NOTE: We expect this group cruise to sell out. Secure your spot today with a refundable deposit.
Are you ready to embark on a tropical paradise adventure in the dead of winter? We’re thrilled to announce our next Postcard Jar Friends Cruise to the Southern Caribbean in January 2027. And this time, we’re offering back-to-back cruises! Pick Week #1, Week #2, or stay on board for both. It’s up to you! Secure your spot HERE! You MUST book through THIS LINK to get the discounted group pricing and perks and be included in group events.
What Islands Will We Visit?
Trade winter gray skies for warm Caribbean breezes as your journey begins and ends in vibrant San Juan, Puerto Rico. We decided to sail out of Puerto Rico this year instead of Florida. It seems that many flights and hotels are actually less expensive there.
Week #1 (Jan. 9–16, 2027)
Charlotte Amalie – St. Thomas
A shopper’s paradise with stunning harbor views, beautiful beaches, and easy island vibes—perfect for a relaxed first taste of the Caribbean. Magen’s Bay is one of the island’s most famous beaches, known for its calm, clear water and long stretch of soft white sand—perfect for an easy, relaxing beach day (and a very popular cruise stop for a reason).
Philipsburg – St. Maarten
A unique island split between Dutch and French culture, known for lively beach bars, turquoise waters, and the famous planes landing at Maho Beach.
St. John’s – Antigua
Bright, colorful, and surrounded by 365 beaches—one for every day of the year—this island is all about sunshine, sailing, and soft sand.
Castries – St. Lucia
Dramatic Piton mountains, lush rainforests, and breathtaking coastal views make this one of the most scenic stops in the Caribbean.
St. George’s – Grenada
Known as the “Spice Island,” Grenada offers fragrant markets, rolling hills, waterfalls, and some of the Caribbean’s most beautiful beaches.
Week #2 (Jan. 16–23, 2027)
Charlotte Amalie — St. Thomas
Beautiful beaches, island vibes, and fantastic shopping.
Basseterre – St. Kitts/Nevis
A relaxed island filled with history, scenic views, and the unique chance to see both the Atlantic Ocean and Caribbean Sea from one spot.
Roseau – Dominica
The “Nature Island” is rich with waterfalls, hot springs, and rainforest adventures—perfect for those who love exploring the outdoors.
Castries – St. Lucia
A repeat favorite for a reason—stunning scenery, iconic Pitons, and unforgettable experiences both on land and sea.
Bridgetown – Barbados
A lively mix of British heritage and Caribbean charm, with gorgeous beaches, rich culture, and plenty to explore.
Each stop offers its own unique rhythm and beauty, blending vibrant culture, stunning beaches, and unforgettable scenery. And, for those of you considering the back-to-back, the only repeated island stop is St. Lucia. After days filled with island-hopping adventure and relaxation, you’ll return refreshed to San Juan—the perfect ending to a truly idyllic winter escape. This is your chance to explore 10 different islands while only unpacking your suitcase once!
About the Celebrity Constellation
Indulge in a more intimate and classic cruising experience aboard the elegant Celebrity Constellation. As part of Celebrity Cruises’ Millennium Class—and our very first Postcard Jar group cruise on this class of ship—you’ll enjoy a smaller, more relaxed atmosphere than the larger ships we’ve sailed together in the past. Think fewer crowds, a slower pace, and more space to truly unwind while still enjoying the elevated touches Celebrity is known for.
You’ll find comfortable accommodations, excellent dining, and inviting spaces to gather or slip away for quiet moments—whether that’s lounging by the pool, enjoying a spa treatment, or catching a show in the theater. And of course, we’ll be hosting special events just for our Postcard Jar friends throughout the cruise, creating a warm, connected experience you won’t find anywhere else.
Why Join Our Group Cruise to the Southern Caribbean?
- Exclusive Experiences: As part of our group, you’ll have access to special events, activities, and discounted group rates.
- Like-Minded Travelers: Connect with fellow travelers who share your passion for adventure and relaxation.
- Expert Guidance: As experienced cruisers, Steve and Ann Teget will be available to assist you with planning your trip and ensuring a seamless experience. In addition, now that we are travel advisors with Dream Vacations, we handle your booking, as well.
Still unsure if group travel is right for you? Check out THIS BLOG POST we wrote to help you decide.
Dates and Itinerary
Our cruise will depart from San Juan, Puerto Rico both Jan. 9 and Jan. 16. The complete itineraries are below. As with all cruises, it is subject to change.
Secure your spot on the Southern Caribbean Cruise(s) today!
Don’t miss out on this incredible opportunity to explore the Southern Caribbean with Steve, Ann, and other friends of Postcard Jar. Here’s how you can join us.
- Secure your spot(s) on our Celebrity Constellation cruise by filling out THIS FORM. Space is limited, so don’t delay.
- Enjoy your hassle-free vacation with old and new friends.
- Cross three amazing destinations off your bucket list!
