We recently returned from an unforgettable family trip to St. John, and it was truly the ideal destination for our last big adventure before our eldest, John, heads off to college. Having visited St. John once before for our anniversary, my husband Luke and I knew we wanted to share its magic with our sons. This trip was more than just a vacation; it was a special milestone for our family.
Family vacation memories at Maho Bay Beach in St. John, USVI
St. John offered us the perfect escape. We spent our days relaxing on pristine beaches, snorkeling in vibrant coral reefs teeming with marine life (we even saw sea fans as big as 7 feet!), encountering wild donkeys and chickens roaming freely, and exploring the vast trails of the national park. It felt like paradise found. I’m thrilled to share all the details of our trip, packed with photos and helpful tips to inspire your own family getaway to St. John.
St. John: A tiny island, in the middle of a big ocean, that feels like a dream.
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This quote perfectly encapsulates the enchanting spirit of St. John, as I saw it inscribed on a mug at Cinnamon Bay.
Serene Cinnamon Bay Beach, St. John, perfect for family relaxation
Discovering St. John: An Island Paradise
St. John, nestled in the US Virgin Islands alongside St. Thomas, is the smallest yet arguably most captivating of the trio. Uniquely, it’s the only US territory where driving is on the left side of the road, adding a touch of exotic charm to your family vacation.
Remarkably, since 1956, about 60% of St. John has been protected as part of the Virgin Islands National Park, managed by the US National Park Service. This commitment to preservation ensures the island’s natural beauty remains unspoiled for generations of families to enjoy.
A Glimpse into St. John’s Rich History
The history of St. John is as rich and vibrant as its natural landscapes. Long before European arrival, the Taino people inhabited the island from around 700 AD to the late 15th century. During our hikes, we explored ancient Petroglyphs, and archaeological findings at Cinnamon Bay reveal traces of pottery and settlements, connecting us to the island’s indigenous past.
Ancient Petroglyphs in St. John, a historical site for family exploration
Between 1671 and 1718, control of St. John shifted between Danish and English settlements, eventually settling under Danish rule in 1718. The island’s economy thrived on sugar cane, cotton, and other crops, powered by large plantations like the Annaberg Sugar Plantation, established in 1731. Sadly, this prosperity was built on the backs of enslaved people; by 1804, the slave population peaked at 2,604. Denmark emancipated slaves in 1848, leading to the abandonment of many plantations by the 1850s.
In 1917, amidst World War I, the United States purchased the Virgin Islands from Denmark for $25 million to establish a strategic military base. The 20th century saw private investment in St. John, with vacation resorts emerging, notably Laurence Rockefeller’s Caneel Bay development. Rockefeller, passionate about conservation, donated vast tracts of land to the federal government, leading to the creation of the Virgin Islands National Park and ensuring the island’s natural splendor would be preserved.
Iconic straw hat hanging at Honeymoon Beach, St. John, a symbol of island relaxation
While Hurricane Irma significantly damaged Caneel Bay Resort, the Caneel Bay Beach Club and ZosZos are currently open, with hopes for redevelopment to restore the beloved resort to its former glory.
Getting to Your St. John Family Escape
Your journey to St. John begins by flying into St. Thomas (STT), the closest airport. From there, you’ll take a scenic ferry or a private boat taxi to St. John. We opted for the Red Hook ferry upon arrival and the Crown Bay ferry for our departure. The Crown Bay ferry is a bit longer but conveniently located nearer to the airport.
Traveling from Boston, expect a full day of travel. Although our flights were indirect, the reward of reaching St. John is absolutely worth the journey.
Airplane wing view over clouds en route to USVI, starting the family adventure
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Family-Friendly Accommodation in St. John
During our previous visit, we enjoyed a stay at Caneel Bay. This time, for our family vacation, we chose the privacy and space of a private villa with a pool. We booked Elysium Villa in Fish Bay through BookVI.
