We traveled to St. John in the U.S. Virgin Islands for a week with our friends Justin and Katie to celebrate Justin’s 40th birthday, and it turned out to be an incredible island for the kind of trip we love. With much of St. John protected as part of Virgin Islands National Park, we spent nearly every day hiking to panoramic overlooks, snorkeling with turtles and rays, exploring historic ruins and beach hopping around the island. St. John doesn’t have an airport, so getting there requires a boat or ferry from neighboring St. Thomas – but it’s absolutely worth staying longer than a quick cruise excursion. We visited in September during peak hurricane season, which was definitely a gamble, but we lucked out with almost perfect weather and the huge bonus of surprisingly quiet beaches and trails. Our home base at Thalassa Seaside Retreat gave us gorgeous ocean sunrises, a private pool and plenty of space to relax between adventures, while having our own Jeep – plus a day captaining our own dinghy along the North Shore – gave us the freedom to explore St. John from just about every angle.
🗓️ Itinerary: A Week in St. John
We spent six nights on St. John September 12–18, 2026, using our Jeep to explore a different part of the island each day while still leaving plenty of time to relax at Thalassa. Our itinerary mixed hiking, snorkeling, beaches and a full-day dinghy adventure, with a flexible final day to adjust for weather and revisit a few favorites.
✈️ Day 1 – Arrival + Villa
- ✈️ 5:20 AM – Depart St. Louis
- 🛫10:15 AM – Leave Orlando
- ✈️ 1:20 PM – Arrive St. Thomas
- 🚙 2:00 PM – Pick up Jeep rental
- 🌮 2:30 PM – Lunch at Agave
- 🛒 3:30 PM – Grocery stop at Cost U Less
- ⛴️ 5:00 PM – Car ferry to St. John
- 🚙 5:30 PM – Drive (~30 min) to Coral Bay
- 🏡 6:00 PM – Check in at Thalassa Seaside Retreat
- 🍽️ 7:00 PM – Dinner at villa
🥾 Day 2 – Ram Head + Windmill
- 🥾 8:10 AM – Hike Ram Head Trail (~3 mi, ~1.5h total)
Read more: Ram Head Along Salt Pond Bay - 🤿 10:30 AM – Snorkel Salt Pond Beach
- 🏖️ 11:30 AM – Picnic lunch and relax on the beach
- 🏊 2:30 PM – Return to villa for pool and relaxation
- 🚙 4:45 PM – Drive (~30 min) to Cruz Bay
- 🌅 5:15 PM – Dinner at Windmill Bar over sunset (6:15 PM)
🚤 Day 3 – Dinghy North Shore Beach Hopping
- 🚤 10:00 AM – Full-day Wharfside Watersports dinghy boat rental (🎟️ BOOK)
Read more: Renting a Dinghy in St. John, USVI - 🏊 5:00 PM – Return to villa for pool and relaxation
- 🍽️ 7:00 PM – Dinner at villa
🥾 Day 4 – Cinnamon Bay + America Hill + Trunk Bay
- 🌿 9:10 AM – Cinnamon Bay Nature Loop (~0.7 mi, 30 min plantation ruins)
- 🥾 9:45 AM – Cinnamon Bay Trail + America Hill Trail (1.3 – 2.3 mi out-and-back, steep, ~1.5h total with stop at Cinnamon Bay Trail viewpoint)
- 🏊 11:00 AM – Cinnamon Bay swim and picnic lunch
- 🤿 1:30 PM – Trunk Bay snorkel the Trunk Bay Underwater Snorkel Trail and relax on beach
Read more: America Hill, Cinnamon Bay & Trunk Bay - 🚙 4:00 PM – Return to villa for pool and relaxation
- 🌮 6:00 PM – Taco night at villa
🐠 Day 5 – Annaberg + Leinster Bay + Waterlemon Cay + Hansen Bay
- 🏛️ 8:30 AM – Explore Annaberg Sugar Plantation (~30 min, walk through the windmill, sugar factory & ruins)
- 🥾 9:00 AM – Leinster Bay Trail (~1 mi, ~30 min each way)
- 🥾 9:20 AM – Johnny Horn Trail spur to Guardhouse ruins
- 📸 9:50 AM – Windy Hill Greathouse ruins with stunning overlook
