Caribbean Cruises from San Juan

Cruising from San Juan, Puerto Rico, offers an exciting gateway to the Southern Caribbean with minimal sea days and maximum island time. Caribbean cruises from San Juan in 2025, 2026, and 2027 typically range from 7 to 14 nights and visit exotic destinations such as St. Lucia, Barbados, St. Kitts, Aruba, and Curaçao. As a turnaround port closer to the action, San Juan sailings often include more ports than traditional Caribbean cruises from Florida. Major cruise lines including Royal Caribbean, Celebrity Cruises, and Norwegian Cruise Line operate from here year-round. With Hello Cruise, you can compare itineraries, cruise lines, and the best prices from trusted travel agents.
264 cruises
Discover new experiences on every shore – and on every deck.If you love next-level thrills, world-class dining and stellar entertainment, you’ll love a holiday getaway onboard Brilliance of the Seas®. This headliner levels up adventure with exciting destinations and favourite onboard activities. Reach new heights and take on the signature Rock Climbing Wall 12 metres above deck. Sip craft cocktails at a rotating bar with spectacular views. And catch non-stop entertainment that will make you sing along and laugh out loud.TIME FOR A LATITUDE ADJUSTMENTIf you’re looking for one-of-a-kind ways to experience distinct cultures, savour exotic flavours and soak up views that’ll give even the most seasoned travellers wanderlust, this is the cruise ship for you. Brilliance of the Seas® offers year-round adventures for every kind of explorer.
- Mega Ship
- Fun-filled
- Family-Friendly
Cruise: San Juan (Puerto Rico) – Tortola – Oranjestad – Oranjestad – Willemstad – San Juan (Puerto Rico)
7 nights
Wander to the world’s most captivating destinations onboard Jewel of the Seas®.Between scenery scoping and memory making, you’ll have the time of your life while sailing from one breathtaking location to another. Reach new heights with thrilling rock climbing. Watch showstopping entertainment and stellar Broadway musical productions. And treat your tastebuds to an epicurean feast ranging from Italian specialities to delicious teppanyaki prepared tableside.
- Large Ship
- Fun-filled
- Family-Friendly
Cruise: San Juan (Puerto Rico) – Charlotte Amalie – Philipsburg – Saint Croix Island – Roseau – Bridgetown – San Juan (Puerto Rico)
7 nights
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The Azamara Quest is a mid-sized ship with a deck plan that’s intimate but never crowded, and offers everything modern voyagers are looking for—plus some unexpected extras.Your boutique hotel at sea, the Azamara Pursuit® is a mid-sized ship with a deck plan that’s intimate but never crowded, and offers everything modern voyagers are looking for—plus some unexpected extras.Seven restaurants, cafes, and lounges, a refreshing pool, sun-drenched decks, a revitalising spa…the list goes on. With so many areas to explore onboard Azamara Pursuit, it’s a good thing we have deck plans.One of the best ways to experience the jaw-dropping sights of the Fjords of Norway, and the mesmerising Mediterranean Sea coast lines is from your private veranda. It’s just one of the many benefits exclusive to your wonderfully spacious suite aboard Azamara Pursuit.Escape to a private retreat of polished style, featuring contemporary décor, luxurious linens, plush cotton robes and slippers, French bath products, fresh flowers, turndown treats, and 24-hour room service. (Perhaps we should arrange for a wake-up call
- Small Ship
- All Inclusive
- Premium
Cruise: San Juan (Puerto Rico) – Charlotte Amalie – Saint John's – Saint Pierre – Port Elizabeth, Bequia – Saint George's – Scarborough – Bridgetown – Castries – Roseau – Basseterre, Saint Kitts – Charlestown – Philipsburg – Road Town, Tortola – San Juan (Puerto Rico)
14 nights
Norwegian Epic® is sure to dazzle with her contemporary design, world-class performances and endless onboard activities. Cruisers of all ages can enjoy everything from an Aqua Park to a towering Climbing Wall. Take a break from all the action at Mandara Spa® and enjoy the Thermal Suite – designed for ultimate relaxation. Speaking of grown-ups, Vibe Beach Club and Spice H2O are adult-only venues that provide for an oasis during the day and a party at night. Multiple dining destinations ensure a happy palette at mealtime, whilst drinks can be enjoyed at unique bars like Ice Bar, Shaker’s Martini & Champagne Bar and Maltings Beer & Whiskey Bar. Explore the history of the Mediterranean, relax on the waters of the Transatlantic, or feel the balmy breezes of the Caribbean.. No matter what type of cruise you desire or what group you’re with, prepare for an Epic holiday.
