Special Events On & Off The Vineyard

Sail from St. Thomas to Florida


April 27-May 5, 2020

Don't miss this great opportunity to learn & experience Downwind Spinnaker Sailing on an amazing voyage from St. Thomas, USVI to West Palm Beach, Florida!

Gain real-life cruising knowledge and hands-on training as you sail through the northern Caribbean waters past Puerto Rico and north of the Dominican Republic then onward to pass near the Turks & Caicos, the Bahamas and finally into the port of West Palm Beach, Florida. We offer education for those seeking live-aboard experience as well as those seeking formal training thru American Sailing Association curriculum.

4 students maximum

Meals, accommodations & instruction included.

$2500 per person

4th of July Sail to Edgartown


July 4th, 2020

6:00 -10:00 pm

 Join us for the best seat on the island this 4th of July. This one-way sail starts in Vineyard Haven harbor, includes a sail along the coast past Oak Bluffs & State Beach and ends with a beautiful anchorage just off of the fireworks barge. Hors d'oeuvres, soda, water and ice is included and guests are welcome to bring additional foods and beverages. Guests will return to Edgartown dock via the water taxi. 

$750 for up to 6 guests

Pirate Full Moon Sail


 July 5th and August 3rd, 2020

8:00 - 10:00 pm

Arrrrr - calling all pirates, fairies, lost boys and mermaids! Dress in your best flogs, eye patches and bandannas and join us for a full moon sail. We'll serve champagne and heavy hors d'oeuvres and award a prize to the best dressed guest. Bring yer best pirate jokes or we'll make ya walk the plank, me hardy! 

4 people minimum.

50% deposit required with reservation. 

$150 per person 

Dress to Impress Full Moon Sail


July 6th and August 4th & 5th, 2020

8:00 pm - 10:00 pm

Join us for a "Dress to Impress" Full Moon sail. Celebrate a special occasion or enjoy champagne and heavy hors d'oeuvres with new friends under the beautiful Martha's Vineyard night sky. 

4 people minimum. 

50% deposit required with reservation. 

$150 per person 

Illumination Fireworks Sail


August 19, 2020

6:00 - 10:00 pm

Truly one of the best events of the summer, the Oak Bluffs Grand Illumination fireworks are a Martha's Vineyard must! There is no better display than the bursts of color cascading over the water. As we depart Vineyard Haven Harbor, enjoy sailing along the coastline to Oak Bluffs where we'll drop the anchor and offer you a front row seat to this amazing annual fireworks display! 

Fireworks begin at 8:00 pm.  Guests will be returned to Oak Bluffs after the fireworks.

$700 for up to 6 guests

Sail South With Us


October 15, 2020*

Set sail with us from Martha's Vineyard for a 5-7 day offshore passage to Bermuda.  Practice dinghy skills, offshore vessel preparation & provisioning, routing, weather assessment, sail planning, watch schedules and more.  Sailors can gain real-life experience and knowledge, and earn an American Sailing Association certification if desired.  

Email us for full details.

Includes all meals aboard, accommodations and instruction.

*Exact dates may vary due to weather conditions

$2000 per person