Explore Portland’s Old Port, visit Portland Head Light, and sail Casco Bay on a classic schooner with scenic views and local wildlife.

Begin with a scenic drive through the quaint streets of Old Port up the rocky coast of Cape Elizabeth. After a quick stop at America's oldest lighthouse, return to Portland and board an authentic Maine-built, wooden schooner for a leisurely sail on Casco Bay. The schooners are the ideal way to experience the beauty of Maine’s rugged coastline featuring lighthouses, seals, and seabirds. Join the crew as they hoist the sails, take command at the ship’s wheel, or simply relax and enjoy the scenery.

Energy Level

Duration

4 Hours

Type

CULTURED

Accessible

Shore Thing Highlights

Sail a classic schooner on Casco Bay and spot scenery and wildlife
Stop at Portland Head Light, the oldest lighthouse in Maine
A scenic drive through the quaint streets of the Old Port

Need to know

Sailors in wheelchairs or with limited mobility should not select this Shore Thing
Sailors prone to motion sickness should take precautions prior to this Shore Thing
Weather may be chilly on the water, jackets are recommended
Wildlife sightings are likely but not guaranteed
The order of sites visited may vary

Experience shores the Virgin way

Local & Immersive Tours
Authentic experiences curated with local operators
A Sustainable Cause
Select tour bookings to help social charities
Peace of Mind
Modify/cancel up to 48hrs before where applicable
Priority Debark in Port
Be first ashore in all our ports of call
Safe and Insured
Our partners are licensed and insured
Transparent Pricing
No hidden costs, all-inclusive Shore Thing prices
Expert Travel Support
Pre-voyage to onboard assistance, always there
Stress-Free Returns
Ship will wait for you in the event of a delay
Convenient Collection
Convenience of one location to shop for your calls

Shore Things are fully refundable to the original form of payment. However, please note that Shore Things are only fully refundable if they are canceled within 48 hours prior to the booked Shore Thing taking place, unless stated otherwise in a specific Shore Thing 'Need to Know' section. If you fail to either (a) cancel within 48 hours of the booked Shore Thing (or alternative time period as may be stated in a specific Shore Thing 'Need to Know' section), or (b) show up for a booked Shore Thing, you will be charged for 100% of the Shore Thing price.

If you make a cancellation prior to the first day of your voyage and within 48 hours (unless otherwise stated in the tour details) of your Shore Thing, you will be refunded to the original form of payment after midnight Eastern Standard Time (EST) on the day of cancellation.

If you make another purchase prior to midnight EST, after canceling a booking eligible for a refund, the credit from the canceled booking will be applied to your new booking. Therefore, you’ll only be charged for the price difference between the canceled and new experience. If you have remaining temporary credit left on your account after you’ve made another experience purchase, the remaining credit will be refunded to your original form of payment after midnight EST.

If you cancel a Shore Thing during your voyage and are eligible for a refund, a credit will be applied to your folio and not to your original form of payment.

Shore Things departure times and/or meeting locations are subject to change. We will make every effort to notify Sailors in advance via the Sailor App of any tour departure and/or meeting changes.

Schooner Adventure on Casco Bay

Explore Portland’s Old Port, visit Portland Head Light, and sail Casco Bay on a classic schooner with scenic views and local wildlife.

Shore Thing Highlights

Need to know

Experience shores the Virgin way

Our Shore Things Policies