2027 Boston-to-Caribbean Group Cruise
Boston → San Juan | October 20–29, 2027 | Celebrity Summit
This isn’t a “sit still and do nothing” cruise — unless that’s exactly what you want that day.
We’re sailing straight out of Boston on Celebrity Summit for a longer Caribbean itinerary that mixes active sea days, really good food, and just enough structure to make it feel like something special without turning it into a forced group experience.
What’s Included
• Ocean View stateroom
• Classic Drinks Package
• Premium Wi-Fi + VIP Access
• Gratuities, taxes & port fees
• Photo + water bottle package
• Airport transfer in San Juan
• 4 curated group excursions
🏓 Pickleball at Sea
Yes — real pickleball courts on board.
We’ll have casual open play on sea days and a few friendly group matchups for anyone who wants in. Nothing competitive, nothing awkward. Play a game, grab a drink, come back later if you feel like it.
Bring your paddle or borrow one onboard. Or don’t play at all — this part is optional, not mandatory fun.
🍽️ The Food
World-Class Dining by Daniel Boulud
Celebrity Cruises’ culinary program is designed by Daniel Boulud, one of the most respected chefs in the world.
• Restaurant-level main dining menus nightly
• Global cuisine nights + elevated classics
• Famous Indian curries, fresh seafood, house-made pastas
• European café with espresso & pastries
• High-quality casual dining that still feels upscale
⭐Chef’s Table by Daniel Boulud (optional add-on $)
A limited-capacity, five-course tasting experience featuring:
• Champagne & canapés
• Private galley tour
• Chef-designed menu
• Keepsakes + commemorative photo
** We plan to reserve this experience as a group for those interested.
🛳️ Sea Days (3 Total)
Sea days are the whole point.
• Pools, hot tubs, and the adults-only Solarium
• Live music, shows, comedy, trivia, and random things you didn’t plan to attend but will anyway
• Casino, rooftop movies, silent disco
• Gym, fitness classes, open deck space
• Pickleball courts, sun, snacks, repeat
Do a lot. Do nothing. Both count.
🌴 Ports of Call
Puerto Plata, DR
Dominican culture tour + Coconut Cove beach (included)
Samaná, DR
Open day for beaches or excursions
St. Thomas
Magens Bay, Drake’s Seat, Skyride gondola (included)
Antigua
Open beach day; famous 365 beaches
Tortola, BVI
Cane Garden Bay (included) or optional zipline
San Juan, PR
Old & New San Juan tour + airport transfer (included)
✈️ Not Included
Return flight (~$360 total for 2; SJU to BOS)
Travel Insurance (recommended) ~ $563/cabin
🚢 Who This Cruise Makes Sense For
• People who like travel with a little structure but plenty of freedom
• Food-motivated travelers
• Pickleball players who want games without taking it too seriously
• Friends, couples, and solo travelers
• Anyone who likes sailing out of Boston and skipping the flight at the start
💬 Ready to Book?
$5,255.44 per cabin (2 guests; double occupancy)
Deposit: $50
Final payment due: June 22, 2027
Group space is limited and this sailing will fill.
Offer expires Jan 5, 2026. Terms and Conditions apply. Please request more details. Pricing, availability, itinerary, and included amenities are subject to change at any time and are not guaranteed until a deposit is received and booking is confirmed.
