Four Islands, Four Moods: A Leeward Islands Yacht Journey
The YCN destination guide / St. Maarten, St. Barth, Antigua & Guadeloupe
A French lunch by the sea. A harbor full of sailing stories. A reef that persuades you to stay in the water. Find your own Leeward Islands rhythm.
Your next Caribbean chapter
A different island.
A different kind of perfect.
Some islands ask you to dress for dinner. Others make you forget where you left your shoes. A Leeward Islands yacht charter can give you both: the restaurants and lively shore scenes of St. Martin and St. Barth, Antigua’s sailing heritage, and Guadeloupe’s lush coast and island villages.
This guide focuses on the four destinations in YCN’s St. Maarten, St. Barth, Antigua, and Guadeloupe group. St. Maarten is the Dutch side of the island shared with French Saint-Martin; St. Barth is also commonly called St. Barts. Each deserves time beyond its headline attraction.
Choose a compact island pairing or a carefully planned longer passage itinerary. These destinations are not all neighboring lunch stops, and a week spent enjoying two places can be far more satisfying than a week spent chasing four.
Explore YCN’s St. Maarten, St. Barth, Antigua & Guadeloupe yacht charters to find a yacht for the journey you have in mind.
St. Maarten / Saint-Martin
Two cultures, one very tempting coastline
Start with a beach, then follow your appetite.
01 · Grand Case, Saint-Martin
Let lunch choose the destination
Best for: French-Caribbean dining
Grand Case is a strong argument for going ashore hungry. Wander the seaside village, choose between an easy local grill and a more leisurely restaurant lunch, and enjoy a different kind of island discovery: one made around a table.
Leave time for a beach stroll before returning aboard. A meal tastes even better when nobody is trying to fit it into a forty-minute stop.
Make it happen: Reserve popular restaurants and coordinate the landing. French-side formalities and local operating rules still need attention.
02 · Pinel Island, Saint-Martin
Make a tiny island feel like a proper escape
Best for: A beach-and-lunch outing
Pinel offers the simple appeal of stepping away from the main island for a few hours. Enjoy the view back across the water, settle into a beach afternoon, and take a gentle walk where access allows. Keep the plan light enough to match the setting.
If lunch ashore is part of the dream, arrange it beforehand. The best version of a laid-back day often begins with a little preparation.
Make it happen: Confirm protected-area rules, permitted access, and restaurant operations; weather determines whether the outing works.
03 · Tintamarre, Saint-Martin
Trade the busy shore for open space
Best for: A quieter island excursion
Tintamarre makes a lovely change from town. The attraction is the feeling of space: low land, a beach, and water that keeps drawing your attention away from everything else. Enjoy a swim where conditions allow and let the scenery remain uncomplicated.
Bring what you need and leave nothing behind. A visit feels more special when the island still looks untouched after you depart.
Make it happen: Use approved access and anchoring arrangements in the protected area. Exposed conditions can require another choice of bay.
04 · Marigot, Saint-Martin
Give the morning a French accent
Best for: A waterfront stroll and café stop
A warm pastry, a good coffee, and a walk along the waterfront can be quite enough to justify going ashore. Marigot offers a town morning to balance the beaches, with a chance to browse and enjoy the everyday rhythm of the French side.
Choose a few things that interest you rather than turning the outing into a checklist. You have a yacht to return to, not a bus to catch.
Make it happen: Agree on a suitable landing and transport. Market schedules and individual shop hours vary.
St. Barth
A little glamour, a lot of sea
Enjoy the shore scene and the quieter bays in equal measure.
05 · Gustavia, St. Barth
Arrive with time to wander
Best for: Harbor atmosphere and boutiques
Gustavia makes arriving by sea feel especially fitting. Enjoy the harbor view, walk the compact town, and let a little shopping or a café stop lead naturally into lunch. There is room here for both a polished afternoon and a wonderfully casual one.
After dark, a reservation ashore can give the charter a celebratory note. Let the crew manage the return so dinner stays relaxed.
Make it happen: Book berthing or tender arrangements early during busy periods, and confirm restaurant reservations separately.
06 · Shell Beach, St. Barth
Slip a beach break into a town day
Best for: An easy change of pace
Near Gustavia, Shell Beach brings a different texture to the usual stretch of sand. Enjoy the shoreline, take in the sheltered-looking setting, and decide whether the day’s sea conditions suit a swim. It is a pleasing way to interrupt a shopping afternoon.
You do not need to make the stop elaborate. A towel, some water, and time to enjoy the view can be the whole plan.
Make it happen: Watch your footing on shells and stones, and use locally advised access rather than assuming a tender can land anywhere.
07 · Colombier, St. Barth
Choose the quieter side of the island
Best for: A scenic bay and a slower afternoon
Colombier is a reminder that St. Barth has more than one personality. Enjoy the bay from the yacht, then make a swimming or shore plan that suits the conditions. The draw is the landscape and the feeling of being removed from the town scene.
