*Both deposits are refundable for tryp credits up until 60 prior to the start date of your Tryp.

*Final balance is non-refundable.

Boat Tryp Payment Schedule

*Both deposits are refundable for tryp credits up until 60 prior to the start date of your Tryp.

*Final balance is non-refundable.

*Both deposits are refundable for tryp credits up until 60 prior to the start date of your Tryp.

*Final balance is non-refundable.

COVID-19 Travel Update - Steps We Are Taking to Prioritize Your Health and Make Travel Flexible & Easy!

Boat Tryp

Sail the warm seas. Connect with your crew. Explore unique destinations. 

Customer Reviews

Tryp Highlights

Traveling the tropics the right way.

Sailing

Travel by sea on board your private yacht through three different countries: St Maarten, Anguilla, and St Bart’s. This is the most unique way to experience the islands of the Caribbean Sea.

Snorkeling

The Caribbean Sea will be your backyard and your yacht comes equipped with snorkeling gear. Swim in the warm sea surrounding you and connect with the diverse marine life at your fingertips.

Local Culture & Cuisine

Discover local customs and feast on the freshest seafood. Your tastebuds will be ecstatic as we explore restaurants and local food markets throughout the journey.

Island Hopping

Explore three countries and six islands in one shot. Everyday you’ll sail to a new destination with the opportunity to adventure in-land and along the beautiful coast.

Private Yacht

 You and your crew will be sailing on a private yacht navigated by a professional and internationally certified Skipper (your captain)! The yacht is equipped with everything that you need for the most comfortable and epic week at sea.

Activities & Excursions

Get off the beaten path for some unforgettable experiences. For those looking for some extra fun, you can partake in optional activities that include Mountain Ziplining, ATV Excursions, Rum Tours, and Island Night Crawls.

About Your Tryp

This is the most unique vacation at sea, bringing together like-minded travelers to discover the world differently - on board a sailboat.

Over the course of seven days, 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 sail through the multicultural nation of St Maarten, witness the precious nature of Anguilla, and experience the celebrity island of St Barts. 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.

How it works

Never sailed before? Don’t worry! Here’s what you need to know.

1. Choose Your Group Size

Full Yacht (9 People): Book your own private yacht with a group of friends.

Cabin (2 People): Book a two person cabin on a shared yacht.

Solo Traveler: Grab your adventurous spirit and book yourself an individual spot on a yacht. You’ll share a same-sex bunk cabin with another like-minded solo traveler.

*Note: All yachts include a Certified Skipper on board with you.

2. Fly Down & Meet Your Crew

On Day 1 of your Boat Tryp, you’ll be greeted by your Skipper and Boat Tryp Crew. This first day will be dedicated to settling into your sailboat, doing a grocery run with your crew, and preparing for your sailing adventure.

3. Orientation

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.

4. Set Sail

 And away you go into the big blue sea. Your Skipper will navigate you safely through paradise alongside other Boat Tryp yachts. Most meals will be enjoyed on board with your crew, with the occasional in-land restaurant dinners. Your yacht is fully equipped with a kitchen, dining area, front deck, patio, audio system, sleeping cabins, bathrooms, and everything that you need for the most comfortable and epic week at sea.

5. Return Home

After the adventure, your boat will dock at the same location it started. You head back home with a hot tan and a new family of international travelers.

(before April 30TH)

*Taxes and fees included. Airfare to and from Egypt not included.

Looking for a Private Tour?

Let’s customize a personally-tailored experience for your group!

CONTACT US

Health & Safety

Steps We Are Taking to Prioritize Your Health

As per the protocols of these countries, all Tryppers must provide proof of vaccination and a negative PCR test upon entry. For passengers who require a PCR test to return home: Tryps can facilitate your PCR test before returning to your home country.

At Tryps we’re grateful to welcome back our Tryppers! To ensure we can continue to move on the right path as a global community while traveling safely, we’ve meticulously evaluated all of our experiences and protocols to make sure we respect and protect the wellbeing and safety of our community. In consultation with public health and the government of Canada, we have developed a series of protocols to keep you safe.

