Planning Your Trip to St. John – A Timeline

Planning Your Trip to St. John – A Timeline

Happy Monday!  We just wrapped up another spectacular weekend here on St. John.  On Friday, we did a little happy hour at Lovango Rum Bar with Kenny Floyd on stage and then headed over to The Beach Bar for an incredible night of music from a superstar lineup.  There were so many good people around and we got to get some masked up dancing in…Which was a true highlight!  It was relatively quiet in town on Friday night…But, on Saturday we went over to St. Thomas to pick up some boat parts and stock up on produce at Moe’s and the ferry ride home was ANYTHING but quiet.  It was PACKED.  Like, literally standing room only.  And the holiday check ins don’t really start until next week.  Which leads me to the purpose of this article….

Planning Your Trip to St. John - A Timeline 1
Two of my favorite guys on the planet: Captain Teddy and Kenny Floyd enjoying pizza and good times at Lovango Rum Bar.

It is going to be another abnormally busy season here on St. John.  I have mentioned countless times how important it is going to be this year to get your reservations in advance for activities, dining, rental cars and accommodations.  I’m standing by that today with a few guidelines for you to use when planning your upcoming St. John vacation.

The general rule of thumb for all of this is that you should be booking most of your travel plans at least a month out.  But, even then, you may run into some scheduling restrictions and maybe not your ideal dining time or charter vessel.  Additionally, the entire island is vastly understaffed and in order to give staff a day off each week, a lot of places will continue to run with limited hours and be closed on certain days of the week.  So, if you have your heart set on a certain restaurant at sunset or a set day of the week you want to go sailing, it is best to plan ahead.  And, I know for some of you that may be a bummer and you would rather just roll with the days while you are visiting, but look at it like this…You will not have to worry or stress about a thing by the time you arrive because you will have already done the work prior to your visit!

Planning Your Trip to St. John - A Timeline 2
Save the stress- Enjoy the sunsets! Plan ahead for your next trip to St. John

Nine-Twelve Months Prior to Your Arrival – Accommodations

My folks come down to visit every year and my mom generally is booking their stay for the following year as soon as she gets home.  They have the places that they enjoy staying and want to make sure that they can reserve at one of their preferred accommodations.  If you are a little more flexible and like to try different things every time you come, you may be able to find deals closer to your arrival than this recommended window of time.  But, if you have your heart set on a certain location or condo, you’ll want to start researching and communicating with booking agents and property management companies close to a year out from your arrival.  If you aren’t sure where to start, we have some amazing properties and management companies that advertise with us here on the site.  Take a look at some recommended accommodations here.

Planning Your Trip to St. John - A Timeline 3

Seven to Ten Months Prior to Your Arrival – Rental Car

Rental cars are scarce on St. John and during peak times of the year, you may not find something within two to three months of your stay.  DO rent on St. John if you can find a vehicle!  The hassle of the car barge and waiting for a rental car on St. Thomas after an already long day of travel can be stressful (You’re here to de-stress, right?).  We have family visiting in a few weeks and they had originally booked a rental on St. Thomas.  They are traveling with an infant and we persuaded them to rent on St. John instead so they wouldn’t be dealing with potential hassles and delays during their inaugural arrival to Love City.

Planning Your Trip to St. John - A Timeline 4
The barge can be a pain- Rent on St. John and skip the hassle

If you are staying at the Westin, they offer some great transportation services that get you and your bags delivered straight to your room with little to worry about in between.  Many rental car agencies on St. John will meet you right at the ferry dock with your car.  Renting on St. John is simply easier and it supports our businesses here on island.  We have compiled a list of St. John car rental companies for you to reference while making your reservations…If you are visiting this Spring or Summer, you should be making those calls now!

Five Months Prior to Arrival – Boat Excursions

We have noticed over the past year that people LOVE to try to book our boat, Asante, very last minute.  And, sometimes we can happily accommodate that.  But other times, we have to turn people away due to lack of availability.  Even if we aren’t booked on the day in question, we may have maintenance scheduled or other commitments that can’t be re-scheduled last minute.  Additionally, everyone down here is working multiple jobs, so finding last minute crew, even if the boat is available, may be an issue for some companies.

Planning Your Trip to St. John - A Timeline 5
Go boating! But book your trip before your visit! – Image: Flyaway Charters

So, don’t spend hours of your vacation on the phone trying to find a last minute boat trip.  Book a few months in advance in order to ensure that you get some time on your vessel of choice and don’t waste a moment of your on island time scrambling to do so!

Once again, if you are at a loss of where to start, take some time to review the ads on the site or take a look at the spotlights we have featured.  We have some awesome charter companies represented here!

Planning Your Trip to St. John - A Timeline 6
Check out Voodoo for your next boat day!

Three Months Prior to Arrival – Other Activities

Looking for an in villa massage?  How about a day on a guided kayaking tour?  These other activities may be something you think about last minute while you are here and maybe you can find luck into some availability.  But, if you have your heart set on one of these additional experiences, its best to do the research and book them ahead of time as well.

Planning Your Trip to St. John - A Timeline 7
Kayakers with VI Eco Tours at Honeymoon Beach

One-Three Months Prior to Arrival – Dining

This is a big one.  The number of fine dining restaurants on island pales in comparison to the number of visitors we have had on island.  I called three restaurants a month out to make reservations for our visiting family members and was limited on choices of time and day at each one.  You’ll likely have not much issue walking into the Beach Bar or getting on the wait list at Lovango Rum Bar or Longboard while you are here (Don’t be surprised if there is a wait…But who minds waiting with a cocktail in your hand and your toes in the sand?).  But, if you plan to do some nicer dinners out, do call ahead to reserve your table at least a month in advance.

Planning Your Trip to St. John - A Timeline 8
Waterfront Dining at Lovango Beach Club + Resort

The above is merely a recommended framework for planning your vacation.  Maybe you aren’t a planner and you don’t have anything particular in mind for your upcoming trip.  If so, this probably doesn’t apply to you!  And, I’m not saying that you need to schedule out every hour of your trip.  But, if dinner at Zozo’s or The Terrace is a must-have or you have the exact accommodation or excursion in mind.  It is best to look to the future and book those things in advance in order to avoid the headaches of missing out on your favorites while you are here!

Planning Your Trip to St. John - A Timeline 9
Enjoy the beach!

3 thoughts on “Planning Your Trip to St. John – A Timeline”

  1. Hi Hillary, thanks for the great advice.
    As far as every business being short handed, some of it is lack of housing. My wife and I would be there right now if we could find a place, I’ve been looking for 2 months. I’m not going to give up yet!

  2. Hi All! Thanks for these great updates. My family and our friends have been going to St John from the last 10 years. We’re heading down for thanksgiving and this is gonna sound like a crazy question but figured I put it out there. We heard their is limited Corona on the island is that true? We have someone in our party that only drinks Corona and are just trying figure out if we should BYOD for Corona. Can’t wait to be down there and thanks for all you do News id St John

Leave a Comment