St. Thomas Girl's Trip: 6 day Itinerary with Real Prices
Six days, four of them doing real work. Most itineraries pretend your arrival day counts. It does not. You land, you find the rum, you go to bed. Here is what the middle four days should actually look like, with the prices nobody else will print.
Pick Your Lodging and Make it Sapphire Beach
Not saying we're biased or anything. Beachfront condos, a dozen dining options without getting in a car, a marina full of excursions sitting right outside your door and live music on Sundays. Can't beat that.
The thing that actually matters for a girls trip is that you stop negotiating. Nobody is driving. Nobody is the designated anything. Your boat leaves from the marina you can see from your balcony, your coffee is a two minute walk and your dinner is on the sand. That is the whole argument.
Sleeps: 2 to 6 per unit, so one or two units covers most crews
Walk: Buildings A through C sit right in front of the beach
On site: marina, pools, restaurants, watersports
Sundays: live music at the beach
Have the Condo Stocked Before You Land
Have the condo stocked before you land
Here is how the first evening usually goes without this. You land at 3pm, you are in a taxi by 4 and you stop at the store with five tired women and one cart. You get to the condo at 6 having spent your first two hours on island buying paper towels.
Or the groceries are already in the fridge when you walk in. Coffee for the morning, wine for the balcony, breakfast things, water, ice, the stuff you would have forgotten anyway. Time Saver Provisions shops it and delivers it to the unit before you arrive.
What: grocery and liquor provisioning delivered to your condo before check in
Order by: well ahead of your arrival date, especially in high season
Day One: Arrival, Expect Nothing of Yourselves
Day One: arrival. Expect nothing of yourselves
Most flights land midday to late afternoon. By the time you have bags and a taxi it is 5pm and somebody is hangry. Plan for that instead of fighting it.
Provisions already delivered. See above. This is the single best thing you can do for your first evening.
Get in the water before dark. Even for ten minutes. It resets everybody and it is the moment the trip actually starts.
Keep dinner walkable. Nobody wants a car ride on night one.
Sort Your Ride before You Sort Anything Else
Call Jermaine Petty at 340.642.3904. He is a friend of ours and the driver we put every one of our own guests with. Airport pickup, the run to Red Hook, the late night one nobody wants to think about at 10pm. Text him your flight number and stop worrying about it.
Check the Ship Count for Your Arrival Day
Four ships in port means the road through town and the taxi line at the airport are both slower. It does not change your plans. It changes how early you stop panicking about the delay.
Day Two: The Full Island Tour that Ends at the Beach
Do the island on day two, while you still have the energy for it and before you've decided the water is the only thing that matters. You'll understand where you are for the rest of the week, which makes everything after it land better.
Jammin' Jeep picks you up at your door at 9am and has you back by 3pm. Historic Charlotte Amalie, the 99 Steps, Fort Christian, Mountain Top, Drake's Seat, then a ferry to Water Island and Honeymoon Beach for turtles, a paddle board and a cocktail with your feet in the sand.
Day Three: The Boat Day & It Needs to be Private
This is the day you'll talk about at the next birthday. Book it private. On a shared boat you go where twenty strangers go, on somebody else's clock, with a soundtrack you did not choose. On a private boat you run your own itinerary.
Which means you get to pick. St. John beaches and Lime Out, the floating taco bar everyone wants a photo at. Or point the bow east and do the BVI for the day. Both are good. They are not the same day and you should decide before you book.
OceanRunner: Private Charter
Fast, comfortable and the crew knows which beach is empty on a given day, which is the actual product you are buying. Tell them what kind of day you want and let them route it.
Price: Ocean Breeze, seats 10, from $1,175. Sunny Daze, seats 12, from $1,325. Axopar, seats 11, from $1,450
Splits to: about $196 each for six on the Ocean Breeze
Add for BVI: around $80 per person for customs, on top of the charter
Duration: 8:30am to 4pm. Closer to 5pm if you are doing the BVI
Suits: crews who want the boat, the route and the playlist to themselves
Then...Walk Straight to Dinner
You will come off that boat salted, sunburnt in one spot you missed and very pleased with yourselves. This is the right night for the nice dinner, because it asks nothing of you. Rinse off, put on the dress, walk down.
