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Spring Sail 2023:
Saint Martin, Anguilla and St Barts!

Week 1: Wednesday March 29th (Evening) - Sunday April 9th (Morning)

Spring Sail 2023 is hosted in the most picturesque of the Caribbean Islands - Saint Martin, Sint Martin, Anguilla and St. Barts!  These islands have a long and storied history.  

Our rough itinerary will start in Saint Martin then head over to Anguilla followed by a stop in Sint Martin and end the trip heading to St. Barts.  This is packed itinerary-so packed that we needed to extend the trip by 3 days!  Instead of being our now week long trip, we're doing 10 days.  

Each part of the island is a unique experience - the Dutch side is more more known for it's duty free shopping, nightlife and waterfront views.  The French side is quieter, more relaxed with clothing optional beaches.  Anguilla has plenty of sandy islands, great snorkeling and picturesque anchorages.  St. Barts is filled with amazing free diving and amazing Caribbean cuisine.

Never sailed? No problem! Join another group who has an experienced sailor. Just kick back, apply some sunscreen and enjoy a beverage. Want to sail the boat yourself? We can also arrange that.

This will blow any other spring trip out of the water. Every single day you will wake up to a sunrise either over a beautiful beach or across the ocean. You won’ t have to see the same island twice. Want that morning swim? That's only 10 feet away.

Before we dive into the itinerary, let's talk a quick local legend:  Two men representing the two respective countries met on the island to define the border. Both men wanted the majority of the land for their nation, so they decided to have a contest. They would both start at the same point and walk along the coast in separate directions. When they both met on the other side of the island, they would draw a line from point to point, and that would serve as the border. However, the Dutchman was a drunk and was hammered when they started the contest. He was stumbling and kept falling down, which is why the Netherlands has less of the land.

Trip Itinerary

Spring Sail 2023


Gather at the Marina!

Sail to Sandy Island

If your expectation was to spend the week on a sandy spit surrounded by clear blue ocean water, great snorkeling, and a drink in hand - the Sandy Island will not disappoint.  Located off the coast of Anguilla, we'll stop here for lunch and a relaxing afternoon!

Anchor at Prickly Pear Island

After you've spent the day lounging on a sandy island, we'll depart to another sandy island.  This offers slightly more protection than the Sandy Island for the night as well a trail system which allows you to explore a post card like island!

Day 1 (Evening)

Day 2

Day 3

Anchor at Pinel Island

After a slow relaxing morning, you'll head down to Orient Bay.  Orient Bay is host to Pinel Island and a wide variety of water sports activities.  You'll be able to rent a wind surfer, kite board or any other water sport.  There are also a variety of bars and restaurants for a quick drink on the beach!

We will receive all provisions and then congregate for 1-2 (limit strictly not enforced) beverages the evening of the trip!

Day 4

Annual YachtXP Regetta

It's back!  After a thrilling regatta in the British Virgin Islands last year, we're returning to the Hobie cats for another year.  We'll divide up into several crews and race a combination of Hobie Cat variations.  If racing isn't you pace, you can join the spectator boat, grab a wind surfer or kayak and explore Pinel Island.

Day 5

St Barts here we come!

After a quick 20 mile sail, you'll be at Gustavia, the main entry point to St. Barts.  St. Barts is a highlight of the trip.  The combination of great hiking as well as diving gives a combination for either the land lover or the mermaid in all of us.

Day 6

St. Bart Exploration

St. Barts has long been considered a playground of the rich and famous and is known for its beautiful pristine beaches, gourmet dining in chic restaurants and high-end designer shopping. There is one small airport that can only accommodate small prop planes from St. Martin and San Juan, and the harbor is too small to accommodate cruise ships. The fact that it is hard to get to is part of the island's appeal.  We should feel right at home.  

Rent a 4x4 and explore the entire island!

Day 7


This small uninhabited island off the coast of St. Martin is home to two exceptional SCUBA diving sites as well as a few secluded beaches. A quick walk from the powdery sand along a dirt trail will lead you to an abandoned airstrip and remnants of an airplane that may have crashed on the island.  The stories are varied on whether the plane was abandoned or it is the result of a crash. Nonetheless, an afternoon to explore this island is well spent.

2 Extra Days!

Shopping, Lounging, Fishing, Kiting, Wind Surfing, Kayaking You Pick!

While we try to provide a guide of what to expect, there are always places people want to spend more time.  Sometimes you find the perfect beach, the perfect bar tender, the perfect drink, or fishing spot.  The flex days give us the ability to spend more time where you want!  

Option for Extra Day

The Bottoms & Saba (Optional)

If there was one place we're excited about - it's the Bottoms & Saba.  Amazing diving, an incredible 1000M volcano to hike, and away from the crowds.  Depending on the crew, we may or may not reach the Bottoms as this adds approximately 60 miles.

Day 10

Return to Marina

Sadly, every amazing week comes to an end.  We must disembark by 10 AM.  Please plan appropriately to make your flight.  It takes at least 30 minutes to get to the airport.


Never Sailed?  Check out the boat!

The Catamaran provides plenty of comforts on a stable platform where you can stare at the beaches while you cook.  You'll have berths with windows looking into the ocean and plenty of areas for sun bathing.  If you prioritize comfort for adventure, the catamaran is for you.

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Saint Martin FAQ

Saint Martin Basics

Where are we leaving from?

Saint Martin (French Side).  The Marina is located near Anse Marcel.

How do I get to St Martin?

Three ways to get to St Martin:

  1. Fly to St. Maarten’s Princess Juliana International Airport; take a taxi to the base; distance is approximately 20 minutes
  2. Fly to St. Martin’s Grand Case Airport (in Grand Case, French side); take a taxi to the base; distance is approximate 20 minutes.
  3. Take a ferry from Anguilla to Marigot Port, capitol of the French side of St. Martin. (Every 30 min. From St.Barths to Marigot daily 7:30am, 11:30am and 5:00pm

What time do we expect to leave?

7 AM on Thursday Morning.  Please arrive Wednesday night!  A "sleep aboard" is included as part of the charter Wednesday night.

When do we return?

Sunday, April 9th in the morning.  Please do not plan on making a flight earlier than noon!

What is St Martin's COVID Policy

The COVID policies of St Martin have varied greatly. as it is affected by both the French and Duetch side.  As we get closer to the trip, we will provide any knowledge of the policies we have.  Sadly, unless the charter company offers a refund, we are unable to offer refunds for changes related to COVID policies.

Is there a security deposit for the boat?

A security deposit must be paid at the base by Visa or Master Card and is refundable at the end of your charter subject to there being no loss or damage. This varies by boat however usually ranges in the $200-300 per person.