care of the details so you can focus on making memories. While many villas offer amenities, few deliver this kind of personalized care—where your vacation truly feels effortless.

5. Close to It All, Yet Totally Secluded

Castle at Cabrita is just minutes from Red Hook’s dining, beaches, and ferry access to St. John—but once you’re here, it feels like your own private hideaway. You get the best of both worlds: adventure at your fingertips, and a serene escape whenever you want it.

Ready to experience Castle at Cabrita for yourself? 
Book your stay now and discover what makes our villa so unforgettable.

Why Celebrate Thanksgiving in the U.S. Virgin Islands (Not Just at Home)

When you think of Thanksgiving, you might imagine turkey, family, football—and maybe a fire you don’t have to shovel out of. But what if your next Thanksgiving could feel like a tropical memory rather than a cold-weather chore? Here’s why more travelers are choosing the U.S. Virgin Islands to celebrate gratitude, connection, and calm—and how you can make it your own.

Tropical Weather That Outshines Autumn Chill

While much of the U.S. is already cooling down, the VI offers breezy warmth, reliably sunny skies, and mild evenings. That means your holiday photos will feature palm trees, not barren branches—and your morning coffee might come with seawater views.

Winter trade winds are gentle by this point in the season, so sea conditions are ideal for snorkeling, paddleboarding, and catamaran sails.

Holiday Energy With Island Character

Thanksgiving in the VI isn’t a ghost town. Local restaurants often offer special holiday menus, and island communities host markets, live music, or cultural events. While it may not look like your hometown’s Thanksgiving parade, you’ll find a warm, authentic vibe—carefully blended with beachy ease.

You might discover a pop-up seafood feast, local bands playing calypso, or rooftops lit for sunset dinners. And because it’s a quieter travel window than December, many vendors are open and ready to host.

Endless Things to Do (Beyond the Turkey Day Table)

  1. Sunrise / Beach Time – Start Thanksgiving morning with a dip or stroll before the holiday eating begins.
  2. Boat Day to BVIs or St. John – Island hop to hidden beaches, caves, and reef snorkeling — many boat tours run daily.
  3. Water Sports & Snorkeling Clearer water visibility, fewer crowds, ideal for beginners and experienced alike.
  4. Local Dining / Private Chef – Sample Caribbean flavors with seafood, island sides, or hire a chef to bring the feast to your villa.
  5. Sunset Moments – No football game time limits—watch the sky, share a toast, soak in the view.

Each of these gives you more than something to cross off your list—they become moments people remember.

Travel Practicalities You’ll Appreciate

  • Easier logistics: Fewer holiday crowds than December means better flight and ferry availability.
  • Better planning window: Because it’s not yet peak season, you can lock in charters, chefs, and transport ahead without frantic demand.
  • Proximity to home: For U.S. travelers, the USVI is domestic territory—no passport needed (unless you sail to the BVI)— and many times you may find a direct flight from your local airport hub! (Just think you may be one flight away from relaxing in paradise!)

Why the Virgin Islands (and Castle at Cabrita) Make Thanksgiving Feel Extraordinary

Choosing a tropical Thanksgiving isn’t just about escaping cold—it’s about creating a holiday that shifts the narrative. It’s about laughter under string lights, ocean breezes after dessert, and stories whispered under stars.

Castle at Cabrita is designed with intimate gatherings in mind. Its layout, amenities, and service make it ideal for those who want togetherness without crowds: group dining, spaces to gather and retreat, ocean views from many angles, and the capacity to weave in private chef experiences or curated island adventures.

While many places feel like vacation rentals, the Castle is built to feel like home for the holiday.

How to Make It Happen (Your Island Thanksgiving Checklist)

Book early (November-December window is often snapped up).

✓ Reserve key experiences in advance — e.g. boat charters, private chefs, guided tours.

✓ Coordinate menus to include island flavors — Connect with a private chef or let us help you explore local thanksgiving day restaurant offerings – think tropical sides, seafood, local produce (maybe even trading in that turkey for a caribbean lobster)

✓ Pack for versatility — sunny days, breezy evenings; light layers + reef-safe sunscreen.

✓ Plan for downtime — leave space for lounging, storytelling, and quiet reflection.

If you’re ready to explore spending Thanksgiving where the views compete with the company, keep this blog as your guide. I’d be happy to help you weave in available dates, suggested experiences, or make a booking strategy that fits your group’s style.

