Sail The Caribbean

8 Days, 7 Nights
Start
Finish
Status
Price
Deposit
December 2023

Saturday

Dec 9, 2023

Dates

Saturday

Dec 16, 2023

Status

Limited Spots

Price

$2195 CAD

Deposit

BOOK
BOOK
SOLD OUT
NOT AVAILABLE
December 2024

Saturday

Dec 7, 2024

Dates

Saturday

Dec 14, 2024

Status

Available

Price

$2,725 CAD

Deposit

$300 CAD

BOOK
BOOK
SOLD OUT
NOT AVAILABLE

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We’ll send you the detailed Sail Caribbean Itinerary and other useful info to plan your adventure.

Sail the St Maarten

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

SeND ME Itinerary

Sail the Caribbean

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

SeND ME Itinerary
See Dates & Prices
7 Days | From $2,195
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CHECK AVAILABILITY
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.

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

Get Detailed Itinerary

Package Includes

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

Fully equipped yacht (includes mileage, marina fees and insurance)

Professional & internationally certified skipper

5 unique island visits

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

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Sites You Will See in the Caribbean

The Coast Line
Tintamarre
Open Sea
St Martin
Sunset
Tintamarre
Sandy Beaches
Anguilla
Majo Beach
Sint Maarten

Next Available Trip

December 9-16, 2023

SEE DATES & PRICES

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

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

Cabin For 2

Kitchen

Indoor Dining Area

Outdoor Patio

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

Pat Flood
Los Angeles, USA
Sailing with Tryps
Watch Video

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 Available Trip

December 9-16, 2023

SEE DATES & PRICES

Travel Solo, Adventure Together.

Travel Solo, Adventure Together.

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DATES & PRICES