TSheeka Ruffin

Pleasant Point Travel LLC

Bucket List Getaway - Saint (Isles) & Seas of the Caribbean

Dec 13, 2024 to Dec 21, 2024
Sails from San Juan Puerto Rico
 
 
Set out from San Juan on this epic 7-night voyage to some of the Caribbean’s most beautiful islands. Start in Road Town, the capital of Tortola in the British Virgin Islands, where you can visit local rum distilleries, or relax at Cane Garden Bay Beach. Then complete your whirlwind Caribbean tour by heading to Barbados, St. Lucia, Antigua, and St. Maarten. 

Cruise Itinerary

Map of Saint (Isles) & Seas of the Caribbean itinerary
Saint (Isles) & Seas of the Caribbean • 7 Nights
Sailing on Resilient Lady
The Virgin Voyages Experience
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Easy port access in San Juan

Have all the must-see spots within walking distance with the ship docked in the heart of Old San Juan, and soak up Puerto Rico’s effervescent vibes.

Hassle-free embarkation

Hassle-free embarkation

Pre-upload your travel docs to the Virgin Voyages app, get Ready to Sail before leaving home, and make boarding a (sea)breeze in just a few minutes.

5 ports in 7 nights icon

5 ports in 7 nights

Make the most of your time off, experiencing the culture of 5 unique cities in an epic 7-night cruise with people just as hungry for adventure as you.

Keeping It Local Icon

Keeping it local

We’ve teamed up with locals in each of our ports to reveal sides of places you’ve yet to explore — from the people who know the destinations best.

What's included in this trip

Fair & Flexible Fares

Over $1000 in value and flexible policies. The luxury you deserve — without the nickel and diming from the others. Look (far) beyond the headline rate
Food

All Food

From refined dining to relaxed casual, all of our 20+ eateries featuring menus curated by Michelin star chefs are yours to enjoy.

 
Drinks

Soft Drinks & Water

Stay hydrated with still and sparkling water, non-pressed juices, sodas, teas and even drip coffee.

 
Wifi

Wifi

Browse, post, and stay connected with wifi — whenever you want, and wherever you are on the ship.

 
Tips

Tips

We've taken care (of taking care) of your servers, so we cover the gratuities for your onboard experiences.

 
Group Fitness Classes

Group Fitness Classes

Yoga, meditation, cycling, HIIT classes, and more — all your group fitness classes are covered.

 
Entertainment

Shows & Entertainment

Developed by the world’s most-talked-about producers and artists, you have a ticket to all of our awe-inspiring shows.

 
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Flexible Booking

Unlike other places, you can change your voyage dates — meaning you get the flexibility you need when life (as it does) happens.

 
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No-Fuss Name Changes

Change the name on your voyage up to 48 hours before you head out if you can’t make it, or want to change whoever is sailing with you.

 
 

What's not included

✅ Travel Insurance 
✅ Spa treatments
✅ Phone calls.
✅ anything off of personal nature, not mention above
 
 

 Cabins & Suites
 

Insider

 

Designed with a Sailor’s many moods in mind, our cabins are revolutionizing ship design to create a personal retreat complete with modern aesthetics, yacht-like sensibilities, and functional living space. The ultimate go-to for relaxation and rejuvenation, our cabins stand out for the flexible furnishings, and upgraded bathrooms with Roomy rain showers, and sensory mood lighting, creating comfy quarters that are way more than just a place to crash.

INCLUDED FOR ALL SAILORS

  • Shows & Entertainment
  • Wifi
  • All Food
  • Tips
  • Group Fitness Classes
  • Soft Drinks & Water
 
 

Sea View

Designed with a Sailor’s many moods in mind, our cabins are revolutionizing ship design to create a personal retreat complete with modern aesthetics, yacht-like sensibilities, and functional living space. The ultimate go-to for relaxation and rejuvenation, our cabins stand out for their flexible furnishings, upgraded bathrooms with Roomy rain showers, and sensory mood lighting, creating comfy quarters that are way more than just a place to crash.

