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Passage Offshore + Sailing School

Grenadine Islands (Sailing School)

American Sailing Association

PASSAGE OFFSHORE, A TRUE SAILING SCHOOL | Cruising + Bareboat Certification

Earn your ASA Skipper certifications during a 10-day passage sailing from Grenada to St Vincent in the Windward Islands with a legendary skipper. This voyage will take you through the elements and you’ll walk away with an authentic experience as a true sailor. The course prepares you with hands-on practical knowledge designed to offer the confidence and experience to accelerate your sailing endeavors and elevate your sailing aspirations.


Single Cabin: Full Price $4900* per student | 1 cabins available

Double Cabin: Full Price $3,675* per student | 0 cabin available

* All-Inclusive | room, board, ASA material

  • Basic Costal Cruising (103)

  • Bareboat Cruising Certification (ASA 104)

Sailing students who have already completed your ASA 103 course, you will receive a 10% discount on the list price and the 103 material is an excellent opportunity for hands on practical learning

Start & Finish: Grenada, West Indies, Maurice Bishop International Airport


November 1st — 10th 2024

10 days, 9 nights


Passage Offshore + Sailing School
Sailing School


0 Double Cabin

0 Single Cabin


$4900 Single Cabin price per cabin

$7350 Double Cabin price per cabin



This EPIC itinerary takes us cruising through five sovereign Caribbean island nations cruising over 250 nautical exploring some of the most remote and under-explored islands in the sea. From chart plotting, overnight passages, customs and immigration, students will experience true and authentic cruising.

Kingstown, St. Vincent -> Bequia, Grenadines

Bequia, Grenadines -> Mustique, Grenadines

Mustique, Grenadines -> Canouan, Grenadines

Tobago Cays, Grenadines -> Carriacou, Grenada

Carriacou, Grenada -> St. George's, Grenada


Jon Bickford

Jon Bickford


A native to Maine and unabashed thalassophile, Jon has worked on the water for over 12 years and has sailed over 15,000 miles. On land he has walked the width and breadth of two nations and has lived in cities from New York to Honolulu to Bangkok. While solo journeys have incredible value, for him, it is the communal expeditions in outdoor settings that have defined Jon’s time in the wilderness as they provide the rare combination of camaraderie and growth that only can be known through group adventure. He holds a USCG masters license, and has participated in international competitions on traditional 18th century wooden Bantry Bay Gigs, canoed Alaska's Inside Passage rain forest, and operated a marine research vessel for Cornell University. When not on the move, he enjoys living in small island communities off the New England coast.


Sailing Collective's Passage Offshore program is proud to be working with American Sailing Association to offer ASA certifications. This means that your experience gained has international recognition, and you are eligible for an IPC (international proficiency certificate), which is commonly accepted by charter companies as a qualification to captain your own cruising boat. Your next vacation could be with you at the helm!

Why learn the Sailing Collective way? We practice a style of sailing that has been honed over thousands of days at sea, an elixir of fun and adventure balanced by safe seamanship and relaxation. We teach the ways of passagemaking without losing sight of all of the wonderful reasons why we want to be out here in the first place.

The American Sailing Association (ASA) curriculum has structured levels of sailing pedigrees that are examined through progressive certification courses. Students who learn to sail through the PASSAGE OFFSHORE program receive an ASA Logbook that lists the certification qualifications and records sailing experience. When your certification is successfully completed, your ASA Logbook is notarized by your ASA instructor any charter or vessel rental operator can view your credentials and level of competency.



ASA qualified instructor captain • Room aboard vessel • Provisioning for all onboard meals excluding 3-6 meals ashore • Moorings & dockage • Fuel, water, ice • All ASA material including qualifying exams & exam materials • Vessel Insurance

Not included

Travel & flights • Customs & immigration • Ashore activities including any recreational tours, meals, and drinks • Gratuity


Plan to be at the boat by 5 pm on day 1 (March 1st)


The final night will be spent in the marina, and sailors will be asked to be off the boat by 9 am on March 10th.


Unlike other Sailing Collective voyages, instructors & students will be preparing meals. Part of the Bareboat Charter ASA 104 requirements is voyage provisioning and preparation. We will be following the guided menu created by SC Culinary Director Flannery Klette-Kolten and a customized and unique Sailing Collective-style journey menu.


Please book your flights to and from: Maurice Bishop International Airport - Grenada (airport code GND)


Port Louis Marina is a 15-minute taxi ride from the airport. Taxis in Grenada are all shared vehicles billed per person, and rates from the airport are pre-set by the taxi association. It should be around $20 USD to the Marina.