- Large Ship
- Relaxed
- Family-Friendly
Cruise: San Juan (Puerto Rico) – Road Town, Tortola – Saint John's – Bridgetown – Castries – Philipsburg – Saint Thomas – San Juan (Puerto Rico)
7 nights
Discover new experiences on every shore – and on every deck.If you love next-level thrills, world-class dining and stellar entertainment, you’ll love a holiday getaway onboard Brilliance of the Seas®. This headliner levels up adventure with exciting destinations and favourite onboard activities. Reach new heights and take on the signature Rock Climbing Wall 12 metres above deck. Sip craft cocktails at a rotating bar with spectacular views. And catch non-stop entertainment that will make you sing along and laugh out loud.TIME FOR A LATITUDE ADJUSTMENTIf you’re looking for one-of-a-kind ways to experience distinct cultures, savour exotic flavours and soak up views that’ll give even the most seasoned travellers wanderlust, this is the cruise ship for you. Brilliance of the Seas® offers year-round adventures for every kind of explorer.
- Mega Ship
- Fun-filled
- Family-Friendly
Cruise: San Juan (Puerto Rico) – Tortola – Willemstad – Oranjestad – Oranjestad – San Juan (Puerto Rico)
7 nights
Norwegian Epic® is sure to dazzle with her contemporary design, world-class performances and endless onboard activities. Cruisers of all ages can enjoy everything from an Aqua Park to a towering Climbing Wall. Take a break from all the action at Mandara Spa® and enjoy the Thermal Suite – designed for ultimate relaxation. Speaking of grown-ups, Vibe Beach Club and Spice H2O are adult-only venues that provide for an oasis during the day and a party at night. Multiple dining destinations ensure a happy palette at mealtime, whilst drinks can be enjoyed at unique bars like Ice Bar, Shaker’s Martini & Champagne Bar and Maltings Beer & Whiskey Bar. Explore the history of the Mediterranean, relax on the waters of the Transatlantic, or feel the balmy breezes of the Caribbean.. No matter what type of cruise you desire or what group you’re with, prepare for an Epic holiday.
- Large Ship
- Relaxed
- Family-Friendly
Cruise: San Juan (Puerto Rico) – Road Town, Tortola – Saint John's – Bridgetown – Castries – Philipsburg – Saint Thomas – San Juan (Puerto Rico)
7 nights
Discover new experiences on every shore – and on every deck.If you love next-level thrills, world-class dining and stellar entertainment, you’ll love a holiday getaway onboard Brilliance of the Seas®. This headliner levels up adventure with exciting destinations and favourite onboard activities. Reach new heights and take on the signature Rock Climbing Wall 12 metres above deck. Sip craft cocktails at a rotating bar with spectacular views. And catch non-stop entertainment that will make you sing along and laugh out loud.TIME FOR A LATITUDE ADJUSTMENTIf you’re looking for one-of-a-kind ways to experience distinct cultures, savour exotic flavours and soak up views that’ll give even the most seasoned travellers wanderlust, this is the cruise ship for you. Brilliance of the Seas® offers year-round adventures for every kind of explorer.
- Mega Ship
- Fun-filled
- Family-Friendly
Cruise: San Juan (Puerto Rico) – Castries – Basseterre, Saint Kitts – Saint John's – Tortola – Charlotte Amalie – San Juan (Puerto Rico)
7 nights
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Expect the extraordinary as you step aboard and discover the captivating possibilities, all true to her nameWith top deck dining venues, Slice Pizzeria, The Mix, Salty Dog Grill and Coffee & Cones you’ll have even more options to choose from during your stay on board Grand Princess. Relax at The Sanctuary, a tranquil haven reserved for adults, enjoy Movies Under the Stars® poolside or see an award-winning Broadway-style production show in the Princess Theatre, showcasing an even more immersive audio experience.
