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Join Charles Onboard

Serious SailorsTM
Signature Sailings

Charles has 300+ nights on Virgin ships and is a 2x Virgin Voyages Top 10 First Mate (2024 & 2025). These are the voyages he's booked for himself. Sail with him to join Serious Sailors Secret Suppers and someone onboard who knows the ship better than the app does.

See Charles’s sailings

300+ Nights Onboard

Charles knows these ships the way others know their hometowns. Cabins, venues, shortcuts — all tested.

Sea Day Office Hours

Meet with Charles daily in The Sip Lounge on sea days to ask questions or plan your next voyage.

Secret Suppers

Invite-only dinners and off-menu tables the booking app will never show you — Serious Sailors guests only.

Charles's Calendar

Pick the route. He's already picked the ship.

Charles is personally booked on every sailing listed here. Itineraries repeat through the year, so check the date.

View all Serious Deals
Sep62026
Iceland & Greenland to NYC Charles is onboard

Iceland & Greenland to NYC

September 6, 2026 13 nights Valiant Lady

Reykjavik, Iceland → Ísafjörður, Iceland → Prince Christian Sound (Cruising), Greenland → Qaqortoq, Greenland → Nuuk, Greenland → St. John's, Newfoundland → Halifax, Nova Scotia → New York City, New York

View sailing
Oct42026
Mediterranean: Athens to Barcelona Charles is onboard

Mediterranean: Athens to Barcelona

October 4, 2026 7 nights Scarlet Lady

Athens (Piraeus), Greece → Mykonos, Greece → Catania, Sicily, Italy → Amalfi Coast (Salerno), Italy → Rome (Civitavecchia), Italy → Barcelona, Spain

Sea View from
$2,660/sailor
Sea Terrace from
$2,800/sailor
View sailing
Oct112026
Spain to Morocco & Miami Transatlantic Charles is onboard

Spain to Morocco & Miami Transatlantic

October 11, 2026 14 nights Scarlet Lady

Barcelona, Spain → Casablanca, Morocco → Las Palmas de Gran Canaria, Spain → Santa Cruz de Tenerife, Spain → Miami, Florida

Insider from
$1,540/sailor
Sea Terrace from
$1,820/sailor
View sailing
Oct192026
Bermuda & Caribbean: NYC to San Juan
Solo Deal
Charles is onboard

Bermuda & Caribbean: NYC to San Juan

October 19, 2026 12 nights Valiant Lady

New York City, New York → Royal Naval Dockyard, Bermuda → The Beach Club at Bimini, Bahamas → St. Croix, U.S. Virgin Islands → Philipsburg, St. Maarten → Tortola, British Virgin Islands → San Juan, Puerto Rico

Solo from
$1,694 /sailor
View sailing
Oct292026
Panama Canal: LA to Miami Halloween Charles is onboard

Panama Canal: LA to Miami Halloween

October 29, 2026 17 nights Brilliant Lady

Los Angeles, California → Cabo San Lucas, Mexico → Puerto Quetzal, Guatemala → Puntarenas, Costa Rica → Panama City, Panama → Panama Canal (Cruising), Panama → Cartagena, Colombia → Miami, Florida

Sea View from
$2,380/sailor
Sea Terrace from
$5,355/sailor
View sailing
Jan112027
Eastern Caribbean & Bimini Beach Club
Serious Deal
Charles is onboard

Eastern Caribbean & Bimini Beach Club

January 11, 2027 10 nights Brilliant Lady

Miami, Florida → Philipsburg, St. Maarten → Tortola, British Virgin Islands → St. Croix, U.S. Virgin Islands → San Juan, Puerto Rico → Puerto Plata, Dominican Republic → The Beach Club at Bimini, Bahamas → Miami, Florida

Sea Terrace from You save $31
$1,700 $1,669 /sailor
View sailing
Jan232027
Southern Caribbean Cruise
Serious Deal
Charles is onboard

Southern Caribbean Cruise

January 23, 2027 6 nights Valiant Lady

San Juan, Puerto Rico → Tortola, British Virgin Islands → Basseterre, St. Kitts and Nevis → St. John's, Antigua → Castries, St. Lucia → San Juan, Puerto Rico

Sea Terrace from You save $308
$1,200 $892 /sailor
View sailing
Jan292027
Southern Caribbean & Aruban Nights
Serious Deal
Charles is onboard

Southern Caribbean & Aruban Nights

January 29, 2027 8 nights Valiant Lady

San Juan, Puerto Rico → Oranjestad, Aruba → Willemstad, Curaçao → Kralendijk, Bonaire → Fort-de-France, Martinique → Philipsburg, St. Maarten → San Juan, Puerto Rico