Collapsible bags in place of large rigid suitcases are advised for ease of transport on and off the boat. Loading and unloading from the dingy can be a wet activity, a pair of shoes such as flip-flops that you can get wet if we are landing on a beach.

As the vast majority of your time will be spent outside, prepare for the elements - bring a light raincoat just in case, a hat to shield yourself from the sun, and a warm layer.  Sunglasses are important; polarized is recommended.

Overpacking is more common than underpacking. You will be well-outfitted for the journey if you have the following things.

  • A few bathing suits

  • Shorts and Pants, one or two pairs of each

  • a warm layer

  • sun hat and sunglasses

  • comfortable sneakers

  • sandals or shoes that can get wet

  • a lightweight beach towel (bath towels will be provided)

We also encourage guests to bring ecologically appropriate products into ocean environments. You can read more about those recommendations on the Sailing Collective Journal here: Packing for a Healthy Ocean


ASA 103, Basic Coastal Cruising

Able to skipper a sloop-rigged auxiliary powered (inboard or outboard engine) keelboat of approximately 25 to 35 feet in length by day in moderate winds (up to 20 knots) and sea conditions. Knowledge of cruising sailboat terminology, basic boat systems, auxiliary engine operation, docking procedures, intermediate sail trim, navigation rules, basic coastal navigation, anchoring, weather interpretation, safety, and seamanship.

ASA 104, Bareboat Cruising

Able to skipper a sloop-rigged, auxiliary powered keelboat of approximately 30 to 45 feet in length during a multi-day cruise upon inland or coastal waters in moderate to heavy winds (up to 30 knots) and sea conditions. Knowledge of provisioning, galley operations, boat systems, auxiliary engine operation, routine maintenance procedures, advanced sail trim, coastal navigation including basic chart plotting and GPS operation, multiple-anchor mooring, docking, health & safety, emergency operations, weather interpretation, and dinghy/tender operation.


Q. What is ASA?

The American Sailing Association is a coalition of sailors, professional sailing instructors, sailing schools and charter companies promoting safe recreation in the United States with an internationally recognized certification education system.

Q. What are the advantages of certifications?

Internationally recognized credentials, quality educational materials, professional instructors, and targeted goals for each level of the program.

Q. What certifications will I earn during this course?

Bareboat Cruising [104]

Q. What are the Prerequisites?

Basic Keelboat [101] Basic Coastal Cruising [103] is required. If you have completed Basic Keelboat from another reputable sailing school certifier [US Sailing or similar], you are able to take the ASA 101 Qualifier Exam. Please contract us if you have additional questions.

Q. Should I study the ASA material prior to the start of the course?

YES! You are expected to read through the sailing text books and familier with the information prior to the start of the course. The more knowledge you have the better equipped you will be to implement the knowledge during the course.

Q. What is the deposit?

A 25% deposit is required. You can place your deposit by clicking on the BOOK NOW button at the top of the page.

Q. Will there be meals ashore?

Yes, there will be 3 to 4 meals enjoyed ashore and you are expected to cover

Q. How much sailing will there be daily?

Depending on the coursework, there will be 5 to 8 hours of sailing each day. Certain days will cover less water to practice maneuvering and other activities such as anchoring, chart plotting, safety, and docking.

Q. Will there be downtime?

Yes, you bet! PASSAGE OFFSHORE is a course designed to explore the joys of sailing and a big part of that is rewarding yourself with the fruits of your labor. Whether it is a splendid beachside restaurant or rum shack, snorkeling, hiking, exploring a magnificent seaside village, or relaxing with a book aboard, there will be plenty of downtime from the educational curriculum.

Q. Who cooks?

Unlike other Sailing Collective adventures, PASSAGE OFFSHORE teaches you how to provision and cook for a voyage. Together, we will go to the local markets and seek out quality ingredients to be prepared aboard. Recipes will be based on the guidebook provided by the Sailing Collective culinary director. Please be prepared to bring two to three of your favorate recipes to prepare. The instructor will facilitate the provisioning.

Q. How many students?

There will be 4 students per session with 1 instructor. We keep the student count to a minimum to maximize your time learning and hands-on experience.

Q. Gratuity

Not only is your captain your educational instructor, but he is also providing high levels of hospitality. It is customary in the yachting industry to offer gratuity to your crew. 10% of your ticket price is a standard amount.


Oceanis 51.1

Oceanis 51.1

With sleek lines, a new stepped hull and a stylish deck plan, the Oceanis 51.1 is the first of a new generation. The Oceanis 51.1 is spacious, elegant, cleverly designed, and fast, and successfully revisits the cruising yacht.

Grenadine Islands (Sailing School)

Sailing School


November 1st — 10th 2024


Sailing School

Only 0 Cabins Left

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