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Sail St Maarten

8 Days, 7 Nights
Start
Finish
Status
Price
Deposit
December 2025

Saturday

Dec 6, 2025

Dates

Saturday

Dec 13, 2025

Status

Available+

Available+

This trip is available. Once you book your spot, your trip leader will reach out within 72 hours and provide you with the next steps in preparing for your adventure.

Price
EARLY BIRD Price

$3,185 CAD

$2,495 USD

Deposit

50%

50%

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BOOK
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SOLD OUT
NOT AVAILABLE

Sail St Maarten

This Is a 7-Day Sailing Trip Across St Maarten & Anguilla for Solo Travelers!

Sail St Maarten

This Is a 7-Day Sailing Trip Across St Maarten & Anguilla for Solo Travelers!

7 Days | From $2,195
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Sail St Maarten | 7 Day Sailing Trip | December 7-14, 2024
Itinerary
Accommodations
FAQs
Trip Dates
STARTING FROM  $2,475 USD
4 SPOTS LEFT
DATES + BOOK
3 Day Trip | From $705 CAD
SEE PRICES
4 SPOTS LEFT
 |  FROM $2,475 USD
DATES & BOOK
Black Friday Sale | $500 OFF | Nov. 23 - 29
DATES & BOOK
What To Expect

29° C

Average temperature in high season.

Beaches & Adventure

Incredible beaches, open-ocean sailing, remote islands.

Local Cuisine

Seafood, tropical fruits, plantain, local rums.

10 people per yacht

Average age is 32; even mix of male and female.

How Tryps Sails St Maarten!

This is not your typical Caribbean resort vacation. You and your crew will experience the Caribbean like never before. Your yacht will be your home and vehicle throughout this adventure. Alongside your crew and private Skipper, you’ll discover 3 countries and 6 different islands. 

You’ll first sail along the multicultural nation of St Maarten which is uniquely split in two halves - one side French, and the other Dutch. You will then witness the precious nature of Anguilla and its surrounding islets where you will enjoy the freshest seafood and true tranquility of virgin beaches that can only be reached by sailboat. And then there is the majestic wilderness of Tintamarre Island which is a haven for biodiversity and known for its prominent sea turtles. Along the way you’ll relax on the finest white-sand beaches, discover local culture, feast on the freshest seafood, snorkel with marine life in turquoise water, and witness the most stunning sunsets from the middle of the sea. 

DAY 01

Welcome to St Maarten!

Your journey begins on the island of St Maarten in the tropical West Indies. You’ll land at Princess Juliana International Airport (SXM), located on the Dutch side of the island. Upon arrival you'll make your way to the marina where you’ll be greeted by your Skipper and sailing crew. This first day will be dedicated to settling into your yacht, gathering groceries with your crew, and preparing for your sailing adventure on the Caribbean Sea.

DAY 02

Anguilla

After breakfast on your yacht, your crew will undergo a brief orientation led by your Skipper. You’ll learn some basic sailing etiquette, lingo, and skills. Sailing is a team effort and everyone in your crew will be given a role and responsibility throughout the adventure. All aboard! We set sail towards the gorgeous island of Anguilla. With its powdery white beaches, crystal-clear turquoise waters, and vibrant local culture, this island will feel like a dream. Today you will relax at sea under the Caribbean sun, explore the island by scooter, or go horseback riding along the beach side.

DAY 03

Prickley Pear Cays

When islands have little babies, we call them islets! We will spend the day exploring the gorgeous islets off the coast of Anguilla. Known for their rugged beauty, the uninhabited miniature islands are described as tropical paradises, with tons of marine and bird life. It’s meant to be a day of relaxing, snorkeling, and swimming with sea turtles. For lunch, we’ll stop by the Prickly Pear Island for a beachside seafood feast! Get your fix of lobster, crab, fried cod, plantains and tasty local punch. We’ll spend the evening on our very own tropical private island, finishing the night with a bonfire and gazing at the stars.

DAY 04

Marigot

We now sail to the other end of St Maarten to explore the French capital of Marigot. Nestled along the picturesque shores of the Caribbean Sea, Marigot is a blend of French flair and Caribbean charm. Wander through the cobblestone streets of the Old Town, where colorful colonial buildings house boutique shops, sidewalk cafes, and artisanal markets offer handmade treasures and local delicacies. Here, you’ll witness the bustling marina, local fishermen, and the waterfront restaurants that serve up delicious French and Creole cuisine with stunning ocean views. In the evening, we’ll dine on local fresh fish, roam the streets, and experience the bars and live music venues to get a taste of French-Caribbean culture.

DAY 05

Tintamarre

We’ll anchor by the wild and tropical island of Tintamarre. This tiny uninhabited island is a protected natural gem, with pristine white sandy beaches, crystal-clear turquoise waters, and lush greenery. It’s a paradise for nature lovers and beach lovers alike. Today’s dedicated to kicking our feet back, soaking up the sun, swimming in the turquoise sea surrounding us, and living the ultimate boat life. We’ll do snorkeling where you may encounter curious marine animals and happy dolphins playing in the waves. Dinner will be enjoyed on the yacht and the night will end with a cocktail party aboard.

