Our Tradewinds’ Experience

Why Tradewinds?

I’ve known about Tradewinds for about 10 years through a family member who frequently sails with this company. My husband and I always wanted to try a trip like this, where we could visit remote areas of the world – with a guide – and see sites we wouldn’t usually get to see while leaving the planning to someone else. Tradewinds checked all those boxes for us, and many more. To put it in simply, Tradewinds is the unicorn of luxury travel.

Selecting a Tradewinds' Destination

Tradewinds has a ton of options. They have trips just on the water (AQUA) or just on land in their villas (TERRA) or a combination of both in their AQUATERRA excursions. For us, we wanted the sailing experience somewhere with clear waters without any concerns about weather interruptions. We chose the Grenadines. (see map here)

A Private Yachting Vacation

Sailing with Tradewinds is for owners, members, and referrals only. People who choose to buy into the membership get points to use against trips, all over the world. Their business model is that they attract a certain type of people who love adventures and water, and they assume our friends enjoy the same. So as a member, I can invite friends to try Tradewinds at a 50% discount (which is what we did when we became a member). There’s no hard sales pitch, it’s more like you trying to figure out how the heck to book your next trip while you’re still on your current trip! Kris and I chose to get a membership to invest in us, in a way that’s different than date nights or ski trips with the kids. Both of us love boating, food, and exploring new places, so this membership was a gift just for us.

The Boats

We didn’t really know what to expect. We knew we were going to be sharing a luxury catamaran with 4 other couples and just before the sail we learned we were traveling in a 60-foot boat named “Swept Away”. When we boarded, we were met with hugs from our crew, beverages, and appetizers while we got to know each other and toured the boat.

The crew provides all meals at three set times per day sourcing local food and preparing everything on the boat. The food really blew us away, as did the professionalism and kindness from the crew.

I thought I might get bored on a boat for 7 days, but there were options to go ashore, snorkel or dive in a new location, or just relax. We were able to visit new locations almost every day and we had the perfect balance of stuff to do (if we wanted) and relaxation.

Regarding the boats, there are different classes with different amenities, we were on a luxury class which is somewhere in the middle. My description of the boats won’t come close to doing it justice as the features and comforts were beyond. If you want to know more about their boats, a breakdown of their class system can be found here.


We really didn’t know our itinerary until we got on board. We knew the general area we’d be sailing, but the captain customizes the locations based on weather, wind, and what type of adventures we are looking for. I mentioned I wanted some beach time, and they made every effort at multiple locations to let me walk along the sandy beaches.

Day 1: Canouan

We ‘caught’ the boat in the Canouan Marina, once you land in your departure city, they handle all the local transportation and activities. They set us up for the day at the marina club house on the most beautiful beach. We all flew in at different times and arrived at the club house separately, but were able to meet and make introductions. We anchored in a quiet bay for the night to unpack, snorkel, visit, eat dinner, and settle into our new home for the next 7 days.

Day 2: Mayreau

We sailed to the island of Mayreau. I had read some about the Caribbean before I went on this trip and learned a lot about how important socializing and gatherings are for these small communities. When we went ashore, I noticed that the beach was lined with coconut trees and in between and around all the trees there were firepits where you could see people had previously hung out and drank from coconuts. We hiked up the hill to the small church with a 360’ view of the Grenadines, chatted with some of the locals, and went back to the boat. My impression of Mayreau was that whatever this island might be lacking in monetary wealth, they made up for with color.

We left Mayreau for Union Island with plans to anchor there for the night. Arriving in Union Island, we learned the story of a local man who couldn’t find any land to build his bar, so he started collecting Conch shells and stacking them in the middle of the shallow areas off shore. It’s now a bar for boaters fondly named “Happy Island’. The proprietor is known for his drink called the “pain killer” customized with blended fruit-of-the-moment. We watched the sun start to set from Happy Island and talked to people from all around the world on this tiny piece of land no bigger than our boat. It was a very memorable experience.

Day 3 – Bequia

Sailing to Bequia we got an up-close view of the architectural wonder that is Moonhole. What started in the 60’s as a husband-and-wife team wanting to create a sanctuary and protected area around the western tip of Bequia, turned into a lot larger project. I’m not going to do the story justice here, but I encourage you to read through the website linked above if you’re interested. The 17 structures along the cliffs are made from repurposed materials such as whale bones and native wood, shells, and stones. There are no roads, only walking paths. It’s truly a sight to see.

We anchored overnight in a quiet bay in Bequia and did some snorkeling. We swam with turtles, and at one point were surrounded by at least 2 dozen baby squid with giant eyes and saw so many fish.

