About Your Tryp

This is a 7-day sailing trip in the Caribbean Sea for solo travellers.

Alongside your crew and private Skipper, you’ll discover 2 countries and 5 different islands aboard a sailboat. You’ll sail through the multicultural nation of St Maarten and witness the precious nature of Anguilla. 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 out at sea. We take care of all the nitty gritty planning so you can focus on living your best life at sea, and connecting with other adventurers!
‍
This is the ultimate experience at sea!

Sailing Facts

What’s the Weather Like?

The weather in the Caribbean Sea averages around 29°C during the day and 24°C at night.

24°C

Average Temperature in high season

Do I Need To Know How To Sail?

Nope! You’ll be in great hands with our internationally certified skipper. They’ll take care of the sailing business so you can focus on living your best life at sea!

Will We Sleep In Open Waters?

No, each night we dock in a marina or off the shore. You’ll have ample opportunities to go on land and check out the different islands and cities we visit.

Timezone

Eastern Time Zone

Top 5 Experiences

Learning the Basics of Sailing
Sunsets at Sea
Beach Bonfires
Island Hopping
Snorkeling

Top 5 Dishes To Try

Fresh Seafood
Conch and Dumplings
Codfish Fritters
Local Rum! (it’s that good!)
Locri

Subscribe to our Sail Caribbean mailing list!

Drop us your email to hear updates on our upcoming sailing trips to Caribbean and to access some great travel deals!

Package Includes

Spectacular sailing, breath-taking landscapes, and an incredible group of other solo travellers.

Fully equipped yacht (includes mileage and insurance)

Professional & internationally certified skipper

5 unique island visits

Max 10 travellers per yacht

Experienced Tryp Leader with you from start to finish

Remember, flights and food aren't included and prices are based on sharing a cabin. Single room upgrades are available. 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

Itinerary

DAY

01 Welcome to St Maarten!

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 Anse Marcel Marina where you’ll be greeted by your Skipper and Sailing Crew. This first day will be dedicated to settling into your sailboat, gathering groceries with your crew, and preparing for your sailing adventure on the Caribbean Sea.

DAY

02 Sail to Anguilla

After breakfast on your sailboat, you and 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.

DAY

03 Islet Hopping

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 a large abundance of marine and bird life. It’s meant to be a day of relaxing, snorkeling, and swimming with sea turtles.

DAY

04 Two for One!

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. Today you’ll visit two countries in one single day, lounging on as many of the island’s 37 beaches as possible.

DAY

05 Exploring Philipsburg

The journey takes us to Philipsburg, the Dutch capital of
St Maarten. Today we will spend most of the day on land. You could take a stroll through the colourful city, discover the inland, or spend the day at the nearby Great Bay Beach.

DAY

06 Heading to the French Side

We now sail to the other end of the island to explore the French capital of Marigot. Here, you’ll see the rich culture, the local fishermen on the bay and the live music along the strip.

DAY

07 Boat Life

We’ll anchor our sailboat by the wild and tropical island of Tintamarre. It’s our last full day in the tropics. 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.

DAY

08 Until Next Time...

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

DAY

01 Welcome to St Maarten!

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 Anse Marcel Marina where you’ll be greeted by your Skipper and Sailing Crew. This first day will be dedicated to settling into your sailboat, gathering groceries with your crew, and preparing for your sailing adventure on the Caribbean Sea.

DAY

02 Sail to Anguilla

After breakfast on your sailboat, you and 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.

DAY

03 Islet Hopping

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 a large abundance of marine and bird life. It’s meant to be a day of relaxing, snorkeling, and swimming with sea turtles.

DAY

04 Two for One!

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. Today you’ll visit two countries in one single day, lounging on as many of the island’s 37 beaches as possible.

DAY

05 Exploring Philipsburg

The journey takes us to Philipsburg, the Dutch capital of St Maarten. Today we will spend most of the day on land. You could take a stroll through the colourful city, discover the inland, or spend the day at the nearby Great Bay Beach.