- Mega Ship
- Great Value
- Premium
Cruise: San Juan (Puerto Rico) – Saint Thomas – Sint Maarten – Saint John's – Dominica – Bridgetown – San Juan (Puerto Rico) – Bridgetown – Castries – Saint John's – Tortola – Saint Kitts – San Juan (Puerto Rico)
14 nights
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Introducing Seabourn Ovation, the sister-ship to the prestigious Seabourn Encore. Seabourn Ovation represents another stage in the evolution of small ship cruising, which Seabourn pioneered and has consistently expanded and enriched. Both ships deliver a wealth of new concepts, a fresh vision and a host of illuminating ideas to delight the world’s most discerning travelers.
- Small Ship
- All Inclusive
- Luxury
Cruise: San Juan (Puerto Rico) – Aruba – Curaçao – Bonaire – Trois-Ilets – Roseau – Montserrat – South Friars Bay – Antigua – Tortola – San Juan (Puerto Rico)
12 nights
Introducing Seabourn Ovation, the sister-ship to the prestigious Seabourn Encore. Seabourn Ovation represents another stage in the evolution of small ship cruising, which Seabourn pioneered and has consistently expanded and enriched. Both ships deliver a wealth of new concepts, a fresh vision and a host of illuminating ideas to delight the world’s most discerning travelers.
- Small Ship
- All Inclusive
- Luxury
Cruise: San Juan (Puerto Rico) – Aruba – Curaçao – Bonaire – Trois-Ilets – Roseau – Montserrat – South Friars Bay – Antigua – Tortola – San Juan (Puerto Rico) – Frenchman's Cay – South Friars Bay – Terre-de-Haut – Saint Pierre – Port Elizabeth, Bequia – Saint George's – Bridgetown
20 nights
The Azamara Quest is a mid-sized ship with a deck plan that’s intimate but never crowded, and offers everything modern voyagers are looking for—plus some unexpected extras.Your boutique hotel at sea, the Azamara Pursuit® is a mid-sized ship with a deck plan that’s intimate but never crowded, and offers everything modern voyagers are looking for—plus some unexpected extras.Seven restaurants, cafes, and lounges, a refreshing pool, sun-drenched decks, a revitalising spa…the list goes on. With so many areas to explore onboard Azamara Pursuit, it’s a good thing we have deck plans.One of the best ways to experience the jaw-dropping sights of the Fjords of Norway, and the mesmerising Mediterranean Sea coast lines is from your private veranda. It’s just one of the many benefits exclusive to your wonderfully spacious suite aboard Azamara Pursuit.Escape to a private retreat of polished style, featuring contemporary décor, luxurious linens, plush cotton robes and slippers, French bath products, fresh flowers, turndown treats, and 24-hour room service. (Perhaps we should arrange for a wake-up call
- Small Ship
- All Inclusive
- Premium
Cruise: San Juan (Puerto Rico) – Charlotte Amalie – Saint John's – Saint Pierre – Port Elizabeth, Bequia – Saint George's – Scarborough – Bridgetown
7 nights
The Azamara Quest is a mid-sized ship with a deck plan that’s intimate but never crowded, and offers everything modern voyagers are looking for—plus some unexpected extras.Your boutique hotel at sea, the Azamara Pursuit® is a mid-sized ship with a deck plan that’s intimate but never crowded, and offers everything modern voyagers are looking for—plus some unexpected extras.Seven restaurants, cafes, and lounges, a refreshing pool, sun-drenched decks, a revitalising spa…the list goes on. With so many areas to explore onboard Azamara Pursuit, it’s a good thing we have deck plans.One of the best ways to experience the jaw-dropping sights of the Fjords of Norway, and the mesmerising Mediterranean Sea coast lines is from your private veranda. It’s just one of the many benefits exclusive to your wonderfully spacious suite aboard Azamara Pursuit.Escape to a private retreat of polished style, featuring contemporary décor, luxurious linens, plush cotton robes and slippers, French bath products, fresh flowers, turndown treats, and 24-hour room service. (Perhaps we should arrange for a wake-up call
- Small Ship
- All Inclusive
- Premium
Cruise: San Juan (Puerto Rico) – Charlotte Amalie – Saint John's – Saint Pierre – Port Elizabeth, Bequia – Saint George's – Scarborough – Bridgetown – Castries – Roseau – Basseterre, Saint Kitts – Charlestown – Philipsburg – San Juan (Puerto Rico)
13 nights
Norwegian Epic® is sure to dazzle with her contemporary design, world-class performances and endless onboard activities. Cruisers of all ages can enjoy everything from an Aqua Park to a towering Climbing Wall. Take a break from all the action at Mandara Spa® and enjoy the Thermal Suite – designed for ultimate relaxation. Speaking of grown-ups, Vibe Beach Club and Spice H2O are adult-only venues that provide for an oasis during the day and a party at night. Multiple dining destinations ensure a happy palette at mealtime, whilst drinks can be enjoyed at unique bars like Ice Bar, Shaker’s Martini & Champagne Bar and Maltings Beer & Whiskey Bar. Explore the history of the Mediterranean, relax on the waters of the Transatlantic, or feel the balmy breezes of the Caribbean.. No matter what type of cruise you desire or what group you’re with, prepare for an Epic holiday.