Learn More

The Route

7 Nights, 6 Islands, & 1 Unforgettable Sailing Experience!

Itinerary

Day 1
Arrive in St Maarten (flight not included)

Day 2
Sail to Anguilla

Day 3
Islet Hopping through Prickly Pear Cays

Day 4
Beach Discovery

Day 5
Exploring Philipsburg

Day 6
Celebrity Status in St Barts

Day 7
Boat Life at Île Fourchue

Day 8
Farewell

Group Discounts

For groups of 2 and groups of 4!

BOOK NOW

What’s Included?

Multiple countries, island hopping, and your private yacht at sea!

Transportation / Accommodation

Fully Equipped Yacht
Mileage
Insurance

Staff

Professional & Internationally Certified Skipper
Tryps Director

Island Visits

St Maarten
Anguilla
Prickly Pear Cays
St Bart’s
Île Fourchue

Equipment

Dinghy & Outboard Engine
Yacht Audio System
Bed Linens
Pillows
Towels
Plates, Cups, and Cutlery
Kitchenware
Life Jacket
Branded Tryps Drawstring Bag

Tryp Dates

Oct. 1ST - 14TH 2020

Cities

5

Nights

13

All for

$3,100 CAD $3,700 CAD

(before April 30TH)

*Taxes and fees included. Airfare to and from Egypt not included.

Additional Costs

The below costs are not included in the listed prices.

Flight

Transfer to and from airport

Food/groceries

Meals for Skipper

Port fees, yacht fuel, & water

Water taxis

Optional activities

Refundable yacht deposit

*For an estimate of additional costs, click here.

Boat Tryp Itinerary

We are now booking for our 2021 Boat Tryps!

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 andBoat Tryp Crew. This first day will be dedicated to settling into your sail boat, gathering groceries with your crew, and preparing for your sailing adventure on the Caribbean Sea.

DAY

02

Sail to Anguilla

After breakfast on our sailboat, you and your crew will undergo a brief orientation led by your Skipper. You’ll learn some basic sailing etiquette, lyngo, 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 37 beaches that the island has to offer.

DAY

05

Exploring Philipsburg

The journey continues as we make our way 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

St Barts - Celebrity Status

We now sail to St Barts, the destination of choice for the world’s most influential individuals and celebrities. Officially known as St Barthelemy, this French island blends the sophistication of St. Tropez with the laissez-faire Caribbean lifestyle.

DAY

07

Boat Life

En route back to St Maarten, we’ll anchor our sailboat by the wild and tropical island of Fourchue. 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 Boat Tryp 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 our sailboat, you and your crew will undergo a brief orientation led by your Skipper. You’ll learn some basic sailing etiquette, lyngo, 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 37 beaches that the island has to offer.

DAY

05

Exploring Philipsburg

The journey continues as we make our way 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

St Barts - Celebrity Status

We now sail to St Barts, the destination of choice for the world’s most influential individuals and celebrities. Officially known as St Barthelemy, this French island blends the sophistication of St. Tropez with the laissez-faire Caribbean lifestyle.

DAY

07

Boat Life

En route back to St Maarten, we’ll anchor our sailboat by the wild and tropical island of Fourchue. 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.

DOWNLOAD PDF

The Next Boat Tryp

We’ll be hitting the seas once again in 2021! Leave your email below to be the first to know about the next Boat Tryp.

Accommodations

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

Yacht Exterior

Your yacht is equipped with:
4 Cabin Rooms
4 Bathrooms & Showers
1 Single Loft
Full Kitchen
Outdoor Patio
Indoor Dining Area
Front Deck

Cabin for 2

There are 4 private cabins onboard your yacht. The private cabin includes a comfortable bed for 2 and a private bathroom equipped with a toilet, sink, and shower.

Bathroom

There are 4 bathrooms onboard your yacht, 1 per cabin. Bathrooms are equipped with a toilet, sink, shower, and storage space for your belongings.

Indoor Dining Area

This area is equipped with seating, a dining table, storage space, and is surrounded by windows for the best of views.

