Now wind-aware — point of sail on every passage

Plan a charter that sails with the wind

Chief Stew is your AI planning assistant for bareboat charters. Describe your trip and it builds a day-by-day itinerary grounded in real wind data — so the long passages run downwind, not upwind — then coordinates your crew and watches the forecast for you.

chiefstew.app/trip/bvi-week-2026

BVI Week 2026

Feb 22 – 28 · Lagoon 47 · 4 crew

Active
1
Road Town, Tortola → The Bight, Norman Island
Sun, Feb 22 · 8 nm · ~1.5 hours 27°C, mostly clear ≈12 kt ESE · broad reach
10:00
logistics

Charter check-in & boat briefing

Pick up at Village Cay Marina. Complete inventory, safety briefing, and chart review.

12:00
passage

Sail to Norman Island

8 nm south through Sir Francis Drake Channel. Mooring: $30/night.

14:30
activity

Snorkel The Caves

Swim into the sea caves at Treasure Point. Excellent snorkeling with fish and coral.

18:30
dining

Pirates Bight Restaurant ★ 4.3

Dinner on the beach. Great rum punch and grilled lobster.

2
Norman Island → Cooper Island
Mon, Feb 23 · 6 nm · ~1 hour 28°C, sunny ≈14 kt E · beam reach
3
Cooper Island → Virgin Gorda Yacht Harbour
Tue, Feb 24 · 10 nm · ~2 hours 27°C, partly cloudy ≈10 kt SE · broad reach
4
Virgin Gorda → North Sound
Wed, Feb 25 · 5 nm · ~1 hour 29°C, clear ≈8 kt E · close reach
+ 3 more days · Anegada · Jost Van Dyke · Road Town
Wind-aware sailing intelligence

Plan with the wind, not against it

Every passage is grounded in real wind data — worldwide, no setup. ChiefStew reads the forecast near departure and typical climate further out, then shows you the point of sail for each leg so you know whether you're reaching, running, or beating before you ever leave the dock.

Start · Road Town
Anegada
Wind direction per leg
North Sound → Anegada forecast

≈15 kt E · 14 nm · broad reach — longest passage of the week, and it's downwind.

Compare route options

For a round trip, the win isn't avoiding upwind — it's putting the longest passages downwind. ChiefStew scores candidate route directions by wind and shows you which one sails best.

Reverse direction Recommended

Longest passage downwind · 0 upwind legs · 82% favorable

82%
favorable wind
0
upwind legs
Current order

3 upwind legs · 54% favorable

54%
favorable wind
3
upwind legs

Pick a route and Chief Stew rebuilds the plan for your review — nothing changes until you confirm.

Chat with Chief Stew

Describe your trip in plain English. Chief Stew, your AI assistant, builds a complete day-by-day itinerary with anchorages, restaurants, activities, and wind-aware passage planning.

It interviews your crew to learn everyone's preferences, then personalizes the plan so every day has something for everyone. Ask it to adjust anything — it works through changes with you and waits for your go-ahead.

CS
Copilot
CS

Welcome! Tell me about your charter trip — where are you sailing, when, and who's coming?

We're doing a week in the BVI starting Feb 22. Four of us on a Lagoon 47 — me as captain, my wife Sarah, and our friends Jake and Emma.

CS

Great — a 7-day BVI trip on a Lagoon 47! I'll route it to keep your longest passages downwind. Any must-sees? And should I send crew questionnaires to learn everyone's preferences?

Definitely The Baths and Soggy Dollar. Yes, send the crew questionnaires!

Building wind-aware itinerary Sending crew invites
Tell me about your trip...
5
North Sound → Anegada
Thu, Feb 26 · 14 nm · ~3 hours 26°C, partly cloudy ≈15 kt E · broad reach · forecast
08:00
passage

Sail to Anegada

14 nm across open water. Navigate the Anegada reef approach carefully. Anchor: Setting Point (free).

12:00
activity

Loblolly Bay Beach

Best beach in the BVI. Crystal-clear water, snorkeling right off the sand.

18:00
dining

Lobster Trap Restaurant ★ 4.5

Famous Anegada lobster dinner. Fresh-caught, grilled to order. Reservation recommended.