Sea Terrace from You save $542
$2,120 $1,578 /sailor
View sailing
Feb82027
Sisters at Sea: Brilliant Lady Charles is onboard

Sisters at Sea: Brilliant Lady

February 8, 2027 10 nights Brilliant Lady

Miami, Florida → Philipsburg, St. Maarten → Tortola, British Virgin Islands → St. Croix, U.S. Virgin Islands → San Juan, Puerto Rico → Puerto Plata, Dominican Republic → The Beach Club at Bimini, Bahamas → Miami, Florida

Sea View from
$2,500/sailor
Sea Terrace from
$2,750/sailor
View sailing
Feb132027
Sisters at Sea: Valiant Lady Charles is onboard

Sisters at Sea: Valiant Lady

February 13, 2027 7 nights Valiant Lady

San Juan, Puerto Rico → Samaná, Dominican Republic → Grand Turk, Turks and Caicos → Cabo Rojo, Dominican Republic → San Juan, Puerto Rico

Insider from
$1,680/sailor
Sea Terrace from
$1,750/sailor
View sailing
Mar262027
Panama Canal: Miami to Los Angeles
Serious Deal
Charles is onboard

Panama Canal: Miami to Los Angeles

March 26, 2027 16 nights Brilliant Lady

Miami, Florida → Cartagena, Colombia → Colón, Panama → Panama Canal (Cruising), Panama → Puntarenas, Costa Rica → Puerto Quetzal, Guatemala → Cabo San Lucas, Mexico → Los Angeles, California

Sea Terrace from You save $364
$3,200 $2,836 /sailor
View sailing
May22027
Miami to Morocco & Spain Transatlantic
Serious Deal
Charles is onboard

Miami to Morocco & Spain Transatlantic

May 2, 2027 14 nights Resilient Lady

Miami, Florida → Santa Cruz de Tenerife, Spain → Tangier, Morocco → Málaga, Spain → Barcelona, Spain

Sea Terrace from You save $86
$1,750 $1,664 /sailor
View sailing
May302027
Greek Isles & The Adriatic
Serious Deal
Charles is onboard

Greek Isles & The Adriatic

May 30, 2027 11 nights Scarlet Lady

Athens (Piraeus), Greece → Mykonos, Greece → Kotor, Montenegro → Corfu, Greece → Dubrovnik, Croatia → Santorini, Greece → Bodrum, Turkey → Chania (Souda Bay), Crete, Greece → Athens (Piraeus), Greece

Sea Terrace from You save $705
$3,465 $2,760 /sailor
View sailing
Jun32027
Alaska: Glacial Fjords & Coastal Views
Serious Deal
Charles is onboard

Alaska: Glacial Fjords & Coastal Views

June 3, 2027 7 nights Brilliant Lady

Seattle, Washington → Ketchikan, Alaska → Sitka, Alaska → Tracy Arm Fjord (Cruising), Alaska → Prince Rupert, British Columbia → Seattle, Washington

Sea Terrace from You save $148
$1,820 $1,672 /sailor
View sailing
Jun102027
Greek Isles, Turkey & Cairo Overnight
Serious Deal
Charles is onboard

Greek Isles, Turkey & Cairo Overnight

June 10, 2027 10 nights Scarlet Lady

Athens (Piraeus), Greece → Santorini, Greece → Ephesus (Kuşadasi), Turkey → Alexandria (Cairo), Egypt → Rhodes, Greece → Mykonos, Greece → Athens (Piraeus), Greece

Sea Terrace from You save $646
$3,650 $3,004 /sailor
View sailing
Jun202027
The Adriatic, Albania & Greece
Serious Deal
Charles is onboard

The Adriatic, Albania & Greece

June 20, 2027 7 nights Scarlet Lady

Athens (Piraeus), Greece → Dubrovnik, Croatia → Kotor, Montenegro → Sarandë, Albania → Mykonos, Greece → Athens (Piraeus), Greece

Sea Terrace from You save $199
$2,240 $2,041 /sailor
View sailing
Jul42027
Red Hot Sailing Club Voyage from Athens Charles is onboard

Red Hot Sailing Club Voyage from Athens

July 4, 2027 7 nights Scarlet Lady

Athens (Piraeus), Greece → Santorini, Greece → Chania (Souda Bay), Crete, Greece → Ephesus (Kuşadasi), Turkey → Mykonos, Greece → Athens (Piraeus), Greece

Insider from
$1,470/sailor
Sea Terrace from
$1,855/sailor
View sailing
Aug292027
Mediterranean: Athens to Rome
Serious Deal
Charles is onboard

