Free Returns & Exchanges

Use code GIFT10 for 10% off

e-Gifts Delivered Instantly

Chesapeake Bay Private Sailing Experience for up to 6 People

Chesapeake Beach, Maryland

0/0

Chesapeake Bay Private Sailing Experience for up to 6 People

Chesapeake Beach, Maryland

0 (0)

Duration: 2 hours and 30 minutes

Package: For up to 6 People

Overview

Set sail on a private daytime cruise along the Chesapeake Bay in Annapolis, Maryland! This 2.5-hour sailing experience offers scenic waterfront views, relaxation, and the perfect setting for a fun group outing or peaceful escape.

🛥️ Enjoy a private 2.5-hour sail on the Chesapeake Bay from Annapolis, MD

🌊 Take in stunning views of the coastline and calm bay waters

🥪 Bring your own food or pre-order catering for a personalized onboard picnic

🧃 Relax with complimentary snacks and water provided during the cruise

Read More

Full description

Sail away for a few carefree hours on a private day cruise along Maryland’s Chesapeake Bay. This 2.5-hour sail is a laid-back way to enjoy Annapolis from the water—perfect for catching up with friends, hosting out-of-town guests, or just unwinding in the fresh breeze. The boat is all yours during this private experience, offering the ideal setting for everything from low-key celebrations to spontaneous getaways.

Bring your own food and drinks or pre-order something ahead of time to enjoy onboard. Light snacks and water are provided, and there’s plenty of space to spread out and relax. Whether you're sunbathing, sipping, or snapping photos of the scenic shoreline, this Chesapeake Bay sailing experience is a relaxed way to spend a memorable afternoon in Annapolis, Maryland.

Availability

When do I choose a date?

After purchase, you can request your preferred dates and times by following the instructions in the email you receive. If it's a gift, the recipient will also get an email with booking instructions.

Seasonal,
Mid-May -October:
Tuesday - Sunday 9:00am, 12:00pm, 3:00pm, 6:00pm

Practical information

Any restrictions to participate?

• Age: All age groups are welcome
• Physical limitations: Must be able to board a boat; not wheelchair accessible

Who can you accommodate for?

• Children: All participants must be booked; children included
• Pets: Sorry, no pets allowed

What to expect on the day of the experience?

• Duration: 2.5 hours
• What’s included: Private sailing cruise for up to 6 guests, complimentary snacks and water, option to bring your own food or pre-order catering
• Who will be present: A captain will be present; cruise is private and limited to your party (up to 6 total participants)
• Spectators: No spectators allowed, all guests must be included in the reservation
• Photo/ video: Photography is encouraged; guests may take their own photos
• Specific rules to follow: Arrive 15 minutes early for check-in; boarding begins 10 minutes before cast-off

How to prepare?

• Weather dependency: The cruise runs rain or shine; cancellations due to extreme weather will be rescheduled
• Arrival: Plan to arrive at least 15 minutes in advance
• Parking: Parking may be available on site.
• What to wear: Comfortable, weather-appropriate clothing and soft-soled shoes recommended
• What to bring:
  • BYO food and non-alcoholic drinks or pre-order catering
  • Personal items such as sunscreen, sunglasses, and cameras
  • No large coolers or glass bottles
• Restrooms/ lockers/ changing rooms: Bathrooms likely available at the dock area.

Returns, exchanges and cancellation

Unused Experience Vouchers can be returned within 15 days for a full refund to the original purchaser, no questions asked.

If you have any unused Experience Vouchers, you can exchange them for anything else in our marketplace, no matter when. If you choose an experience that's more expensive, you'll need to pay the difference, but if you choose one that costs less, you'll receive a credit towards your next booking.

No refunds are allowed once the experience is booked, but you can reschedule up to 7 days before your experience, for a date within a year of the original booking. To reschedule, contact the experience provider directly. No-shows or rescheduling less than 7 days in advance means losing the value of your experience.

How it works

Find the perfect gift

Choose from 5000+ experience gifts for your recipient - or treat yourself!

Send with ease

Email it to their inbox or yours. Enjoy a free printable voucher or upgrade to a premium gift box.

Book and enjoy

Follow the booking instructions in your email or gift box. We’ll handle the rest!

Includes all fees & taxes

Buy Now Buy Now ...

Buy Now

Trustpilot

Buy Now Buy Now ...