- 🤿 10:30 AM – Waterlemon Cay snorkel
- 🥾 11:30 AM – Hike back to Annaberg along Leinster Bay Trail (~1.1 mi, 30 min)
Read more: Leinster Bay & Waterlemon Cay – Ruins, Reefs & Ridiculous Views - 🚙 12:00 PM – Drive (~30 min) to Hansen Bay
- 🏖️ 12:30 PM – Hansen Bay for picnic lunch and beach time
- 🏊♂️ 3:30 PM – Return to villa for pool and relaxation
- 🍽️ 6:00 PM – Dinner at Surf Club Cantina
🌦️ Day 6 – Flex Day
- 🏊♂️ Morning – Relax at villa and have breakfast/lunch while weather clears
- 🫏 11:30 AM – Cinnamon Bay Beach
- 🤿 Snorkel to Little Cinnamon
- 🐢 3:00 PM – Maho Bay: more turtle snorkeling
- Optional:
- 🌴 Jumbie Bay – 30 minute stop if one of the tiny parking spaces is open
- 📸 Peace Hill – very short walk to the windmill ruins/view
- 🏖️ Francis Bay – quieter beach, easy swimming/snorkeling, good place to relax
- 🏡 Head back to villa for final pool/chill time
🛫 Day 7 – Departure
- 🧳 8:00 AM – Pack and relax
- 🚙 9:00 AM – Drive to ferry (arrive at least 30 min early)
- ⛴️ 10:00 AM – Car ferry to St. Thomas
- 🌴 10:30 AM – Arrive in St. Thomas
- 📸 Stop at Drake’s Seat and Mountain Top viewpoints on drive to airport
- ✈️ 11:30 AM – Arrive at STT airport (3h recommended during busy season, refill gas & return rental car)
- 🛫 2:35 PM – Depart STT
- 🛬 8:00 PM – Arrive STL
💡 Tips: Island Lessons From St. John
- 🚙 Stay on St. John With a Jeep: Having a villa on the island and our own Jeep gave us maximum flexibility to explore beaches, hikes and snorkeling spots without relying on taxis or ferrying back and forth from St. Thomas.
- ⛴️ Ferry a Rental Car from St. Thomas: We rented our Jeep at the St. Thomas airport and brought it across on the car ferry. If you buy a cheaper round-trip ferry ticket, remember that you’ll need to return with the same ferry company, so check its schedule first.
- 🛒 Stock Up on St. Thomas: Cost U Less was considerably cheaper for our main grocery run than shopping on St. John. Calabash Market and Dolphin Market were convenient for restocking during the week, but prices were noticeably higher.
- 🌀 Know the September Trade-Off: September is hurricane season and many restaurants close for the off-season, but our gamble paid off with almost perfect weather, quiet trails, easy parking and some beaches nearly to ourselves. Build in flexibility, check seasonal restaurant closures and consider travel insurance that covers relevant weather disruptions.
- 🌦️ Build in a Flex Day: Even with our great weather, our final morning started rainy. Leaving one day relatively open gave us room to wait it out and revisit Cinnamon and Maho once conditions improved.
- 🚢 Check the Cruise Ship Schedule: Cruise passengers frequently visit St. John from St. Thomas, so we checked the St. Thomas cruise schedule when deciding when to visit popular spots like Trunk Bay.
- 🥾 Hike Early & Carry Plenty of Water: Trails like Ram Head become considerably hotter as the sun climbs, while America Hill and Johnny Horn add more elevation than their mileage might suggest. Starting earlier and carrying plenty of water made the hiking much more comfortable.
- 👟 Bring Real Hiking Shoes or Sandals: St. John’s trails range from rocky shoreline paths to steep forest climbs and exposed terrain. Good footwear was especially useful for Ram Head, America Hill and the Johnny Horn Trail spurs.