Top 10 Things to Do on St. Thomas for Luxury Travelers

St. Thomas is more than just a postcard-perfect paradise—it’s a playground for luxury travelers craving adventure, indulgence, and unforgettable experiences. Whether you’re planning a romantic escape or a family getaway at Castle at Cabrita, here are ten elevated ways to explore the island in true Virgin Islands style.

1. Charter a Private Yacht for the Day

Sail through turquoise waters, discover secluded coves, and explore untouched beaches aboard a private yacht. Whether you’re craving a champagne sail, a guided snorkeling adventure, or a relaxing day island-hopping, this is the ultimate way to see the USVI and beyond.

Our Concierge Recommends:

  • Vibin VI – Exceptional service and onboard luxury

  • Northside Charters – Known for their cliff-jumping in secret coves to snorkeling with turtles.

  • Stormy Pirates – One of the most versatile fleets in the Virgin Islands.

Concierge Tip: We can arrange half- or full-day charters directly from Red Hook, just five minutes from the Castle.

2. Dine at St. Thomas' Best Upscale Restaurants

St. Thomas’ culinary scene is a delightful surprise for many visitors, offering an impressive variety of gourmet dining options. From Caribbean lobster to fresh-caught snapper, the island’s food scene combines bold island flavors with elevated techniques.

Don’t Miss:

  • Sea Salt – A modern rooftop dining experience with fresh seafood and panoramic views

  • Blue 11 – Chef Benji’s seasonal tasting menus are unforgettable

  • Oceana – A romantic oceanfront gem featuring Caribbean-inspired dishes and fine wines

Bonus: Ask us for reservations—we’ll get you the best seat in the house.

3. Book an In-Villa Private Chef Dinner

Why leave paradise when the chef can come to you? Enjoy a gourmet multi-course meal on the Castle’s oceanview terrace, perfectly paired with wine and candlelight.

Partner Chefs We Love:

  • Chef Faye – Perfect for food lovers, families, & celebration groups!

  • Ultimate Chef Services – Perfect for families, foodies & celebration groups!

  • Island Edge Culinary – Customizable Luxury Chef Experience

Whether it’s a birthday, honeymoon, or just another night in paradise, a private chef dinner is always a good idea.

4. Take a Scenic Helicopter Tour

Experience the USVI from above with a thrilling aerial tour. Soar over St. Thomas, St. John, and the BVIs for a whole new perspective on the islands’ beauty.

Fly With:
Caribbean Buzz Helicopters – They offer everything from scenic flights to full-day excursions.

Perfect for honeymooners, milestone birthdays, or a bucket-list adventure.

5. Island Hop to St. John

Hop over to the neighboring island of St. John for the day—it’s only a short ferry or private boat ride away. St. John is known for its lush national park, serene beaches, and laid-back charm.

Must-Sees on St. John:

  • Trunk Bay – One of the most photographed beaches in the world

  • Reef Bay Trail – A scenic hike with petroglyphs and waterfalls

  • Extra Virgin Bistro – Mediterranean-inspired dining with local ingredients

 

Pro Tip: Let us help book a boat charter so you can explore the island by sea, stopping at the best snorkeling spots and hidden beaches.

6. Schedule an In-Villa Spa Day

Unwind in total serenity with a spa treatment right at the Castle. Picture a relaxing massage on your private terrace, the ocean breeze blowing and waves crashing nearby.

We Recommend:
Spa to Go – Our go-to mobile spa partner offering massage, facials, and body treatments using island-inspired botanicals.

 

Add it to your arrival day or mid-trip reset—you’ll thank yourself later.

7. Explore Coral World Ocean Park

This isn’t your typical marine park. Go behind the scenes to feed a sea lion, pet a stingray, or even try the Sea Trek underwater helmet walk.

 

Great for families and ocean lovers alike, it’s an elevated take on a classic experience with marine life.

8. Sunset Cocktails at Secret Harbour or The Easterly

Golden hour in St. Thomas is an event of its own. Sip a perfectly mixed rum punch while watching the sun dip below the horizon.

Local Favorites:

 

  • The Easterly – Tucked into lush palms, this hidden spot serves up innovative cocktails

  • Secret Harbour – A serene beach just five minutes from Castle at Cabrita, ideal for sunset sips

9. Hit the Shops in Yacht Haven Grande and Main Street

From designer labels to handmade island jewelry, shopping in St. Thomas blends upscale elegance with local charm.

What You’ll Find:

  • Local jewelry from Cruzan Gold or Cardow

  • Home décor and island gifts

  • Artisan soaps, candles, and island-made treats

 

Support small businesses while treating yourself.