- Large Ship
- Relaxed
- Family-Friendly
Cruise: San Juan (Puerto Rico) – Road Town, Tortola – Saint John's – Bridgetown – Castries – Philipsburg – Saint Thomas – San Juan (Puerto Rico)
7 nights
Discover new experiences on every shore – and on every deck.If you love next-level thrills, world-class dining and stellar entertainment, you’ll love a holiday getaway onboard Brilliance of the Seas®. This headliner levels up adventure with exciting destinations and favourite onboard activities. Reach new heights and take on the signature Rock Climbing Wall 12 metres above deck. Sip craft cocktails at a rotating bar with spectacular views. And catch non-stop entertainment that will make you sing along and laugh out loud.TIME FOR A LATITUDE ADJUSTMENTIf you’re looking for one-of-a-kind ways to experience distinct cultures, savour exotic flavours and soak up views that’ll give even the most seasoned travellers wanderlust, this is the cruise ship for you. Brilliance of the Seas® offers year-round adventures for every kind of explorer.
- Mega Ship
- Fun-filled
- Family-Friendly
Cruise: San Juan (Puerto Rico) – Kralendijk – Willemstad – Oranjestad – Tortola – San Juan (Puerto Rico)
7 nights
Introducing Seabourn Ovation, the sister-ship to the prestigious Seabourn Encore. Seabourn Ovation represents another stage in the evolution of small ship cruising, which Seabourn pioneered and has consistently expanded and enriched. Both ships deliver a wealth of new concepts, a fresh vision and a host of illuminating ideas to delight the world’s most discerning travelers.
- Small Ship
- All Inclusive
- Luxury
Cruise: San Juan (Puerto Rico) – Frenchman's Cay – South Friars Bay – Terre-de-Haut – Saint Pierre – Port Elizabeth, Bequia – Saint George's – Bridgetown
8 nights
Norwegian Epic® is sure to dazzle with her contemporary design, world-class performances and endless onboard activities. Cruisers of all ages can enjoy everything from an Aqua Park to a towering Climbing Wall. Take a break from all the action at Mandara Spa® and enjoy the Thermal Suite – designed for ultimate relaxation. Speaking of grown-ups, Vibe Beach Club and Spice H2O are adult-only venues that provide for an oasis during the day and a party at night. Multiple dining destinations ensure a happy palette at mealtime, whilst drinks can be enjoyed at unique bars like Ice Bar, Shaker’s Martini & Champagne Bar and Maltings Beer & Whiskey Bar. Explore the history of the Mediterranean, relax on the waters of the Transatlantic, or feel the balmy breezes of the Caribbean.. No matter what type of cruise you desire or what group you’re with, prepare for an Epic holiday.
