Sample Itineraries

As a Sleepy Sailor, you set your own itinerary. Just let you captain know where you want to go and be ready to lend a hand. To help you make you up your mind, please feel free peruse the sample itineraries below.

Each itinerary includes destinations, schedule, and recommended preparations for guest crew (that's you!).

Keep in mind that you go where (and as fast) as the wind will take you so the provided durations are estimates only. It is recommended that you don't make any plans on the day of your sail that you can't cancel.

Head to Sea

10-12 hours: An all-day adventure where you'll cruise the entirety of San Diego and make it out to open water to enjoy amazing views of Coronado, downtown, and Cabrillo Point.

Heart of the Bay

5-8 hours: A great way to get to see the highlights of San Diego Bay, enjoy a bite, and introduce yourself to sailing. No sea legs required.

1000 Departure

1000-1045 Motor cruise

1045-1145 Sail Battleship Row

1200 Shoot the Bridge

1300 Lunch - Dock & Dine

1415 Depart Embarcado

1630 Return to Slip

1700 Guest Crew Departures

0730 Breakfast

(from the Rambler Coffee, call ahead with order if checking in today)

0900 Prepare for departure

1000 Departure

1300 Light lunch aboard

1800 Dock & Dine, guests choice

1930 Sunset cruise to slip

2100 Return to Slip

Sea Trial - w/ Dock & Dine Lunch

5-6 hours: A great way to get to see the highlights of San Diego Bay, enjoy a bite, and introduce yourself to sailing. No sea legs required.

Schedule

0900-1000 Arrivals & boat orientation (arrive any time)

1000 Departure

1000-1045 Motor cruise

1045-1145 Sail "Battleship Row "

1230 Lunch - Dock & Dine

1400 Depart Pier 32

1445 Return to Slip

1500 Guest Crew Departures

  • Itineraries may be modified at guest crew's request - at the captain's discretion.

Guest Crew Preparations

  • Bags - soft sided luggage is preferred

  • Hat & Sunglass

  • Shoes

    • Light soled/non-marking are preferred but not required

Barefoot or secured shoes recommended when walking on deck to minimize tripping hazard. (walking on deck not required)

  • Wind breaker and light sweatshirt - please be sure to check the weather ahead of time. Consult your captain as needed.

  • A comfy change of clothes for the drive home

  • Showers are available

  • Captain provides soft drinks, water, and light snacks. You are more than welcome to pack along any additional snacks and beverages. Alcohol is permitted.

Sea Trial - w/ Lunch on Deck

3-4 hours: A great way to get to see the highlights of San Diego Bay, enjoy a bite, and introduce yourself to sailing. No sea legs required.

Schedule

0900-1000 Arrivals & boat orientation (Arrive any time)

1000 Departure

1000-1045 Motor cruise

1045-1145 Sail "Battleship Row"

1200 Lunch on Deck

To maximize your sailing time, pack a sandwich and enjoy lunch at sea.

1300 Return to Slip

1330 Guest Departures

  • Upon request, sailing time and destinations can be changed At the captain's discretion.

  • Captain provides soft drinks, water, and light snacks. You are more than welcome to pack along any additional snacks and beverages. Alcohol is permitted.


Guest Crew Preparations

  • Bags - soft sided luggage is preferred

  • Hat & Sunglass

  • Shoes

    • Light soled/non-marking are preferred but not required

Barefoot or secured shoes recommended when walking on deck to minimize tripping hazard. (walking on deck not required)

  • Wind breaker and light sweatshirt - please be sure to check the weather ahead of time. Consult your captain as needed.

  • A comfy change of clothes for the drive home

  • Showers are available

  • Captain provides soft drinks, water, and light snacks. You are more than welcome to pack along any additional snacks and beverages. Alcohol is permitted.

Bruce's Lunch

Full Day: Take in all the San Diego Bay has to offer and enjoy lunch with a unique view.

Schedule

  • 0800-0900 Arrivals & boat orientation (arrive any time)

  • 0930 Departure

  • 0930-1015 Motor cruise

  • 1015-115 Sail "Battleship Row "

  • 1230 Bruce's Lunch (Lunch at anchor)

Drop anchor off of Zuniga Point and serve your captain a well deserved lunch.

  • 1400 Return to Bay

  • 1530 Return to Slip

  • 1800 Guest Crew Departures

  • Itineraries may be modified at guest crew's request - or at the captain's discretion.


Guest Crew Preparations

  • Easy prep lunch
    - Suggestions: sandwiches, charcuteuterie, ready to heat soup

  • Rose and/or light beer

  • Bags - soft sided luggage is preferred

  • Hat & Sunglass

  • Shoes

    • Light soled/non-marking are preferred but not required

Barefoot or secured shoes recommended when walking on deck to minimize tripping hazard. (walking on deck not required)

  • Wind breaker and light sweatshirt - please be sure to check the weather ahead of time. Consult your captain as needed.

  • A comfy change of clothes for the drive home

  • Showers are available

  • Captain provides soft drinks, water, and light snacks. You are more than welcome to pack along any additional snacks and beverages. Alcohol is permitted.