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Caribbean (multi-stop: Saint John and surrounding islands) Demo Portal · Airplane Mode
Caribbean Island-Hopping Adventure
✨ BUILD MY OWN
Nov 21, 2026 → Nov 29, 2026 · Caribbean (multi-stop: Saint John and surrounding islands)
Nine days of turquoise water, jerk smoke, rum punch, and the Caribbean that locals actually live in.
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STILL TO BOOK
Lock in the rest of your trip
Lock it in before the prices move.
✈️ Book now
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STEP 3 · MAKE IT YOURS
Add your documents
Drop in a PDF, we file it on the right day.
📎 Upload
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POINTS OF INTEREST
Hidden gems and must-sees
Vetted spots, and it works offline.
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PACK SMART
Your packing list is ready
Built for your trip and your real weather.
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PLACES TO EAT
Curated, vetted local food
Vetted, so you never waste a dinner.
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RECEIPT SCANNING
Snap receipts to split expenses
Snap a receipt, settle up in a tap.
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EXCURSIONS
Tours actually worth your time
Only the tours worth a day of your trip.
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MEET OTTO
Your travel companion
Ask anything about your trip.
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CURATED STAYS
Hotels for every budget
Picked by area, not by ad spend.
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JOURNAL ENTRIES
Capture each day as it happens
It becomes your printed memory book.
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KNOW BEFORE YOU GO
The story behind each town
Know each stop before you arrive.
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GET IN THE MOOD
Watch before you go
Get the group excited before you fly.
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A NOTE FROM SCOTT & JENNIFER
Thank You ✈️
Why we built this, from us to you.
TAP TO READ ›
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DAYS
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FLIGHTS
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TOWNS
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MAP
🍽️
FOOD
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HOTELS
🎫
BOOK
💬
CHAT
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EXPENSES
🧳
PACK
📺
WATCH
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DOCS
NOV
21
Cruz Bay, Saint John
Day 1 of 9 · Saint John, USVI · Sat, Nov 21
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NOV
22
Trunk Bay and North Shore, Saint John
Day 2 of 9 · Saint John, USVI · Sun, Nov 22
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NOV
23
Coral Bay and East End, Saint John
Day 3 of 9 · Saint John, USVI · Mon, Nov 23
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NOV
24
Charlotte Amalie, Saint Thomas
Day 4 of 9 · Saint Thomas, USVI · Tue, Nov 24
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NOV
25
Coki Beach and Water Island, Saint Thomas
Day 5 of 9 · Saint Thomas, USVI · Wed, Nov 25
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NOV
26
Road Town and The Baths, British Virgin Islands
Day 6 of 9 · Tortola and Virgin Gorda, BVI · Thu, Nov 26
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NOV
27
Jost Van Dyke
Day 7 of 9 · Jost Van Dyke, BVI · Fri, Nov 27
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NOV
28
Sint Maarten and Grand Case
Day 8 of 9 · Sint Maarten and Saint Martin · Sat, Nov 28
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NOV
29
Maho Beach and Departure, Sint Maarten
Day 9 of 9 · Sint Maarten · Sun, Nov 29
🎟️ 1
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Otto
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