Pineapple Express | San Diego – Hawaii

Pineapple Express | San Diego – Hawaii

March 14 – April 3 | Finished

Limited Availability
Trip is Complete

We have already Sailed this trip!  If you’re interested in a long voyage, what about crossing from Hawaii to Canada in August on our North Pacific Gyre trip?

Join us aboard Sea Dragon for the classic Pacific crossing! We’ll follow the sunset all the way to Hawaii. We’ll have plenty of time to practice downwind sail handling, helming, and even some celestial navigation if you’re keen. The last time we sailed this voyage we had a very fast week out of Ensenada, racking up well over 200nm a day for the first 5 days of the trip before we got to the trades.  The rest of the voyage was warm and beautiful, with spinnaker sailing in light wind and wing-on-wing running as the trades strengthened.  If you’re interested in celestial navigation, this is the best voyage of the season to learn from us or hone your skills – clear skies in the trades and a smooth downwind voyage.  We’re looking forward to what should be a spectacular ocean crossing – a perfect opportunity to get away from it all and cross the Pacific!

This trip is an RYA Yachtmaster Ocean and IYT MOY Unlimited qualifying voyage – contact us to discuss.

  • Cost: Already Sailed
  • Date: March 14 – April 3, 2021
  • Start: Chula Vista Marina, San Diego, California
  • End: Ko Olina Marina, Hawaii
  • Length: 21 days, 20 nights
  • Focus: Offshore Passagemaking | Ocean Crossing | Sail Training
Due to the remote nature of this trip, we are aiming for a higher standard of risk reduction than what airlines and others are requiring. While we can’t guarantee that our protocol will 100% prevent a COVID infection onboard, we are hopeful that with these constraints, it will seriously reduce the risk of the possibility of a serious COVID infection part way to Hawaii, far from advanced medical care. 
COVID Protocol
March 1 (14 days before trip):






Please begin to take maximum precautions to minimize your risk of infection with COVID-19 by following CDC guidelines. Please review CDC guidelines here, and minimize or eliminate nonessential activities which may expose you to COVID.

March 10:  Arrive in San Diego no later than this date.  
The CDC classifies air travel as a “higher risk activity” and air travel with connections in its “highest risk” travel category.  Please do all you can to minimize risk during your flight: follow CDC recommendations, social distance when feasible, book direct if possible, wash your hands or sanitize according to CDC guidelines, and wear the best fitting and highest filtration mask you are able to.

Once you have arrived in San Diego, we ask that you get a PCR COVID test, then self quarantine in a hotel until boarding.  This means avoiding crowded outdoor spaces, avoiding indoor spaces with others, and generally trying to avoid any possibility of picking up an infection prior to boarding.

As of today, San Diego PCR tests are taking 72 hours to get results, so please take the PCR test on March 11.  If testing times improve, we may change when this test is taken in order to reduce the gap between the test and boarding. With the information we have now, taking the test on March 11 is the closest day to boarding to take the test and get results back in time. We will provide some suggestions of where PCR tests are available. 

March 14:  Arrive at boat.  
We will provide you with a COVID symptoms questionnaire to complete before boarding. We will take your temperature, review your questionnaire, and administer a rapid antigen test to you on the dock before boarding. With proof of a negative PCR result (from March 11), a negative COVID screen from the questionnaire and temperature check, and a negative rapid test on the dock, you will be able to board Sea Dragon. Once everyone is on board, we will fall into the normal routine for trip operations. We’ll become a “bubble” with no masks required on board. You’ll choose your bunk, we’ll have a group dinner on board and go through safety briefings for departure the next morning to Ensenada. 

With the possible risk of infection, shore activities and exploration of Ensenada will not be possible. We will ask that all crew members stay within the marina and hotel area.  We will retest everyone on board with rapid tests before departing from Ensenada for sea.  If anyone tests positive, the trip will be cancelled, and the vessel will return to San Diego. 

In the event that you test positive on either the PCR test or your pre-boarding rapid test, you will not be allowed aboard the vessel, and we will be happy to transfer your payment to a trip of your choosing at a later date.

If the trip is cancelled due to a crew member testing positive on the rapid test in Ensenada before departure to sea, we will be happy to transfer your payment to a trip of your choosing at a later date or refund your money. 

We understand that by March some of you may have been able to get vaccinated. As this becomes a reality, we will reassess these requirements based on CDC guidelines and our medical support team in the UK. 


Contact Us

Call Us: +1 ‪(305) 330-4212‬




If you want a lifetime experience and adventure, sail on Sea Dragon with Eric & Shanley. They are by far two of the most qualified and professional sailors on the planet and terrific hosts who look after every detail in making their passengers feel comfortable during a voyage. Sea Dragon is an exquisitely maintained, seaworthy vessel and fun to sail in all weather conditions.”

-Tom B.


Tentative Itinerary

Day 1:  Arrive at Sea Dragon

You’ll join your professional crew and other guest crew members on Sea Dragon between 1500 and 1700. This evening gives you time to settle into your bunk and unpack and before everyone joins together for our first meal on board. After dinner, your Captain and Mate will take you through essential things to know for life on board. You’ll then have time to get to know the others on board with you or to explore the surrounding area. We’ll spend the night on the dock.

Day 2:  Shakedown Cruise to Ensenada

Today we’ll be off the dock early for the trip down to Ensenada.  En route we’ll practice safety procedures, learn the basics of sail handling and helming, and get used to the boat. You’ll get fitted for a lifejacket, and if you haven’t brought foul weather gear, have some assigned to you for the trip to Hawaii. We’ll spend the night on the dock.

