Guadeloupe Sailing Vacation

Guadeloupe Overview

Upcoming Voyages:

• Dec 1st to 8th 2018 - Fully booked
• Dec 8th to 15th 2018 - Fully booked
• Dec 15th to 22nd 2018 - Fully booked

Vessels: Helia 44 Catamaran & Lipari 41

Price: $3,250 per single-occupancy stateroom - bring a spouse or friend for only $250! ($3,500 double-occupancy stateroom, $1750/person)

Certification Options*: Crew, Skipper, Bareboat Charter Master
*new* International Sailing License & Credentials (SLC, with Bareboat)

Prerequisite: No prior experience required

register now for sailing classes, courses and clinics

The Guadeloupe Archipelago

Guadeloupe is considered among the best sailing grounds and ecotourism destinations in the world.  Les Saints is considered "the most beautiful bay", and for snorkeling and diving - suffice that Cousteau named the Archipelago as one of the top 10 diving spots in the world!

Guadeloupe's known for balancing modernity with its culture, heritage and natural resources. IDEAL catamaran sailing with easterly Trade Winds and line-of-sight sailing while weaving through the archipelago.... And once you reach your island destination: French Creole culture, fertile rainforests, mountainous slopes, coral reefs, mangrove swamps - and a Gallic cuisine followed by dancing the night away to zouk and ragga!  ....Crystal blue waters and white sandy beaches.

A perfect playground for island hopping Sailors!

Discovered by Christopher Columbux in 1493, Guadeloupe's butterfly shaped islands are unique as part of the Leeward Islands.  As a French "Departement", Foodies will delight in the French Creole as a distinct blend that includes West Indian cooking.   The mix of African, European and East Indian cultures makes Guadeloupe the melting pot of the Caribbean.

Information on joining the cruising groupA few island hopping itinerary examples: Read More

Sailing Guadeloupe Les Saintes• Iles Des Saintes ("Island of the Saints") - a volcanic archipelago encircled by shallow reefs (ahem, snorkeling & diving), and otherwise "the most beautiful bay in the world"

• Deshaies - a charming fishing village

• Marie Galante - discovered by Columbus in 1493, and now know for its Rum (Argh, 59 proof "Rhum"!). Of course, beaches and snorkeling....

• Portsmouth, Dominica

• Llet a Gosier - explore the primordial forests...

An Ecotourism Paradise:

Sailing Guadeloupe Cousteau reserve• Each island is a unique ecosystem, from volcanic to arid to tropical...  Nature reserves abound.

• Cousteau named Guadeloupe archipelago islands as one of the world's TOP 10 Dive sites

• Preservation is a pillar of Guadeloupe - a plethora of fortresses, colonial buildings, etc....

• Guadeloupe is part of the "old way" of agricultural life, from oxcarts to cuisine - music, dance, markets, crafts, etc...

A few tasty teasers of the French Creole for more adventurous sailors:

Sailing Guadeloupe French Creole cuisine• "Accras" seafood & vegetable fritters

• "Colombo" classic meat/fish except prepared with a Creole (not Indian) curry

• "Crabes Farcis" spicy stuffed crabs, cooked perfectly to be moist....

• "Bokit" savory deep fried naan like bread stuffed with meat, vegetable or fish.

Guadeloupe Voyage Information

Helia 44 SailingNo prior sailing experience required: Kick back and enjoy the ride and the scenery, take the helm and handle the lines, train & learn as much as you'd like, or take a nap on the trampoline with ear buds in - it’s all up to you... 

Notably this is a small group and personalized Adventure Sailing Vacation, and so all participants should come a willingness and capacity to actively participate in all aspects of sailing the yacht. How much is up to you!  As sailors we love sharing the fun, freedom and discovery of casting off, deciding where to go, how to get "there", and what to do.

Sailing can be adventurous, rigorous and challenging, but the rewards of freedom of the open water, connecting with nature, disconnecting from the modern world, discovering islands and new ports, and self-confidence are tremendous. If you enjoy adventures, then once on the water you'll wonder why you haven't been sailing all along!

And, please bring a fair share of jokes and stories!

Included in the stateroom price are linens and towels, all meals and snacks while aboard, water and soft beverages, fuel and moorage.

Not included are transportation, meals ashore, hotels, excursions, alcoholic beverage of your choice, and additional certification training materials. We'll coordinate travel arrangements with all participants.

Sailing Certification

You'll receive training from one of the World's foremost experts and regardless of certifications. For those wanting certifications: Crew, Coastal Skipper, Bareboat Charter Master, and International SLC certifications are available.

NauticEd 21st Century Sailing EducationFor knowledge, we offer NauticEd's online courses to prepare you with the most advanced and current online sailing education available. Start immediately, take your time with interactive content, and test online - this allows you to enjoy more fun sailing and practical instruction on your cruise!

Depending on the certification and your sailing background - the knowledge training may be an additional cost. Every sailor has unique backgrounds, needs and goals - and so we'll review your background and make specific preparatory training recommendations. Our goal's to save you time and money; and focus on what's individually needed.