This is a good day to let the chef prepare lunch aboard. With a view like this, going somewhere else may seem unnecessary.
Make it happen: The bay lies within a marine reserve. Follow current mooring, anchoring, and visitor rules, and use an alternative if conditions are unsuitable.
08 · Saline Beach, St. Barth
Take the long view of a beautiful beach
Best for: A land-based beach escape
Saline offers a broad sweep of shoreline and a welcome excuse to put the phone away. Make the approach on foot after a road transfer, find your place on the sand, and enjoy the beach as a landscape as much as a swimming stop.
It pairs well with a leisurely drive around the island and a late lunch. There is no need to circle the entire coast by yacht to appreciate it.
Make it happen: Bring shade and water, check surf conditions, and arrange a driver. This is not a guaranteed tender-landing stop.
Antigua
Where sailing stories come ashore
Historic harbors, high viewpoints, and time for another swim.
09 · Nelson’s Dockyard, Antigua
Walk into Antigua’s sailing story
Best for: Harbor heritage and architecture
Stone buildings, rigging, and the sheltered shape of English Harbour make Nelson’s Dockyard a shore visit with a strong sense of place. Take time to explore the historic setting and learn about the people who built and worked within it.
Follow the visit with lunch nearby. The pleasure is in the combination of a living yachting harbor and a past that still shapes the waterfront.
Make it happen: Check site admission and opening arrangements. Reserve marina space separately if your yacht will berth here.
10 · Shirley Heights, Antigua
See your holiday from above
Best for: A memorable harbor panorama
A trip up to Shirley Heights changes your understanding of the coastline. The harbors open out below, the boats become tiny, and the sea stretches far beyond the scene you have been exploring from deck level.
Go for the view, then decide whether a scheduled music or dining event fits your plans. Sunset is appealing, but it does not have to be the only good hour to visit.
Make it happen: Arrange a road transfer, confirm event dates, and avoid assuming entertainment happens every evening.
11 · Pigeon Point, Antigua
Keep a beach afternoon close and easy
Best for: A relaxed shore break
Pigeon Point suits the day when you would like a swim and a stretch of sand without a grand expedition. Enjoy a gentle beach visit from the English Harbour area, perhaps followed by a simple meal and a return to the yacht before the afternoon becomes busy.
It is an especially useful reminder that the most enjoyable stop is not always the farthest one away.
Make it happen: Let local conditions determine swimming and access. Use a shore transfer when it is simpler than a tender approach.
12 · Half Moon Bay, Antigua
Find a beach with a wilder mood
Best for: A scenic island drive
Half Moon Bay gives an Antigua shore day a different feel from the enclosed harbors. Enjoy the curve of the beach, the open horizon, and a walk that leaves plenty of room for stopping simply because the view is good.
Treat it as a land outing rather than a promise of calm-water swimming. Some landscapes are at their best when you enjoy them from the shore.
Make it happen: Arrange a driver and assess surf locally; the Atlantic-facing setting can be exposed.
Guadeloupe
Let the landscape get greener
Creole villages, island bays, and underwater adventures.
13 · Deshaies, Guadeloupe
Linger over a Creole lunch
Best for: Village charm and bay views
Deshaies is made for a pleasant lack of urgency. Step ashore, enjoy the village, and choose a meal that gives you time to look out over the water between courses. This is where a charter can feel less like travel and more like briefly belonging somewhere.
If you want a little more activity, arrange a visit to the botanical garden as part of the shore day.
Make it happen: Check tender access and restaurant opening days; the garden requires separate transport and admission planning.
14 · Malendure & Pigeon Islets, Guadeloupe
Spend the morning beneath the surface
Best for: Guided snorkeling or diving
The marine area commonly called the Cousteau Reserve invites you to look closely: fish moving across the reef, changing light, and the quiet concentration of being underwater. Choose snorkeling or diving according to your experience and the day’s conditions.
Afterward, a relaxed lunch around Malendure can be a very satisfying way to return to dry land.
Make it happen: Use an appropriate operator and follow national-park rules. Confirm the exact site rather than assuming all reef areas have the same access.
15 · Terre-de-Haut, Les Saintes
Let an island village steal your afternoon
Best for: A beautiful bay and gentle exploring
Terre-de-Haut has the sort of bay that makes you slow down before you even step ashore. Wander the village, browse a little, and taste a local tourment d’amour pastry while deciding whether the next stop should be a viewpoint or another café.
Stay long enough to enjoy the change in light over the water. A place this pretty deserves more than a quick arrival photograph.
Make it happen: Confirm a suitable mooring and landing. Arrange transport or a walking plan that suits the heat and your group.
