St Martin and Leewards Voyage

Dates: Nov – June |  Departure: St Martin  |  Group Size: Flexible |  Price: Starting at $2450 per person

Join MountainSea for a one week sailing adventure through the Leeward Islands of the Caribbean. We will embark from St. Martin to the islands of Tintamarre, Ile Fourche, St. Barths, and Anguilla. The package will include all food catered and prepared by your professional chef, a trained skipper with expert knowledge of the cruising grounds, sailing, snorkeling, paddleboarding, hiking, sunny beaches, town time… all experienced from the comfort of a luxury sailing catamaran.

Create Your Own Adventure…Do as much or as little as you would like throughout the week. If you are interested in learning how to sail, your captain is a certified sailing instructor and can give you a certification through the American Sailing Association. If you want to relax and enjoy the sights only, thats okay too! You may decide to help sail the yacht one day, but not the next. It is all completely up to you. 

This voyage is led by MountainSea head crew Captain Colin and Chef Sarah. They bring years of experience leading yacht charters all over the world, and can’t wait to share their love of the Leeward Islands with you!

St Martin and the Leewards Highlights

  • Enjoy French Caribbean cuisine onboard and ashore
  • Sample St Martin’s guavaberry rum     
  • Sunbathe on the beaches of St Barths
  • Go cliff jumping in Anguilla
  • Snorkel with sea turtles, sting rays, and colorful reef fish
  • Hike a cliffside trail from beach to beach
  • Feed iguanas on Ile Pinel
Day 1 – St Martin and Ile Tintamarre

We’ll meet at Port Louis Marina in Marigot on the French side of St. Martin. After a quick yacht briefing and settling in, we’ll sail to Ile Tintamarre, a small island with a long, pristine, white sandy beach. Swim, hike or relax while the sun sets! Tonight, we will have an easy dinner of salad, French cheeses, fresh baked baguettes.

Day 2 – Columbier, St Barths

After a breakfast of local fruits, granola and yogurt, relax and put your feet up or go for a snorkel on the tugboat in Tintamarre, which sits in about 35’ of water. See amazing marine life from spotted eagle rays to gigantic lobster. This afternoon, we will sail to Colombier, a popular bay in St. Barths for locals to spend the weekend boating, partying and relaxing. There is an excellent hike over to the windward side where we can bodysurf in the waves or walk down the long white sand beach to stretch your legs. There is great snorkeling in our anchorage if you didn’t get enough this morning.

Day 3 – Gustavia, St Barths

Wake up to a small breakfast, save your appetite though because where we’re going has some of the best crepes and bakeries in the Caribbean! We will sail to Gustavia, the main town and capital of St. Barths. It’s a swanky little harbour known for its celebrity sightings. A must to walk through once, enjoy brunch at the creperie and provision as necessary. Next, we’ll motor around the corner to Shell Beach where there is a cliff to jump for all levels depending on your appetite for adventure! Tonight, we’ll head to town for dinner at Pipiri Palace, known for their fresh lobster.

Day 4 – Ile Fourchue

A marine protected and uninhabited island of St. Barths, Ile Fourche is a great place to snorkel with excellent, easily accessible reefs. The island offers one of the best places around to take in a sunset after hiking up to the highest point on the island. For dinner, we’ll barbecue some local fish over rice and veggies. Wind down by watching shooting stars up on the trampoline!

Day 5 – Anguilla

Today is our longest sail, over 30NM. On this trip feel free to pull the lines, hoist the sails and crank the winches. Your skipper is a trained sailing instructor, so pick his brain about all that is sailing. If you prefer to relax, kick back on the trampoline with a book, however keep your eyes open for playful dolphin and flying fish.

Day 6 – Marigot, St Martin

We’re off to Sandy Island for a lazy day of relaxing under the palm trees in a hammock, swim around the tiny spit of an island and grab a frozen drink at the one bar here. Today choose how adventurous you feel. Stay around the pristine quintessential Caribbean cay or head slightly north to explore Prickly Pear. It’s then back to St. Martin with another fantastic sail to windward around Anguilla. Test those sailing skills you learned a couple days ago while we tack back and forth. We arrive in the late afternoon to Marigot Bay. Tonight, we celebrate our last night onboard by going out to eat at Calypso, a favorite restaurant in the area.

Day 7 – Farewell!

Unfortunately, today we must leave our beloved yacht and head off to new adventures. It was a pleasure having you all onboard and we look forward to sailing with you again in the near future!


What’s Included:

  • Captain
  • Chef
  • All breakfasts, lunches, and snacks
  • 3 Dinners onboard
  • Water and all non-alcoholic beverages onboard
  • 6 Nights in double stateroom with ensuite lavatory
  • Snorkeling equipment
  • Water toys
  • Kayak/Paddleboard
  • Yacht fees, fuel costs, marina fees
  • MountainSea hat

Optional Services:

  • American Sailing Association Certifications
    • ASA 101 – Basic Keelboat Sailing
    • ASA 103 – Coastal Cruising
    • ASA 104 – Bareboat Chartering
    • ASA 114 – Cruising Catamarans
  • Scuba Diving
  • Airport transfers

Not Included:

  • 3 Meals onshore
  • Attraction entrance fees
  • Alcoholic beverages (Many places to buy throughout the voyage)
  • Airfare
  • Travel insurance
  • Crew gratuity

“What an amazing experience! This trip took us out of our comfort zone just enough to be a great adventure. We saw beautiful sunrises and sunsets over the horizon, swam in clear blue waters and slept out on the deck under the stars. Our guide and Captain, Ted did a great job sailing the boat while sharing his knowledge of the process and the islands we visited. Highly recommend a trip like this with MountainSea for families or a group of friends!”

Randy and Jen