Sail St Maarten

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!

Sail St Maarten
7 DAY SAILING TRIP | FROM $2,825 CAD
What To Expect

Itinerary

You’ll discover 3 countries and 5 different islands aboard a sailboat!

DAY

01

Welcome to St Maarten!

Start your vacation right! Hot sun, sandy beaches and Caribbean vibes.

Meet Your Crew

Check-in to Yacht

Welcome Dinner

DAY

02

Sail to Anguilla

Set sail to Anguilla - home of some of the world’s top beaches!

Sailing Orientation

Sail to Anguilla

Scooter Rentals

DAY

03

Islet Hopping

Spend the day island hopping and snorkeling - living your best life at sea!

Island Hopping

Snorkeling

Raft Party

Patrick Flood

“It was easily the best vacation decision of my life!”

DAY

04

Two for One!

Discover St Maarten - boutique shops, live music and plenty of Caribbean rum.

Sail to St Maarten

Majo Beach

Bar Crawl

DAY

05

Exploring Philipsburg

Tour the island and all of its hidden gems via your own ATV!

ATV Touring

Phillipsburg Exploration

Local Rum Tasting

DAY

06

Heading to the French Side

Discover the rich local culture in the streets of Marigot.

Sail to Marigot

Seafood Buffet

Live Music Tour

DAY

07

Boat Life

Take in the sun, sandy beaches and crystal clear waters.

Sail to Tintamarre

Beach Day

Farewell Bonfire

Salma Abou-Aly

“What a unique way to visit the Caribbean! I’ll never forget this experience!”

DAY

08

Until Next Time...

Head home with a hot Caribbean tan and life-long memories!

Sail to Ansel

Yacht Checkout

Airport Transfer

DAY

01

Welcome to St Maarten!

Start your vacation right! Hot sun, sandy beaches and Caribbean vibes.

Meet Your Crew

Check-in to Yacht

Welcome Dinner

DAY

02

Sail to Anguilla

Set sail to Anguilla - home of some of the world’s top beaches!

Sailing Orientation

Sail to Anguilla

Scooter Rentals

DAY

03

Islet Hopping

Spend the day island hopping and snorkeling - living your best life at sea!

Island Hopping

Snorkeling

Raft Party

Patrick Flood

“It was easily the best vacation decision of my life!”

DAY

04

Two for One!

Discover St Maarten - boutique shops, live music and plenty of Caribbean rum.

Sail to St Maarten

Majo Beach

Bar Crawl

DAY

05

Exploring Philipsburg

Tour the island and all of its hidden gems via your own ATV!

Sail to St Maarten

Majo Beach

Bar Crawl

DAY

06

Heading to the French Side

Discover the rich local culture in the streets of Marigot.

Sail to Marigot

Seafood Buffet

Live Music Tour

DAY

07

Boat Life

Take in the sun, sandy beaches and crystal clear waters.

Sail to Tintamarre

Beach Day

Farewell Bonfire

Salma Abou-Aly

“What a unique way to visit the Caribbean! I’ll never forget this experience!”

DAY

08

Until Next Time...

Head home with a hot Caribbean tan and life-long memories!

Sail to Ansel

Yacht Checkout

Airport Transfer

Package Includes

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

Before You Travel

Flight Booking Assistance

Packing Checklist

Detailed Itinerary run through

Budgeting & Spending Tips

Online Orientation Session with your Tryp Leader

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

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

Safety Resources

Dietary Restrictons & Food Allergy Accommodations

Branded Tryps Dry Bag

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

Once You're Home

Curated Photo Album of your Tryp

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

Next Available Trip

December 7-14, 2024

Sites You Will See in the Caribbean

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

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

FAQs

Next Available Trip

December 7-14, 2024