INCLUDED FOR ALL SAILORS

  • Shows & Entertainment
  • Wifi
  • All Food
  • Tips
  • Group Fitness Classes
  • Soft Drinks & Water

 

 

Sea Terrace

 

Designed with a Sailor’s many moods in mind, our cabins are revolutionizing ship design to create a personal retreat complete with modern aesthetics, yacht-like sensibilities, and functional living space. The ultimate go-to for relaxation and rejuvenation, our cabins stand out for their flexible furnishings, upgraded bathrooms with Roomy rain showers, and sensory mood lighting, creating comfy quarters that are way more than just a place to crash.

INCLUDED FOR ALL SAILORS

  • Shows & Entertainment
  • Wifi
  • All Food
  • Tips
  • Group Fitness Classes
  • Soft Drinks & Water
 
 
ROCK STAR QUARTERS
Rates will be provided upon request
 
Brilliant Suite - Rockstar Quarters

 

With a view of the European king bed from the indoor Peek-a-Boo shower through a dichroic glass window, the only sensual rival is the ocean itself. Sailors can crank up the music from the record player, serve up drinks from the fully stocked in-room bar, and then take the party to the terrace to enjoy more stunning sea views while relaxing around the Champagne table.

Max 4 sailors
Suite 396 sq ft

Terrace 86 sq ft

 

Exclusive access and VIP treatment fit for a star.

ROCKSTAR PERKS
✅ Richard's Rooftop access
✅ Curated in-room bar, on us
✅ Early Booking/Priority Access
✅ RockStar Agents

 

 

A taste of what's onboard - Our distinctive and delicious specialty eateries offer dishes designed to crush any craving. Here’s a taste of what to expect from our 20+ foodie-approved eateries - and the places that'll host all of your toasts.

 

 

STEAK & SEAFOOD - The Wake
The perfect mix of sophistication, nostalgia, and cool — entering The Wake is an event in and of itself. And once you've made your way down the grand staircase, you'll enter a world that harks back to the old steakhouse, three-martini-lunch days of Madison Avenue ad men. But ya know, now with, thankfully, gender equality. And less cigar smoke.

COOKING LAB & RESTAURANT - The Test Kitchen
Inspired by Escoffier’s Ma Cuisine, this laboratory-like eatery is part cooking school and part restaurant. It's educational, experiential, and social. With classes and evolving tasting menus, this is for the curious, boundary-pushing tastebuds on board.

VEGETARIAN-FORWARD - Razzle Dazzle Restaurant
So your best friend wants something light and healthy and you want to get really weird? This is that place. Boasting a bold interior, this restaurant offers creative surprises on some classic, comfortable go-to's. Whether you're looking for something familiar (#basic can be good) or something spicy and out of the left field, this place does all of that with a twist (breakfast, lunch, dinner, baby).

KOREAN BBQ - Gunbae
If you're into hands-on meat-grilling and soju drinking, our Korean BBQ is the perfect spot to do all that with maximum social engagement (IRL, but feel free to 'gram it if you want). It's a catalyst for great conversation since we all have that one friend who insists on being the meat master. Go ahead and roast the master while they roast the meat. 🔥

 

 

UPSCALE MEXICAN - Pink Agave
Inspired by the capital city's red-hot street food scene, sailors are treated to an immersive odyssey of Mexican cuisine. Personal, intimate, and educational, a master of ceremonies will guide you through a highly curated dining and drinking experience. Mezcal dinner pairings equipped with a history lesson? Yes pls. 

ELEVATED ITALIAN - Extra Virgin


Deeply rooted in Italian Culinary traditions, our trattoria serves regionally inspired food punctuated by our fresh, handmade pasta. Start with a shared antipasto - and follow that with any of our pasta-centric favorites and worship the carb gods like a good vacation begs of you. Top if off with a traditional Italian aperitif to make your night complete...or help it get started.