DAY 06

Phillipsburg

The journey takes us to Philipsburg, the Dutch capital of St Maarten - a city of colorful streets, a bustling waterfront, and lively atmosphere. Today we will spend most of the day on land. Take a stroll through the vivid city, discover the hilly interior, or spend the day at the nearby Great Bay Beach. There are a number of optional activities you can choose from like the Flying Dutchman (the world’s longest zip line!) or renting ATVs and touring the island at your own pace. We won’t  have to remind you to indulge in the flavourful Caribbean cuisine at beachfront restaurants and open-air cafes, where fresh seafood and tropical cocktails are served with a side of island hospitality. For those looking to shake their hips to some Caribbean beats, we invite you to join a night crawl of the local music venues in the capital. 

DAY 07

Simpson Bay

Fun fact - St Maarten is the smallest inhabited island in the world that is shared among two nations (France and Netherlands). We’ll sail to Simpson Bay Lagoon which shares a border with the French and Dutch side of the island. That’s right, you’ll visit two countries in one single day, lounging on as many of the island’s 37 beaches as possible. You’ll also have the opportunity to explore Simpson Bay Village, active with lively bars, waterfront restaurants, and charming boutiques offering local crafts and souvenirs. We’ll visit the Topper’s Rum Distillery where we’ll taste every possible type of infused rum you can imagine! On this final night of the adventure, we’ll enjoy a farewell feast with the entire crew at a delicious local restaurant.

DAY 08

Farewell

Today we dock the boat at port and pack our bags. We head back home with amazing memories and a new travel family. A sailor’s salute to the crew! Where one journey ends, another Tryp begins.

DAY 01

Welcome to St Maarten!

Your journey begins on the island of St Maarten in the tropical West Indies. You’ll land at Princess Juliana International Airport (SXM), located on the Dutch side of the island. Upon arrival you'll make your way to the marina where you’ll be greeted by your Skipper and sailing crew. This first day will be dedicated to settling into your yacht, gathering groceries with your crew, and preparing for your sailing adventure on the Caribbean Sea.

DAY 02

Anguilla

After breakfast on your yacht, your crew will undergo a brief orientation led by your Skipper. You’ll learn some basic sailing etiquette, lingo, and skills. Sailing is a team effort and everyone in your crew will be given a role and responsibility throughout the adventure. All aboard! We set sail towards the gorgeous island of Anguilla. With its powdery white beaches, crystal-clear turquoise waters, and vibrant local culture, this island will feel like a dream. Today you will relax at sea under the Caribbean sun, explore the island by scooter, or go horseback riding along the beach side.

DAY 03

Prickley Pear Cays

When islands have little babies, we call them islets! We will spend the day exploring the gorgeous islets off the coast of Anguilla. Known for their rugged beauty, the uninhabited miniature islands are described as tropical paradises, with tons of marine and bird life. It’s meant to be a day of relaxing, snorkeling, and swimming with sea turtles. For lunch, we’ll stop by the Prickly Pear Island for a beachside seafood feast! Get your fix of lobster, crab, fried cod, plantains and tasty local punch. We’ll spend the evening on our very own tropical private island, finishing the night with a bonfire and gazing at the stars.

DAY 04

Marigot

We now sail to the other end of St Maarten to explore the French capital of Marigot. Nestled along the picturesque shores of the Caribbean Sea, Marigot is a blend of French flair and Caribbean charm. Wander through the cobblestone streets of the Old Town, where colorful colonial buildings house boutique shops, sidewalk cafes, and artisanal markets offer handmade treasures and local delicacies. Here, you’ll witness the bustling marina, local fishermen, and the waterfront restaurants that serve up delicious French and Creole cuisine with stunning ocean views. In the evening, we’ll dine on local fresh fish, roam the streets, and experience the bars and live music venues to get a taste of French-Caribbean culture.

DAY 05

Tintamarre

We’ll anchor by the wild and tropical island of Tintamarre. This tiny uninhabited island is a protected natural gem, with pristine white sandy beaches, crystal-clear turquoise waters, and lush greenery. It’s a paradise for nature lovers and beach lovers alike. Today’s dedicated to kicking our feet back, soaking up the sun, swimming in the turquoise sea surrounding us, and living the ultimate boat life. We’ll do snorkeling where you may encounter curious marine animals and happy dolphins playing in the waves. Dinner will be enjoyed on the yacht and the night will end with a cocktail party aboard.