Day 3:  Explore Ensenada

After clearing into Mexican customs and immigration, we’ll have a day to explore in Ensenada.  We’ll do a bit more training in the morning, then have the rest of the day to explore – surfing, wine tasting, street tacos and more!

Day 4:  Departure for the Big Blue

After clearing out of Mexican customs & immigration, we’ll set sail for Hawaii!

Day 5 – 19:  Offshore Sailing

We all find our rhythm to life at sea, and the days will fade in and out upon big blue. No two days, sunrises, sunsets or watches will be the same. Hopefully, we’ll see some good sea life, including dolphins, whales, albatross and boobies. As we adjust our sails along the way, things that seemed so foreign in the beginning will quickly become second nature, and the miles will fall behind as we continue west.

Day 20:  Estimated Arrival in Hawaii

After more than two weeks at sea, we’ll arrive in Oahu into Ko Olina Marina. The green hillsides rise up to the clouds from the sea, and our senses will be re-introduced to the attributes of land. While we wait to get cleared through customs and immigration, we’ll tidy Sea Dragon. After we’re cleared, it will be time for a nice cold beverage, a dip in the sea, and a group dinner on shore to celebrate our arrival!

Day 21:  Departure Day

After a fun night out, it will be time to disembark Sea Dragon at 0900. We’ll all say so long, but not goodbye, and you’ll find yourself free to explore the tropical and volcanic Hawaiian island chain as you wish.  

 What's Included

Contribution Includes:
– 20 nights accommodation on Sea Dragon
All meals (vegetarian), snacks, and drinks on board
– Sailing instruction
– Safety equipment and foul weather gear
– Mask, snorkel, fins


Contribution does not include:
– Transportation to and from San Diego and Hawaii
– Transportation to and from the boat
– Additional nights spent ashore
– Personal expenses while in port

 Packing List
 Travel Details

You will join the boat in San Diego between 1500-1700 on the first day.    You will depart the vessel in Ko Olina at 0900 on the last day. We’ll try to avoid motoring on this voyage, so our actual passage time is dependent on the winds.  If we have a fast passage, we could arrive as early as March 2.   Our slowest voyage time would be arriving the afternoon of the 6th, and you could depart the boat on the 7th as per the itinerary.  If we arrive early, you are welcome to stay aboard until the final day, but are by no means required to – take a few days and have a mini Hawaiian vacation!

San Diego International Airport (SAN) is a 20-30 minute drive from Chula Vista Marina.  You can also take the transfer bus from the airport to connect to the trolley, which lets off about 1 mile from the marina at H Street.  Honolulu International Airport (HNL) is about 30 minutes from Ko Olina by car.  

All crew members will require a passport and visas from their home country that will allow them to travel to/from Mexico and the USA. Please note that many nationalities which can enter the US by air on the ESTA visa waiver program need a B1/B2 visa to enter by sea.    If you are NOT from the USA, Canada, or Bermuda, you will need to get a B1/B2.    Please ensure you have the appropriate paperwork completed before joining the vessel, or you will not be allowed to board.    Please look into the specific type of visa you need for arriving at these destinations by sea, or contact us directly to discuss.

 Boat Tour

 Your Crew

ANNA STRANG and MAGGIE KERR – Skipper and First Mate

Anna and Maggie met as Skipper and First Mate on a 74ft science expedition yacht, sailing from the UK to Tahiti researching ocean plastic pollution. 

Anna, born in 1990 was taught to sail in the Cadet fleet in Poole harbour, UK, by her grandfather at the age of 6. From a competitive dinghy racing background, she became an RYA Yachtmaster instructor and has worked full time in the industry for 14 years; teaching a range of ages in all aspects of watersports. 

Alongside her professional sailing career, Anna also gained a BA in Architecture from Brighton University. However, having grown up on a farm in the south-west of England, living and working outdoors, she chose to pursue a passion for the outdoors and adventure.

Anna has worked in most areas of the industry from race Captain on luxury yachts in the Maxi Worlds, to teaching and managing an RYA Training Centre. She has sailed over 75,000nm in the Atlantic, Pacific, Mediterranean and Caribbean. She loves being offshore and has competed in many ocean crossing races with teams of novice crew which she thoroughly enjoys. She first sailed Seadragon in 2017 across the Atlantic and then again across the Pacific in 2018. 

Maggie, born in 1992 grew up in Australia’s Whitsunday Islands and Great Barrier Reef. She started racing sabots from the age of 5, then progressed to pacers and lasers later in her youth. She coached her school sailing team which is where she developed a passion for teaching sailing. Maggie completed a Bachelors degree in Business Public Relations but chose a career offshore with an undying passion for ocean sailing.

Maggie started her career as a teenager, working in her family business which ran adventure sailing charters. Every school break, when she wasn’t competing in dinghy regattas, she spent her time working on a traditional square rigger, classic schooner and ex americas racing cup racing yacht. In 2013 she sailed to Antarctica and rounded Cape horn and fell in love with ocean sailing. 

In 2017 Maggie left Australia to travel and continue sailing. She worked in the Mediterranean on a range of luxury yachts between 28 and 92m. She has sailed over 30,000nm all over the world in the Pacific, Atlantic, Arctic and Southern Oceans. 

When they are not sailing, they enjoy travelling by land in their yellow camper-van which they converted themselves. They also love to dive and are currently learning to kite-surf.


Anna is an Ocean Yachtmaster with commercial endorsement, an RYA Yachtmaster Instructor, a PADI Open Water Diver, and holds her STCW endorsed Proficiency in Medical Care at Sea.  Maggie is an MCA Master of Yachts < 200 tons, MCA Officer of the Watch to 500 tons, Australian Master Class 5, and holds a certificate in Advanced First Aid & CPR.