Chartering in Thailand With Sailing Club Friends
When Matt Smith moved to Washington, DC, in 2015, he joined DC Sail where he began teaching adult sailing on Flying Scots. Aware of the existence of several sailing clubs in the area it became apparent that there was very little social interaction between members of those clubs, and none of the clubs appeared to offer opportunities for large-format group sailing beyond the occasional overnight or long weekend on the Chesapeake Bay.

Matt formed DC Sailing Community (DCSC) in 2017 to bridge that divide, giving members of various sailing clubs in the DC area an opportunity to make friends outside of their own club, with local, like-minded people that share their passion for sailing. Through DCSC, annual flotillas became twice-per-year sailing charters. This is how Matt and an eight-boat flotilla sailed in Phuket, Thailand, for seven days in late February. Here are his answers to SpinSheet’s questions about the journey:
SpinSheet: Tell us about the boats.
Matt: We chartered seven boats from The Moorings and Sunsail, and an eighth private boat owned locally joined our flotilla. The boats ranged from 40 to 45 feet in length.
How did you choose this particular charter boat and location?
There’s a fun saying in chartering: “Once you go cat, you never go back!” While most of our sailors love the thrill of a monohull heeling in stiff breeze, the majority of them prefer a catamaran for this type of sailing adventure. The stability, ease of handling, and rather luxurious comfort levels that modern charter cats offer these days are hard to beat.

Did your charter include a captain, cook, or other crew?
We bareboat all our flotillas, so we are responsible for skippering and crewing the yachts ourselves and preparing our own meals. Typically, we plan for three dinners onboard and three ashore. Most breakfasts and lunches are onboard.
Could you summarize where you went and favorite anchorages?
We sailed a clockwise loop around the Andaman Sea, taking in the must-see stops along the way. Highlights included Ko Phing Kan (known as James Bond Island since it was used as the location for Scaramanga’s base in ‘The Man with the Golden Gun’), Rai Le Beach, Ko Lanta (where we held our flotilla-wide dinner), and the Phi Phi Islands, made famous by the Leonardo DiCaprio movie, “The Beach.”

Was the sailing exciting? Conditions summary?
We began the week with a rather dreary and wet forecast, and indeed the first day delivered cloudy skies, thunderstorms, fog, and very little wind. The conditions improved markedly as the week progressed, with beautiful 25-knot winds for a couple of days and plenty of blue sky. Sea states were for the most part calm; although a large storm passing south of us pushed a lot of water our way which meant a lot of swell and a couple of rolly anchorages. The main anchorage at Phi Phi Don, Ton Sai Bay, was so rolly that the entire fleet upped anchor and moved around the corner to a more protected anchorage on the other side of the island.
The most significant thing to be aware of here is the 10-foot tidal range. We reminded ourselves frequently to scope for high tide when dropping anchor. Many of the bays dry out close to shore at low tide, so you have to be very deliberate that you park far enough away from shore to avoid grounding at low tide.
Tell us about your excursions.
We organized a morning dive trip for about 20 people in the Phi Phi Islands and several private longtail tours that took crews snorkeling and sightseeing to Ko Phi Phi Li. James Bond Island is an extraordinary place to visit; although you need your wits about you in the dinghy when arriving and departing as there are hundreds of tour boats and longtails zipping about full of tourists. Not the quietest spot. At Ko Lanta we had an extraordinary fire show on the beach after our flotilla dinner. (Several of our crews took advantage of being in southeast Asia and booked additional tours before or after the sail. I went with a group of nine to Cambodia, which was truly a magical experience.)

Three highlights on sea or land?
The landscape is stunning, particularly in Krabi province which we covered during the first couple of days. You pass by and sometimes are surrounded by remarkable limestone cliffs that soar up to the sky. It’s jaw dropping.
Maya Bay on Phi Phi Le was just stunning. You do have to try to ignore that there are a lot of tourists, but it is still a remarkable place and fun to visit another movie location.
The people we met at our various stops throughout our sail were so welcoming. There is very little crime, and it seems to be because everyone is just so content!
Did anything surprise you about the trip?
I wasn’t quite prepared for just how busy the main tourist spots in the islands are. James Bond Island and Phi Phi Le were especially crowded. However, I think through good planning we had the right mix of busier and quieter anchorages, so we had an itinerary to please all tastes.
Would you do anything differently if you could do it over?
I would take a boat for two weeks instead of one! The Andaman Sea is vast, and there are thousands of anchorages where you could be the only boat there. While we tried to hit the ‘must see’ spots, on another occasion I would take the time to visit some of the more remote areas.
I would also be a little more careful about who we enlist locally for help in setting up onshore activities. I always find it tremendously helpful to connect with locals while planning a flotilla. In this case, my contact there did not consistently deliver. Some events went down without a hitch, while others he organized for us did not deliver to expectations or were cancelled altogether with no notice. You can’t always know 100 percent what you are getting from local contacts in terms of reliability, but it was a lesson to be as diligent as possible in vetting whom we ask for help.
How do we learn about your future trips?
Click to dcsailingcommunity.com to find out about upcoming flotillas, where to sail in Washington, DC, and our partnerships with the Potomac Riverkeeper Network in being good stewards of the river and with Chronic Sailing, for ASA training.
Upcoming flotillas include Sicily, BVI, Croatia, Mexico, and in summer 2027, Tahiti, where we will celebrate 10 years of building friendships and camaraderie one stunning sailing location at a time!
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