Pineapple Express | Ensenada – Hawaii

Pineapple Express | Ensenada – Hawaii

May 25 – June 13 | $3950 

Already Sailed

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. On our voyage from Mexico to Hawaii in 2018, we had almost a week of beautiful spinnaker sailing before the breeze filled in and we finished strong, running downwind wing-on-wing in 20-30 knots of breeze to Oahu.  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: $3950
  • Date: May 25 – June 13, 2019
  • Start: Ensenada, Mexico
  • End: Ko’Olina Marina, Hawaii
  • Length: 20days, 19 nights
  • Focus: Offshore Passagemaking | Ocean Crossing | Sail Training

Sign up Now!  When you book, the $500 deposit is non-refundable.  Please read our crew contract before booking.

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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 joins everyone 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 and you’ll then have time to get to know those on board with you or to explore the surrounding area.

Day 2: Getting to Know Home

Today we’ll all go through safety procedures, watch schedule, and structure for life at sea before heading out out for a day sail. 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.

Day 3: Departure for the Big Blue

After clearing out of Mexican customs and immigration, we’ll cast off the lines and head out to sea. We’ll set the sails just as we did the day before, only this time we’ll point the bow west, with our sights set to Hawaii! We’ll fall into our watch schedule and have our first night at sea.

Day 4 – 18: Offshore Sailing

We will 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 19: Estimated Arrival in Hawaii

After more than two weeks at sea, we’ll arrive in Oahu into Ko’Olina Marina. The green hillsides will rise up to the clouds from the sea and at once our senses will be re-introduced to 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 20: 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. 

More Information:

Contribution Includes:
– 19 nights accommodation on Sea Dragon
– All meals, snacks, and drinks on board
– Sailing Instruction
– Safety equipment and foul weather gear

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

Kit: Tropical


Travel Details:

You will join the boat in Ensenada between 1500-1700 on the first day.   You will depart the vessel in Ko’Olina at 0900 on the last day.  If we have a fast passage, we could arrive as early as June 10.  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 90 minute drive from Ensenada, but the border crossings can be slow.  Tijuana International Airport (TIJ) is about a 70 minute drive.  Honolulu International Airport (HNL) is about 30 minutes fro Ko’Olina.

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 likely 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:




Eric Loss and Shanley McEntee have been with Pangaea Exploration since 2012. They have extensive experience working with scientific and non-profit research groups and enjoy running educational adventures for school groups. Eric and Shanley have taken Sea Dragon through the Panama Canal, up the St. Lawrence Seaway to Chicago, and to the Baltic, the Caribbean, and West Africa.

Shanley, born in 1987, grew up surfing and swimming in the Pacific in Del Mar, California. Throughout her youth, she worked with the Surfrider Foundation to protect California’s coastlines. She has a BA in Environmental Policy and Marine Science from Western Washington University. Her love and curiosity for the sea also extends underwater, where she is a PADI Rescue Diver.

After college she learned to sail, combining her passion for science, the environment, and the sea by spending several months aboard Sea|Mester’s schooners Ocean Star and Argo. Soon after she earned her Ocean Yachtmaster license. Shanley is the medical officer onboard Sea Dragon while on expedition and, alongside Eric, runs and maintains her both on and off program.

Eric, born in 1985, grew up in Laguna Beach, California. During his youth, he sailed dinghies, raced CFJ’s, Larks, and C420’s, and taught sailing to children in Dana Point, California. As a member of the Sea Scouts, Eric gained experience sailing and repairing cruising sailboats, 80’ to 130’ schooners, ketches, and brigs, locally and on several ocean crossings. He also earned the Sea Scout Quartermaster Award.

After graduating from Bowdoin College, Eric became a PADI Divemaster while working for ActionQuest and Sea|Mester, developing his teaching skills as he progressed from running summer programs on 50’ yachts to skippering 88’ and 113’ schooners throughout the Eastern Caribbean and across the Atlantic. In 2011, Eric took a break from professional sailing to buy and refit Odyssey, an Islander 36, to attempt a non-stop solo circumnavigation. Eight months later, he returned to Los Angeles, having sailed past the Great Capes of the Southern Oceans and back up the Pacific to his home port.

When not aboard Sea Dragon, Eric and Shanley have sailed throughout the Caribbean, across the Atlantic, and to the Arctic Circle aboard their own Pouvreau 42 Cutter, Fleur Australe.




A soon-to-be graduate of Northeastern University, Sarah Tokos spent her childhood sailing, swimming, and kayaking in and around Minnesota’s 10,000 lakes. While on her family’s 34-foot Ericson, she has experienced overnight sails, foul weather conditions, and a variety of necessary maintenance procedures–from ripped sails to emergency yahtzee dice recovery. When she’s not on a body of water (and even when she is), Sarah enjoys a good book and a strong pot of coffee. An advocate for outdoor adventures, she believes experiencing this beautiful world is the first step in appreciating and respecting its existence.