DAY

06 Heading to the French Side

We now sail to the other end of the island to explore the French capital of Marigot. Here, you’ll see the rich culture, the local fishermen on the bay and the live music along the strip.

DAY

07 Boat Life

We’ll anchor our sailboat by the wild and tropical island of Tintamarre. It’s our last full day in the tropics. 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.

DAY

08 Until Next Time...

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

EMAIL ME THE ITINERARY

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Drop us your email to hear updates on our upcoming sailing trips and to access some great travel deals!

Chat with Your Tryp Leader

Meet Kimo: A travel aficionado based in Toronto.

“Think crystal clear water, white sand and good times. Over 7 days, we’re island hopping across 2 countries. This trip is all about beautiful beaches, remote islands and local Caribbean vibes!”

@kimobythetree

book a call

Caribbean Highlights

Island hopping on our own private yachts!

The Coast Line

Tintamarre

Open Sea

St Martin

Sunset

Tintamarre

Sandy Beaches

Anguilla

Majo Beach

Sint Maarten

Accommodations

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

Yacht Exterior

Front Deck

Bathroom

Cabin For 2

Kitchen

Indoor Dining Area

Outdoor Patio

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

Pat, Caribbean 2021

“The most special trip I’ve been on in my life!”

“Took my first Tryp last week. 11 people on a boat sailing the Caribbean for 7 days. It was easily the best vacation decision of my life. We hit 3 countries, spent nights by a fire on completely secluded beaches, laughed hysterically and found new friends that I now get to call my family. Moving forward, I’d do any Tryp I can get my hands on. This is unmatched boutique tourism!”

Watch Video

Pat, Caribbean 2021

“The most special trip I’ve been on in my life!”

Watch Video

As Captured on Instagram

The latest from our Tryppers

@salma.527

@pure_patties

@strzkrzysiek

@couma_dan

@lifeisatryp

Sail The Caribbean

Saturday

Dec 9, 2023

Saturday

Dec 16, 2023

Limited Spots

$2195

$600

Saturday

Dec 7, 2024

Saturday

Dec 14, 2024

Available

$2195

$600

Drop Your Info

Sail the Caribbean

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

Sail the Caribbean

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

About Your Tryp

This is a 7-day sailing trip in the Caribbean Sea for solo travellers.

What’s the Weather Like?

24°C

Do I Need To Know How To Sail?

Will We Sleep In Open Waters?

Timezone

Top 5 Experiences

Top 5 Dishes To Try

Subscribe to our Sail Caribbean mailing list!

Package Includes

Spectacular sailing, breath-taking landscapes, and an incredible group of other solo travellers.

DAY 1

DAY 2

DAY 3

DAY 4

DAY 5

DAY 6

DAY 7

DAY 8

Itinerary

DAY

01

Welcome to St Maarten!

DAY

02

Sail to Anguilla

DAY

03

Islet Hopping

DAY

04

Two for One!

DAY

05

Exploring Philipsburg

The journey takes us to Philipsburg, the Dutch capital of St Maarten. Today we will spend most of the day on land. You could take a stroll through the colourful city, discover the inland, or spend the day at the nearby Great Bay Beach.

DAY

06

Heading to the French Side

We now sail to the other end of the island to explore the French capital of Marigot. Here, you’ll see the rich culture, the local fishermen on the bay and the live music along the strip.

DAY

07

Boat Life

We’ll anchor our sailboat by the wild and tropical island of Tintamarre. It’s our last full day in the tropics. 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.

DAY

08

Until Next Time...

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

DAY

01

Welcome to St Maarten!

DAY

02

Sail to Anguilla

DAY

03

Islet Hopping

DAY

04

The journey takes us to Philipsburg, the Dutch capital of
St Maarten. Today we will spend most of the day on land. You could take a stroll through the colourful city, discover the inland, or spend the day at the nearby Great Bay Beach.

Are you
ready?