Seas the Bay Sailing

Seas the Bay Sailing Seas the Bay Sailing is a premier captained charter service that provides private day and sunset sai Not only are you on a beautiful fully equipped 54 ft.

Seas the Bay Sailing Charters is a captained charter service that provides our guests with a private day or sunset sail on the Bay without the crowds and worries of trying to sail your own boat. We provide you with an experience that has everything you need to enjoy, relax and take in all that Annapolis “on the water” has to offer. sailing vessel, you can be assured that Captain Chris is highly ex

perienced and certified for safe and deft handling of this yacht in all conditions. First Mate Susan has years of experience taking care of guests on holiday in Italy, and she will make sure you have fun memories that will last a lifetime.

Happy Independence Day from us here at !Hope everyone has a safe and enjoyable holiday!🇺🇸🌭
07/04/2025

Happy Independence Day from us here at !Hope everyone has a safe and enjoyable holiday!🇺🇸🌭

06/20/2025

Our beloved Captain Chris is back on the mainland! He had some words of wisdom to share post race!

8 years ago, he sailed into my life and made me his First Mate forever. Happy Anniversary to my adventure partner, my co...
06/17/2025

8 years ago, he sailed into my life and made me his First Mate forever. Happy Anniversary to my adventure partner, my compass and my calm in every storm❤️🌊⛵️🧭

Love is in the air and on the water this season! Let us be the backdrop to your once in a lifetime moment!💍
06/16/2025

Love is in the air and on the water this season! Let us be the backdrop to your once in a lifetime moment!💍

06/11/2025

🌊Wish Captain Chris luck as he sails in the legendary Annapolis to Newport Race! Battling it out with 68 boats in the open sea!

⛵️Don’t you worry he’ll be back soon! In the meantime our crew is ready to get YOU on the water for your own adventure!⚓️

Seeing the flag reflected in the grill today was a powerful moment — a reminder of the sacrifices made by heroes who gav...
05/25/2025

Seeing the flag reflected in the grill today was a powerful moment — a reminder of the sacrifices made by heroes who gave everything so we could enjoy days like this. 🇺🇸❤️⛵️

Wind in your hair, sun on your skin, and nothing but open water ahead. Whether it's your first date or your forever pers...
04/28/2025

Wind in your hair, sun on your skin, and nothing but open water ahead. Whether it's your first date or your forever person — a sail on the Bay is the kind of memory that lingers. Just you, your love, and the rhythm of the waves. ✨

Book a private couples sail and make the moment last💙 www.seasthebaysailing.com

Birthdays, anniversaries, engagements, or just because... Life’s too short not to celebrate on a sailboat. Private chart...
04/25/2025

Birthdays, anniversaries, engagements, or just because... Life’s too short not to celebrate on a sailboat. Private charters are our specialty — you bring the joy, we’ll bring the wind. 🥂 www.seasthebaysailing.com

Happy ! We are so grateful to appreciate this beautiful earth and all that she offers - from stunning sunsets that refl...
04/22/2025

Happy ! We are so grateful to appreciate this beautiful earth and all that she offers - from stunning sunsets that reflect off of calm waters to gentle sea breeze we are so grateful. Join us, to see what we are talking all about ⛵️🌎 www.seasthebaysailing.com

Annapolis is beautiful from land — but from the water? She’s unforgettable.Sail by the Naval Academy, historic harbors, ...
04/19/2025

Annapolis is beautiful from land — but from the water? She’s unforgettable.
Sail by the Naval Academy, historic harbors, and hidden coves most tourists never see. Make us a part of your visit this spring/summer! www.seasthebaysailing.com

📍 Depart from downtown Annapolis🧊 BYOB + snacks welcome👒 Dress for the breeze📷 Bring your camera — trust us💬 Book in adv...
04/17/2025

📍 Depart from downtown Annapolis
🧊 BYOB + snacks welcome
👒 Dress for the breeze
📷 Bring your camera — trust us
💬 Book in advance (we fill up fast!)

Ready to Seas the Bay? Your perfect sail awaits ⛵️ www.seasthebaysailing.com

Address

326 First Street
Annapolis, MD
21403

Opening Hours

Monday 9am - 9pm
Tuesday 9am - 9pm
Wednesday 9am - 9pm
Thursday 9am - 9pm
Friday 9am - 9pm
Saturday 9am - 9pm
Sunday 9am - 9pm

Telephone

+14108813264

Website

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About Us

Captain Chris has been sailing for over 40 years, and has sailed offshore for over 25 years. His sailing adventures have taken him from Maine to Key West, Bermuda, Guadalupe, Puerto Rico, and Cuba to name a few. Safety at sea is his number one priority and you will be in excellent hands.

Susan Is co-owner and operator of Rosapepe Retreats, a boutique Italian tour company that accompanies visitors to her family hotel in Italy, and provides a unique and authentic experience in southern Italy.

With her husband Chris, Susan discovered the joys of sailing many years ago, and couldn’t be happier sharing this passion and experience with anyone who dreams of a day on the Bay!

Susan and Chris will make your sailing experience a day to remember, with comfortable accommodations, wonderful food and breathtaking sights.