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St. M, One Cool Island

Updated: Jun 19, 2023

St. M is a super cool island. The options are endless while you’re there. We’ve stopped there 3x while cruising over the years. A friend of a friend suggested we look into an excursion with Random Winds Charters to get out on the water and see the coastline and swim. Wow – I can’t even begin to tell you how amazing this experience was. We loved them so much, we actually booked with them during our visit a second time.



In choosing an excursion, you need to do a lot of research. You don’t just grab the first thing you see Random Winds Charters hosts small groups on a 50 ft Catamaran. A woman and her little dog live on the boat and host tourists who want a private and unique experience. We were blown away.


When your ship docks in the port, you walk through a very pleasant, small port area. Leaving the port is very safe and super easy. We walked about 15 minutes to the marina where we boarded. (The

grandparents took a taxi). The marina has a few little shops. One is a cheese shop. Yes, free samples!


When everyone arrived, we kicked off our shoes and boarded the boat. Our son was 7 or 8 on this trip and it was fantastic. Two crazy once-in-a-lifetime things happened during our first trip. 1 – I actually swung off a rope swing from the boat and lived to tell about it! 2 – we sailed right into the Heineken Beer Annual Regatta. An actual Regatta was in progress. It was amazing.



When we arrived in the open sea, we pulled our sail down and all decided to stay and watch for a bit. Amazing doesn’t describe it. Regatta boats listing and spraying water – it was the best. We also saw some of the most expensive sailing boats in the world. Think Russian Oligarchs and some of the wealthiest celebrities on the planet. (I could tell you, but I’d have to kill you.)



When traveling with multigenerational travelers, you need to be sure that the vendor you’re working with understands the needs of each family member. Being sure that there is seating, shade, water, and a

variety of types of food are all things that can really make a difference. Don’t just assume… check with the professionals.

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