MEZZE LOUNGE - The Dock
Okay, frankly we'd be wild to build a ship and not have a restaurant with a sun-drenched lounging area so you can combine all the things you love in one place (eating and views, obviously) so yep — we did that. The Dock feels like an elegant cabana caught between the chill, seaside perfection of Ibiza and the rustic-chic resorts of Brazil.

SCOOP SHOP - Lick Me Till Ice Cream
Our whimsical ice cream shop harks back to that magical hometown, summer nostalgia, just with a Virgin Voyages twist and some complimentary scoops. That includes six seasonal home (or ship) made, artisanal flavors like the vegan Green Machine or Gianduiotto Chocolate. All with a featured daily flavor announced from our nearby record shop DJ booth, guaranteed to be unlike anything you might remember seeing at your local hometown shop.

COFFEE SHOP - Grounds Club
It’s early. You’re still a bit blurry and coffee is the only thing you can focus on right now. Luckily Grounds Club isn’t far, exclusively pouring one of the most satisfying, and tasty brews we’ve ever had, from direct-trade pioneers, Intelligentsia Coffee. It’s like your favorite coffee shop with the best almond milk, double shot, latte you’ve ever had just with ocean views.

 
 

TAP ROOM - Draught Haus
A selective beer drinker's go-to, the Draught Haus features eight seasonal on-tap varieties plus a wide range of artisanal bottles. This part British pub, part modern craft brewery-inspired taproom, provides plenty of chill eclectic places to sit back and sip, or just grab a growler for those ‘bring your brew with you’, kind of days. Chill, casual but discerning beer connoisseur-approved.

CHAMPAGNE LOUNGE - Sip
Our curated champagne lounge, Sip, was designed to satisfy many needs. Craving a posh early breakfast, high tea in the afternoon, or caviar and an effervescent nightcap in the evening? Whatever the time, you can be sure bubbly will be on the menu all day at this glamorous lounge for Sailors in need of a sparkly refresher.

CASUAL MEDITERRANEAN - Dock House
An effortlessly elegant, yet cozy counterpart to the view-focused scene outside, The Dock House, delivers bright flavors that are anything but laid back while live acoustic sounds round out each taste. Select from choice cuts and fresh fish for the tableside open flame, or try bites like house-made pita and dips. Detox mocktails, Mediterranean-inspired cocktails, or selections from the specially curated Rosé program promise to quench all thirst. Part elegant Ibiza cabana, part rustic-chic resort, always full-on delicious specialty dining.

COCKTAIL BAR - On The Rocks
Why not challenge our mixologists to make you something special? Forget the menu and simply tell the bartender the flavors you love, then watch as a unique masterpiece is created before your very eyes. Kickstart the evening or round out the night with a cocktail that’s perfectly crafted for you.

SOCIAL CLUB - Loose Cannon
Here, an opening gun salute signals the singing of an old sea shanty which can be heard far and wide. This salty sea dog, the nautically-themed bar boasts lively music and animated processions with equally spirited bar keeps, ready to ignite a hearty chant, at a moment’s notice.

 

 
 

$100 Bar tab for your Sailors - Must book and deposit by March 25, 2024

We love finding reasons to raise our glasses — so this year, we’re celebrating Eat & Drink Month for the very first time. From new menu items to specialty cocktails in every bar, we’re adding tasty surprises to every voyage and gifting a $300 Bar Tab per cabin to your Sailors, Rock Stars, and Mega RockStars who sail this year.

THE DETAILS

A Bar Tab is onboard credit your Sailors can use on any beverages not already included in their voyage fare. From drinks to barista coffee, pressed juices, or smoothies, your Sailor calls the shots. And if you tell your November Sailors to double up on their $200 prepaid Bar Tab, we’ll top it off with an extra $100, to spend at any bar on board or at The Beach Club at Bimini. It’s a win-win for everybody. 

How does the Bar Tab work?
Pre-voyage, Sailors can purchase a Bar Tab in $200 increments, and any premium beverages will be deducted from their Bar Tab. They can check their balance in The Sailor App.

What’s already included?
Filtered still and sparkling water, non-pressed juices, sodas, tea bags, and drip coffee are always on us.

