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Three Perfect Days in St. John

Three Perfect Days in St. John

St. John, fondly known by locals as Love City for being so safe and friendly, is an American paradise. Though the smallest of the U.S. Virgin Islands, it’s a very special place with over two-thirds of the island’s land protected as Virgin Island National Park. This conservation effort ensures this unspoiled gem maintains its immaculate landscape while providing visitors an abundance of outdoor activities so they may observe the island’s wildlife, nature, celebrated history, and vibrant scenery in its most organic form. 

Not only is St. John one of the most beautiful Caribbean islands you’ll ever visit, it’s also the friendliest. St. John is peppered with over a dozen beaches, hundreds of acres of tropical forests, shopping and nightlife in lively Cruz Bay, and top-rated restaurants. Whether it’s paddling through the bay in search of sea turtles, snorkeling with tropical fish in the reefs, dancing to live music, or sailing through the waves in a catamaran, there’s plenty of fun in the sun on this inviting island. 

Picturesque Trunk Bay – St. John’s most famous beach – is consistently rated one of the top in the world. It’s also one of the most photographed places in the Virgin Islands because of its pristine beauty with sugar sand beaches. 

Our Destination Manager Danielle was fresh off an action-packed trip in St. John when we asked her to share her ideal itinerary for three perfect days in this island paradise. Snorkeling, paddling, hiking, and delicious food await!   

DAY 1: Canvasing the Beauty of Conservation Land

Start your morning off at Provisions in Cruz Bay where you’ll fuel up with a hearty breakfast sandwich. We suggest the sausage and egg on a cheddar biscuit. For those with a sweet tooth, their fresh banana bread is a winner every time. Don’t forget to grab a few chilled bottles of water to go. 

A locals’ favorite,  Ram Head Trail is a great morning hike before the afternoon heat arrives. A little over two miles long, this trail head takes about an hour and offers amazing ocean and bay views. You will pass two different beaches where you can stop to take a dip, or canvass for shells. If you’d prefer to have a tour guide on your hike, we’ll gladly arrange one for you. 

For lunch we suggest Skinny Legs Bar & Grill.  After all that hiking, you definitely earned their specialty – the cheeseburger. Whether you opt for the simple cheddar or the blue burger, you won’t be disappointed. The relaxed vibe makes it easy to enjoy the company of locals and vacationers alike as you sip a chilled raspberry lemonade with your juicy burger.  

A trip to St. John isn’t complete without exploring the gorgeous blue waters of the island’s East End by kayak or paddleboard. Your Local Host made afternoon reservations for you with Virgin Islands Expeditions Company, so all you need to do is show up ready to learn how to paddle. You’ll see amazing sea life, including nurse sharks, barracuda and squirrel fish. You’ll glide over colorful coral reefs, turtle grazing beds and a shipwreck as you sail through turquoise waters and tranquil sea breezes under the afternoon sun. 

After taking a dip and enjoying a cocktail poolside back at the Equity Estates home, you’ll head to the dazzling alfresco eatery Morgan’s Mango in Cruz Bay where we’ve made reservations for your group. The flavorful Neo-Caribbean cuisine will delight your tastebuds. For a real treat, we recommend you share the octopus appetizer, and for the main course try the Panko Grouper. Danielle said the fish was the best she’s ever had. 

DAY 2: Tropical Fish, Turtles & Reefs!

With so much to do at St. John’s famed Trunk Bay, it’s important to start your day with a satisfying breakfast. At Cruz Bay Landing, the favorites are the banana and blueberry stuffed pancakes and the mouthwatering house benny (ham eggs benedict with a Caribbean kick). Cold brew coffee lovers line up to enjoy the perfection of their ten hour brew.

Trunk Bay is the most iconic spot in St. John, named after the largest sea turtle in the world, which is known to locals as “trunks.” With a 650-foot self-guided snorkeling trail, stunning coral formations and bountiful sea life, there’s plenty to do. Lifeguards watch over swimmers and snorkelers, making it a safe place for beach lovers of all ages. 

The Equity Estates residences are stocked with all the necessities for your day at the beach. Bring the chairs, snorkel gear, tents and sunscreen, and find a comfy place to camp out and take in the sun and surf.

