Illustration of small wooden boats carrying sailors in Santa hats on a blue harbor near a snowman and glowing cottages (Jolly Express Cruise)

Jolly Express Cruise

Passengers take a 45-minute on-water sleigh ride along Spa Creek with Captain Santa or Mrs. Claus at the helm. An onboard elf serves hot cocoa while guests stay warm under available blankets. A portion of ticket proceeds is donated to Historic Annapolis.

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Plan Your Visit

Tickets

$28 per adult; $15 per child, with children’s pricing applying to anyone 11 and under. A ticket includes the cruise and the first cup of hot cocoa. A private cruise for up to 21 passengers can be purchased by selecting Private Tour at checkout; no price for that option is stated.

Ages

Children 11 and under

Food & Drink

Hot cocoa is served by an onboard elf, and your ticket includes your first cup.

Accessibility

There's limited room on board, so leave large strollers in the car.

Going?

Location

The Piers at 1 Prince George Street · 1 Prince George St, Annapolis, MD 21401 Get Directions

Local Insight & Ratings

Family Friendly

🎄 🎄 🎄 🎄 🎄 (5/5)

Best For

Families with children

Vibe

Festive and cozy

Energy Level

Low

Photo Friendly

Moderate

Weather Sensitivity

Moderate

Tips & Advice

  • Reserve online or call the sales office ahead of time, because walk-up tickets for the Jolly Express are limited.
  • Leave large strollers in the car, since the boat has limited room and there's nowhere on board to store them.
  • Dress warmly for 45 minutes on the water. Blankets are on board and your ticket includes the first cup of hot cocoa.
  • Groups of up to 21 can book the whole boat by choosing Private Tour at checkout instead of buying individual tickets.
  • If the time you want is sold out online, call the Watermark office at 410-268-7601 and staff will help with your booking.

Special Events & Promotions

  • A private cruise for up to 21 passengers is available by choosing Private Tour at checkout.

Links & Contact

Run by Watermark

Christmas Events Near Me is an independent guide, not the organizer of this event. For tickets, entries, vendor spots or questions, contact the organizer directly through their contact page.

Frequently Asked Questions

How long is the cruise?

45 minutes on Spa Creek, with Captain Santa or Mrs. Claus at the helm.

Will it be cold on the water?

Blankets are on board to keep you warm. An elf serves hot cocoa, and your ticket includes the first cup.

Can I bring a stroller?

Leave large strollers in the car, because there isn't much room on the boat.

Can our group have the boat to ourselves?

Yes. Choose Private Tour at checkout to book a private cruise for up to 21 passengers.

Does the cruise support a cause?

Yes. Part of the proceeds goes to Historic Annapolis.

Browse Christmas in Annapolis

Always check the official website for the most current information.

We've done our best to keep details up-to-date, but event schedules, prices, and policies can change. For the latest updates, please visit the official website or contact the organizers directly. Christmas Events Near Me is an independent guide and isn't affiliated with the events we list.

Contributors & Updates

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