Simplicity Charters Videos

One of our favorite stops on our 25th anniversary cruise. Simplicity Charters was an awesome day....

Chamber music

Simplicity Charters sailing the beautiful caribbean waters off the coast of St. John's National Park.

Simplicity Charters' star crew member, Hinckley the sailing dog shows the family how she tacks.

Members of Team Skimcaribbean get stuck on Bermuda while delivering a sail boat to Rhode Island. Grabbing two scooters Josh and Charlie set out to ...

75 ft. Titan sailing in the BVI spring regatta day 2. Titan went on to win it's class.

On the Caribbean 1500 cruising rally, from Virgina to the British Virgin Islands the crew of Nepenthe got a dolphin escort. enjoy the pod.

Bob Read and crew deliver Nepenthe a J40 from Rhode Island to the Virgin Islands. They meet the locals, join the Caribbean 1500 Cruising Rally, sai...

Amazing sailboat charter in St. Thomas (to St. John) on Simplicity Charters. Then an Atlantis VIP alumni party, a hilarious show by Miss Richfield,...

Simplicity Charters visits Lameshire Bay in St. John's National Park, USVI. Enjoy our encounter with some friendly Hawksbill Turtles, reef squid, a...

Simplicity Charters visits Carvel Rock off the northside of St John's National Park. US Virgin Islands snorkeling at it's finest.

Simplicity Charters daysails to Christmas Cove, Great St. James USVI. A beautiful snorkel with the local marine life, southern Atlantic stingrays,...