ST JOHN SAILING CHARTER

CIMARRON YACHT CHARTER
LEAVING FROM CRUZ BAY
WESTIN ST JOHN PICKUP AVAILABLE

  • "Slam-Dunk Experience. Easily the highlight of our trip"

    Evan B.

  • "Incredible Snorkeling and beautiful sail"

    TravelerWithOpinions

  • "Highlight of my summer, what an amazing time!!!"

    Breanna B.

  • "The best sailing experience on St. John!"

    Aubrey S.

Family gathered on a Cimarron Yacht Charter sailboat, sailing through the beautiful waters of Cruz Bay, St. John.

FULL DAY PRIVATE SAIL

6 Hours on the Water. Just Your Crew

Claim the entire boat for your group and spend the day exploring the stunning waters around St. John at your own pace. Captain Rick will take you to secluded coves, hidden reefs, and snorkeling spots that most visitors never find. The kind of places that make you wonder why you ever spend a vacation on land.

What's included:

  • Open bar all day

  • Snorkel gear and instruction

  • Exclusive use of the vessel; no strangers, just your group

  • Up to 6 guests included (up to 8 available)

  • Lunch at Pizza Pi, VI or from North Shore Deli

From $1,300 for up to 6 guests ·
$185 per additional guest (up to 8)
10am – 4pm · Departs St. John, USVI

SUNSET SAIL ST JOHN

GOLDEN Hour in the Caribbean.

There's nothing quite like watching the sun sink into the Caribbean Sea from the deck of a sailboat, glass in hand, with the warm trade winds filling the sails. This is St. John at its absolute best and you don't need to plan an entire day to experience it.

Join a small group of St John lovers, or book the whole boat for your crew.

What's included:

  • Open bar throughout the sail

  • Stunning views of the Virgin Islands at golden hour

  • Captain Rick's expert guidance and local stories

Shared: $100 per person
Private: From $700 for up to 6 guests · $100 per additional guest

Departs 4:30pm · Sails until sunset · Departs St. John, USVI

Our Story

What started as a passion became Cimarron Yacht Charter, a small sailing charter business built on one simple idea: that the best way to see St. John is from the deck of a sailboat, with someone who knows every cove, current, and hidden beach by heart.

Captain Rick didn't end up in St. John by accident, he followed the water. After years of sailing the Atlantic coast, he found himself anchored in one of the most beautiful places on earth and decided to stay.

A
ST JOHN
WEDDING AT SEA.

Simple.
Romantic.
Stress Free.