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New York, NY

We are parents, too. We think traveling well and traveling with children shouldn’t be mutually exclusive. We have limited vacation time, and we’re not spending our few days of freedom in lousy hotels eating bad food. We know the world is full of wonderful resorts, cool urban escapes and far-flung lodges that can make our time with our kids count. We want it all, and we don’t think it should be so hard to find. So we’re going to share it with you.


St. John Escape with Five Kids

Travel Journal

Travel Journal

Dispatches from around the world

St. John Escape with Five Kids

Henley Vazquez


Mama of three and business development extraordinaire at our favorite consignment shopping site, TheRealReal, Elisa Carbone Brown just got back from a fun-filled trip to St. John. She intrepidly brought her brood, Jack, 12, Fin, 10 and Hadley, 7 along with two cousins, ages 14 and 16 to St. John for February break. Yes, she took five kids by herself to an island! Her travel mantra is to "live with passion, travel with purpose." If you're looking for her on a plane, she's the one wrapped in a fabulous Hermès cashmere throw, sipping Essentia Water and totting a Rimowa suitcase. As for her littles, they don't travel without "Apple iPads and Beats by Dre. I somehow forgot them on the last trip and we where on an old Delta plane with no televisions. It almost got ugly." For Elisa, whether you are traveling to a city or an island, the most important thing is to have an itinerary planned that has you and your family eating and discovering like locals. Read on for her take on the US Virgin Islands with the kiddos. 


We booked last minute and swooped up a three bedroom villa at The Westin St. John Villas. It far exceeded my expectations. The whole resort is villas with a full kitchen, washer/dryer, etc. The kitchen is a huge bonus because food in St. John is uber-expensive, as they have to bring everything over by boat. It is easy to walk to a grocery store and pick up fresh fruit and eggs to cook breakfast, otherwise you are dining at the resort and spending $40 per child for an omelet. The resort has a recreation center for kids (pool table, ping pong table, air hockey), kid programs (we did not use them), a generous size pool and a beach that has complimentary paddle boards and kayaks to take out, inflatable trampolines and water slides. It is truly an awesome resort for families. The food is much better then fine, but it's not going to blow your mind. I would stay there again in a heartbeat. 

Caneel Bay Resort is also beautiful (rustic, no television), but it was fully booked. It is a large resort, hosts seven beaches and many restaurants. It's the next level up from the Westin and did not disappoint when we went over for dinner to visit some friends.


Downtown St. John is a five minute cab ride, safe and charming.

Da Livio is a restaurant serving homemade Italian pastas and wood-fired pizzas. Mario Batali, who is often seen on the island, is a regular here. It's tiny, so having a reservation in peak season is important. It's like a small version of Otto in NYC if I had to compare. Loved it!

Longboards is brand new to St. John and blew our minds! Fresh margaritas, fish tacos, shrimp ceviche and kale salad/quinoa bowls that were so yummy we went back a second time. The decor is awesome, upscale beach shack style with surf boards and hip nautical signage. 

Turtle Bay Estate House at Caneel Bay is exquisite. The room, service and food are out of this world. Mitch McConnell and secret service sat at the table next to us. They have a kids' menu that serves a green salad or side of fruit and kids get to pick between steak, lobster, shrimp, mahi mahi and roasted chicken with brown rice. Prices area bit steep. Kids menu starts at $42 and up, but it's worth it. 

I've heard from reliable friends that other options for great food are ZoZo's, Extra Virgin and Las Tapa

St. John's Scoop was a nightly staple for ice cream. 


When traveling alone with five kids, having a plan was a must. I chose to stay at the resort every morning for breakfast and ocean play. Day 1 and Day 5 were partial travel days so we did three days of excursions from 10 AM-5 PM. 

I cannot recommend Good Day Charters enough. While there are many companies that provide good group excursions, with my cast of characters, it was better to go private and customize our experience. Dusty and his father, Lloyd own the company. They have such a passion for island life and are incredibly knowledgeable. They helped customize the trip of a lifetime and provided all the snorkel gear for my crew. Here are the different boat trip highlights:

St. Thomas

  • Swim and climb coconut trees at Skinny Beach
  • Dock at The Abi Beach Shack for lunch and rent paddle boats
  • Snorkel at Happy Lagoon

St. John and Lovango Cay

  • Snorkel at Lovango Cay
  • Lunch on the boat
  • Hang out at Honeymoon Beach and kayak
  • Snorkel at Trunk Bay with the turtles

Best part of day was going to The Pizza Pi Boat as we headed home. They let the kids take turns coming onto the boat and watching the pizzas being made. While you wait for pizza, you can snorkel all around the boats. Definite bucket list experience. 


Best day of the trip (and one of the best days of my life)

Snorkeled in the caves of Norman Island.

Lunch at The Pirates Bight in Norman Island (gorgeous beach shack and beach) Kids can swim, kayak, paddle board and snorkel.

Made a pit stop to the famous Willy T boat. While it's a boat bar and a bit of a rough crowd, the kids climbed to the top and took the famous leap off the boat three times. The Bravo show, Below Deck was filming that day on The Willy T.

Final stop and trip highlight was docking at Jost Van Dyke Island. You need to swim to shore as it's a small island with a beach and four beach shack bars. We swam to shore, hung at beach and got cocktails (Painkiller at the Soggy Dollar is famous) and mocktails for the crew. The crowd energy is awesome and my kids did not want to go home. Another real bucket List experience.