Certifications available:

Bareboat Charter Master - learn to sail and charter big boats read more

Bareboat Course and NauticEd Bareboat Charter Master certification

Prerequisite: Skipper, ASA 103 or equivalent experience required.

Sail big boats and charter in exotic locations with the Bareboat Charter Master Certification. This Course teaches a complete understanding of vessel systems, planning, and large boat handling.

Skippering a large sailboat for multiple days requires a diverse range of knowledge and skills: you're the Skipper, Navigator, Weatherman, Engineer, Cook, Plumber and all while responsible for the proper care, feeding and planning of your crew.

Bareboat Charter Master Certification requires you pass all the competency tests listed below. Each step is recorded in your online resume, and once ALL the required steps are achieved - you're certified.

√ Knowledge: successfully complete Online Bareboat Chartering Clinic, Coastal Navigation Clinic, Anchoring Clinic, and Electronic Navigation Course.
√ Practical Competency: 3-day course
√ Experience: 50 days of qualified sailing experience (prior experience counts).

*Note: The online and practical course completion will be recorded and is the equivalent of an ASA or US Sailing Bareboat Certification. The 50 day requirement is what most Charter companies recommend for the Bareboat Master status, and most charter companies will charter to you with less than the 50 day requirement. The additional days of experience are required to demonstrate that you can successfully Bareboat on your own, utilizing what you learned online and on-the-water.

The days are logged into your NaucticEd online logbook and once completed - you're certified a Bareboat Master Rank!

International Sailing License & Credentials (SLC) - the recreational sailing license valid for yacht charter companies worldwide including more

Prerequisites: Skipper. SLC is earned as part of Bareboat certification.

The International Sailing License and Credentials (SLC) is a recreational sailing license valid for all yacht charter companies worldwide including Europe. To gain an SLC, the candidate must hold a national government boating license, pass a suite of theoretical knowledge courses and tests appropriate for bareboat chartering, log sufficient sailing experience, and demonstrate sailing skills according to internationally established sailing standards.

The SLC is offered as part of the Bareboat training and includes several additional requirements. Learn more about the SLC and requirements ›

Skipper/Coastal Cruising - advance skills past basic sailing read more

Learn to Cruise and sail further and faster with improved sail and boat handling techniques, in heavier weather and with sailboats 25' and larger.

Prerequisite: Skipper-Small Keelboat, ASA101, or equivalent experience required.

Sail further and faster with the Basic Cruising Course and Skipper Certification. Learn improved sail and boat handling techniques, including heavier weather sailing and sailing on sailboats 25' and larger.

After mastering the fundamentals, sailors are introduced to more advanced topics and sailing in diverse conditions. You will learn to cruise: be prepared for extended sailing, planning for new waters, adverse weather and troubleshooting. By the end of the course, students will have the skills to plan a full day or overnight cruise, and the confidence to execute it safely and enjoyably.

Skipper Certification requires you pass all the competency tests listed below. Each step is recorded in your online resume, and once ALL the required steps are achieved - you're certified.

√ Knowledge: Successfully Complete Online Skipper and Maneuvering Under Power classes
√ Practical Competency: 3-day course
√ Experience: 4 days of qualified sailing experience (prior experience counts)

The additional days of experience are required to demonstrate that you can successfully skipper on your own, utilizing what you learned online and on-the-water.

Crew - invite your spouse/friends to gain beginner sailing and crew experience read more

NauticEd Qualified Crew CertificationUpon completion, you will feel confident in your ability to understand the workings on the sailboat and enjoy contributing as a knowledgeable crew member. There are tips on how to hold a straight course when at the helm, sail trimming, rules of the road so you're not second guessing who has to give way, and just what the heck does that blue line do.

Qualified Crew requires you pass all the competency tests listed below. Each step is recorded in your online resume, and once ALL the required steps are achieved - you're certified.

√ Knowledge: Successfully Complete Online Qualified Crew
√ Practical Competency: 3-day course
√ Experience: 4 days of qualified sailing experience (prior experience counts)

The additional days of experience are required to demonstrate that you can successfully crew on your own, utilizing what you learned online and on-the-water.

The Vessels

Helia 44

Helia 44 Catamaran SailboatThe Helia 44, meaning "Sunshine" in Greek, is the ultimate light-filled (360° views) spacious catamaran and is the epitome of live-aboard luxury. Helias are safe and stable "voyaging" multihulls - Fountaine Pajot (the builder) catamarans have crossed the Atlantic well more than 500 times and circumnavigated the World dozens of times.  Performance? She'll outperform most Catamarans in her class.

The Helia 44 is our vessel of choice for this adventure because of it's balance of luxury and performance - stable transiting open water and with the ability to explore skinny (shallow) waters near the islands.