10. Plan a Luxe Beach Day

You’ve never experienced a beach day like this. Let us arrange a fully styled setup—complete with picnic table, umbrella, plush cushions, and a charcuterie spread—at one of St. Thomas’ most beautiful beaches.

Vendor We Recommend:
Picnics Under Palms – Custom luxury beach picnics for proposals, celebrations, or “just because”

 

Pair that with paddleboarding or a snorkel session for the perfect day.

Ready to plan your luxury escape?

Let our team at Castle at Cabrita help you experience the best of St. Thomas.
Book Your Stay or Contact Us to start planning today.

From Ruins to Radiance — The Rebuild Story of Castle at Cabrita

In September 2017, two of the most powerful Atlantic hurricanes ever recorded — Irma and Maria — swept across the Caribbean just fourteen days apart, each packing sustained winds of over 155 mph. The storms left a trail of devastation, and among the structures battered was the property once known as Villa Fantasia, perched high on Cabrita Point in St. Thomas.

What followed wasn’t just a rebuild — it was a rebirth. A revival born through generational collaboration between a father and daughter, bringing together experience, vision, and love for an extraordinary place. Two storms. Two generations. One redemption story.

A Legacy Worth Rebuilding

Originally constructed in the late 1980s by Thomas, the villa’s original builder and steward of the land, the home was crafted as a gathering place for friends and family — a place where hospitality, laughter, and island beauty came together. For more than three decades, Villa Fantasia stood as a symbol of Caribbean joy.

After the hurricanes, Chelsea — Thomas’s daughter — and her husband Connor knew this wasn’t the end of its story. Partnering closely with Thomas, whose knowledge of every beam and stone was unmatched, Chelsea directed the villa into a new era: blending her fresh perspective with his craftsmanship and the history embedded in its walls. Together, they charted a path to honor the past while designing for the future.

Five Years. One Vision.

What began as a storm-damaged shell evolved into a five-year labor of love. Every wall, beam, and window was reconsidered: how could it remain true to the villa’s original soul while offering an elevated, modern experience?

The result is Castle at Cabrita — a fully reconstructed luxury retreat that pairs timeless Caribbean charm with contemporary elegance, giving guests an immersive sense of comfort and wonder.

A rebuild from the heart of connection

After Hurricanes Irma and Maria in 2017, we chose to treat the rebuild as an invitation to reimagine the heart of the villa — flipping the great room, moving the kitchen into the former living space, and tearing down walls so sightlines sweep a full 360° from anywhere in the room. The kitchen now sits in a spacious elevated outlook overlooking the pool and great room as a conversational hub where guests naturally gather, while the living and dining areas flow together to create an open, airy space made for shared meals, stories, and slow afternoons. It was a big overhaul, but the result is a warm, effortless place designed for connection and the kind of memories families come here to make.

Rising Above: From Torn Roof to Rooftop Retreat

When the storms ripped the roof off in 2017, we saw another chance to rebuild with intention — to honor the villa’s stunning original, gazebo-like interior woodwork while reimagining the rooftop as a place for our guests to truly connect with the unique vantage point of Cabrita Point overlooking the USVI and BVI from one place. We preserved the warm, handcrafted details inside, and added a rooftop deck with a circular couch designed for unobstructed 360° views — perfect for sunrise, sunset, stargazing, and lingering conversations. The new roof keeps the villa’s original charm but elevates the experience: a place where the horizon becomes part of your gathering and every evening feels a little more magical.

The Iconic Rock Room

One of the villa’s most memorable spaces is the Rock Room Suite. From the very beginning, a massive boulder naturally embedded in the hillside inspired the original design. During the rebuild, Chelsea, Connor, and Thomas reimagined how this unique feature could make the space even more inviting. The remodel added a freestanding soaking tub and rainfall shower, turning the room into a sanctuary where nature and design meet in perfect harmony.

Guest Comfort, Above All

Every choice throughout the restoration was guided by two goals: enhancing the guest experience and strengthening the villa to withstand future storms.

Chelsea and Connor now live in a nearby home to welcome guests personally and ensure every stay feels seamless and warm. Thomas continues to visit often, sharing stories and making new memories with his family on the very land he once envisioned as a haven.

Ready to stay somewhere with a story?

Come experience the care, history, and craftsmanship that make Castle at Cabrita so much more than just a vacation rental.

Book your dates today and become part of our legacy.