DAY 06

Phillipsburg

The journey takes us to Philipsburg, the Dutch capital of St Maarten - a city of colorful streets, a bustling waterfront, and lively atmosphere. Today we will spend most of the day on land. Take a stroll through the vivid city, discover the hilly interior, or spend the day at the nearby Great Bay Beach. There are a number of optional activities you can choose from like the Flying Dutchman (the world’s longest zip line!) or renting ATVs and touring the island at your own pace. We won’t  have to remind you to indulge in the flavourful Caribbean cuisine at beachfront restaurants and open-air cafes, where fresh seafood and tropical cocktails are served with a side of island hospitality. For those looking to shake their hips to some Caribbean beats, we invite you to join a night crawl of the local music venues in the capital. 

DAY 07

Simpson Bay

Fun fact - St Maarten is the smallest inhabited island in the world that is shared among two nations (France and Netherlands). We’ll sail to Simpson Bay Lagoon which shares a border with the French and Dutch side of the island. That’s right, you’ll visit two countries in one single day, lounging on as many of the island’s 37 beaches as possible. You’ll also have the opportunity to explore Simpson Bay Village, active with lively bars, waterfront restaurants, and charming boutiques offering local crafts and souvenirs. We’ll visit the Topper’s Rum Distillery where we’ll taste every possible type of infused rum you can imagine! On this final night of the adventure, we’ll enjoy a farewell feast with the entire crew at a delicious local restaurant.

DAY 08

FAREWELL

Today we dock the boat at port and pack our bags. We head back home with amazing memories and a new travel family. A sailor’s salute to the crew! Where one journey ends, another Tryp begins.

What’s Included

During The Tryp

Marina & Port Fees

Fully equipped yacht (includes mileage and insurance)

Professional & internationally certified skipper

Experienced Tryp Leader with you from start to finish

24/7 On-Site Support

Dietary Accommodations

Branded Tryps Dry Bag

Dedicated Content Creator to capture the experience so you don’t have to!

Extra Perks

Flight Booking Assistance

Packing Checklist

Online Orientation Session with your Tryp Leader

Direct Contact with your Tryp Leader through email, text and calls to answer your questions

Remember, flights and food aren't included and prices are based on sharing a cabin. Click here for an estimate of additional costs.
ROUTE

DAY 1

Settle on Board

DAY 2

Sail to Anguilla

DAY 3

Islet Hopping through Prickly Pear Cays

DAY 4

Beach Discovery

DAY 5

Exploring Philipsburg

DAY 6

Discover Marigot

DAY 7

Boat Life at Tintamarre

DAY 8

Our Farewells

Watch Our Adventure Come to Life

Pat’s POV Sailing
St Maarten Memories
Sailing with Tryps

Traveling with a group?

Book A Private Yacht!

Get In Touch

Connect with a Trypper

Meet some of the folks that are part of our Tryps community, ask them questions, and get first hand experience.

Maya | 34
Toronto, Canada
Amalfi 2023
Sarah | 31
Cairo, Egypt
Amalfi 2023

Sites You Will See in the Caribbean

The Coast Line
Tintamarre
Sandy Beaches
Anguilla
Majo Beach
Sint Maarten

Stay in the Know!

Leave your info below to learn about our St Maarten sailing trips.

Accommodations

Check out how you’ll be living on your 7-day sailing adventure.

Pyramisa Luxor Hotel (Luxor)
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Yacht Exterior

Front Deck

Bathroom

Bathroom

Cabin For 2

Cabin For 2

Kitchen

Interior Dining Area

Outdoor Patio

WATCH VIRTUAL TOUR

Chat with Your Tryp Leader

Meet Kimo - A travel aficionado based in Toronto. 

Book a call with Kimo and he’ll walk you through the itinerary, discuss flights and pricing, and answer any of your questions.

book a call
Book a call with Kimo and he’ll walk you through the itinerary, discuss flights and pricing, and answer any of your questions.
book a call

Local Cuisine

How It Works

Never travelled with us before? Don’t worry! We got you in 4 easy steps!

STEP 1

Check Dates

STEP 2

Connect With Your Tryp Leader

STEP 3

Pack Your Bags

STEP 4

Book Your Flight

 CHECK Dates

How It Works

Never sailed before? Don’t worry! We got you in 4 easy steps!

STEP 1

 Choose your group size

STEP 2

 Fly down & meet your crew

STEP 3

We teach you the 1s and 2s of sailing

STEP 4

Set sail and away we go!

BOOK NOW

As Captured on Instagram

The latest from our Tryppers

@salma.527

@pure_patties

@strzkrzysiek

@couma_dan

@lifeisatryp

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FAQs

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Do I need to know how to sail?
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What’s the sleeping arrangement?
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Will we sleep in open waters?
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What’s the size of the group?
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What’s the average age within the group?
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Do I get time on my own to explore?
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Is there power on the boat?
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Can I access the boat when we’re docked at the marinas?
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What are the meals like during the trip?
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Is sea sickness common?
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How do I book my flights?
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Do I need a travel visa?
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 Do I need to travel insurance?
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What’s the Cancellation Policy?
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What’s not included in the price?

Next Trip

Dec. 7-14, 2024

BOOK NOW

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Travel Solo, Adventure Together.

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