Your Local Host is happy to arrange for any beach toys you wish to make your day complete. 

When shell seeking and tropical fish finding work up your appetite, the Trunk Bay Snack Shack is ready to serve you a very casual but satisfying hot lunch, refreshing cocktails, and ice cream. The pulled pork nachos are a great starter, and as far as snack shack food goes, the hot dog and burger with fries always hit the spot after a morning of sunshine and swimming. 

If you have enough energy left on your way back to the residence, there are many historic sites nearby for a quick sightseeing adventure, including America Hill Ruins, Annaberg Ruins, Trunk Bay Plantation Ruins, and Cinnamon Bay Sugar Mill Ruins.   

Back at the residence, unwind with a few laps in the pool or happy hour before you head out to dinner where we’ve made reservations at The Terrace. The menu is a rare treat of freshly sourced seafood and hand selected meats with premium ingredients that yield a delectable French-inspired cuisine. Sip from the sommelier’s choice wines while taking in the amazing sunset view from the deck. Oysters Rockefeller paired with a sparkling wine to begin are complemented by the piping hot homemade bread served with shallot butter. Whether you order a steak, fois gras, or fresh fish, you won’t be disappointed. And don’t forget the key lime mango pie for dessert. 

If you’re ready to work off dinner with dancing, live music at the Beach Bar is always an island favorite. Their signature painkiller drink is like a second dessert. 

DAY 3: Sail Away!

This morning you’ll head back to Cruz Bay where you’ll start your day at the North Shore Deli. The north shore scramble and French toast are sure to fill you up before you head out for an exciting day on the catamaran.

Your local host made reservations at Voodoo Charters Pack a towel and sunscreen and hop aboard their sleek catamaran prepared to take your group out for a funfilled day of snorkeling, swimming, and delicious tacos at the world-famous Lime Out. Adults will love the open bar onboard the catamaran, and everyone will have a fantastic time snorkeling several reefs and making new friends throughout the day.  

The catamaran returns to Cruz Bay by late afternoon offering plenty of time for shopping, happy hour, live music or exploring some historic sites. If a day at sea has you worn out, a siesta relaxing by the pool and taking in the spectacular views from your residence is always a perfect way to ease into the evening.   

Whether your home base is the Equity Estates residence in Klein Bay or Chocolate Hole, our favorite chef Vinny will surprise and delight you with a unique menu of your choice. This Chicago-trained culinary master offers delicious canapes, family style menus and theme nights.

As you unwind with your choice of cuisine and cocktails, Vinny will cater to your every whim, offering you the most amazing dining experience as you enjoy your final night sharing your favorite memories of St. John with your family and friends. There’s no better way to spend your last evening than in the comfort of your own home being served by a top-rated chef.

An evening stroll on the beach near the residence listening to the gentle lap of the waves under the stars is the perfect way to end your three perfect days in Love City. 

At Home in St. John with Equity Estates 

Equity Estates offers investors two luxurious residences in St. John. 

The Klein Bay residence is a gorgeous oceanfront villa comprised of a three-level main home and a pool house. With a classic Caribbean flair, pristine ocean views, a private pool and plenty of outdoor living space, this residence is reminiscent of a small luxury resort. With five bedrooms, six bathrooms and over 5,000 square feet of living space, this island stunner offers room to spread out, relax and enjoy the view. 


The newly renovated Chocolate Hole residence offers investors the classic Caribbean experience with breathtaking ocean views, a private pool, and plenty of outdoor living areas to soak in the ocean breeze. Offering six bedrooms, six bathrooms and over 8,000 square feet of living space to accommodate up to 14 guests, this residence is ideal for large groups and multigenerational gatherings. 

Your Destination Manager will work with you to plan your itinerary before you arrive and make sure your stay is effortless by arranging reservations for activities, transportation, and dining. Leave the details to us and arrive to a fully stocked kitchen and bar with groceries of your choice from the local market. Your Local Host is on call to help with anything you need during your island stay. With Equity Estates, comfort and luxury are yours.  

Travel with Equity Estates for a unique and memorable experience. If you would like more information about investing with Equity Estates, please reach out to our Investor Relations team at 404.445.8501 or tap this link to schedule a call. Your incredible St. John getaway awaits!