Cabins and Rates for the Southern Caribbean Cruise
All cabin rates* INCLUDE:
- All meals on board the ship (excluding specialty restaurants)
- Classic Beverage Package
- Basic Wifi
- Gratuities
- Friends of Postcard Jar special events
For Retreat, solo, inside or accessible cabins or additional guest pricing, email Steve Teget for a quote.
Aqua Class Cabins
Double occupancy (total for 2 people in stateroom) = Week #1 – $4,838 | Week #2 – $4,931 | Both – $9,769*
Includes a private veranda (balcony), exclusive access to Blu restaurant, complimentary access to the Persian Gardens spa relaxation area, and spa concierge service. Begin booking your Aqua Class cabin HERE.
Concierge Class Cabins
Double occupancy (total for 2 people in stateroom) = Week #1 – $4,606 | Week #2 – $4,751 | Both $9,357*
As part of Concierge Class, you’ll have a balcony and the opportunity to attend exclusive events, including a welcome aboard Concierge Class lunch and have access to the concierge team for assistance. Begin booking your Concierge Class cabin HERE.
Veranda Cabin
Double occupancy (total for 2 people in stateroom) = Week #1 – $4,668 | Week #2 $4,667 | Both – $9,332*
Celebrity Constellation, CS, Refurbishment, Suite, Penthouse, Stateroom
Your personal veranda lets you greet the day, soak in breathtaking sunsets, and enjoy fresh sea breezes. Begin booking your Veranda cabin HERE.
Oceanview Cabin
Double occupancy (total for 2 people in stateroom) = Week #1 – $3,638 | Week #2 – $3,638 | Both – $7,276*
Celebrity Constellation, CS, Refurbishment, Ocean View, Oceanview stateroom
Enjoy a window view (but no balcony) with a king or two single beds. Begin booking your Oceanview cabin HERE.
The Retreat (Suites), Solo, and Accessible Cabins
Email Steve Teget for pricing and availability on Retreat, Solo, or Accessible cabins.
As a guest of The Retreat, you’ll enjoy a roomier suite, and a long list of thoughtfully curated amenities and perks. Suites also include Premium Wi-Fi and Premium Beverage Package. You’ll also have exclusive access to Luminae restaurant, butler service, Retreat concierge services, and complimentary access to The Retreat Lounge.
Frequently Asked Questions About Our Friends Cruise
Q: How do I sign up?
A: It’s easy! Just complete this POSTCARD JAR CRUISE FORM and we’ll be in touch. Important: You MUST BOOK ONLY through this link or by contacting Steve and Ann (and not directly through the cruise line or another agent) to be included in Postcard Jar Friends Cruise pricing, meetups, & activities.
Q: Is there a secure online payment option?
A: Yes. You can make a secure payment anytime you’d like with Dream Vacations’ secure payment form. Use this link anytime to make payments: DREAM VACATIONS SECURE ONLINE PAYMENT FORM and select Steve Teget as your travel advisor.
Q: Is this a private charter cruise?
A: No. It is an “everybody – all are welcome” cruise. We just reserved a block of rooms at discounted pricing for friends of Postcard Jar and anyone else who would like to join us.
Q: What if I’ve never cruised before?
A: That’s no problem at all. In fact, that’s what we’re here for. Specifically, we will keep you up to date with emails, a Facebook group, and even group Zoom calls before our cruise to help guide you and answer all of your questions and concerns.
Q: Will there be Postcard Jar group events?
A: Yes, there will be events exclusive to our group. In the past, we’ve done events like a sail away party, martini tasting, cooking class, wine tasting, helipad sail away. In addition, those from our group who are in the same cabin categories may dine together, if desired.
Q: Are drinks included?
A: The Classic Drink Package is included in your cruise fare. It includes soft drinks, beers, spirits, cocktails, liqueurs, frozen drinks, wines by the glass, specialty coffee, tea, and generic water up to $10 per serving. If you’d like a drink that exceeds the $10 limit, you just pay the difference, or you can also upgrade to the Premium Drink Package before the cruise or once onboard for an additional fee.
Q: Do I need a passport?
A: Yes. Every passenger needs a passport to board the ship. In addition, your passport must not expire before September, 2027.
Important Celebrity Cruises and Dream Vacations Terms and Conditions
- *Prices are subject to change until confirmed with your deposit with a credit or debit card.
- Refundable $500 per cabin deposit due at time of booking.
- ALL PAYMENTS are non-refundable after Oct. 1, 2026.
- Non-refundable group service fee of $25 per person will be charged in addition to the cabin rates listed at the time of booking. There is a $50 cancellation fee.
Finally, if you have any questions about our Postcard Jar Friends Cruise to the Southern Caribbean, don’t hesitate to let us know. You can email us at a.teget@dreamvacations.com (Ann), s.teget@dreamvacations.com (Steve) or give us a call at 402.575.9624.
