St. John is an island where some planning ahead pays off, but you don’t need to schedule every minute of your vacation. In fact, we encourage you not to over-plan.
As high season approaches, here’s what we’d book ahead on St. John before you arrive…and a few things you can leave to island time.
The Quick Version
Book before you arrive
- Car rental
- That special dinner
- Boat charters
- Must-do excursions
Leave to island time
- Casual dinners
- The passenger ferry
- Everyday taxi rides
What to Book Ahead on St. John
🚙 Car Rental: Book It
Especially during high season and holiday weeks. There are only so many rental vehicles on a very small island, and waiting too long can seriously limit your choices. Once you have your villa and flights, this is your next step.
For where to rent and what to drive on these hills, see our St. John car rental guide.
🍷 That Special Dinner: Reserve It
Have your heart set on a particular upscale restaurant or celebrating something special? Make the reservation. Many restaurants take reservations up to 60 days in advance, so don’t leave your must-have night to chance.
Looking for that one special night? Start with our list of the best restaurants on St. John.
🚤 Boat Charter: Book Ahead
Booking ahead gives you the best choice of boats, captains, itineraries and dates, particularly if you have a larger group or something specific in mind.
Browse the captained boats and self-drive rentals we work with on our St. John day charters page, or let our boat concierge match your group with the right boat.
🤿 Island Excursions: Plan the Must-Dos
Guided hikes, sailing trips, fishing, diving and other experiences can have limited schedules or capacity. If your group would be disappointed to miss it, lock it in.
Need ideas? See our guide to St. John activities and excursions and our favorite St. John hiking trails. For ranger-led programs in the park, check the Virgin Islands National Park website.
And What Can You Leave to Island Time?
🍔 Casual Dinners
You don’t need seven nights of dinner reservations. Some of the best St. John evenings begin with, “Where do we feel like going tonight?” Save room for tacos, burgers, pizza, beach bars and whatever sounds good after a day in the sun.
Planning to cook a few nights at the villa? Our St. John food costs guide will help you plan the grocery run.
⛴️ Ferries
For the regular passenger ferry between St. Thomas and St. John, check the schedule and give yourself enough travel time, but this isn’t something we’d lose sleep over months before arrival.
Our guide on how to get to St. John walks through the ferry options from St. Thomas.
🚕 Taxis
You don’t need to pre-book every ride before your vacation. Traveling with a large group or want private transportation? Sure, book ahead. But ordinary getting-around doesn’t need to become another item on your pre-trip checklist.
The Local Rule
Book the things you’d be really disappointed to miss. Leave enough space for St. John to surprise you.
If you’d like a hand deciding what to book ahead on St. John, that’s what we’re here for. Once your villa is booked, reach out to our team and we’ll point you in the right direction for cars, charters and that special dinner.
Frequently Asked Questions
How far in advance should I rent a car for St. John?
As soon as your villa and flights are set, especially for high season and holiday weeks. The island has a limited number of rental vehicles, and the best choices go first.
Do I need dinner reservations for every night on St. John?
No. Reserve the special-occasion or upscale dinners you have your heart set on (many restaurants accept reservations up to 60 days out) and leave the casual nights open.
Do I need to book the St. Thomas to St. John ferry in advance?
For the regular passenger ferry, no. Check the schedule before you travel and give yourself enough time to make the connection.
Should I book a boat charter before I arrive?
Yes, if you have a specific boat, captain, date or a larger group in mind. Booking ahead gives you the widest choice.
