Name: Out of Office Collective Caribbean Cruise
Start: 2025-11-28
End: 2025-12-05
Location: San Juan, Puerto Rico

Out Of Office Collective

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31 reviews

Nov 28 - Dec 5, 2025

Group size: 30 - 50

Out of Office Collective Caribbean Cruise

San Juan, Puerto Rico

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Out Of Office Collective

Email address verified

31 reviews

£NaN

Nov 28 - Dec 5, 2025

Group size: 30 - 50

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

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
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!
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Day 2
Day 2
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.
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Day 3
Day 3
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.

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Day 4
Day 4
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.
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Day 5
Day 5
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.
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Day 6
Day 6
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.
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Day 7
Day 7
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.
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Day 8
Day 8
San Juan, Puerto Rico, USA
Arrive 6.30am.
Our adventure ends back in San Juan.
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Day 1

Welcome to Puerto Rico!

You will never regret going on an OOOC trip. The organisation, gift bags and communication are top tier. The trip was very good value for money and you can see how much Mel and Tamara care about everyone’s individual experience. Definitely planning another cruise with people I met on the cruise. 10/10 would recommend.

By Alarna F for Out of Office Collective Caribbean Cruise on Dec 14, 2025

If you weren’t there, you definitely missed out on great company, food, countries, vibes on vibes. Enjoyed the cruise 10/10

By Nothando M for Out of Office Collective Caribbean Cruise on Dec 14, 2025

Such an amazing trip. Everything was well organised. The activities were so fun, especially Dominica! It was great being able to enjoy a holiday with everything being planned. Met some amazing people and the vibes wrrr greatWould highly recommend booking a trip with OOOC.

By Joanne M for Out of Office Collective Caribbean Cruise on Dec 14, 2025

Great experience! I thoroughly enjoyed my first OOOC trip and I look forward to future trips. I was very impressed by the organisation of this trip! Thank you Tamara and Mel for ensuring every excursion, transfer and booking went smoothly. Although I was not a solo traveler, I would recommend an OOOC trip to anyone who wishes to solo travel but is still seeking company. We also received a goodie bag and a t-shirt which is also much appreciated!