28th November to 5th December 2025
Caribbean Cruise
Out of Office Collective
Join us on a cruise of the Caribbean .
Join us for a 6-night, modern adults-only voyage as we explore four stunning Caribbean islands!
Our adventure begins in the sunny paradise of San Juan, Puerto Rico, where we set sail from the charming, historic streets of Old San Juan.
Our first stop is the vibrant island of St. Maarten, where Dutch and French cultures meet against a backdrop of breath-taking beaches.
Next, we explore the scenic beauty of St. Kitts and Nevis—known for its lush hillsides, friendly locals, and sweeping coastal views.
We then continue to Dominica, a land of lush, volcanic landscapes—renowned for its natural hot springs, waterfalls, and rainforest hikes.
Our final destination is Barbados, where lively island spirit meets crystal-clear waters, vibrant coral reefs, and a thriving local food scene—an ideal spot to unwind before we return to Puerto Rico.
This cruise promises a perfect mix of tropical tranquillity and cultural discovery at every port.
So, let’s go out of office to the Caribbean!
Accommodation in San Juan, Puerto Rico
Nestled in the historic Old San Juan district, this stylish hotel offers a modern haven infused with the rich cultural charm of Puerto Rico.
Whether you're wandering the cobblestone streets outside or watching the sun dip into the bay from the rooftop pool, every moment here invites you to slow down and soak it all in. The location couldn’t be better—just steps from the cruise piers, vibrant shops, lively cafés, and the city’s most iconic landmarks. And when it’s time to arrive or depart, the airport is just a quick 10-minute drive away.
Each room is thoughtfully designed, blending contemporary elegance with tropical touches. Rooms feature views of either the scenic San Juan Bay or the colourful, historic city streets.
Amenities include complimentary Wi-Fi, air conditioning, mini-fridges, coffee makers, and sleek modern bathrooms. Guests can also enjoy a rooftop pool, whirlpool, fitness centre, and several on-site bars and restaurants.
‘Shared’ rooms have 2 beds, unless a double is requested. 
Deluxe Double Room
Accommodation on the Cruise Ship
Sea Terrace Cabin
The Sea Terrace Cabin—your oceanfront oasis!
Step into a space where sleek modern design meets the calm beauty of the sea. These cabins offer a luxurious retreat with sweeping panoramic views, private balconies complete with signature handwoven hammocks, and cutting-edge amenities to make your stay effortless and unforgettable.
Enjoy the “Roomy Rainshower” for a spacious, invigorating shower experience, and take full control of your environment with an in-room tablet that lets you adjust mood lighting, stream music and movies, and order room service with a single tap.
Unwind in style with a 43” 4K TV offering a wide range of streaming options, relax in the supple saddle leather lounge chair, or toast the sunset at your own champagne table.
Additional thoughtful touches include a well-stocked mini bar, steamer, hairdryer, and plenty of hidden storage to keep things tidy.
‘Shared’ rooms have 2 beds, unless a double is requested. 
Sea Terrace Cabin
Daily Itinerary
Day 1
Welcome to San Juan, Puerto Rico!
To avoid any travel day stress, we’ll be spending the night before the cruise at a beautiful hotel in Old San Juan. This is a great chance to settle in and meet the rest of the group before we sail out!
Day 2
Join us for our group breakfast and spend the morning enjoying the hotel facilities.
In the afternoon, we will have lunch and a welcome social in the hotel, before checking out and literally walking across the road to the cruise terminal, where our Caribbean adventure officially begins.
Day 3
Philipsburg, St. Maarten, 9am to 6pm.
Known for its dual Dutch-French heritage and turquoise bays, St. Maarten is a Caribbean gem.
Join us for a private group tour of the island to learn more about its rich culture!
Day 4
Basseterre, St. Kitts and Nevis, 8am to 6pm.
A perfect mix of laid-back charm and natural beauty, St. Kitts is all about scenic views.
You will have a free day to explore the island!
Day 5
Roseau, Dominica, 8am to 6pm.
Nicknamed “The Nature Island,” Dominica offers waterfalls, hot springs, and lush rainforests.
Join us for a private group island tour to explore the wonders of the island.
Day 6
Bridgetown, Barbados, 8am to 6pm.
Known for its pristine beaches, vibrant culture, and world-famous rum, Barbados is the perfect blend of laid-back island life and rich history.
This is a free day to explore as you please.
Day 7
Day At Sea
This will be a full day at sea, and an excellent opportunity to rest, recover, and enjoy what is on-board the ship.
In the evening, we will have our private farewell dinner, a lovely way to wrap up the memories of an unforgettable week!
Day 8
San Juan, Puerto Rico, 6:30am
Our adventure ends as we return back to San Juan, where the ship will dock around 6:30am and we will say our farewells.