Elegant villa in St. John with lush orchids, perfect for family stays
Elysium Villa comfortably accommodates up to six guests, ideal for our family of four. BookVI provided exceptional service, greeting us upon arrival and guiding us to the villa, and were readily available for any needs. They offer a comprehensive concierge service to enhance your stay.
Fish Bay offered a tranquil setting, and our villa’s cliffside location provided stunning views of Fish Bay and the ocean. We were greeted our first morning with a breathtaking rainbow.
Vibrant rainbow over Fish Bay, St. John, viewed from a family villa
The villa was thoughtfully equipped with everything we needed. A beautiful pool and coral stone patio became our private oasis. The layout was unique, with the open-plan living area on the upper floor and bedrooms downstairs, opening onto the patio level. While this worked well for us, families with very young children might need to consider the separate bedroom access. A washer, dryer, and spare bunk room were also conveniently located downstairs.
Charming Fish Bay villa with a red Jeep, ideal for exploring St. John
The villa felt spacious, relaxed, and impeccably clean. The kitchen was fully equipped, including a grill and large fridge/freezer – essential for family meals. A blender was a must-have for crafting our evening Painkiller cocktails (recipe coming soon!), which tasted even better in the St. John air.
Inviting villa with private pool in St. John, perfect for family relaxation
Beach essentials were also provided: beach towels, coolers, chairs, and toys – they truly thought of everything! And I must mention the beautiful aqua pool tiles:
Close-up of aqua pool tiles, adding a touch of color to the St. John villa
We loved unwinding by the pool after beach days, and it was especially magical at night.
Teenage boys enjoying the pool at night at a St. John villa
Beyond private villas, St. John also offers options like the Westin St. John Resort Villas and the Cinnamon Bay Campground for different family preferences and budgets.
Getting Around St. John with Family
On our first trip, we mainly stayed within Caneel Bay and relied on taxis to Trunk Bay Beach. This time, renting a Jeep was a game-changer, allowing us to explore much more of the island at our own pace. Be aware that St. John roads are known for being curvy and steep. Driving is on the left side with left-hand drive vehicles, which can be a unique experience. While I wouldn’t have been comfortable driving myself, my husband, who grew up navigating narrow Cornish lanes, handled it with ease! If you can drive in Cornwall, you can drive anywhere, as they say!
Family Adventures: Beaches and Hikes in St. John
During our week-long stay, we aimed to maximize our exploration, visiting a different beach and attempting a hike each day. One day, when our son Conor wasn’t feeling well, we enjoyed a relaxed day at the villa with a short trip to Peace Hill. Here are some of our favorite family-friendly beaches and hikes:
Day 1: Lind Point Trail & Honeymoon Bay Beach
We began our vacation with a nostalgic return to Honeymoon Bay Beach, one of the beautiful beaches within the Caneel Bay area that we loved on our first visit. We wanted our sons to experience its charm. Parking in Cruz Bay for the day, we took the scenic Lind Point Trail to reach Honeymoon Beach.
Lind Point Trail sign, marking the start of a family hike in St. John
The Lind Point Trail is an easy, enjoyable hike, perfect for families. Along the way, we spotted crabs, cacti, termite mounds, and impressive giant air plants.
Giant airplants along Lind Point Trail, St. John, a natural wonder for families to discover
The trail opened up to the stunning Honeymoon Beach.
Honeymoon Beach offers the Caneel Bay Beach Club, where you can enjoy lunch, cocktails, and refreshments. They also have a small shop and restroom facilities, making it convenient for families.
Boys playing on the sandy shores of Honeymoon Beach, St. John
Of course, we had to indulge in Painkillers on the beach!
Painkiller cocktails on Honeymoon Beach, a tropical treat for parents
Snorkeling at Honeymoon Beach was fantastic, with an abundance of colorful tropical fish and coral to explore.
