Frequently Asked Questions

BOOKING YOUR SAIL

We accept cash, credit card, and Venmo.
We have a 48-hour cancellation policy. That said, if the weather is truly bad on the day of your sail, we'll work with you.
No fuel fees, no mooring fees. One of the perks of sailing: the wind does most of the work.
Gratuity is never required, but always appreciated. The standard in the charter industry is 20%.
Depending on your vibe, we have two great options for sailing with Cimarron. If you desire a private charter or a romantic sunset cruise with just the two of you, we have a low minimum price to go out. If you are looking to meet some great people, you can join one of our shared sunset sails.

DAY OF SAIL

We've got the snorkel gear, the drinks and the food covered. You should bring a towel and sunscreen or a rash guard.
We pick up and drop off directly on the beach in front of High Tide Bar & Seafood Grill, right in Cruz Bay. It's the first restaurant you'll see as you come off of the ferry dock; you can't miss it!
Insider tip:
High Tide is a great spot for breakfast (see menu) before your charter. They open at 8AM daily.
Cruz Bay is the main hub of St. John and easy to reach from anywhere on the island. If you're coming by ferry from St. Thomas, you'll walk right off the boat and we're just steps away, to your right.
Parking in Cruz Bay is tight, plan a little extra time so you’re not rushing to the boat.
Two spots to check first:
Slim Man’s - in the heart of Cruz Bay, next to Back Bar.
The Lumberyard - above Nella’s and next to STJ Speakeasy .
Don't panic! That's just St John USVI weather doing its thing. Does it rain a lot in St. John USVI? Depends on what you consider a lot:)
Rain is a normal part of life in the Virgin Islands. Showers are typically brief, passing quickly and giving way to sunshine, often within minutes. It's simply the nature of a tropical climate.
One thing Captain Rick will tell you: don't rely on the Weather Channel St. John USVI weather forecast. The models are notoriously unreliable, and a gloomy morning outlook almost never reflects what the day actually brings out on the water.
In over 16 years of running charters, we've cancelled maybe once a year due to heavy rain and even that is rare.
So if you wake up to clouds or a passing shower, get ready anyway. The water is warm, the fish don't mind, and the sun is almost certainly on its way.
On full-day charters you'll either feast on gourmet sandwiches from the North Shore Deli: fresh, local, and home to what just might be the best bacon you'll find anywhere in the Caribbean OR we'll visit the legendary Pizza Pi in Christmas Cove, a floating pizzeria serving hot, homemade pizza straight from their boat anchored in a turquoise cove.

Check out North Shore Deli’s menu before your sail right here.
Check out Pizza Pi’s menu before your sail right here.

ST JOHN

The US Virgin Islands has banned certain chemical sunscreens; specifically spray sunscreens and those containing chemicals harmful to coral reefs.
Please bring reef safe, mineral-based sunscreen in lotion form.
No sprays on the boat.
It's a small thing that makes a big difference for the reefs we're snorkeling on, and we take it seriously.
Sunset in St. John USVI is one of the most talked-about moments of any visit, and for good reason. The light here does something extraordinary as it drops over the British Virgin Islands and open Caribbean horizon.
The timing shifts through the year, but not as dramatically as it does further north. As a general guide:
Winter (December – February): Sunset in St. John falls between 5:45 and 6:15 pm
Spring & Fall: Expect sunset around 6:15 to 6:45 pm
Summer (June – August): Sunset in St. John USVI comes later, between 6:45 and 7:15 pm
Our sunset sails are timed around the actual sunset for the date of your charter, so you're always on the water when the sky is doing its best work.
If a St. John USVI sunset from the deck of a sailboat is on your list, that's exactly what we do. Book your boat day now!
Honestly, the best snorkeling in St. John USVI isn't always where the crowds are and having a boat changes everything.
That being said, our offshore snorkeling secrets stay with the boat but check out these St John snorkeling secrets.

Haulover Bay North on the East End is dramatic and undervisited. The western side of the bay has submerged boulders, small underwater caves, and large sea fans growing right at the water's edge. You'll see big snapper, permit, stingrays, and hard corals in just 5 to 20 feet of water. It requires a short walk through the woods to reach, which keeps the crowds thin.
Yawzi Point, tucked between Great and Little Lameshur Bays on the remote south shore, rewards the effort it takes to get there. The point drops into deep ridges and valleys with some of the most thriving coral on the island, coral competing with coral for real estate. Not a beginner spot, but unforgettable for strong swimmers.
Maho Bay is well-known, but for good reason. It's the single best place on St. John to snorkel with sea turtles. The wide seagrass beds just off the beach are a feeding ground, and on most days you'll find multiple turtles grazing without even having to swim far from shore. Get there early and you may have them nearly to yourself.
St. John operates on Atlantic Standard Time (AST), which is UTC-4. That puts us one hour ahead of Eastern Standard Time during the winter months. However, the USVI doesn't observe Daylight Saving Time, so when the East Coast "springs forward," we're on the same time as New York, Miami, and other Eastern cities from March through November.
The easy rule: If it's summer, we're on the same time as the East Coast. If it's winter, add one hour.

EVERYTHING ELSE

Dress casually. Even on a sunset sail, this isn't a formal affair. Comfortable clothes and a light layer if you run cool in the evening breeze. We pick up on the beach, so you'll be taking your shoes off.
We have a bathroom below deck.
The bar is already stocked and open, so you're covered. If you want to bring something specific, that's fine too - with one exception - no glass beer bottles. Cans are fine, glass isn't a great idea on a boat.
Absolutely. We've had infants on board many times. Families are welcome and we're comfortable with little ones.