Lipari 41

Lipari 41 sailing with AGWE sailing in GuadeloupeThe Lipari 41 offers spacious accommodations, relatively high freeboard, and a raised saloon with excellent visibility. Like similar cruising cats and when off the wind, it'll leave all but full-bore racing monohulls in the dust and without the "bridgedeck pounding" experienced in many boats.  The Lipari 41 is spacious and comfortable both inside and out, and it's no slouch under sail.

The Lipari combines excellent sailing performance with ultra-comfortable interior accommodations. With less than 4 feet of draft, the Lipari can sneak into almost any shallow anchorage - a benefit when exploring Gaudeloupe!

Meet the Captains...

Capt. Stephen Frankland

Capt. Stephen Frankland AGWE Sailing in Guadeloupe"The World's Best Instructor" by NauticEd's student reviews.

Capt. Stephen Frankland is a USCG licensed Captain rated for OUPV Inland and Near Coastal, leading NauticEd and ASA instructor, and arguably one of the highest rated instructors in the NW. Read More

...My name is Stephen Frankland and I love to share the passion of sailing!  I had the great good fortune of spending all my summers growing up on Lake Michigan. I got my first boat, a Sunfish, when I was 10 and have been in love with sailing ever since. At the age of 12 I started sailing on The Northern Light – the 12 meter US14 built in 1938. I was ‘adopted’ by the crew and for the first two summers I worked on and sailed on the boat as much as I could.

At 14 I was invited to join the race crew and for the next four summers we participated in as many of the races around the Great Lakes that we could, the high point of each summer being the Famous Chicago to Mackinac race.

While attending the University of Oregon I got an opportunity to go to Alaska to work on boats and well…, six summers of commercial fishing and working the waters from The Gulf of Alaska (North Pacific) and Prince William Sound all the way out west to Norton Sound at the top of the Bearing Sea had rolled by when I chose to settle down in Portland in the early 90’s and discovered much to my surprise the amazing sailing taking place on The Columbia!

I joined Island Sailing immediately after I found about them and started sailing and racing avidly. It wasn’t long before I joined the crew there, started working at the club, got my instructor certifications, and began teaching at the different locations the club has.

I am currently sailing and sharing my 1978 C&C Lancer 30: “Mahalo” out of Portland – sharing the joy of flying along in 15-20 mph almost daily summer winds with countless friends through the years. In teaching I find the opportunity to share this wonderful world of sailing and the joy it brings with an endless number of wonderful people who like me “have been called by the sea…”

USCG Licensed Captain NauticEd World's Best Sailing Instructor American Sailing Association ASA certified instructor 

Capt. Rob Roy

Island Sailing sailor Rob RoyMy name is Rob Roy, I love to sharing my passion for living a good life and for adventure.

At 13, my dad introduced me to sailing by building 16’ sailboat in our garage. We launched her into the local waters and I learned port from starboard. Tacking and gybing became part of the enduring joy of the warm summer days. Read More

...In college, I found rock climbing and spent years on the sides of mountains covering much of the US. Topping out in Mexico, at 18,500 ft., on Pico de Orizaba.

When I moved to Portland, Oregon, I decided I should run the Portland Marathon, many times, which lead me to Greece to run the original 26 mile course from Marathon to Athens. After an early retirement, from IBM, my sailing passion was ignited. I participated in local club races and became commodore of the Island Sailing cruising group. Last year I decided to walk the Camino de Santiago, a 500 mile pilgrimage across Spain. While in Europe, I traveled from Iceland to Turkey, and Spain to Estonia.

Of course, I fell in love with the Mediterranean sea while sailing with my friend, Mehmet on his Bavaria match 42. Alternating between mooring in stunning turquoise bays and racing in international waters.

These days, after bicycling up to the marina, I sail my vintage restored 1966 Cal 25 Flat Top on The Columbia. There is just something about turning the the motor off.

Price Details & Registration

Single-occupancy stateroom: $3,250

Double-occupancy stateroom: $3,500 (only an extra $250 to bring a significant-other or friend, or $1,750/person)


  • Sailing
  • All meals and snacks while aboard
  • Water and soft beverages
  • Fuel, moorage and boat fees
  • Linens and Towels
  • We assist on travel plans & coordination
  • Capt. Frankland's sea stories


  • Certification & related materials
  • Flights, transfer & custom fees
  • Hotels
  • Alcoholic beverage of your choice
  • Meals ashore
  • Inland park, guide and recreational services
Please note: bookings are first-come/first-serve. The booking process includes some required paperwork and waivers before payment.
For payment, a twenty (20%) per cent deposit is required at time of booking. The balance is due sixty (60) days before departure, or the Balance must be paid in full within 60 days or by Sept. 1st (at the latest).
Please see Booking Conditions, Policies & Release for details.


To register please submit the contact form below and we'll follow-up. Our process begins with answering questions and discussing training, goals and other details related to the voyage and travel. Simply, we tailor these voyages to each sailor's goals and needs.


Need Help? Contact Island Sailing

Alternatively, please contact Chris Black directly at with questions, for more information or to sign-up!

Sailing Guadeloupe Deshaies