With our Chinese Junk rig, we always get noticed wherever we go. Whether it’s an hourly charter in the Inner Harbor, a full-day charter on the Chesapeake Bay or several days visiting different ports around the Bay, you’ll enjoy the privacy of this very unique vessel. It’s a great idea for a birthday, anniversary, vacation or special event. We always have fun on the Summer Wind!

Available By Reservation – Call Cap’n Tom at 844-595-8860

Choose Your Charter:

Hourly Charters

charter-small-picYou can reserve the whole boat for your special affair for as long as you need. Whether it’s a marriage proposal, anniversay, special birthday, family reunion or corporate event, we’d love to have you as our guests. We can work with your caterer or set something special up for you. We’re very flexible on our happy little ship and we’ll make your event a memorable one! Our private charter rate is $150/hour with a 2 hour minimum for up to 6 passengers.

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Hourly Charters

$150per hour
  • 2 hour minimum
  • Up to 6 passengers

Daily Charters

schooner Summer WindCharter the schooner Summer Wind for the whole day and enjoy the best Chesapeake Bay sailing charter anywhere. You’ll love exploring our beautiful Bay aboard this unique little ship. We’ll sail out past the Francis Scott Key Bridge and out into the northern Bay. You can haul on halyards, trim sails, take the wheel or just sit back and relax on this fully crewed sailing charter. Our daily charter rate is only $750 for 8 hours for up to 6 passengers. 

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Daily Charters

$750per day
  • Best rate on the Bay
  • Up to 6 passengers

Chesapeake B&B Charters

B&B ChartersAre you ready for an adventure? Dreaming of a Chesapeake Bay sailing charter? Here’s your next vacation! Our B&B charters are a great way to explore the Chesapeake Bay and some of the best sailing on the east coast! We’ll sail to a different port each day and you’ll stay in a different Bed & Breakfast each night on this unique crewed sailing charter. There are several B&B’s in the Bay right on the water and we sail right up to their docks. You’ll get to explore small historic bay towns, fresh food and fresh sea breezes.

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We have four crewed sailing charters to choose from:

2 days and one night in any of the ports we visit for a quick and easy getaway.

The Weekender

$700per couple*
  • Three Couples
  • 2 Days/1 Night

The Weekender

$900per couple*
  • Two Couples
  • 2 Days/1 Night

The Weekender

$1,600per couple*
  • One Couple
  • 2 Days/1 Night
3 days and 2 nights in any of the ports we visit for a better chance to explore the Bay. You’ll get enough time at the helm to learn to sail the boat yourself.

The Holiday

$1,150per couple*
  • Three Couples
  • 3 Days/2 Nights

The Holiday

$1,500per couple*
  • Two Couples
  • 3 Days/2 Nights

The Holiday

$2,500per couple*
  • One Couple
  • 3 Days/2 Nights
4 days and 3 nights in any of the ports we visit for a better chance to explore the Bay.

The Getaway

$1,600per couple*
  • Three Couples
  • 4 Days/3 Nights

The Getaway

$2,100per couple*
  • Two Couples
  • 4 Days/3 Nights

The Getaway

$3,400per couple*
  • One Couple
  • 4 Days/3 Nights
5 days and 4 nights to get away from it all and really relax. Take in all the sights and enjoy all the Chesapeake Bay has to offer with this great sailing vacation!

The Great Escape

$2,100per couple*
  • Three Couples
  • 5 Days/4 Nights

The Great Escape

$2,700per couple*
  • Two Couples
  • 5 Days/4 Nights

The Great Escape

$4,400per couple*
  • One Couple
  • 5 Days/4 Nights

Talk to your friends about a great group vacation you can all share together! Prices vary by length of trip and the number of couples. Breakfast is included with the lodging and lunch is included on the boat while underway. Fuel and dockage fees are also included.

*Assumes double-occupancy per night

Sample Itinerary:

Day 1: We’ll explore the northern end of the Bay and end up on the Eastern Shore in Rock Hall. If you’ve never been to Waterman’s Crab House or The Kitchen, you’ll have a hard choice to make for dinner. You’ll stay overnight at The Black Duck Inn at Rock Hall Harbor and we’ll sail right up to their dock.

Day 2: After breakfast, we’ll sail across the Bay and down to Annapolis. We’ll tie up at the City Dock and you’ll get a night on the town with lots of shopping and restaurants to choose from. You’ll stay at the top-rated Chez Ami Bed & Breakfast, an easy walk up Fleet Street in the center of town.

Day 3: Now it’s time for some peace and quiet on the Eastern Shore as we make our way to Oxford, one of the best boat towns on the Bay. It’s an old sailing town that’s retained all of its historic charm. You’ll spend the night at Sandaway, right on the water with their own beach.

Day 4: More sailing in the Central Chesapeake, up the Eastern Bay past Kent Island, and down into St Michael’s for the night. If there’s time, you might visit the Chesapeake Bay Maritime Museum. You’ll stay at the historic Dr Dodson House, which started as a tavern in 1799.

Day 5: Back out onto the Bay for our final day, we’ll sail under the Bay Bridge and back to Baltimore with a boatload of memories!

Specific B&B’s included in your charter may vary, depending on their availability and may modify our itinerary. Accommodations are arranged at the time of reservation.