A 6-Day Itinerary to Tropical Bliss in the US Virgin Islands - St. Thomas & St. John

Take the shuttle (associated with the rental company you chose) from the airport to pick up your rental car. It is important to remember that they drive on the left side of the road there. If you ended up skipping the rental car services, there are plenty of taxis all over the island for you to hitch a ride in! This will be a nice day to head towards your hotel, make a pitstop at Lattes In Paradise for a tasty sandwich and afternoon pick-me-up from Emily (who is one of the coolest chicks we met on the island), check-in, change into a swimsuit, apply sunscreen (please!) and chill out on the beach with a drink in your hand for a couple hours.

If you’re the type to celebrate your first night with a fancy dinner, you will not go wrong with this stunning restaurant on the water called Oceana Restaurant & Bistro! I recommend you make reservations before you arrive in St. Thomas, and pick a time right before sunset so you can enjoy the pinky time as you dine in. Oceana is that type of place that you wish you’d gone to early in the trip so you had time to go back for a second time. The staff is incredible, the management is so kind and welcoming and the food truly is divine.

Some menus items that we ordered (and would reorder):

Cocktails: The lavender lemonade, the “O” and the Caribbean old fashioned

Appetizers: Fresh oysters — Chef’s choice, tuna tartar, garlic bread, and on their “specials” menu was a bucket of mussels (which was one of our favorites, so hopefully they still have that)!

Main Courses: Pan-roasted mahi mahi, oceana bouillabaisse

Desserts: Creme brûlée

Sleep in this morning to recover from the long day of travel you just had! A nice, slow morning sipping coffee on the balcony overlooking the beach is the most peaceful way to get ready for the day to come. When you are ready, head out for some breakfast or brunch, either at your hotel restaurant or at a local favorite: Carigas Island Cafe on Red Hook Road.

Head over to Tickles Pier/Crown Bay Marina in Charlotte Amalie to catch the red ferry (cash only) over to Water Island. Water Island is home to Honeymoon Beach, an old WWII Fort and, most importantly, Heidi’s Honeymoon Grill that has the best fish tacos and pudding shots I have had in my life. When we arrived on Water Island, we walked a short distance up the hill and rented a golf cart for the day at Rachel’s Rentals. I recommend the golf cart rental so you can drive up to the fort, down to the beach and over to Heidi’s for some tacos and drinks! Just do not forget to stay on the left side of the road!

After the day gallivanting on Water Island, head back to the landing to catch the ferry. Show up early, because if you miss the last ferry of the day, you’ll be spending the night on the island!

We ended our second day with dinner at The Easterly in Red Hook, where we had a delicious spread of cocktails, appetizers, entrees and my favorite dessert of the whole trip: the smoked chocolate ganache (We came back for this dessert a few times throughout our trip).

This was by far one of my most favorite things we did on this trip! We booked a half-day luxury power catamaran excursion with Someday USVI to snorkel with the turtles that started at 9 am. Captain Joe and Catie are two of the best guides we could have gotten stuck with. They gave us the history of some of the landmarks in the US Virgin Islands and took us on a reverse route of the other charters so the locations were not as packed from all the other tourists on the cruise ships. Catie got in the water with us to guide us through the snorkel locations to find the turtles and taught us about the types of fish we saw. There was an unlimited bar where Catie was making drinks for us and they even had a delicious spread of snacks to eat halfway through our excursion. They even cap the amount of people allowed on the boat at 12, so you’re not packed together like sardines in a can like you could be on other charter boats.

I recommend you swim in a sun hoodie and throw on a think layer of sunscreen on your cheeks and legs, because my partner and I got burnt to a crisp on this day.

We made two friends on our tour and the four of us headed over to the Westin to have drinks at their swim-up bar before saying goodbye to them and heading over to Duffy’s Love Shack for a burger and some drinks before calling it a night.

Wake up early and head to the Red Hook Car Ferry (if you have a rental car) to get loaded up on the boat and taken to St. John. Once we arrived in St. John, we parked our car in a paid lot called Slim Man’s Parking, which was $5.00 for one hour. We grabbed breakfast at High Tide, which was right on the water in Cruz Bay.

We drove about an hour over to the other side of the island to hike Ram Head Peak for some rock climbing (this is also just a good hike if you’re not a rock climber). I highly recommend you only do this hike if you are moderately fit, hydrated and have tennis or hiking shoes. It is a pretty long hike and the humidity and minimal shade is killer. Throughout the hike, though, you will pass a few small private beaches that are quiet and relaxing if you want to stay away from all the crowds in places like Trunk Bay.

We drove around the entire island this day and stopped at most of the larger, more well-known beaches as well to spend 30 minutes to an hour at each of them. We had a really good time at Hawksnest Beach, which was less congested than Trunk Bay and had some beautiful snorkeling if you have gear with you.

To finish our day in St. John, we went to grab some food at Sun Dog Cafe, which has been around since 1994 and has delicious jerk chicken quesadillas, which you should get if you go there. Head back to the ferry and get back to St. Thomas to have some sushi at Buddha Sushi for dinner. This spot has some of the coolest people we met at a dining establishment, and the vibes are hot for dinner. Their menu is large and there really is something for everyone at this sushi restaurant. They also have karaoke on Wednesdays, and it’s the spot to be.

We stopped and got a coffee and breakfast sandwich from Lattes in Paradise before driving from Red Hook all the way over to Botany Bay for a walk down to the private (public) beach called Mermaid’s Chair. On the way there, we stopped at the Charlotte Amalie overlook and met up with the donkey named Lady Gaga for a quick photo op before heading to Mountain Top for a “world famous banana daiquiri.” When you get to Botany Bay, you will see an office that you need to check in at and get your picture taken with security before they let you through the gates to start your 1.5-mile stroll down to Mermaid’s Chair.

This is a great place to go if you are looking for a private and stunning beach when at low tide, you can walk across the sand that disappears at high tide. This is a beautiful spot to plan something special, like an engagement (hint-hint), just in case you were wondering where to do that while on a beautiful tropical vacation.

It is important to mention that the walk back is straight up-hill, so be prepared to get a bit of a cardio workout in when leaving the Mermaid’s Chair!

After our day on the other side of the island, we went over to Sea Salt for cocktails and ceviche before going next door to Paradise Pie for a tasty margarita pizza.

It is a sad, sad day to wake up and know it is the last full day in this tropical heaven. We hit Lattes in Paradise again (this was our spot if you haven’t noticed by now) for breakfast and coffee and started our drive to Meagans Bay to see what the fuss was about at this well-known spot on St Thomas. Now, this is a very beautiful beach with an awesome bar, but if you are taking this vacation to stay away from crowds and maintain your peace, this is not the spot for you. This is the beach that every cruise ship shuttles their guests to when they arrive in port. It is full of large groups and families, and is not the best snorkeling spot since the crowds stir up the bottom and make it very foggy underwater.

After we spent a few hours at Maegan’s Bay, we left to go to a more low-key beach (at least it was when we were there) called Sapphire Beach. We were happy lounging here drinking some mango daiquiris and pain killers before heading out for our last dinner on the island at Oceana Restaurant & Bistro. This was a wonderfully relaxing and delicious way to close out our trip to the US Virgin Islands.

Hit up Lattes in Paradise one last time on the way to return your rental and head to the airport. Ensure that you show up three hours before takeoff to get through customs.

Have some drinks at the airport bar and get on the plane to head home!