You’ve bought your tickets, booked your villa, and your tropical Saint John vacation is looming in front of you, but now what?  We get asked all the time what our customers and friends should see and do while on island, so we have created our idea of a perfect Saint John vacation, obviously with a little local flair thrown in to mix it up! So, here it is, What to do on Saint John, USVI for a week:

Day 1:

  • Travel Day!

    • Arrive at the airport, grab a beer while you wait for your luggage, get a cab, get the ferry, and then relax……ahhhhh you’re almost on Saint John!  We recommend to all our friends to order pizza the first night, our favorite is from Da Livio’s in Cruz Bay, grab wine, beer, or whatever your favorite relaxing cocktail may be, and enjoy your first night of tropical freedom at your villa or hotel! Open a book, or just enjoy cocktails poolside and enjoy the sunset with your loved ones and get ready for a week of fun! 

Day 2:

  • Grocery shop for the week early in the morning. The stores are pretty much empty at that time and you’ll be able to find everything on your list before all the other tourists even get the idea to shop!  It’s an island, so we run out of everything at one point or another.  Remember to improvise and don’t be too shocked at those sticker prices

  • Stock your fridge, pack a lunch and head to the beach! For first timers, Trunk Bay is a must, just ask the travel channel. But Cinnamon Bay is our favorite, there is plenty of room to spread out, bathrooms, showers, a small store, and great snorkeling! 

  • Follow this awesome day with dinner at your favorite Love City Restaurant.  Our pick; Rhumblines! Go all out for your first night out, you deserve it! 

Day 3:


    • We love packing the car with snacks and friends then venturing out to the East End for a hike and a beach, and then ending the day with burgers at Skinny Legs.  Perfect Saint John Day. 

    • Make sure you stop by Vie’s Beach, it’s quaint, sunny, and has great snorkeling.  Her conch fritters are a local favorite, so make sure you get ’em before she runs out

    • For those of you looking for a great dinner IN Coral Bay, we highly recommend Sweet Plaintains.  Amazing food, atmosphere, and who doesn’t love a restaurant with a rum flight on the dessert menu! 

Day 4:

  • BOAT DAY! 

    • You absolutely cannot come to Saint John and NOT visit the British Virgin Islands, so please bring your passport with you! 

    • We obviously recommend a day on CatZilla. And always recommend getting to Jost Van Dyke, the home of the painkiller, so make sure you try one when you get there and say hi to Mic for us. Recommendation: The Nilla Killa

    • A simple dinner back at the villa is highly recommended after a long day of fun in the sun! 

Day 5:

  • Recooperate from said BOAT DAY! 

    • The day after a boat day is a great time to head into Cruz Bay to shop for souvenirs, have a great lunch and catch happy hour (if you’re up for it) or just enjoy a laid back sunset at one of the local restaurants before a great dinner

Day 6:

  • Hit the beaches again! Take a jeep along the north shore and explore! Maho is a fun stop with the beach right next to the road and Francis is a great place to stop and snorkel with turtles! 

  • Finish your vacation off with a really great dinner. Our current favorite is ZoZo’s at the SugarMill at Caneel Bay.  The ambiance is one of high end culinary excellence mingled with island casual friendliness.  It’s quite a combination and if you don’t get the Osso Bouco, you’ll regret it! 


 Day 7: Cry all the way home while secretly planning your next trip down and book marking all your new favorite Saint John websites to look over once winter really hits up North. 

 Enjoy your vacation, we hope you love Saint John as much as we do!