Pineapple Express | San Diego – Hawaii

Pineapple Express | San Diego – Hawaii

Feb 14 – March 6 | $4500

Limited Availability
FULL 0 Berths Remaining

This Trip is FULL, as is the waitlist.  If you’re interested in a longer ocean voyage, take a look at our “North Pacific Gyre” trip from Hawaii to Victoria, BC.  Or if that sounds too cold, what about Tahiti Why Not and Hopping Hemispheres between Kiritimati and Tahiti – they are each over 1000nm of uninterrupted sailing with an equator crossing to boot!

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: $4500
  • Date: Feb 14 – March 6, 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

This trip is FULL, the waitlist is too.  Take a look at our other voyages and see if you can find one that tickles your fancy!

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