Fall Leaves to Miami Scenes
Québec City, Québec • Halifax, Nova Scotia • Saint John, New Brunswick • Eastport, Maine • Boston, Massachusetts • Charleston, South Carolina • Miami, Florida
- Nights
- Brilliant Lady
- October
LIMITLESS EXPLORATION
Why choose a Sail Deeper Voyage?
With our itineraries from 7 to 16-nights, you’ll have time to do it all (and more) thanks to a curated list of specialty experiences designed to help you immerse yourself in each new destination.
76 ports, 35+ itineraries, and over 800 Shore Things – whether you’re a seasoned Sailor or an aspiring adventurer, there’s something for you on every Sail Deeper Voyage. From mouthwatering foodie tours, heart-pumping hikes, and stargazing at an actual eclipse, our hand-picked list of shore excursions and activities are designed to help you sail deeper into each destination.
Experience what the world has been raving about
More Destinations, More to Explore
Our Sail Deeper Voyages mean more experiences and opportunities to explore each jaw-dropping destination.EXPLORE ITINERARIES
Enhanced Entertainment
Sail Deeper itineraries that leave room for exclusive events, new programming, and exciting, new speaker series.EXPLORE EXPERIENCES
More Menu options
Each Sail Deeper Voyage will feature exclusive dining, new dishes, and rotating menus across our fleet.EXPLORE NEW MENUS
Exclusive Pricing & Deals
Thanks to our policy of Always Included Luxury, you won’t have to worry about being charged for extras like onboard dining, non-alcoholic bevs, or wifi.EXPLORE PRICING
Plan ahead with confidence
With Sail Deeper Voyages leaving in 2025 and 2026, you can book your dream vacation on a whim or look forward to something special in the year to come.EXPLORE 2025 & 2026
More Port Time
Sailing Deeper means more ports and time to explore them with overnight and late night stays.EXPLORE OUR PORTS
More Shore Things
When you Sail Deeper you’ll also get a list of expertly curated shore excursions to help you further explore each port.EXPLORE SHORE THINGS
Go deeper with 800+ epic excursions
More ports = more opportunities to explore new terrains, taste new foods, and immerse yourself in new cultures thanks to our curated list of incredible shore excursions.
Autumn Leaves: New York to Quebec
New York City, New York • Boston, Massachusetts • Eastport, Maine • Saint John, New Brunswick • Halifax, Nova Scotia • Québec City, Québec
- Nights
- Brilliant Lady
- Sept - Oct
Southern Caribbean & Aruban Nights
Miami, Florida • Oranjestad • Willemstad • Cartagena • Ocho Rios • George Town
- Nights
- Brilliant Lady
- February
Colorful Curaçao to the Charming Caymans
Miami, Florida • Oranjestad • Willemstad • Cartagena • Grand Turk • Puerto Plata
- Nights
- Scarlet Lady
- November
Pacific Coastal: LA to Vancouver
Los Angeles, California • Catalina Island, California • San Francisco, California • Astoria, Oregon • Victoria, British Columbia • Vancouver, British Columbia
- Nights
- Brilliant Lady
- May
MORE EXPERIENCES ON BOARD & ASHORE
Are you ready to sail deeper?
Immerse yourself in luxury at sea with our uniquely curated Sail Deeper Voyages.
Set sail with us on an unforgettable 7 to 16-night Sail Deeper Voyage through crystal blue waters to jaw-dropping destinations — with the time you deserve to truly discover and explore. What’s the value of a Sail Deeper Voyage? It’s more – 76 more destinations to cross off your bucket list. More time to explore (with overnights and late stays!) on 35+ itineraries. And more opportunities to enjoy our award-winning onboard experiences and 800+ shore excursions.
Let us book your hotels, airfare, and more!
Want to make planning even easier? Our incredible First Mates are here to help you book airfare, hotels, and more!
Contact your travel advisor to learn more.
With this many epic destinations, you’re gonna need more time
Are you a Caribbean cruiser? An Alaskan adventurer? A European explorer? With more experiences onboard and ashore, the choice is yours and the possibilities are endless.
8 nights in the Eastern Caribbean Antilles. 11 nights Greek island hopping to Istanbul. 16 nights from Miami to Los Angeles through the Panama Canal. With Sail Deeper Voyages exploring the waters of the Caribbean, North America, Europe, Alaska, and more, there’s an adventure awaiting every type of Sailor.
Each new year brings new possibilities
North America, Northern Europe, and the Caribbean in 2025. Alaska, the Panama Canal, and Nordic wonders in 2026 — the choice is yours.
Cap off 2025 with a fall foliage tour along the Northeastern coast of the US & Canada or look ahead to an epic transcontinental journey through the Panama Canal in 2026. With each new year, our Sail Deeper Voyages offer new opportunities to embark on the voyage of a lifetime featuring new waters, new destinations, and new life-changing experiences.
MORE MARVELOUS
Once-in-a-lifetime Marvelous Voyages
Sail Deeper on a once-in-a-lifetime voyage that showcases otherworldly beauty from the sea to the land to the cosmos.
Experience an eclipse on the Icelandic sea. Sail through the British Isles to Baltic beauties. Explore Moroccan wonders, or cruise through the iconic Panama Canal. These extraordinary adventures include special programming and epic itineraries that take the idea of sailing deeper to a whole new level.
EXPLORE SAIL DEEPER ITINERARIES
Sail Deeper voyages mean endless possibilities. Who will you be when you’re at sea?