 

Unexpected Entertainment

Blink-or-you'll-miss-it pop-up performances and shows that blur the line between audience and performer. Our motley crew of buzzworthy musicians, globetrotting DJs and audacious drag performers will make you feel so immersed in their world, you'll be glad your friends didn't let you get up and join them (but you can if you want). 

 Two Types of Events + Gigs Onboard:

1. Out Among The Sailors: Events that happen in the real world during a voyage, to either amplify an existing vibe or cater to a type of activity

2. In A Venue: Events in a venue like The Manor or The Red Room

 

A full-on riot of a show

It’s a game show like no other. You'll win points. You’ll lose points. You'll know all the tunes. And you may even surprise yourself as you break into song — all while wondering, “Okay, wait, what exactly is going on?” The Host and Assistant will entertain you while guiding you through to the Grand Prize; a finale like you've never experienced before. And psst, it’s never the same show twice. And if you’re still not clear what you’re about to see… perfect. We promise you’ll love it.

 

A new performance every night

Taking a cue from festival-style performances from around the globe, our rotation of comedians, mentalists, and specialty artists offer their unique style of theatrics and talent, just for our Sailors. From one-time only to limited-run residencies, our showstopping selection of music, comedy, and audience participation-driven performances offer fresh, immersive spectacles — so no matter how many times you come aboard, you’ll be amazed at each new and exciting show.

 
 
Need to Know:
Itinerary
  • Check your specific sailing for exact departure and arrival times. All times are local to the port.
  • Itineraries are subject to change at any time without notice.
 
Embarkation & Desembarkation
  • Due to security reasons, all guests must be on board 2 hours before sailing on Day 1 of the cruise.
  • Disembarkation usually begins 2 hours after docking on the final day of the cruise.

Required Travel Documents

What are the Passport requirements for Voyages departing from San Juan?
Our voyages require Sailors to have a valid passport with an expiration date at least 6 months after the voyage end date. Additionally, depending on your country of citizenship, certain ports may also require a visa for entry. Additional information can be found by clicking here.
 
Cancellation policy:
Our cancellation policy was created to provide a better experience for our Sailors. Here's what you need to know:
 
  • You have the most flexibility outside of 120 days before your voyage. If you're booking at this time, you have a 7-day grace period to request a full refund on your deposit and any other payments made. Refunds will be issued to your original form of payment.
  • After the grace period (but still before the 120-day mark), you can receive a full refund on any payments, not including your deposit. For your deposit, you will receive Future Voyage Credit at this time.
  • Between 119 and 45 days, any funds paid will be converted to Future Voyage Credit, good to use on any voyage 1 year from the original voyage start date. Sweet deal, huh
  • Within 44 days of your voyage, all funds paid are final. But you do have the option to send a mate in your place up to 48 hours before your voyage if you really can't sail. 

 

IF YOU NEED A CABIN OTHER THAN INTERIOR, OCEANVIEW, OR REGULAR BALCONY OR HAVE MORE THAN 2 CRUISERS, PLEASE CONTACT US!

 

TSheeka Ruffin

TSheeka Ruffin

PLEASANT POINT TRAVEL LLC

+1 (630) 974-5621 ext 1

tsheeka@pleasantpointtravel.com

 


Available Packages

Interior Cabin
Unavailable as of May 31, 2024

Starting At: $1,645.00
Deposit: $350.00 per person

Designed with a Sailor’s many moods in mind, our cabins are revolutionizing ship design to create a personal retreat complete with modern aesthetics, yacht-like sensibilities, and functional living space. The ultimate go-to for relaxation and rejuvenation, our cabins stand out for their flexible furnishings, upgraded bathrooms with Roomy Rainshowers, and sensory mood lighting, creating comfy quarters that are way more than just a place to crash.
 
