Tips for Planning Your Trip to St. John

Tips for Planning Your Trip to St. John

Good Morning! It’s hard to believe August is already upon us, which means that stateside the back to school advertising campaigns are in full swing, and our northernmost friends are trying to enjoy the last month of beach days, bonfires, boating, and camping before the weather gets a little iffy. Before we know it, the Halloween decorations and candy will be lining store shelves and Christmas music will be hard to avoid on the radio.

All joking aside, it’s a great time to start planning a trip to St. John, and whether you’re a seasoned St. John veteran or a first timer, we hope that you find a few tips in this article beneficial in doing so. 

Travel Dates

One of the most common questions we get on travel planning from readers is regarding when the best (or worst) time to travel to St. John is. Of course, this comes down to personal preference. If you ask 10 different people you are likely to get 10 different answers, but here are a few things to keep in mind. 

The peak season is generally considered to be December through April. This is when the weather tends to be nice on St. John, and quite cold for our friends up north, especially those brave enough to live in the Midwest or Northeastern states. The island is bustling with tourists, so don’t be surprised when popular beaches and restaurants are quite busy, especially over common school scheduled breaks such as Christmas, New Years, and Spring Break. What’s nice is pretty much everything is going to be open for the entirety of peak season, and if it starts to rain, it probably won’t last long. 

If you travel during low season, you might be able to find some great deals, and save thousands of dollars compared to traveling during the peak season. Flights tend to be cheaper, and you can get some great deals on villas (more on that below). Just keep in mind that many businesses including restaurants and boat charters will shut down for a period of time and/or have more limited hours. As you’re nailing down exact dates, it’s a good idea to check on what will be open. Our Seasonal Restaurant Closing List is a great resource, and is continuing to be updated as more restaurants confirm dates they will be closed. 

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Rum Hut


When booking your accommodations, you should really first decide what things you’d like to do on your vacation to determine what location and amenities you’re looking for. 

If you will be doing a lot of eating, drinking, and shopping, you’ll definitely want to be close to Cruz Bay. If you’re going to be exploring different beaches every day, find something that is a bit closer to the North Shore. If you want something quiet and secluded, there are a lot of great options in Coral Bay. 

When you know what location and what amenities you’re looking for, many travelers will start searching the popular third party booking websites. Although this is an ok place to start, please keep in mind that many short term rentals on St. John have the option to book directly. With third party booking websites, there are often high fees for both the property owner and the renter. Doing a little more research to connect directly with your desired property can save everyone hundreds or even thousands of dollars. 

News of St. John has developed a great resource to connect travelers directly with property owners and managers. You can visit Newsofstjohnvillarentals.com to search properties, availability, then fill out a form to connect directly with them. News of St. John does not charge any booking fees for this service. Additionally, some properties will even offer discounts for booking directly during certain times throughout the year. 

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Limetree at Peter Bay

Transportation and Boats

If you’re contemplating whether it makes sense to rent a vehicle on St. John for your trip, again, you should decide what you will be doing and where you are staying. For example, if you plan to spend most of your time at your villa, and maybe visit a beach once or twice, it might not be necessary or cost effective to rent a jeep. Instead, you could find a taxi on these days. You’ll just want to make sure this is well planned. It might be easy to get a ride from Cruz Bay to a remote beach during the day, but if you’re coming back late afternoon or evening, finding a taxi could be much more difficult and phone service can be iffy depending on where you are. If you’re renting a villa, the owner or manager could be a great resource in hooking you up with a taxi driver. 

If you’ve decided you’ll be renting a vehicle, PLEASE don’t wait until the last minute to find one. There is limited inventory available, and especially during the peak season, they can go very quickly. 

Boat Charters are a wonderful way to spend a day, or multiple days on your vacation. Whether you want to fish, snorkel, explore different islands, or take a sunset sail, there are a number of different options to choose from. Our Boat Charters page is a great place to start your research.

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Island Roots Boat Charters 

1 thought on “Tips for Planning Your Trip to St. John”

  1. My biggest challenge is finding a flight where we can still get to STJ in time to pickup a rental…didn’t quite makes it last time but thankfully Moses came to our rescue!!!

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