Kitchen

The kitchen is fully equipped with a sink, gas stove, oven, fridge, counters, and storage space for food and equipment. All basic kitchen items are also included such as cutlery, plates, utensils, pots, and pans.

Outdoor Patio

This area of the yacht is equipped with comfortable seating and a dining table.

Front Deck

The best seat in the house! The Front Deck is equipped with tanning nets and plenty of space to enjoy the warm sun and fresh breeze from the sea.

Yacht Exterior

Your yacht is equipped with:
4 Cabin Rooms
4 Bathrooms & Showers
1 Single Loft
Full Kitchen
Outdoor Patio
Indoor Dining Area
Front Deck

Cabin for 2

There are 4 private cabins onboard your yacht. The private cabin includes a comfortable bed for 2 and a private bathroom equipped with a toilet, sink, and shower.

Bathroom

There are 4 bathrooms onboard your yacht, 1 per cabin. Bathrooms are equipped with a toilet, sink, shower, and storage space for your belongings.

Indoor Dining Area

This area is equipped with seating, a dining table, storage space, and is surrounded by windows for the best of views.

Kitchen

The kitchen is fully equipped with a sink, gas stove, oven, fridge, counters, and storage space for food and equipment. All basic kitchen items are also included such as cutlery, plates, utensils, pots, and pans.

Outdoor Patio

This area of the yacht is equipped with comfortable seating and a dining table.

Front Deck

The best seat in the house! The Front Deck is equipped with tanning nets and plenty of space to enjoy the warm sun and fresh breeze from the sea.

Costs

North, South, East and West. We’re covering it all!

Tryp Dates

Apr 2ND - 16TH 2020

Cities

5

Nights

14

All for

$2,965$2,660 USD

until Jan 31ST

Tryp Dates

Apr 2ND - 16TH 2020

Cities

5

Nights

14

All for

$3,900 $3,500 CAD

until Jan 31ST

Tryp Dates

Apr 2ND - 16TH 2020

Cities

5

Nights

14

All for

€2,680 €2,405 EUR

until Jan 31ST

*Taxes and fees included. This price does not include airfare to and from Egypt.

BOOK NOW

Book Your Tryp

Confirm your spot with a deposit of only $250 per person!

Solo Traveler 

Total price per person: $2,295 CAD

BOOK SOLO

Cabin

Total price per person: $2,095 CAD

BOOK CABIN

Full Yacht (9 People)

Total price per person: $1,895 CAD

BOOK YACHT

See Full Payment Schedule.

Traveler Details

Please provide the information requested below and proceed to payment.

Special Requirements

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Easy & Flexible Booking

Let’s Take Away the Stress from Planning Your Next Tryp!

Book with
a Micro Deposit!

Yes, that’s right. Secure your spot on an upcoming Tryp with a micro deposit and pay the rest up to 60 days before your Tryp. Book your next Tryp here!

Flexible
Deposits

Plans change, we get it! Book with us and your deposit is refundable for a Tryp Credit up until 60 days prior to your Tryp start date.

No Change
Fees

 Let us know at least 60 days prior to your Tryp start date and you pay zero fees and your deposit is applied to the new Tryp.

Reviews

5-Stars on Google and Facebook. Read more reviews.

“A Dream Come True!”

This tryp was a dream come true! I couldn't have gone with a more incredible group of people! Every day was a feast for the senses; rich cultural and historical experiences, delicious food, and wonderful people - I couldn't recommend this Tryp highly enough!

Olivia
(Italy)

“Great Human Connections”

Off the beaten path, boats almost everyday, ancient history and culture, and best of all...Great human connections! This Tryp is truly one of a kind. If you're looking for a world class, lifelong experience,  this may be for you!

Chris Weber
(Canada)

“Not at all touristy!”

The experience was not at all touristy, and truly felt off the beaten path which was exactly what I was looking for. It would have been very difficult to do this by myself. To top it off, the group was made up of easy-going, like-minded people. Recommend 100%!

Miguel Parma
(Spain)

“Each day was so unique!”

It was everything I could hope for and more. The hosts took care of us from arrival to departure, by being with us every step of the way. I cannot pick a favourite moment from my Tryp because each day was so special and unique :)

Deanne Abby
(Canada)

“A Dream Come True!”