- Large Ship
- Relaxed
- Family-Friendly
Cruise: San Juan (Puerto Rico) – Oranjestad – Willemstad – Castries – Basseterre, Saint Kitts – San Juan (Puerto Rico)
7 nights
Introducing Seabourn Ovation, the sister-ship to the prestigious Seabourn Encore. Seabourn Ovation represents another stage in the evolution of small ship cruising, which Seabourn pioneered and has consistently expanded and enriched. Both ships deliver a wealth of new concepts, a fresh vision and a host of illuminating ideas to delight the world’s most discerning travelers.
- Small Ship
- All Inclusive
- Luxury
Cruise: San Juan (Puerto Rico) – Frenchman's Cay – South Friars Bay – Terre-de-Haut – Saint Pierre – Port Elizabeth, Bequia – Saint George's – Bridgetown – Rodney Bay – Terre-de-Haut – South Friars Bay – Montserrat – Curaçao – Aruba – Bonaire – Saint George's – Port Elizabeth, Bequia – Bridgetown
20 nights
Discover new experiences on every shore – and on every deck.If you love next-level thrills, world-class dining and stellar entertainment, you’ll love a holiday getaway onboard Brilliance of the Seas®. This headliner levels up adventure with exciting destinations and favourite onboard activities. Reach new heights and take on the signature Rock Climbing Wall 12 metres above deck. Sip craft cocktails at a rotating bar with spectacular views. And catch non-stop entertainment that will make you sing along and laugh out loud.TIME FOR A LATITUDE ADJUSTMENTIf you’re looking for one-of-a-kind ways to experience distinct cultures, savour exotic flavours and soak up views that’ll give even the most seasoned travellers wanderlust, this is the cruise ship for you. Brilliance of the Seas® offers year-round adventures for every kind of explorer.
- Mega Ship
- Fun-filled
- Family-Friendly
Cruise: San Juan (Puerto Rico) – Charlotte Amalie – Tortola – Basseterre, Saint Kitts – Saint John's – Castries – San Juan (Puerto Rico)
7 nights
The Azamara Quest is a mid-sized ship with a deck plan that’s intimate but never crowded, and offers everything modern voyagers are looking for—plus some unexpected extras.Your boutique hotel at sea, the Azamara Pursuit® is a mid-sized ship with a deck plan that’s intimate but never crowded, and offers everything modern voyagers are looking for—plus some unexpected extras.Seven restaurants, cafes, and lounges, a refreshing pool, sun-drenched decks, a revitalising spa…the list goes on. With so many areas to explore onboard Azamara Pursuit, it’s a good thing we have deck plans.One of the best ways to experience the jaw-dropping sights of the Fjords of Norway, and the mesmerising Mediterranean Sea coast lines is from your private veranda. It’s just one of the many benefits exclusive to your wonderfully spacious suite aboard Azamara Pursuit.Escape to a private retreat of polished style, featuring contemporary décor, luxurious linens, plush cotton robes and slippers, French bath products, fresh flowers, turndown treats, and 24-hour room service. (Perhaps we should arrange for a wake-up call
- Small Ship
- All Inclusive
- Premium
Cruise: San Juan (Puerto Rico) – Charlotte Amalie – Virgin Gorda – Saint John's – Saint Pierre – Port Elizabeth, Bequia – Scarborough – Bridgetown
8 nights
The Azamara Quest is a mid-sized ship with a deck plan that’s intimate but never crowded, and offers everything modern voyagers are looking for—plus some unexpected extras.Your boutique hotel at sea, the Azamara Pursuit® is a mid-sized ship with a deck plan that’s intimate but never crowded, and offers everything modern voyagers are looking for—plus some unexpected extras.Seven restaurants, cafes, and lounges, a refreshing pool, sun-drenched decks, a revitalising spa…the list goes on. With so many areas to explore onboard Azamara Pursuit, it’s a good thing we have deck plans.One of the best ways to experience the jaw-dropping sights of the Fjords of Norway, and the mesmerising Mediterranean Sea coast lines is from your private veranda. It’s just one of the many benefits exclusive to your wonderfully spacious suite aboard Azamara Pursuit.Escape to a private retreat of polished style, featuring contemporary décor, luxurious linens, plush cotton robes and slippers, French bath products, fresh flowers, turndown treats, and 24-hour room service. (Perhaps we should arrange for a wake-up call
- Small Ship
- All Inclusive
- Premium
Cruise: San Juan (Puerto Rico) – Charlotte Amalie – Virgin Gorda – Saint John's – Saint Pierre – Port Elizabeth, Bequia – Scarborough – Bridgetown – Mayreau Island – Castries – Roseau – Basseterre, Saint Kitts – Philipsburg – Road Town, Tortola – Miami, Florida
18 nights
Wander to the world’s most captivating destinations onboard Jewel of the Seas®.Between scenery scoping and memory making, you’ll have the time of your life while sailing from one breathtaking location to another. Reach new heights with thrilling rock climbing. Watch showstopping entertainment and stellar Broadway musical productions. And treat your tastebuds to an epicurean feast ranging from Italian specialities to delicious teppanyaki prepared tableside.