Mediterranean: Athens to Rome

August 29, 2027 9 nights Scarlet Lady

Athens (Piraeus), Greece → Bodrum, Turkey → Santorini, Greece → Mykonos, Greece → Valletta, Malta → Catania, Sicily, Italy → Amalfi Coast (Salerno), Italy → Rome (Civitavecchia), Italy

Sea Terrace from You save $355
$2,655 $2,300 /sailor
View sailing
Sep72027
Mediterranean: Rome to Athens
Serious Deal
Charles is onboard

Mediterranean: Rome to Athens

September 7, 2027 12 nights Scarlet Lady

Rome (Civitavecchia), Italy → Florence/Pisa (Livorno), Italy → Pompeii/Capri (Naples), Italy → Palermo, Sicily, Italy → Valletta, Malta → Rhodes, Greece → Mykonos, Greece → Santorini, Greece → Ephesus (Kuşadasi), Turkey → Athens (Piraeus), Greece

Sea Terrace from You save $479
$3,480 $3,001 /sailor
View sailing
Oct312027
Halloween Transatlantic from Spain
Serious Deal
Charles is onboard

Halloween Transatlantic from Spain

October 31, 2027 12 nights Scarlet Lady

Barcelona, Spain → Tangier, Morocco → Lanzarote, Canary Islands, Spain → San Juan, Puerto Rico

Sea Terrace from You save $80
$1,500 $1,420 /sailor
View sailing
Nov82027
Red Hot Sailing Club Voyage from Miami Charles is onboard

Red Hot Sailing Club Voyage from Miami

November 8, 2027 5 nights Valiant Lady

Miami, Florida → Costa Maya, Mexico → The Beach Club at Bimini, Bahamas → Miami, Florida

Insider from
$800/sailor
Sea Terrace from
$1,100/sailor
View sailing
Nov122027
Southern Caribbean Cruise
Serious Deal
Charles is onboard

Southern Caribbean Cruise

November 12, 2027 8 nights Scarlet Lady

San Juan, Puerto Rico → Tortola, British Virgin Islands → Basseterre, St. Kitts and Nevis → Bridgetown, Barbados → Castries, St. Lucia → Roseau, Dominica → Philipsburg, St. Maarten → San Juan, Puerto Rico

Sea Terrace from You save $159
$1,840 $1,681 /sailor
View sailing
Nov272027
Panama Canal: Los Angeles to Miami
Serious Deal
Charles is onboard

Panama Canal: Los Angeles to Miami

November 27, 2027 17 nights Brilliant Lady

Los Angeles, California → Cabo San Lucas, Mexico → Puerto Quetzal, Guatemala → Puntarenas, Costa Rica → Panama City, Panama → Panama Canal (Cruising), Panama → Cartagena, Colombia → Miami, Florida

Sea Terrace from You save $400
$3,400 $3,000 /sailor
View sailing
Feb212028
Panama Canal: Miami to Los Angeles
Serious Deal
Charles is onboard

Panama Canal: Miami to Los Angeles

February 21, 2028 16 nights Brilliant Lady

Miami, Florida → Cartagena, Colombia → Colón, Panama → Panama Canal (Cruising), Panama → Puntarenas, Costa Rica → Puerto Quetzal, Guatemala → Cabo San Lucas, Mexico → Los Angeles, California

Sea Terrace from You save $425
$3,520 $3,095 /sailor
View sailing
Apr162028
Miami to Morocco & Spain Transatlantic
Serious Deal
Charles is onboard

Miami to Morocco & Spain Transatlantic

April 16, 2028 14 nights Valiant Lady

Miami, Florida → Ponta Delgada, Azores → Funchal, Madeira, Portugal → Tangier, Morocco → Barcelona, Spain

Sea Terrace from You save $261
$1,960 $1,699 /sailor
View sailing
Apr222028
San Juan to Spain Transatlantic
Serious Deal
Charles is onboard

San Juan to Spain Transatlantic

April 22, 2028 12 nights Scarlet Lady

San Juan, Puerto Rico → Philipsburg, St. Maarten → Funchal, Madeira, Portugal → Tangier, Morocco → Barcelona, Spain

Sea Terrace from You save $214
$1,620 $1,406 /sailor
View sailing

Why people book these

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Know what to book

Straight answers on cabins, decks and fare tiers — including the bits the cruise line's booking flow quietly leaves out.

Someone to actually ask

Missed a booking window? Restaurant showing "full"? Not sure a port day is worth it? He's on the ship — just ask.

Onboard Office Hours

Meet with Charles daily in The Sip Lounge on sea days to ask questions or plan your next voyage.

Ready to plan your voyage? Let's talk ship
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