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Philipsburg

Sailing Trips & Tours

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Our most recommended Philipsburg Sailing Trips & Tours

Simpson Bay: Lambada Sunset Cruise of Sint Maarten

1. Simpson Bay: Lambada Sunset Cruise of Sint Maarten

Enjoy a perfect ending to a beautiful day in paradise on an evening cruise around the coastline of Sint Maarten. This coastal cruise on board the Lambada catamaran is truly spectacular and a tour that you will remember forever. Enjoy sightseeing as the Lambada sails from Pelican Marina on Simpson Bay up the coast to Long Bay, straight into the setting sun. Great music and an array of tasty snacks and drinks are provided for your enjoyment aboard the boat. Enjoy the spacious decks of the boat and relax on the nets set up on the front of the bow while the experienced crew provide excellent service and cater to your needs.

Full-Day Catamaran Sail to Prickly Pear and Anguilla

2. Full-Day Catamaran Sail to Prickly Pear and Anguilla

Enhance your St. Maarten holiday with a full-day sail to the gorgeous and unspoiled islands of sun and sand – Anguilla and Prickly Pear. The Lambada has a 17-year history of party boat fun, family gatherings, and an outstanding crew, and is always a top-ranked excursion. Departing from Simpson Bay Resort, the Lambada sails up the west coast of St. Maarten, and from Plum Point across the channel, and to Prickly Pear Island for snorkeling. Non-swimmers can also enjoy the beach and shallow clear water! Enjoy a tasty meal at Johnno's Prickly Pear. Choose the BBQ chicken, fish, or ribs buffet, and then enjoy some free time beach combing, swimming, or relaxing in the sun. Stop for swim at a beach on the way home. Like all the beaches on Anguilla, the sand is white and the waters a breathtaking turquoise blue. During the nice leisurely sail back you’ll be treated to foot-tapping Caribbean rhythms and a tasty rum punch.

St. Martin: Private Speed Boat Day Charter

3. St. Martin: Private Speed Boat Day Charter

Enjoy a once-in-a-lifetime experience as you enjoy the sensations of a speed boat ride and select your own itinerary for the day. This private day charter is fully personalized to any of your needs, from the pick-up and drop off time, to the places that you visit and the activities that you participate in. That could be a family day full of activities such as snorkeling, cliff jumping and watching large planes few feet above you in Maho Bay, or a romantic cruise out from the crowd or even a beach party with your friends on an uninhabited island! No matter what activities you choose, you will enjoy an open bar and snorkeling gear. You can let your guide recommend some great restaurants for lunch time, or you can bring your own picnic lunch.

St. Maarten: Half-Day Moon Dance Sailing Charter

4. St. Maarten: Half-Day Moon Dance Sailing Charter

Head off shore and explore St. Maarten on a half-day sailing charter. The Moon Dance leaves from Simpson Bay on a voyage of exploration of the St. Maarten coastline, its beaches, and some of the neighboring islands. You can choose to relax on deck and enjoy the beauty of the coastline, or help out and become a part of the crew. You can try your luck fishing with the poles available on board, or use the kayak to access the shore. Whatever you choose to do during the sail the views are guaranteed to be spectacular! Although lunch is not included in the price of the charter you’re welcome to bring along a lunch to enjoy on deck or to opt for a meal at the Lolo Shacks. Make the most of your stay and set sail on a Moon Dance charter!

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What people are saying about Philipsburg

Overall rating

4.7 / 5

based on 42 reviews

The sunset tour was beautiful and the vibes were exactly what you’d hope for. The crew was great and made sure our drinks were never empty. We would absolutely recommend this to anyone visiting Sint Maarten!

Sam, our captain, was awesome. He knew the best places to snorkel, swim and eat. We were able to swim with sea turtles! He even took photos for us. He also took us to watch the planes take off. Very cool.

We had such a great time! Our guide Sam was wonderful. The boat ride was a blast and he took us to beautiful spots all around St. Maarten. If you’re headed to St Maarten, you should book this tour!!

The day has flown by. Sam, our captain, was able to tell a lot about the island and the surrounding area. Put together the day in consultation, seen a lot!

Too much fun for a 90 minute cruise. The crew was over the top dedicated to everyone having a great time.