This Tryp was a dream come true! I couldn't have gone with a more incredible group of people! Every day was a feast for the senses; rich cultural and historical experiences, delicious food, and wonderful people - I couldn't recommend this Tryp highly enough!

Olivia
(Italy)

“Great Human Connections”

Off the beaten path, boats almost everyday, ancient history and culture, and best of all...Great human connections! This Tryp is truly one of a kind. If you're looking for a world class, lifelong experience,  this may be for you!

Chris Weber
(Canada)

“Not at all touristy!”

The experience was not at all touristy, and truly felt off the beaten path which was exactly what I was looking for. It would have been very difficult to do this by myself. To top it off, the group was made up of easy-going, like-minded people. Recommend 100%!

Miguel Parma
(Spain)

“Each day was so unique!”

It was everything I could hope for and more. The hosts took care of us from arrival to departure, by being with us every step of the way. I cannot pick a favourite moment from my Tryp because each day was so special and unique :)

Deanne Abby
(Canada)

Payment Schedule

North, South, East and West. We’re covering it all!

Important Notes

Some tips on how best to plan your Tryp!

Entry Requirements

As per the protocols of these countries, all Tryppers must provide proof of vaccination and a negative PCR test upon entry. For passengers who require a PCR test to return home: Tryps can facilitate your PCR test before returning to your home country.

What is your COVID-19 Policy?

To ensure we can continue to move on the right as a global community while traveling safely, we’ve meticulously evaluated all of our experiences and protocols to make sure we respect and protect the wellbeing and safety of our community. In consultation with public health and the government of Canada, we have developed a series of protocols to keep you safe. Click here to review our COVID-19 travel protocols.

Accomodation

Your crew will be sleeping in double rooms equipped with a bed and a bathroom. If you are travelling solo, you will be paired with another solo traveler of the same gender.

Cancellation

In the case of cancellation, you must notify us at hello@tryps.ca. Deposits / payments are refundable for Tryp Credit up until 60 days prior to your Tryp start date. Afterwards, all payments are non-refundable.

Easy & Flexible Booking

Book your spot with just a $100 refundable deposit. Click here to learn more.

Flights

Airfare to and from the destination is not included in Boat Tryp prices. If you need help booking a flight, we would be happy to help get you the best pricing through our agent at no additional cost.

Food

Our yachts have a fully-equipped kitchen on board. Prior to departure, your crew will make a grocery run. As per sea protocol, cooking is a shared responsibility. A rotating schedule will be made in which two people per day will be responsible to feed the crew. Depending on each itinerary, some meals will take place at restaurants on land.

Passports & Visas

It is your responsibility to have valid travel documents. You must ensure that you have a valid passport and any necessary visas to enter any country you are visiting, including transit stops, prior to your departure. Citizens and holders of a valid residence permit for the United States, Canada, the Schengen Area, the United Kingdom, Ireland or Switzerland do not require a visa to visit St Maarten, Anguilla or St Barts.

Payments

For your convenience, payments are done in 3 simple installments. Upon making your booking, you can view the payment schedule showing due dates. Your booking can be paid online by debit or credit card. Click here to book your spot.

Route

The route as provided to you prior to departure is subject to change as changes in weather and other external factors are out of our control.

Sailing

Absolutely NO sailing experience is required to join Boat Tryp. Nonetheless, you will get a taste of sailing culture. You and your crew will undergo a brief orientation led by your Skipper.

Skippers

All prices include a qualified and licensed Skipper that will navigate safely throughout your adventure. He/She is the captain of your ship!

Travel Insurance

Travel insurance is optional though we highly recommend getting coverage. There are many options and we can certainly point you to our recommended source.

What’s Not Included?

Flight (varies per country of origin)
Transfer to and from airport ($30)
Food/groceries ($100)
Meals for Skipper ($20)
Port fees, yacht fuel, & water ($130)
Water taxis ($50)
Optional activities ($40 to $100)
Refundable yacht deposit ($150)

*Prices are in USD and are approximations

Talk With An Expert

We’re here to answer all of your questions.