We were able to use the dingy from the boat to visit the small town of Bequia. There are some thriving restaurants along the shorefront popular with both the locals and the tourists. It seems the locals make their living mostly through tourism in this area. There’s a path along the beach built into the rock that takes you around part of the island. Some local vendors set up bars along the path, and there’s fine dining as well. Tradewinds also has the Mimosa House along that stretch of beach and is one of their TERRA offerings.

The bay in Bequia seemed to be bustling with local fishermen and fancy yachts. There was a boat that advertised “laundry” services to all the yachts parked in the bay, and a gentleman named Willy who makes carvings from coral, and whale bone that he sells from his boat. Tradewinds has a long friendship with Willey, and they always let him know when they’ll be anchored. He motors out and enjoys a beer while we all bought his handmade keepsakes.

Day 4 – Mustique

Mustique is a privately owned island home to Mic Jagger, Princess Margaret and Tommy Hilfiger – among others. Because it’s privately owned, this island has a completely different vibe than the others. The beaches are untouched, private, and the snorkeling was amazing –  so many rays and turtles. We enjoyed an evening dinner off the boat at the local eatery, Basils.

Days 5-6 – Tobago Cays

Every picture of the Caribbean that looks photoshop’d, I’m convinced was probably actually taken in the Tobago Cays. Crystal Clean blue waters, white sand, uninhabited islands, and sea as far as you can see. We snorkeled in a turtle sanctuary, walked along an empty beach where the rocks were the color of jade, and fed manta rays off the boat.


There aren’t any words that will give the Tobago Cays the justice it deserves; they are one of the world’s wonders. This area is only accessible by boat and thankfully patrolled by a local park ranger to keep the area as pristine as possible for generations to come.

Day 6 – Mayreau & Saltwhistle Bay

Mayreau is a small island in the Grenadines only accessible by boat and has one of the Caribbean’s best beaches, Saltwhistle Bay. The scenery and local flare were mesmerizing. Less than 300 people live on the .46 sq ft island of Mayreau, making it the smallest inhabited island in the Grenadines. Most tourists flock to Saltwhistle Bay where a small stretch of land separates the Atlantic from the calm bay. Locals set up shop selling handmade items, clothing, and variations of the popular Rum punch. We had drinks with a proprietor who shared he lived in a tent behind his bar, his clothing could be seen swinging from the line and his recently acquired puppy joined us as well. This was probably my second favorite stop after the Tobago Cays.


The Friday before you leave the boat, there’s generally a dinner off shore at one of Tradewinds villas. We were lucky enough to get a tour of the Mayreau villas and learned about Tradewinds 28-million-dollar renovations they recently completed. We got to hang out at their infinity pools and ate a three-course meal at their restaurant onsite. We sailed in the evening back to Canouan to dock for the night.

Day 7 – Canouan and Departure

Departure day is a flurry of packing, exchanging contact information with all the new friends you’ve made, and sharing pictures taken throughout the week. Over breakfast we all discuss our next Tradewinds trip and  longtime members offered advice and travel guidance.

Summary & Membership

I’ve been lucky enough to travel to some fun places in my life, but nothing compares to the experience Tradewinds offers. This is an all-inclusive experience. They sent me a survey when the trip was complete, and I really struggled to offer anything in the way of constructive criticism. They have a captain and first mate on board, any alcohol you could want, water activities like kayaks and paddleboarding, and most importantly, AC.  The company is making big strides in the world of sustainable yachting and will be launching its first electric boat hopefully this year. They are continually adding more boats and more locations (both Aqua and Terra). I’m so excited to say we are booked to sail in Greece in 2024.

I’m excited that we decided to buy into a membership and I feel compelled to share this with everyone I know – because it was that amazing. I went on this recent trip as a referral through a current member which gives you 50% off the non-member fee, and I’d be happy to offer that to any of my friends that might be interested, or happy to talk to anyone who may have questions. You can only become a member while on a trip; a weird provision but at least the trip is half off!

Some of the places I saw I might never see again in my lifetime. I feel beyond blessed and grateful to Tradewinds for giving us these memories.

Learn more about Tradewinds here, and please let me know if you end up going. I want the company to know that my raving review encouraged you to consider traveling with them.

For questions about our experience, feel free to email Alaina here.

A huge shoutout to our captain Roly and first mate (and also a captain) Laura for putting up with my frequent requests for iced and long island iced teas and my husband’s inability to keep track of any of his things. You two are the absolute best!

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