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Virgin Voyages ship at sea

Join Charles Onboard

Serious Sailors^TM
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

Aug52026

Solar Eclipse: Iceland & British Isles

Charles is onboard

Solar Eclipse: Iceland & British Isles

August 5, 2026 15 nights Valiant Lady

Portsmouth, United Kingdom → Dublin (Dun Laoghaire), Ireland → Glasgow (Greenock), Scotland → Liverpool, United Kingdom → Belfast, Northern Ireland → Siglufjörður, Iceland → Ísafjörður, Iceland → Reykjavik, Iceland → Edinburgh, Scotland → Portsmouth, United Kingdom

Sea Terrace from

$3,825 /sailor

Aug272026

Northern Europe: Portsmouth to Iceland

Solo Deal

Charles is onboard

Northern Europe: Portsmouth to Iceland

August 27, 2026 10 nights Valiant Lady

Portsmouth, United Kingdom → Amsterdam, Netherlands → Edinburgh, Scotland → Invergordon, Scotland → Akureyri, Iceland → Ísafjörður, Iceland → Reykjavik, Iceland

Solo from

$3,084 /sailor

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

Insider from

$2,405/sailor

Sea Terrace from

$3,250/sailor

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

Insider from

$1,960/sailor

Sea Terrace from

$2,730/sailor

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

$1,400/sailor

Sea Terrace from

$1,820/sailor

Oct192026

Bermuda & Caribbean: NYC to San Juan

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

Sea View from

$1,380 /sailor

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

$2,636/sailor

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 $103

$1,900 $1,797 /sailor

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 $54

$1,380 $1,326 /sailor

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 $327

$2,080 $1,753 /sailor

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

Insider from

$1,950/sailor

Sea Terrace from

$2,601/sailor

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

Sea View from

$1,960 /sailor

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

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

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 $265

$3,025 $2,760 /sailor

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 $149

$1,821 $1,672 /sailor

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 $596

$3,600 $3,004 /sailor

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

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

$1,400/sailor

Sea Terrace from

$1,785/sailor

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 $265

$2,565 $2,300 /sailor

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 $359

$3,360 $3,001 /sailor

Oct242027

Mediterranean: Athens to Barcelona

Serious Deal

Charles is onboard

Mediterranean: Athens to Barcelona

October 24, 2027 7 nights Scarlet Lady

Athens (Piraeus), Greece → Mykonos, Greece → Amalfi Coast (Salerno), Italy → Cannes, France → Barcelona, Spain

Sea Terrace from You save $53

$2,030 $1,977 /sailor

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 $85

$1,500 $1,415 /sailor

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

$750/sailor

Sea Terrace from

$1,025/sailor

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

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

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 $426

$3,521 $3,095 /sailor

Why people book these

Expert help, minus the clipboard.

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

Serious Sailors™ Travel Agency was created by Charles Conroy, Top 10 travel advisor for Virgin Voyages.

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