Where: SeaSalt at Sapphire Beach
Timing: cocktails at golden hour, table after
Getting there: you walk
Book it: weeks ahead in season, not the day of
Day Four: And the Next Day, We Rest...
Every crew wants to fill this day. Every crew that doesn't fill it says afterward it was their favorite. You are not here to be exhausted in a nicer climate.
Resting properly still takes a reservation though and ours is Lovango Beach Club. It sits on its own island between St. Thomas and St. John, the water taxi is included in the price and it picks you up from Red Hook or Cruz Bay. Ten minute ride and you are somewhere that looks like a magazine.
Lovango Beach Club Day Pass
Get the poolside cabana. I know it is the expensive line on this page and I am telling you anyway. Six women, one shaded base, your own space all day and nobody hunting for a fourth chair at noon. It is so worth it.
Chaise: $150 per adult, $175 on holidays
Pool cabana: $245 per adult, minimum 4 people, up to 6 guests
Beach cabana: $245 per adult, minimum 2 people
Ferry: included. 10 minutes from Red Hook or Cruz Bay
Suits: a crew of exactly four to six, which is why the cabana math works
Day Five: Chill and then We Sail Off into the Sunset
Last full day. Keep the daylight hours completely open. Beach, pool, the shopping somebody has been quietly wanting to do, a nap. Put the pretty thing at the end of it.
A sunset dinner sail is the right closer. Two hours is short enough that nobody gets tired of it, dinner is handled and you are watching the island get smaller and gold at the same time. Best way to cap off a week here.
The VI Cat Sunset Dinner Sail
Sixty five foot catamaran and the sunset from the water is a different thing than the sunset from a restaurant. Worth the drive over to Frenchman's Cove.
Price: $109 per adult
Duration: about 2 hours, evening departure
Departs: Frenchman's Cove
Getting there: taxi from the East End, about 40 minutes. Book the return.
Suits: everyone. This is the photo that ends up framed.
Arrange the Ride to and from the Sunset Sail
Frenchman's Cove to the East End after dark is not the moment to start looking for a taxi. This is exactly what Jermaine is for. Book the return when you book the ride out and confirm the time.
Day Six: Departure...do the math backwards
STT is a small airport that gets very busy, very suddenly. Work backwards from your flight, add a buffer, then add the buffer you will pretend you don't need.
Two and a half hours before departure at the airport in season, minimum. Three if a full crew is checking bags.
Forty five minutes from Sapphire to the airport, more on a heavy ship day when the road through town is crawling.
You can still swim. Bags packed the night before, one last hour on the sand, rinse off, go. Set the alarm.
Duty free rum has a generous limit. If anybody wants some, this is the moment, not a scramble at the gate.
What the four booked days cost, per head, crew of six
Lodging, food and drinks sit on top of this. These are the things you reserve in advance, which are also the things that make or break the week.
What I Would Skip
The rental car. You are on a boat, in a jeep or on a water taxi four days out of six. It will sit in a lot and you will pay for it. Call Jermaine instead and keep the parking money.
A shared group boat. Cheaper per head and a completely different day. If the boat day is the centerpiece, private is the whole point.
Two water days back to back. Sounds amazing on paper. In practice the second one is six women being quiet and slightly nauseous.
Booking the rest day. Lovango IS the rest day. Do not add a second thing to it.
The grocery run on arrival day. Provision ahead. You will never go back.
The BVI crossing with one unconfirmed passport. Already said it. Saying it again.
Book in this Order
Four to six months out: flights and the Sapphire unit. Good units for six go first.
Three to four months out: the private boat. This is the real deadline.
Two to three months out: Jammin' Jeep, the Lovango cabana, the sunset sail, the SeaSalt table.
Two months out: confirm every passport if BVI is on the list.
Three to four weeks out: place the provisioning order.
Two weeks out: text Jermaine your flight numbers for both directions and book the ride to the sunset sail.
The week before: check the cruise ship calendar for your arrival and departure days.
Use this as a full guide or jsut grab your favorites from the list! If you need personalized help, you can always reach out to our in-house travel planner, Getaway Girlfriend!
Prices checked September 2026 and quoted as each operator listed them. They move between seasons, so treat them as the shape of the cost rather than a quote. Confirm at booking.
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