- 🤿 Keep Snorkel Gear in the Jeep: Snorkeling opportunities are everywhere, so having our gear with us made it easy to add an unplanned swim or snorkel. For Waterlemon, we carried ours along Leinster Bay but left it near the Johnny Horn junction while climbing to the Guardhouse and Windy Hill ruins rather than hauling it up and down.
- 🌊 Respect the Water: Conditions can change quickly. We turned around when the water became rougher at Trunk Bay and avoided circling Waterlemon Cay because of the stronger current on its Tortola-facing side.
- 🪸 Protect Yourself – and the Reef: Two people in our group stepped on sea urchins at Trunk Bay. Watch where you’re swimming and entering the water, but never stand on or touch coral even when the reef becomes shallow.
- 🫏 Expect Wildlife Everywhere: Sea turtles, rays, donkeys, goats and birds ended up being some of our favorite surprises. Keep food secured – although apparently even a zipped backpack wasn’t enough to stop one determined Leinster Bay goat from getting into my trail mix!
- 🚤 Consider a Dinghy Day: Renting and captaining our own dinghy was one of our favorite adventures and gave us a completely different way to experience the North Shore, particularly harder-to-reach beaches like Scott and Oppenheimer.
📸 Summary: St. John Highlights
🏡 Thalassa Seaside Retreat: Our Home Base
We spent all six nights at Thalassa Seaside Retreat, a tropical villa overlooking Coral Bay and Friis Bay that gave us a relaxing home base for Justin’s 40th birthday trip. The outdoor space was our favorite part, with a private pool surrounded by tropical landscaping and beautiful ocean views, plus incredible sunrises that made getting up early considerably easier. Inside, the villa had colorful tropical décor, huge king bedrooms with extremely comfortable beds and a modern kitchen with an induction cooktop, which was especially useful for preparing our own GF meals and packing picnic lunches for hiking and beach days. We spent plenty of downtime swimming, cooking and hanging out together at the villa, spotted a double rainbow, and had regular visits from Rosie, the very sweet resident cat. Between the views, pool and peaceful setting, Thalassa felt like part of the vacation rather than simply somewhere to sleep – and our drone footage really shows off its beautiful location above the water.
🎥 Thalassa Tour: Short, TikTok, Reel
🥾 Ram Head Along Salt Pond Bay: Desert Meets the Caribbean
Ram Head Trail was one of the most distinctive hikes of our trip, taking us from Salt Pond Bay through a surprisingly dry and exposed landscape to dramatic Caribbean views from the summit. After hiking back, we spent several hours relaxing and snorkeling at Salt Pond Beach, where we saw a stingray and blacktip shark, before returning to Thalassa and heading to Windmill Bar for sunset.
Read more: Ram Head Trail Along Salt Pond Bay – Desert Meets the Caribbean
🚤 Dinghy Day: Beach Hopping the North Shore
Renting our own dinghy from Wharfside gave us an entirely different way to explore St. John’s North Shore, with stops at Scott Beach, Gibney/Oppenheimer and Maho Bay. Scott Beach was a priority because it’s accessible by boat, while reaching Oppenheimer by water avoided its extremely limited parking, making the dinghy one of our favorite ways to beach hop around St. John.
Read more: Renting a Dinghy in St. John, USVI – North Shore Beach Hopping
🌴 Cinnamon Bay, America Hill & Trunk Bay: Hike + Snorkel Day
We combined the Cinnamon Bay Nature Loop with the steep climb toward America Hill, including the spur to the America Hill ruins, before cooling off at Cinnamon Bay and spending the afternoon snorkeling at Trunk Bay. The combination of plantation ruins, sweeping views, swimming and the Trunk Bay Underwater Snorkel Trail made this one of our most varied days.
Read more: Cinnamon Bay, America Hill & Trunk Bay – Ruins, Reefs & Remarkable Views
🐠 Leinster Bay & Waterlemon Cay: Ruins, Reefs & Ridiculous Views
Starting at Annaberg Sugar Plantation, we followed Leinster Bay Trail and added the steep Johnny Horn Trail spurs to the Guardhouse and Windy Hill Greathouse ruins before snorkeling Waterlemon Cay. We finished the adventure with a picnic and beach time at Hansen Bay, making this another full day of history, hiking, snorkeling and beach hopping.