Iguana strolling on Honeymoon Beach, St. John, a wildlife encounter for families
After a full day at the beach, we walked back via the Lind Point Trail and explored Mongoose Junction for some shopping and delicious frozen treats at Irie Pops.
Refreshing Irie Pop popsicle in Cruz Bay, St. John, a treat for a family day out
We highly recommend Irie Pops’ homemade popsicles. For dinner, we had an early meal at High Tide, a restaurant we loved so much we returned on our last night. The views are simply incredible!
Breathtaking view from High Tide Restaurant in Cruz Bay, St. John
The food at High Tide was consistently excellent. My son Conor enjoyed a wrap sandwich:
Delicious wrap sandwiches at High Tide Restaurant, St. John
I couldn’t resist the Coconut Shrimp and ordered it with a salad – it was so good I had it twice!
Basket of golden Coconut Shrimp at High Tide Restaurant, St. John
Day 2: Lameshur Bay Trail, Petroglyphs & Lameshur Bay Beach
Lameshur Bay, recommended by a friend as a “hidden gem,” lived up to its reputation. It was incredibly peaceful and secluded. However, a Jeep is essential for this excursion due to the rough, unpaved road leading to the bay.
Historic ruins at Lameshur Bay, St. John, adding a touch of history to a beach day
We started by exploring the fascinating ruins near the beach.
Scenic view through a window in the ruins at Lameshur Bay, St. John
Then, we hiked the Lameshur Bay Trail to see the Petroglyphs.
Entrance to Lameshur Bay Trail, St. John, a hiking adventure for families
Hiking shoes are definitely recommended for this trail. The initial steep incline rewarded us with stunning ocean views.
Expansive ocean view from Lameshur Bay Trail, St. John
Cactus and wasps along Lameshur Bay Trail, St. John, highlighting the natural environment
Further along, the trail transitioned into a more shaded, forest-like path leading to the Petroglyphs.
Petroglyphs trail sign in St. John, guiding families to historical art
Father and son hiking to Petroglyphs in St. John, a bonding experience
These ancient carvings, dating back to 900 AD, were created by the Taino people and are a truly remarkable site. For an easier option, the National Park Service offers a downhill tour to the Petroglyphs that includes a boat ride back.
Detailed Petroglyphs carvings in St. John, ancient art to admire
Petroglyphs informational sign in St. John, providing context for visitors
On our return hike, we were caught in a sudden downpour. We were drenched, but it was a refreshing cool-down!
Mother and sons hiking in the rain on Lameshur Bay Trail, St. John, embracing the island weather
The rain shower was brief, and soon the sun was shining again.
Scenic views from Lameshur Bay Trail after the rain, St. John
After our hike, we spent time at Lameshur Bay Beach. It was secluded and shady, but we found the snorkeling less vibrant compared to other beaches.
Boy walking along Lameshur Bay Beach, St. John, enjoying the tranquility
Father and sons relaxing on Lameshur Bay Beach, St. John, family time in paradise
For a late lunch, we visited the Windmill Bar, which offered breathtaking views of Lovango Cay.
Family enjoying the views at Windmill Bar, St. John
Their Mahi Mahi Bowl was a highlight – absolutely delicious!
Mahi Mahi bowls at Windmill Bar, St. John, a flavorful lunch option
Day 3: Beach Day at Trunk Bay
This day was dedicated to pure beach relaxation at Trunk Bay. My son Conor prepared amazing BLTs for a beach picnic.
Family picnic on Trunk Bay Beach, St. John, enjoying homemade lunch
Trunk Bay is renowned for its beauty and underwater snorkel trail.
Iconic Trunk Bay Beach, St. John, famous for its beauty and snorkeling
Rated as one of the world’s top 10 beaches by Condé Nast, Trunk Bay truly is stunning.
Mother and sons enjoying the clear waters of Trunk Bay Beach, St. John
We arrived early, around 8:30 am, and enjoyed a peaceful beach before it became busier later in the day with more visitors, including content creators.
