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Legends Cruise 2027

May 15 - 22, 2027

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Andrew Cabrera

High Seas Cruise Co

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Overview

Seven nights in the Caribbean with Matt Mitcham, Schwartz, and Cookie aboard the brand-new Margaritaville at Sea Beachcomber. Sailing roundtrip from PortMiami, this sailing visits Key West, Grand Cayman, Ocho Rios, and Nassau — with exclusive Legends at Sea events, hosted games, meet-and-greets, and surprises throughout the week.

May 15–22, 2027 · PortMiami · Margaritaville at Sea Beachcomber

Trip Details

Cabin Options

Starting at $1,500

May 15 - 22, 2027

8 room options

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Prepaid Gratuities

Prepaid gratuities cover the daily service charges distributed to the crew members who take care of you throughout your cruise. This includes your stateroom attendant, dining room team, and other behind-the-scenes staff who help make your experien...

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Optional

Select Your Cabin Location

Margaritaville at Sea assigns cabins by default. Upgrade to request your preferred location for $150 per cabin. After booking, submit your preferences through your trip link (example: near elevator, specific deck, forward or mid-ship). Requests ar...

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Day 1 · Sat, May 15 · Miami

PortMiami

May 15

Miami is one of the world’s most popular holiday spots. It has so much to offer; from its countless beach areas, to culture and museums, from spa and shopping days out, to endless cuban restaurants and cafes. Miami is a multicultural city that has...

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Optional

The Legends Bundle (Drinks + Wifi)

Kick back, drink up, and stay connected. The Legends Bundle includes a Premium Drink Package with 15 drinks per day plus Basic WiFi — everything you need to make the most of your week at sea. At $599 per person, it's the easiest way to go all-in o...

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Day 2 · Sun, May 16 · Key West

Key West

May 16

Enjoy a day in Key West, Florida. Arrival: 7:00 AM Departure: 3:00 PM

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Day 3 · Mon, May 17 · At Sea

At Sea

May 17

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Day 4 · Tue, May 18 · George Town

George Town, Grand Cayman

May 18

Spend the day in George Town, Grand Cayman Arrival: 8:00 AM Departure: 4:00 PM

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Optional

Beach Day with the Legends - Grand Cayman

Spend the afternoon at Kaibo Beach Club — one of Grand Cayman's most iconic beachfront destinations — with Matt Mitcham, Schwartz, Cookie, and your fellow Legends at Sea guests. Four hours of sun, sand, and island vibes with the people who make th...

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Day 5 · Wed, May 19 · Ocho Rios

Ocho Rios, Jamaica

May 19

Visit Ocho Rios, Jamaica Arrival: 8:00 AM Departure: 4:00 PM

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Day 6 · Thu, May 20 · At Sea

At Sea

May 20

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Day 7 · Fri, May 21 · Nassau

Nassau, Bahamas

May 21

Discover Nassau, Bahamas Arrival: 9:00 AM Departure: 5:00 PM

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Day 8 · Sat, May 22 · Miami

PortMiami

May 22

Miami is one of the world’s most popular holiday spots. It has so much to offer; from its countless beach areas, to culture and museums, from spa and shopping days out, to endless cuban restaurants and cafes. Miami is a multicultural city that has...

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