Read more: Leinster Bay & Waterlemon Cay
🏖️ St. John’s Beaches: Our Favorites & What They’re Best For
St. John has an incredible variety of beaches, and rather than picking a single favorite, we’d recommend different beaches depending on what you want to experience. We visited beaches across the island by Jeep, hiking trail and dinghy, with everything from easy turtle snorkeling to secluded stretches of sand and rocky bays leading to more adventurous snorkeling.
🫏 Cinnamon Bay: Best All-Around Beach
Cinnamon Bay was the largest and one of the most beautiful beaches we visited, with very few people during our visit, great swimming and our best donkey interactions of the trip. It’s also an excellent base for exploring beyond the beach, with direct access to the Cinnamon Bay Nature Loop, plantation ruins and trails toward America Hill. We returned to Cinnamon Bay and snorkeled over to Little Cinnamon hoping to find its submerged airplane propeller, but we weren’t able to locate it.
🐢 Maho Bay: Best for Sea Turtles
Maho Bay was our favorite for spotting sea turtles, with four turtle sightings between our two visits – plus a massive ray! The calm, relatively shallow water makes it easy to snorkel over the seagrass beds where turtles feed, and we liked it enough to visit once by dinghy and return again by Jeep on our final day.
🤿 Leinster Bay & Waterlemon Cay: Best for Advanced Snorkeling + Views
Leinster Bay and Waterlemon Cay were our pick for more adventurous snorkeling, with deeper water, reef exploration and a more challenging swim than places like Trunk or Maho. The surrounding trails also led to the best overlooks of our entire trip from the Guardhouse and Windy Hill ruins. The shoreline itself is rocky and wouldn’t be our choice for lounging on a beach, but the combination of hiking, ruins, views and snorkeling made it one of our favorite areas.
🐠 Trunk Bay: Best for Beginner Snorkeling
Trunk Bay is our pick for beginner snorkeling thanks to its marked Trunk Bay Underwater Snorkel Trail, which makes it easy to know where to explore. We saw a ray, jellyfish, a camouflaged flatfish, a squid-like creature and schools of fish, although conditions became rougher as we approached the point. It’s also one of St. John’s most famous beaches, which means it was the most crowded beach we visited.
🏝️ Scott Beach: Best for Seclusion
Scott Beach was the most secluded beach we visited, with beautiful sand and very few people around. Reaching it by dinghy was one of the reasons we prioritized it during our North Shore boating day – and, of course, Scott was a fan before we even arrived simply because the beach had excellent taste in names.
🏚️ Oppenheimer Beach: Best for Seclusion + History
Oppenheimer Beach combined a remote feel with an interesting historical connection, and arriving by dinghy made it much easier since parking from land is extremely limited. We stopped here for our picnic lunch and enjoyed having a quieter place to relax before continuing along the North Shore.
🥾 Salt Pond Bay: Best Reward After a Hike
Salt Pond Bay was our favorite reward beach, especially after completing the phenomenal Ram Head Trail. We returned from the hike, cooled off in the water, snorkeled with a ray and then spent several hours relaxing and eating lunch on the beach before making the final climb back to our Jeep.
🪨 Hansen Bay: One We’d Probably Skip
Hansen Bay was the one beach we probably wouldn’t recommend based on our experience. It’s a fairly long drive, the beach was somewhat rocky with short palms, and access was confusing because the property typically charges for beach access while the shoreline can also be reached through a public boat-access point. We attempted to use the public access and had a man yell at us and accuse us of felony trespassing, which certainly didn’t help the experience! With so many other beautiful beaches on St. John, we’d spend that time elsewhere next time.
🌴 North Shore Beaches: Still on Our List
Our dinghy ride gave us a chance to see many of St. John’s other North Shore beaches from the water, but there are still several we’d like to properly visit. Honeymoon and Salomon Beaches, Hawksnest, Denis Bay, Jumbie Bay and Francis Bay are all on our list for another trip, giving us plenty of reasons to come back.