Peaceful morning at Trunk Bay Beach, St. John, before the crowds arrive
Father and sons enjoying Trunk Bay Beach, St. John, quality family beach time
Day 4: Relaxing at Maho Bay Beach
Maho Bay Beach is known for its calm waters, making it ideal for families with younger children.
Calm waters of Maho Bay Beach in the morning, St. John, perfect for families
We found a shady spot to set up our beach chairs. Maho Bay felt more laid-back than Trunk Bay, with many families enjoying the snorkeling. Restrooms were conveniently located, and across the street were shops, a snack bar, rentals, and a bar.
Boy digging a giant hole on Maho Bay Beach, St. John, family fun in the sand
Maho Bay is famous for sea turtle sightings. Although we didn’t see any turtles, the boys spotted a stingray while snorkeling.
Day 5: Peace Hill & Denis Bay
This was a more relaxed day as Conor wasn’t feeling well. We spent most of the day at the villa, painting and resting. In the afternoon, we ventured out for a short trip to Peace Hill.
Sugar Mill ruin atop Peace Hill in USVI, a historical landmark
Peace Hill is a short 10-minute drive from Cruz Bay with a small parking area. The trail to the top is only 1/10 of a mile, making it an easy walk even when feeling under the weather.
Teenager exploring the ruins on Peace Hill, St. John
At the summit of Peace Hill are the ruins of a sugar mill, once part of the nearby Denis Bay Plantation. A short trail from Peace Hill leads down to Denis Bay Beach, which my husband and son John explored.
Peace Hill offers stunning views of Trunk Bay.
Panoramic view of Trunk Bay from Peace Hill, St. John
The views from Peace Hill are truly spectacular.
Sweeping Caribbean seas and views from Peace Hill, St. John
Here’s a glimpse of Denis Bay Beach from above:
Denis Bay Beach as seen from Peace Hill, St. John
While waiting for Luke and John to return from the beach, we encountered some of St. John’s famous wild donkeys.
Close-up of wild donkeys in St. John
On our way back to the villa, we picked up pizza from Ronnie’s Pizza (our second time!) near the Westin. Excellent pizza and subs!
Ronnie's Pizza storefront in St. John
Enjoying take-out Ronnie's Pizza at the villa in St. John
Day 6: America Hill Ruins, Cinnamon Bay Sugar Factory Ruins & Cinnamon Bay Beach
Our last full day on St. John was extra special. We started at Cinnamon Bay (also a campground) and hiked the America Hill Ruins Trail.
Cinnamon Bay Campground and Beach facilities, St. John
Map of Cinnamon Bay Trail system, St. John, for planning family hikes
Sneakers or hiking shoes are essential for the America Hill Ruins Trail, as it’s steep and rocky in sections.
Trail signs for Cinnamon Bay trails, St. John, guiding hikers
The trail is beautifully wooded and shaded, filled with the scents of cinnamon and jasmine.
Family hiking up a steep staircase on Cinnamon Bay Trail, St. John
At the summit, we explored the ruins and even spotted a deer!
The ruins offer views of Maho Bay and Francis Bay.
Scenic view from America Hill Ruins overlooking Maho Bay, St. John
Coral used in the construction of America Hill Ruins, St. John
Palm trees and Caribbean views from America Hill Ruins, St. John
After hiking back down, we took a short walk around the Cinnamon Bay Sugar Factory Ruins.
Sign for Sugar Factory Ruins at Cinnamon Bay, St. John
Sugar Factory ruin with a palm tree growing inside, Cinnamon Bay, St. John
It’s fascinating to see coral used as a building material in the ruins.
Cinnamon Bay Ruins showcasing coral construction, St. John
Sugar Factory Ruins at Cinnamon Bay, St. John, historical site for families to explore
Then we spent the afternoon at Cinnamon Bay Beach, which we absolutely adored. It’s a long stretch of soft white sand beach, about half a mile. We walked towards the end and found a secluded spot just for ourselves.
