Out of Office Collective Caribbean Cruise

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Overview

Out of Office Collective Caribbean Cruise
San Juan, Puerto Rico
Nov 28 - Dec 5, 2025
Out Of Office Collective image
Out Of Office Collective
£1,750
Deposit: £550

About your trip

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

San Juan, Puerto Rico


On the night of Friday 28th November, we will be staying in a modern and stylish hotel, right by the departure port in Old San Juan.


Cruise Ship


We will be staying in the top tier and luxurious 'Sea Terrace' rooms, all of which have an ocean-view with a spacious balcony.



There are 2 room options: Shared and Solo.


Shared rooms can be booked by solo travellers and will be shared with another solo traveller. They can also be shared with a person of your choice. These rooms will have twin beds and are same gender unless requested otherwise. 


Solo rooms are single occupancy, so the room is your own. These rooms will have a double bed.


For those in shared rooms, you will have the same roommate for both the San Juan hotel and the cruise.

Terms & Conditions

Any payment made towards booking your place on the holiday is non-refundable, except in the case that the trip is cancelled. If you can no longer attend and wish to get refund, you are responsible for selling your space to another party.


Attendees may be photographed or filmed during the trip. By booking this holiday, attendees grant permission for the organisers to use such media for promotional and documentation purposes.

What's included

One-way airport transfer

Airport transfer from San Juan Airport (SJU) to the hotel in Old San Juan, on Friday 28th November

Accommodation

1 night at a hotel in Old San Juan property

Breakfast

Breakfast in the San Juan hotel on Saturday 29th November

Lunch and welcome social

Lunch in the San Juan hotel on Saturday 29th November

Cruise Accommodation

6 nights in a Sea Terrace cruise cabin (ocean view with balcony)

All-inclusive meals

All-inclusive meal package at 20+ onboard eateries for 6 nights on the cruise, including breakfast, lunch, dinner, snacks and soft drinks

Alcohol drinks allowance

$200 per cabin, for the duration of the cruise

Amenities on-board

20+ eateries, wi-fi, fitness centre, entertainment, and much more!

Tips

All gratuities on-board the ship

Island tour - St Maaten

A private group excursion, including return transportation to the ship

Island tour - Dominica

A private group excursion, including return transportation to the ship

Private farewell dinner

A final dinner on-board the ship exclusively for the group

Recommendations

Excursion, activity and sight-seeing recommendations for the islands where we do not have private group tours

Goodie bag

Exclusive OOOC merch

What's not included

Flights

Flights are not included and will need to be booked separately. Please book your flight to arrive into Luis Muñoz Marín International Airport (SJU) on Friday 28th November.

Some alcoholic drinks

Any alcoholic drinks outside of the $200 per room allowance will be self-funded.

Island expenses

Any food, activities, excursion or expenses during the island stops, that are not included as part of the tours in St Maarten and Barbados.

Travel insurance

Travel insurance is not included and MUST be booked. Proof of insurance may be required.

Any applicable visas

If you need a visa, you will be required to cover the cost yourself. Please leave enough time to apply and receive the visa.

Other

Anything else that isn't covered in the 'What's Included' section.

Day 1

Day 1 image

Welcome to 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

Day 2 image

San Juan, Puerto Rico, USA

After a relaxed morning breakfast and an early afternoon welcome social, we will check out and head to the nearby cruise terminal. 


The cruise departs at 8pm local time, so we must be on board 4 hours before departure. 

Day 3

Day 3 image

Philipsburg, St. Maarten

9am - 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

Day 4 image

Basseterre, St. Kitts and Nevis

8am - 6pm.

A perfect mix of laid-back charm and natural beauty, St. Kitts is all about scenic views.

This is a free day to explore.

Day 5

Day 5 image

Roseau, Dominica

8am - 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

Day 6 image

Bridgetown, Barbados

8am - 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 7 image

Dat at Sea

Enjoy a free day on board to enjoy everything the ship has to offer! 

Join us in the evening for a farewell dinner.

Day 8

Day 8 image

San Juan, Puerto Rico, USA

Arrive 6.30am.

Our adventure ends back in San Juan.

Location

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1. San Juan, Puerto Rico

San Juan, Puerto Rico

About your organizer

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