🍽️ Restaurants & Food: Gluten-Free in the USVI
With Scott having celiac disease, strict gluten-free (GF) accommodation is always an important part of our travel planning. We ate at Agave, Windmill Bar and Surf Club Cantina during this trip, and all three were able to accommodate him without any issues afterward. We also made many of our meals at Thalassa and packed picnic lunches for our adventure days, which worked especially well in September when several St. John restaurants were closed for the off-season.
🌮 Agave: Our First Island Meal
We stopped at Agave on St. Thomas shortly after landing, making it an easy first meal before our big grocery run and the car ferry to St. John. They were able to accommodate Scott’s strict GF needs without any issues, and my shrimp tacos were delicious. The location also worked perfectly with our arrival-day logistics, letting us eat before stocking up at Cost U Less and continuing to Red Hook for the ferry.
🌅 Windmill Bar: Painkillers, Plantation History & Caribbean Sunset
After hiking Ram Head, we headed to Windmill Bar at historic Estate Susannaberg for dinner and sunset. The bar sits beside the stone remains of the Susannaberg windmill, built in the 1780s as part of a former sugar plantation, and we were even able to step inside the old windmill for a photo. Its hilltop location delivered beautiful views across St. John and the surrounding islands as the sun went down, making it one of our favorite settings for a meal. We celebrated with our first Painkillers of the trip and had mahi mahi, jerk chicken and a milkshake – a pretty perfect way to end our Ram Head day.
🔄 360 Photo: Click and drag to look around
🌮 Surf Club Cantina: GF Near Thalassa
We ate at Surf Club Cantina in Coral Bay after our Waterlemon adventure, and its location near Thalassa made it especially convenient after a full morning of hiking and snorkeling. They were able to accommodate Scott’s strict GF needs without any problems, and the mahi mahi tacos were wonderful. Between the casual island atmosphere, good food and a very cute dog hanging around, it was an easy, laid-back dinner to finish one of our busiest days.
🛒 Groceries: Stock Up Before St. John
We did our main grocery run at Cost U Less on St. Thomas before taking the car ferry, stocking up on GF foods, breakfasts, drinks, picnic supplies and ingredients for dinners at Thalassa. Prices were considerably better than what we found on St. John, so we’d recommend doing a larger grocery run before taking the ferry if you have room in the Jeep. During the week, Calabash Market and Dolphin Market were convenient for restocking and had additional GF options, but expect to pay more for the convenience.
⛴️ Getting to St. John: Taking the Car Ferry
Because St. John doesn’t have an airport, we flew into St. Thomas, picked up our rental Jeep and drove to the Red Hook car ferry, which made bringing the Jeep over to St. John surprisingly easy. We drove directly onto the ferry – backing in, which was an experience in itself – and even ventured up to the top deck to enjoy the views along the short ride across Pillsbury Sound to Cruz Bay. Having our own vehicle on St. John was absolutely worth it for reaching trailheads, beaches and more remote parts of the island on our own schedule. On our return to St. Thomas, we simply drove back onto the car ferry in Cruz Bay for the trip to Red Hook, making the ferry feel less like a transfer and more like the official start and finish of our St. John adventure.
📞 Transfer, Tour & Guide Info
- 🚙 Jeep Rental: We rented our Jeep on St. Thomas from the airport and brought it to St. John for the week, giving us the flexibility to explore independently.
- ⛴️ Love City Car Ferries: We used the vehicle ferry between Red Hook, St. Thomas and St. John. Arrive early (~30 minutes) when you need a particular departure, especially when returning to St. Thomas for a flight. Round-trip tickets are cheaper than buying two one-way fares, but you must return on the same ferry company, so check the return schedule before purchasing.
- 🚤 Wharfside Watersports: We rented a dinghy from Cruz Bay for a full day (7 hours, 10:00 AM–5:00 PM) for $295 + $25 fuel, accommodating up to four people. After a quick orientation, we captained the dinghy ourselves along St. John’s North Shore, with the ability to pull directly onto many beaches instead of worrying about parking. This was especially useful for reaching Scott Beach and Gibney/Oppenheimer, and gave us the flexibility to beach hop and snorkel at our own pace.
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