Crew highlights for today

Sarah — Vegetarian option noted at Lobster Trap (grilled mahi-mahi)

Jake — Paddleboarding at Loblolly Bay (gear on board)

Emma — Flamingo colony birdwatching at the west end

Day-by-day itinerary

Every day planned with stops, passage distances, mooring costs, and crew-personalized highlights — each leg tagged with its wind and point of sail. Expand any day to see the full schedule.

An interactive map plots your whole route, from pickup to final anchorage, with a wind arrow on every passage. Export the trip to PDF or CSV for offline reference on the water.

Crew coordination

Invite your crew with a link. AI interviews each member to learn preferences — dietary restrictions, allergies, interests, activity levels.

Everything is tracked so the itinerary reflects what everyone actually wants.

Rick captain

Experienced bareboat captain. Loves exploring new anchorages.

sailing fishing photography
Adventure
Foodie
Activity
Joined
Sarah crew

Avid snorkeler and yoga enthusiast. Loves discovering local cuisine.

snorkeling yoga hiking
vegetarian
Luxury
Foodie
Culture
Joined
Jake guest

Teenager who loves water sports and non-stop adventure.

paddleboarding swimming
shellfish allergy
Adventure
Activity
Social
Pending
Emma guest

Photographer and birdwatcher with a passion for history.

photography birdwatching history
gluten-free nut allergy
Culture
Luxury
Social
Joined
Documents 6/8
Compliance 2/5
Provisioning 0/6
Packing 4/7

Smart checklists

Auto-generated from your itinerary. Compliance scanning flags what you need for your route — customs forms, cruising permits, park fees.

Assign items to crew with due dates. Dietary needs and allergy accommodations are built right in from crew profiles.

Captain's log

Digital logbook with passage tracking. Log weather, sea state, crew on watch. Running totals for nautical miles, hours at sea, and night passages.

Export for your records — build your sea time log over multiple trips.

80
Total NM
7
Days at Sea
4.5
Night Hours
Feb 26 Partly cloudy, 26°C, winds 15kt E Moderate seas 14 nm coastal

North Sound → Anegada

Departed Bitter End 0800. Crossed the Dog Islands passage with 15kt easterlies and 1m swell on beam. Picked up Anegada on radar at 8nm. Anchored Setting Point 1100. Excellent visibility for reef approach.

Skipper: Rick Watch: Sarah Jake Emma
3h
At sea
0h
Night
Yes
Tidal
Feb 25 Clear, 29°C, winds 8kt E Calm seas 5 nm

Virgin Gorda → North Sound

Forecast changed for Fri, Feb 27

North Sound → Anegada now shows 28 kt gusts from the NE on an exposed passage — a beat the whole way. Chief Stew can delay departure, reef, or reroute through sheltered water.

Delay departure Sheltered route Discuss with Chief Stew
CS
ChiefStew SMS · 06:02

Weather alert for BVI Week 2026: strong NE wind building Friday on your Anegada passage. Open the app to review your options.

Alerts before the weather turns

ChiefStew keeps watching the forecast after you've planned. When conditions on an upcoming passage turn dangerous — a sudden strong wind, a passage that flips to a hard beat — it sends you a heads-up by SMS and email.

Then Chief Stew proposes fixes: delay the departure, reef, or take a sheltered route. You stay in command — nothing on your itinerary changes until you approve it. Turn alerts on or off any time.

Local knowledge for every port

Tap a stop and Chief Stew researches the harbour in real time: the VHF channel to call, how to enter and what to watch for, mooring options, and how to reserve a berth — with the sources it used, so you can verify.

For restaurants and marinas it pulls the phone, website, hours, and rating — tap to call or book. Recommendations are tuned to your crew's taste, so you get the right spots, not the same canned list everyone else gets.

Port guide — Hvar Town

VHF: Channel 17 (marina), 16 calling/distress

Entering: Approach from the north via the Hvar Channel; harbour is open and exposed to southerlies.

Reservations: Town quay is first-come, first-served — arrive early in season.

Hazards: Pakleni Islands shoals to the SW; heavy ferry traffic; Sirocco swell in the harbour.

Sources: [1] [2]

Konoba Menego

Traditional Dalmatian konoba

★ 4.6 Call Website

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