Border Run | San Diego – Guadalupe Island – Ensenada

Border Run | San Diego – Guadalupe Island – Ensenada

May 8 – May 14 | $1475

Already Sailed

Join the team of Sea Dragon on a quick cross-border hop from San Diego to Ensenada, Mexico, before heading offshore to remote Guadalupe Island, world renowned as a Bisophere reserve and a major stomping ground of great white sharks. This trip should feature relatively calm seas and coastal sailing, adventurous hiking ashore, and a chance to explore the remote island of Guadalupe.

  • Cost: $1475
  • Date: May 8 – May 14, 2019
  • Start: Chula Vista, CA, USA
  • End: Ensenada, Mexico
  • Length: 7 days, 6 nights
  • Focus: Adventure Sailing | Hiking | Exploration

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: Afternoon Arrival on Sea Dragon

You’ll meet us on the dock in Chula Vista anytime between 1500 and 1700 and come on board to settle in. Everyone will come together for our first dinner on board and have the opportunity to chat to your fellow crew members. After dinner, your professional crew will go through life on board and safety procedures in prep for departure the following morning. You’ll be fitted with your own lifejacket and assigned foul weather gear if you haven’t brought your own.

Day 2: Sunrise Sail to Ensenada

Just after the sun rises we’ll cast off the lines and head to another country! Off to Mexico we go on a lovely full day’s sail. We’ll run watch teams and schedules for this hop, so you’ll have plenty of time to get a feel at the helm and trimming the sails, but also to keep an eye out for sea creature friends as we sail coastally to Ensenada. We’ll arrive with the sunset and spend the night on the dock.

Day 3: Customs and Departure for Guadalupe

Welcome to Mexico! First thing we’ll do in the morning is clear customs and immigration. After that you’ll have the opportunity to check out the surrounding area and perhaps find yourself a delicious taco or two for lunch. In the late afternoon, we’ll depart to sail overnight to the remote offshore island of Guadalupe. With 190NM to sail, we’ll once again fall into our watch schedule and sail into the sunset.

Day 4: Blue Water Sailing and Arrival

By this time, you’ll have had your first overnight sailing experience on Sea Dragon and will wake up with nothing in sight but the endless horizon. As we sail through the morning and into the afternoon, we’ll see who spots our destination first, being the one to yell ‘Land Ho’. As we get closer, the island, seemingly small from afar, will grow in size and detail to reveal dramatic cliffs and black sand beaches. In the afternoon, we’ll find our anchorage and take in the pristine and remoteness of Isla de Guadalupe.

Day 5: Remote Island Exploration

After resting up from the overnight sail and getting a nice sleep on anchor, we’ll wake up and be able to explore an island that few come to visit. There will be hiking, beaching, swimming (watch out for sharks!  maybe better to stick to beaching!) and chatting to the local fisherman and families. We’ll have a wonderful dinner on board watching the sun go down and be able to lie on deck to watch the stars come out after a wonderful day.

Day 6: Back on the Big Blue

Today we depart Guadalupe after a morning breakfast on anchor. We’ll get underway and into watches once again to sail overnight back to Ensenada. The island will fall away and we’ll have our 360-degree endless horizon view once again, watching the sunset at sea giving way to another gorgeous night at sea.

Day 7: Mainland Arrival

After our final overnight sail, we’ll arrive in Ensenada early afternoon and say farewell to one another and our communal home of Sea Dragon. Although you’ll disembark at 1500, time is yours and if you wish to stay and explore Mexico further, you’re in a perfect place to do so. 


More Information:

Contribution Includes:
– 6 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 San Diego and Ensenada
– 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 Chula Vista Marina between 1500-1700 on the first day.   You will depart the vessel in Ensenada at 1500 on the last day.

San Diego International Airport (SAN) is about 20 minutes north of Chula Vista, and Tijuana International Airport (TIJ) is about a 30 minute drive south, but border crossings can be slow.  It’s about a 70 minute drive from Ensenada back to TIJ, and 90-100 minutes back to SAN, exclusive of time waiting at the border.

All crew members will require a passport and visas from their home country that will allow them to travel to/from the USA and Mexico. Please ensure that you have the appropriate paperwork completed before joining the vessel, or you will not be allowed to board.




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.