- Large Ship
- Fun-filled
- Family-Friendly
Cruise: San Juan (Puerto Rico) – Charlotte Amalie – Philipsburg – Saint Croix Island – Roseau – Bridgetown – San Juan (Puerto Rico)
7 nights
Expect the extraordinary as you step aboard and discover the captivating possibilities, all true to her nameWith top deck dining venues, Slice Pizzeria, The Mix, Salty Dog Grill and Coffee & Cones you’ll have even more options to choose from during your stay on board Grand Princess. Relax at The Sanctuary, a tranquil haven reserved for adults, enjoy Movies Under the Stars® poolside or see an award-winning Broadway-style production show in the Princess Theatre, showcasing an even more immersive audio experience.
- Mega Ship
- Great Value
- Premium
Cruise: San Juan (Puerto Rico) – Tortola – Pointe-à-Pitre – Dominica – Saint George's – Bridgetown – San Juan (Puerto Rico) – Saint Thomas – Sint Maarten – Saint John's – Saint Vincent – Bridgetown – San Juan (Puerto Rico)
14 nights
Norwegian Epic® is sure to dazzle with her contemporary design, world-class performances and endless onboard activities. Cruisers of all ages can enjoy everything from an Aqua Park to a towering Climbing Wall. Take a break from all the action at Mandara Spa® and enjoy the Thermal Suite – designed for ultimate relaxation. Speaking of grown-ups, Vibe Beach Club and Spice H2O are adult-only venues that provide for an oasis during the day and a party at night. Multiple dining destinations ensure a happy palette at mealtime, whilst drinks can be enjoyed at unique bars like Ice Bar, Shaker’s Martini & Champagne Bar and Maltings Beer & Whiskey Bar. Explore the history of the Mediterranean, relax on the waters of the Transatlantic, or feel the balmy breezes of the Caribbean.. No matter what type of cruise you desire or what group you’re with, prepare for an Epic holiday.
- Large Ship
- Relaxed
- Family-Friendly
Cruise: San Juan (Puerto Rico) – Road Town, Tortola – Saint John's – Bridgetown – Castries – Philipsburg – Saint Thomas – San Juan (Puerto Rico)
7 nights
With a name derived from the Latin, valère meaning strong, our second lady ship is calling Barcelona home before setting sail on our first Virgin Voyages Mediterranean cruise, with three irresistible itineraries across Europe.
- Mega Ship
- Informal
- Adults Only
Cruise: San Juan (Puerto Rico) – Philipsburg – Basseterre, Saint Kitts – Castries – Bridgetown – Frederiksted, Saint Croix – San Juan (Puerto Rico)
7 nights
Expect the extraordinary as you step aboard and discover the captivating possibilities, all true to her nameWith top deck dining venues, Slice Pizzeria, The Mix, Salty Dog Grill and Coffee & Cones you’ll have even more options to choose from during your stay on board Grand Princess. Relax at The Sanctuary, a tranquil haven reserved for adults, enjoy Movies Under the Stars® poolside or see an award-winning Broadway-style production show in the Princess Theatre, showcasing an even more immersive audio experience.
- Mega Ship
- Great Value
- Premium
Cruise: San Juan (Puerto Rico) – Saint Thomas – Sint Maarten – Saint John's – Saint Vincent – Bridgetown – San Juan (Puerto Rico) – Saint Thomas – Saint Kitts – Castries – Saint George's – Bridgetown – San Juan (Puerto Rico)
14 nights