Guadeloupe Sailing Vacation

Sail the Guadeloupe Archipelago's steady trade winds & hop the French Creole Îsles

Coastal Skipper & Bareboat Charter Master certifications available

Need Help? Contact Island Sailing

Contact us with questions or to register.

Guadeloupe Overview

Upcoming Voyages:

• Dec 2nd to 9th 2017 - Fully Booked
• Dec 9th to 16th 2017 - Fully Booked
• Dec 16th to 23rd 2017- Fully Booked

Vessel: Helia 44 Catamaran

Captain/Instructor: Capt. Stephen Frankland

Price: $3,250 per single-occupancy stateroom - bring a spouse or friend for only $250! ($3,500 double-occupancy stateroom, $1750/person)
($100 discount if paying directly by cash or check)

Certifications Options*: Skipper, Bareboat

Prerequisite: No prior experience required

The Guadeloupe Archipelago 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.

A few island hopping itinerary examples: Read More

  • 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:

  • 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:

  • "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

No 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!

*Certifications: You'll receive training from one of the World's foremost experts and regardless of certifications. For those wanting certifications: Coastal Skipper and Bareboat Charter Master certifications are available upon merit.Read More

By merit we mean successfully completing any prerequisite knowledge requirements, and more importantly successfully passing the instructor's assessment of your skills and competence.

Depending on the certification and your sailing background, the knowledge training may be an additional cost. For knowledge, we utilize NauticEd online and interactive courses - an advantage because your knowledge training and testing can be completed prior to the trip (i.e., more fun time).

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.

Click on the course page below to learn more about each certification:

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

Basic Cruising, "Skipper" Certification

Bareboat Course and NauticEd Bareboat Charter Master certification

Bareboat Charter Master certification

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.

Helia 44 Sailing


Helia 44 Catamaran Saloon


Helia 44 catamaran interior


Vessel: The 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.

Meet Captain & Instructor Stephen Frankland

Capt Stephen Frankland at the helm

"The World's Best Instructor" by NauticEd's sailor reviews (read reviews here>)

USCG Captain, NauticEd Instructor & ICC Licensed. Offshore Delivery Captain, Keelboat & Catamaran Expert.

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. Capt Frankland is the Principle of AGWE Sailing, specializing on empowering new and existing sailors with sailing experiences, chartering, private instruction and sail coaching.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 

Price Details

• $3,250 per single-occupancy stateroom (i.e., your own stateroom)

• $3,500 per double-occupancy stateroom (i.e., bring a spouse, significant-other or friend for only $250 more ($1,750/person)

• Book the boat! There are 3 double-occupancy cabins available, perfect for families or a group of friends.  Contact us for additional discounting and group pricing.

• $100 discount if paying by cash or check


  • 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

Registration & Questions

To register or if you have questions, 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 SailingAlternatively, you can contact De Henderson directly at with questions, for more information or to sign-up!

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.