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Come Learn to Sail (and enjoy a Caribbean Island) on PILAR with USCG Master Captain Stephen and First Officer Dawn !

We offer private captained Catamaran Sailing Experience Charters in various locations on our Leopard 48 Catamaran.  These are longer trips with overnight sailing from 1-5 days on the open ocean that may also include deep sea fishing, beach visits, dolphin sightings, and more.  Rates vary depending on the days and locations. Contact us to arrange your custom sailing adventure.

Pilar Sailing Catamaran


Learn how to sail a catamaran, how to plan routes, navigation, sail trim, harnessing the wind, and more!

Experience the open ocean, meals served on board, sailing, swimming, beach walks, snorkeling, fishing, remote island exploration and just chilling!

See Yacht Pictures here

Message us for more details or call 704.870.7091.

LONGER TRIPS

Sail from Charleston to Bermuda – November 12025. The trip will take between 5-7 days and nights. We will then stay in Bermuda for a week. Join us for sailing only or add the option to stay in Bermuda for vacation time as you wish. BOOK NOW!

Sail from Bermuda to St. Martin/ St. Barts/ Anguilla/ St. Kitts/ – November 152025. The trip will take between 5-7 days and nights. We will then stay in St. Martin for two weeks. Join us for sailing only or add the option to stay in St. Martin for vacation time as you wish. BOOK NOW!

Sailing around Virgin Islands – BVI/ USVI/ St. Thomas/ St. Croix – December & January 2025 Christmas in the Virgin Islands anyone?

Sail from Virgin Islands to Puerto Rico to Turks & Caicos – February 2026

Sail from Turks & Caicos to Bahamas – March 2026

Sail from Bahamas to Florida Gulf Stream Crossing Experience – April 2026

France – July 2026

ATLANTIC CROSSING – Sail from France to Canary Islands to Antigua – November 2026

Sail from Antigua to Panama – December 2026. The trip will take between 7-9 days and nights. We will then be cruising around Panama through January. Join us for sailing only or add the option to cruise Panama for vacation time as you wish. Depending on the weather, we may stop in Santa Marta Columbia, staying at the marina there until the next best sailing wind to head to Panama.

Cruising San Blas & Panama – January & February 2026

Panama Canal Transit – February 2026

PACIFIC OCEAN CROSSING – March 2026

LOCAL CHARLESTON AREA SAILING EXPERIENCES

ONE DAY

$1800.00 for up to 4 guests for 1 day includes full lunch and drinks, sailing, swimming, beach walks, remote island exploration, fishing and just chilling! Also includes sailing instruction as desired.

TWO DAYS AND ONE NIGHT

  • 1 Cabin with queen bed and private head (up to 2 guests).
    • ONLY $2500 includes all meals and drinks, sailing, swimming, beach walks, remote island exploration, fishing, sailing instruction and chilling.
  • 2 Cabins – one queen, one full with 2 private heads. (3-4 guests).
    • ONLY $3500 includes all meals and drinks, sailing, swimming, beach walks, remote island exploration, fishing, sailing instruction and chilling.

Charter Terms

  • Customary 15%-20% gratuity (the industry standard) is not included.
  • Off-vessel charges such as airfare, taxi fares, on-shore meals & beverages are not included.
  • Bottled waters are not included in the rates. We have charcoal filtered Reverse Osmosis water of high quality.  We support eco-friendly “green” and plastic-free options by avoiding use of single-use plastic bottles wherever possible. 
  • Rates include all prepared meals and snacks, soft and alcoholic drinks, linens and towels, snorkel gear, fishing gear and 12 ft. inflatable RIB dinghy with 30 HP outboard.
  • A 50% deposit payable to Blue Dot Voyages LLC will confirm your charter dates.
  • Full balance due 30 days before the trip starts.
  • No refunds for cancellation within 30 days unless we can rebook your dates on another charter

Videos of past guest trips

SAILING NEW YORK CITY EAST RIVER | NEW YORK HARBOR ANCHORING
WE SAIL OVER 1700 MILES IN 12 DAYS TO ANTIGUA - SALTY DAWG 2023 RALLY
8 DAYS CATAMARAN SAILING & SNORKELING - DOLDRUMS, STORMS, THEN PERFECT WIND & FOLLOWING SEAS
Sailing PILAR to Everglades? Refugee Boat - Grounding & Gaters - Port of the Islands - Naples FL
Downwind Sailing and the MV Golden Ray in St. Simons Sound - November2020 - EP49
Beam Reach Sail - 10 Knots SOG - Charter Guests - Charleston to Savannah - EP39
Sailing a 50 Knot Gale | Dinghy Falls off Davit | New L48 Helm Enclosure
St. Simons, GA to Seabrook/Kiawah Island, SC - Sailing with the Farleys | 54 | Sailing PILAR
3500 Monkeys on this Island plus Sailing Lessons for Kylee & James - Blue Dot Voyages PILAR - EP46
HOT HOT HOT August Sailing PILAR with Charles and Allison - (and an Engagement!)
11 day Sail from Grand Cayman to Cuba to Charleston SC - EP27
Catamaran PILAR Sails - Dry Tortugas - Cuba - Grand Cayman - EP22
Catamaran PILAR Sails from Marco Island FL to Dry Tortugas FL.  EP20