16 · Îlet du Gosier, Guadeloupe
Make room for one more island swim
Best for: A compact shore-and-water outing
A small island close to the main coast can still feel like a change of world. Îlet du Gosier offers an appealing setting for a beach visit and time looking back across the water. Keep the outing simple, with a swim only where conditions and local guidance suit.
It works best as part of a Grande-Terre-based plan, not as an automatic extra after exploring the opposite coast.
Make it happen: Use an approved transfer or captain-arranged access, and account for boat traffic, currents, and the return trip.
From wish list to holiday
Planning your St. Maarten, St. Barth, Antigua & Guadeloupe yacht charter
Choose your cruising area first
A multi-day yacht charter works best when the route supports the holiday you want. Start with the places and activities that excite you, then ask YCN to match them with a suitable yacht, departure point, and amount of time aboard.
- For a shorter holiday, consider St. Maarten/Saint-Martin with St. Barth, subject to yacht permissions and weather.
- Antigua can fill a charter on its own. Guadeloupe and Les Saintes also offer enough variety for a dedicated regional plan.
- Combining all four destinations needs a longer itinerary, realistic passage estimates, and clearance planning. Avoid measuring the holiday only by the number of flags visited.
Three days, five days, a week—or longer?
| Time aboard | A comfortable approach |
|---|---|
| 3 days | Stay close to your embarkation port. Choose one or two shore highlights and time to enjoy the yacht, subject to availability and minimum booking periods. |
| 5 days | Explore a compact stretch of coast or island cluster, with space for a relaxed afternoon and a change in the forecast. |
| 7 days | Build a regional circuit with a balance of passages, shore visits, and time aboard. Avoid making every day a long transfer. |
| 10–14 days or more | Consider a broader route or a carefully arranged one-way charter. Extra time can also mean longer stays in your favorite places. |
When is the best time to go?
Winter and spring are popular for Leeward Islands charters, but trade winds and north swells can change the best choice of bay. Holiday periods and major sailing events can increase demand for yachts, berths, and restaurants. Atlantic hurricane season runs June through November; confirm the yacht’s seasonal location and the flexibility built into the booking.
What should your quote include?
Ask for the charter fee and applicable taxes, plus a clear explanation of fuel, berths or moorings, meals, drinks, and shore excursions. If the arrangement uses an operating allowance or Advance Provisioning Allowance, confirm what it covers and how the final account is reconciled. Crew gratuities and special requests should also be discussed before booking.
A route with longer passages may have different operating costs from a compact local circuit. For the wider booking process, read YCN’s luxury yacht charter guide.
Plan the shore days as carefully as the yacht days
Confirm the tender, suitable landing points, walking distances, transport, and any attraction bookings. A place being close to the water does not mean a charter yacht can dock there. Local excursion boats, ferries, or a short car journey can make the experience easier and more enjoyable.
National parks and protected areas may have separate visitor and commercial-operator requirements. The charter team should check these before including an excursion. Reserve activities such as guided kayaking, diving, fishing, cycling, or golf with appropriate providers, and confirm any equipment your group needs.
Tell us what your perfect day looks like
More beach time or more towns? A family museum outing or a quiet afternoon aboard? A restaurant worth planning around, or a chef-prepared dinner with the best view already outside? Share your priorities, mobility needs, and dietary preferences before the route is finalized.
The most enjoyable charter does not need to be the busiest. Leave a little space for an extra coffee ashore, a longer conversation over lunch, or the simple pleasure of staying exactly where you are.
Before you set sail
St. Maarten, St. Barth, Antigua & Guadeloupe yacht charter FAQs
Are St. Martin and St. Maarten the same island?
Yes. French Saint-Martin and Dutch Sint Maarten share one island. They have different administrations, so the crew still needs to manage the appropriate local arrangements.
Is St. Barth the same as St. Barts?
Yes. Both names refer to Saint-Barthélemy. St. Barth is commonly used in French, while St. Barts is also widely used in English.
Can we visit all four destinations in seven days?
That may create more passage time than the holiday needs. Ask for actual cruising-hour estimates on the selected yacht, then choose a smaller area or allow a longer charter.
Does a charter include beach-club and restaurant access?
Not automatically. Restaurants, resort facilities, admission, and transfers may need separate reservations and charges. Ask the charter team to confirm your priorities.
How long should I charter for?
Three or five days suit a compact local plan, where available. A week allows more variety within a region. For longer passages or several jurisdictions, allow more time and request cruising-hour estimates on the actual yacht.
What should a yacht charter quote include?
Ask for the yacht rate, taxes, fuel arrangements, meals and drinks, berths or moorings, local fees, transfers, and excursions. Clarify crew arrangements, any operating allowance, and gratuities before confirming the booking.
Your next chapter starts here
A different island.
A different kind of perfect.
A French lunch by the sea. A harbor full of sailing stories. A reef that persuades you to stay in the water. Find your own Leeward Islands rhythm.
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