What’s Included
-
![]()
1 night in San Juan hotel
4* hotel in Old San Juan
including breakfast & lunch -
![]()
6 nights on a cruise ship
Sea Terrace cabin with
ocean view and balcony -
![]()
All-inclusive meals
20+ onboard eateries for breakfast, lunch, dinner and snacks
-
![Essential drinks package]()
Soft drinks package
Still & sparkling water, non-pressed juices, sodas, teas & drip coffee
-
![]()
Bar tab for drinks
$200 bar tab for alcoholic
drinks per cabin -
![]()
On-board amenities
Wi-fi, fitness centre, games room, basketball court, spa, pools & more
-
![]()
Sint Marteen tour
Private group island
tour of Sint Marteen -
![]()
Dominica tour
Private group tour
in Dominica -
![]()
Welcome social
Afternoon social at the
hotel in Old San Juan -
![]()
Farewell dinner
Group farewell dinner at
one of the ship’s eateries -
![]()
Tips
All tips & gratuities onboard
the ship are covered -
![]()
One-way airport transfer
From SJU airport to hotel
on day of arrival (28th) -
![]()
OOOC goodie bag
Exclusive OOOC tote goodie
bag with gifts & essentials -
![]()
OOOC trip t-shirt
Exclusive OOOC t-shirt
with trip branding
Prices
Shared Room*
£1750 pp
Secure your shared room with a
non-refundable deposit of £250.
Pay the balance in 5 instalments.
Solo Room*
£2650 pp
Secure your solo room with a
non-refundable deposit of £400.
Pay the balance in 5 instalments.
*Inclusive of all specified activities and transfers
There are 2 types of room - Shared and Solo:
Shared - for people travelling solo or with a friend/partner, who wish to share a room (2 people, 2 beds unless 1 requested).
Solo - for people travelling solo, who want their own space (1 person, 1 bed).
You can either choose to make the upfront deposit payment to secure your space and then pay the balance in 5 instalments or pay the fully upfront.
Shared room
Upfront deposit: £250
5 instalments: £300 due on 1st July, 1st August, 1st September, 1st October & 1st November
OR
Full payment: £1750
Solo room
Upfront deposit: £400
5 instalments: £450 due on 1st July, 1st August, 1st September, 1st October & 1st November
OR
Full payment: £2650
To book one of these rooms:
Click ‘Book now’ to take you to our We Travel booking page.
Select your desired room type, fill in your details and make the required payment.
Your reservation is confirmed up receipt of the booking confirmation email.
Fill in the ‘Booking Details’ form linked in the confirmation to finalise your booking.
Subsequent payments will automatically be taken, as part of your payment plan.
How to book
FAQs
-
The trips are for people aged 21 - 35.
-
No, flights are not included as part of the package.
You will need to book your own flight to Luis Muñoz Marín International Airport (SJU).
We recommend using Kayak or Skyscanner to find the cheapest flights.
-
Flights should be booked to Luis Munoz Marín International Airport (SJU).
Please arrive as early as possible on Friday 28th November.
-
Click here to view the visa requirements for your country for the US (including Puerto Rico). British citizens will need an ESTA here.
You will have to confirm the visa requirements for each Caribbean destination depending on your citizenship, but British citizens do not require visas for the Caribbean.
-
There are 2 types of room - Shared and Solo:
Shared - for people travelling solo or with a friend/partner, who wish to share a room (2 people, 2 beds unless 1 requested)
Solo - for people travelling solo, who want their own space (1 person, 1 bed).
You can either choose to make the upfront deposit payment to secure your space and then pay the balance in 5 instalments or pay the fully upfront.
Please see above to reserve your place on the trip via our We Travel page. -
You can either choose to make the upfront deposit payment to secure your space and then pay the balance in 5 instalments or pay the fully upfront.
Shared room
Upfront deposit: £250
5 instalments: £300 due on 1st July, 1st August, 1st September, 1st October, 1st November.
OR
Full payment: £1750
Solo roomUpfront deposit: £400
5 instalments: £450 due on 1st July, 1st August, 1st September, 1st October, 1st November.
OR
Full payment: £2650
-
Yes! Travel insurance is a must - make sure that it covers water related activities.
This can be purchased from insurance comparison sites.
-
If you have a friend you want to share a room with, we recommend booking together by selecting 2 for quantity on the booking page. You will then have to pay 2 deposits.
If you are a solo traveller who has booked a shared room, you can find someone to share with either through the group chat, events, or we can facilitate pairing you up.
-
They are not included as part of the all-inclusive.
Each cabin will receive a $200 allowance for alcoholic drinks for the trip.
-
Aboard this adults-only voyage, there is a fitness centre, fitness classes (including yoga), spa, 20+ eateries, basketball courts, 2 pools, a games room, live entertainment, a nightclub, and so much more! You will never be bored!