Expansive Cinnamon Bay Beach, St. John, perfect for a long beach walk
Further down the beach, I found this charming sharing chair.
Sharing chair at Cinnamon Bay Beach, St. John, a sweet beach detail
We brought our own lunch, but food trucks, a bar, and a general store are available. We even bought Cinnamon Bay t-shirts as souvenirs!
Greetings from Cinnamon Bay t-shirt, a souvenir from St. John
We snorkeled twice at Cinnamon Bay. First, to the right, hoping to find plane wreckage we had read about, but we were unsuccessful.
Calm turquoise waters of Cinnamon Bay Beach, St. John, inviting for snorkeling
Our second snorkeling adventure was out to Cinnamon Cay, which proved to be the best spot, with huge 7-foot sea fans and abundant tropical fish. We spent the entire day soaking up the magic of Cinnamon Bay.
Boys playing at Cinnamon Bay Beach, St. John, enjoying the clear waters
View of Cinnamon Bay Beach through a ruin window, St. John
After the beach, we returned to the villa to freshen up for dinner. John loved High Tide, so we went back for our final dinner on the island.
I finally wore my new block print dress from Coastal Brahmin (now on sale!), paired with the beautiful St. John sunset.
Woman wearing a block print dress by the pool at sunset in St. John
I was amazed at how grown-up Conor looked in the evening light!
Teenager leaning against a wall with palm tree shadows in St. John
Family enjoying dinner at High Tide in Cruz Bay, St. John
Most nights, we were in bed early, but on our last night, we enjoyed strolling through Cruz Bay, which has a lively nightlife.
Charming architecture in Cruz Bay at night, St. John
That concludes our St. John itinerary, but here are a few more helpful tips for planning your family trip.
License plate reading "Beach It St John" on a Jeep, St. John
Essential Tips for Your St. John Family Vacation
- Driving: Be prepared for steep and bumpy roads. Driving is on the left side, but cars are American left-hand drive. Ensure you are comfortable with this before renting a car.
- Jeep Rentals: Jeeps are popular and practical due to the island’s terrain.
- Reef-Safe Sunscreen: The sun is very strong! Use reef-safe sunscreen to protect yourself and the coral reefs. We learned the hard way and got sunburned on our first day.
- Snorkel Gear: You can rent gear, but we brought our own snorkel gear from Amazon.
- Parking in Cruz Bay: Parking can be limited and expensive. We paid $70 for a full day of parking.
- Food Costs: Food is expensive due to imports. Consider buying fresh produce and cooking some meals at your accommodation. Starfish Market in Cruz Bay was slightly more affordable than Dolphin Market.
- Cocktails at Home: Making your own cocktails can save money, but Painkillers on the beach are a must-try!
- Jewelry: We loved Caravan Gallery in Mongoose Junction for unique jewelry. I purchased a handmade St. John Hook Bracelet.
- Concierge Services: If your villa offers concierge services, take advantage of them to enhance your experience.
Handmade St. John Hook bracelet, a local jewelry piece
Chicken roaming freely in St. John
Why St. John Stole Our Hearts
Usually, towards the end of a vacation, I’m ready to return home. But this time, I didn’t want to leave St. John! It was an incredible trip.
- Spectacular Nature: St. John’s natural beauty is breathtaking.
- Pristine Beaches & Trails: Every beach and trail we explored was amazing.
- Friendly Locals: The people are welcoming and friendly.
- Clean and Safe: The island is clean and feels safe.
- Relaxed Vibe: St. John has a wonderfully relaxed atmosphere.
Husband and wife on Cinnamon Bay Beach in St. John, enjoying the island beauty
I hope this guide to our family getaway in St. John inspires your own trip! Save this post for future planning. Next time, we’d love to rent a boat and visit Lime Out for tacos on the water.
Rainbow over St. John, a beautiful island moment
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