Prices Include:
  • Cruise fare
  • 1 Pre-night hotel stay at the Condado Palm Inn San Juan
  • Roundtrip Airport/Cruise Transfers 
  • Gratuities, taxes, fees, and port charges. 
  • All meals on board Virgin Voyages 
  • $200 Bar Tab per cabin
  • $50 Additional Sailor Loot

Seaview Cabin
Unavailable as of May 31, 2024

Starting At: $1,700.00
Deposit: $360.00 per person

Designed with a Sailor’s many moods in mind, our cabins are revolutionizing ship design to create a personal retreat complete with modern aesthetics, yacht-like sensibilities, and functional living space. The ultimate go-to for relaxation and rejuvenation, our cabins stand out for their flexible furnishings, upgraded bathrooms with Roomy Rainshowers, and sensory mood lighting, creating comfy quarters that are way more than just a place to crash.
 
Prices Include:
  • Cruise fare
  • 1 Pre-night hotel stay at the Condado Palm Inn San Juan
  • Roundtrip Airport/Cruise Transfers 
  • Gratuities, taxes, fees, and port charges. 
  • All meals on board Virgin Voyages 
  • $200 Bar Tab per cabin
  • $50 Additional Sailor Loot

Sea View Terrace
Unavailable as of June 15, 2024

Starting At: $1,844.00
Deposit: $420.00 per person

Designed with a Sailor’s many moods in mind, our cabins are revolutionizing ship design to create a personal retreat complete with modern aesthetics, yacht-like sensibilities, and functional living space. The ultimate go-to for relaxation and rejuvenation, our cabins stand out for their flexible furnishings, upgraded bathrooms with Roomy Rainshowers, and sensory mood lighting, creating comfy quarters that are way more than just a place to crash.
 
Prices Include:
  • Cruise fare
  • 1 Pre-night hotel stay at the Condado Inn San Juan
  • Roundtrip Airport/Cruise Transfers 
  • Gratuities, taxes, fees, and port charges. 
  • All meals on board Virgin Voyages 
  • $200 Bar Tab per cabin
  • $100 Additional Sailor Loot

Interior Cabin with Flights from O'Hare Airport
Unavailable as of May 31, 2024

Starting At: $2,388.00
Deposit: $450.00 per person

Designed with a Sailor’s many moods in mind, our cabins are revolutionizing ship design to create a personal retreat complete with modern aesthetics, yacht-like sensibilities, and functional living space. The ultimate go-to for relaxation and rejuvenation, our cabins stand out for their flexible furnishings, upgraded bathrooms with Roomy Rainshowers, and sensory mood lighting, creating comfy quarters that are way more than just a place to crash.
 
Prices Include:
  • Roundtrip flights from Chicago O'Hare Airport
  • Cruise Accommodations
  • 1 Pre-night hotel stay at the Condado Palm Inn San Juan
  • Roundtrip Airport/Cruise Transfers 
  • Gratuities, taxes, fees, and port charges. 
  • All meals on board Virgin Voyages 
  • $200 Bar Tab per cabin
  • $50 Additional Sailor Loot
 
Flight Airports Departs Arrives Airline
# Ref From   To        
1 AA2268 ORD   SJU 13-Dec-2024 08:20 13-Dec-2024 14:52 American
2 AA2268 SJU   ORD 21-Dec-2024 16:17 21-Dec-2024 19:40 American
TERMS & CONDITIONS
  • THE DEPOSIT IS NON-REFUNDABLE.
  • Balance Due August 5, 2024. 
  • 100% PENALTY AFTER AUGUST FIRST

Seaview Cabin with flights from O'Hare Airport
Unavailable as of May 31, 2024

Starting At: $2,440.00
Deposit: $470.00 per person

Designed with a Sailor’s many moods in mind, our cabins are revolutionizing ship design to create a personal retreat complete with modern aesthetics, yacht-like sensibilities, and functional living space. The ultimate go-to for relaxation and rejuvenation, our cabins stand out for their flexible furnishings, upgraded bathrooms with Roomy Rainshowers, and sensory mood lighting, creating comfy quarters that are way more than just a place to crash.
 
Prices Include:
  • Roundtrip flights from Chicago O'Hare Airport
  • Cruise Accommodations
  • 1 Pre-night hotel stay at the Condado Palm Inn San Juan
  • Roundtrip Airport/Cruise Transfers 
  • Gratuities, taxes, fees, and port charges. 
  • All meals on board Virgin Voyages 
  • $200 Bar Tab per cabin
  • $50 Additional Sailor Loot
  •  
Flight Airports Departs Arrives Airline
# Ref From   To        
1 AA2268 ORD   SJU 13-Dec-2024 08:20 13-Dec-2024 14:52 American
2 AA2268 SJU   ORD 21-Dec-2024 16:17 21-Dec-2024 19:40 American
TERMS & CONDITIONS
  • THE DEPOSIT IS NON-REFUNDABLE.
  • Balance Due August 5, 2024. 
  • 100% PENALTY AFTER AUGUST FIRST

Sea View Terrace with flights from O'Hare Airport
Unavailable as of June 15, 2024

Starting At: $2,115.60
Deposit: $525.00 per person

Designed with a Sailor’s many moods in mind, our cabins are revolutionizing ship design to create a personal retreat complete with modern aesthetics, yacht-like sensibilities, and functional living space. The ultimate go-to for relaxation and rejuvenation, our cabins stand out for their flexible furnishings, upgraded bathrooms with Roomy Rainshowers, and sensory mood lighting, creating comfy quarters that are way more than just a place to crash.
 
Prices Include:
  • Roundtrip flights from Chicago O'Hare Airport
  • Cruise Accommodations
  • 1 Pre-night hotel stay at the Condado Palm Inn San Juan
  • Roundtrip Airport/Cruise Transfers 
  • Gratuities, taxes, fees, and port charges. 
  • All meals on board Virgin Voyages 
  • $200 Bar Tab per cabin
  • $100 Additional Sailor Loot
 
Flight Airports Departs Arrives Airline
# Ref From   To        
1 AA2268 ORD   SJU 13-Dec-2024 08:20 13-Dec-2024 14:52 American
2 AA2268 SJU   ORD 21-Dec-2024 16:17 21-Dec-2024 19:40 American
TERMS & CONDITIONS
  • THE DEPOSIT IS NON-REFUNDABLE.
  • Balance Due August 5, 2024. 
  • 100% PENALTY AFTER AUGUST FIRST

Solo Insider Cabin with Flights from O'Hare Airport
Unavailable as of June 15, 2024

$2,950.00
Deposit: $500.00 per person

Designed with a Sailor’s many moods in mind, our cabins are revolutionizing ship design to create a personal retreat complete with modern aesthetics, yacht-like sensibilities, and functional living space. The ultimate go-to for relaxation and rejuvenation, our cabins stand out for their flexible furnishings, upgraded bathrooms with Roomy Rainshowers, and sensory mood lighting, creating comfy quarters that are way more than just a place to crash.
 
Prices Include:
  • Roundtrip flights from Chicago O'Hare Airport
  • Cruise Accommodations
  • 1 Pre-night hotel stay at the Condado Palm Inn San Juan
  • Roundtrip Airport/Cruise Transfers 
  • Gratuities, taxes, fees, and port charges. 
  • All meals on board Virgin Voyages 
  • $200 Bar Tab per cabin
  • $50 Additional Sailor Loot
 
Flight Airports Departs Arrives Airline
# Ref From   To        
1 AA2268 ORD   SJU 13-Dec-2024 08:20 13-Dec-2024 14:52 American
2 AA2268 SJU   ORD 21-Dec-2024 16:17 21-Dec-2024 19:40 American
TERMS & CONDITIONS
  • THE DEPOSIT IS NON-REFUNDABLE.
  • Balance Due August 16, 2024. 
  • 100% PENALTY AFTER AUGUST FIRST

Extra Options

Travel Trip Insurance
Unavailable as of August 25, 2024

$0.00

Enhance your travel experience by adding travel protection, providing added security against unforeseen events. Opting for this feature is available during the booking process, and the applicable quote will be provided at that time.
 
ONCE PURCHASED INSURANCE IS NON_REFUNDABLE