HANDS-ON APOSTLE ISLANDS SAILING ADVENTURES
• Sailboats at City Dock
• Office at Corner of Rittenhouse and Broad
Bayfield, WI 54814
(800) 682-1587
The secrets of the Apostle Islands reveal themselves to those who slowly, quietly explore.

Dreamcatcher's Apostle Islands Sailing Adventures from Bayfield, Wisconsin

Please select from one of the following trips below to see more information or scroll down the page and read about all of them.
Day Trips:
  Overnight Trips:

The Island Landing Excursion
9:30 A.M. to 2:30 P.M. Daily
Includes lunch. Help sail Dreamcatcher in the morning, eat fresh catered lunch at anchor in the protection of one of the Islands near Bayfield, either Basswood, Long, Oak or Hermit, use the inflatable zodiac dinghy to explore the clear water beaches and Lake carved sandstone shorelines, and even take a swim on a warm day. Then help sail her back to Bayfield. This trip is for people of all levels of ability with an adventurous spirit.

$115/person, includes lunch or $550/exclusive boat trip for up to six, includes lunch.
Larger groups can be accommodated by taking our second boat. Prices $920/7-8, $1035/9 and $1100 for 10-12


Specials:
20% off all exclusive boat trips and overnight trips in May, June and after Labor Day through the end of September as well as SUNDAYS all season long! Active duty military personnel on leave recieve 10% discount.

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The Afternoon Sail
3:00 P.M. to 5:30 P.M. Daily
Get a taste of what makes Bayfield the most popular sailing port in the Great Lakes. Take the wheel, help handle lines, etc., or just relax. Refreshments included.

$57/person or $275/exclusive boat trip for up to six
Larger groups can be accommodated by taking our second or third boat. Prices $456/7-8, $513/9 and $550 for 10-12


Specials:
20% off all exclusive boat trips and overnight trips in May, June and after Labor Day through the end of September as well as SUNDAYS all season long! Active duty military personnel on leave recieve 10% discount.

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All Overnight Trips
You can either come as a group of two who wishes to join another group for the per person price or take the exclusive boat option for just your group and the captain. If you choose to take the per-person option and we do not fill the trip, we will go with just your group. All food is provided by a local caterer. The exclusive boat trips have the option of bringing their own food for a discount. In the spirit of this type of adventure, all guests are encouraged to become the crew, including learning to sail, handle the boat, anchor, dock, cook in the galley (which is a snap with our catered meals), etc. Personal preference and skills determine the role each guest chooses to fill.
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Sand Island Overnight
(sample itinerary)
Courtesy boarding the evening before the trip, sleep in the boat in the harbor the first night, walk to dinner and breakfast in town within a couple blocks of the boat. Depart Bayfield at 9:30 A.M. for a day of sailing and several stops at caves, sand spits, pristine beaches or lighthouses. Anchor at either Stockton, Oak, Sand or Rocky Islands, depending on the wind. Grill dinner, watch the sunset and sleep on the boat while gently swaying in a calm natural anchorage. In the morning, have coffee and breakfast as the Islands wake up—by then everyone is so relaxed, there is little point in rushing off. The last day is spent sailing, swimming (in season) and exploring before returning to Bayfield by mid to late afternoon. An additional night is available on the boat, if you choose, for a small fee.

$475/person or $1580 exclusive boat for up to 4 adults or a family $1380 exclusive boat trip, bring your own food.

Specials:
Before June 30 and after Labor Day Special
$1264 exclusive boat, $1064 w/out food.

June and September Weekday Super Special
$895, no meals included for up to four adults or a family

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Dreamcatcher at anchor for lunch, cyclists Rick and Debbie, along with friends Jim and Lori, Bob the Chicken on his cross country bicycle trip takes the wheel.

Stockton/Rocky Tour
Four nights, three days

Arrive at Bayfield City Dock in the evening for a night in the harbor aboard Dreamcatcher. Set sail in the morning for a tour of the interior of the Islands. On this trip, you can really get the feel of the boat, with as much sailing instruction as you want. Learn sailing, seamanship, boat handling, navigation and anchoring. After a day of sailing the Islands, anchor at Presque Isle Point of Stockton Island. There are two mile long beaches with dunes and a coastal wetland as well as bedrock slabs that stick out into the water. Next morning, depending on weather, sail toward Outer Island and Cat Island or Hermit, Manitou and Otter Islands. Visit an old fish camp or hike on Oak Island and then sail to a cove between Rocky and South Twin Islands for another night at anchor or at a dock. Grill dinner and walk on the beach and sandspit for a fantastic sunset. After a great breakfast, pull the hook and sail to Raspberry Island Lighthouse for a tour of the house and gardens and a game of croquet in the tradition of the Island. Sail back to Bayfield Harbor in the afternoon for a shower and dinner in Bayfield. Stay on Dreamcatcher in the harbor for one last night and depart in the morning.

$2295 exclusive boat for up to 4 adults or a family
$1995 exclusive boat trip, bring your own food.


Specials:
Before June 30 and after Labor Day Special
$1836 exclusive boat, $1536 w/out food.

June and September Weekday Super Special
$1275 no meals included for up to four adults or a family

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Black River Harbor
Five night sail

Four days on the water in the Apostle Islands just starts to scratch the surface in the many places to explore, so we do many trips without leaving the Islands. For those who want to get the open water experience, one option for a four day trip is to strike out across the open Lake and cross to Black River Harbor. A sample trip might go like this: Board the night before the trip and sleep in the harbor. Head out in the morning for a the first two days training and sailing in the Islands, exploring sea caves, lighthouses, secluded beaches and weathered shorelines, anchoring at one of our favorite protected coves for the first night and at Stockton Island the second night. Then very early AM on the third day, set sail for a twenty five mile crossing of the open lake to Black River Harbor, Michigan. This crossing will include watches, navigating, rotational napping with the water splashing up against the hull, and a real feeling of being off-shore and will take about 6 hours. This secluded little natural harbor is the home only to several fishing boats and a couple of spaces for visitors. After noon, hike up the Black River to the secluded waterfalls and the watch the sun setting on the horizon from the harbor. Early AM departure again—late risers can sleep in while we depart--and a glorious 7-8 hour sail back to the Islands and Bayfield. Stay in the harbor aboard Dreamcatcher for the last night if you choose. This trip could be done in three days with the right weather. However, four days will not only provide a better trip with more time in the Islands, but also a wider weather window for crossing the Lake. If the weather does not cooperate, this trip will be converted to a four day trip in the Islands, which is every bit as fun.

$2900 exclusive boat for up to 4 adults or a family.
$2500 exclusive boat trip, bring your own food.


Specials:
Before June 30 and after Labor Day Special
$2320 exclusive boat, $1920 w/out food.

 

Other weather-dependent options for overnight itinerary:

Devil’s Island
When the seas are calm, which happens often in the middle of summer, Devils Island can be reached. Devil’s sticks out into the open lake and it is a real treat when the weather cooperates. The caves there are spectacular, with rich colors, extensive "rooms" and a glow in the middle of a sunny day that defies description.
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Outer Island
Another Island that sticks out into the open lake is Outer Island. It is a large Island and has very few visitors because it is so far away from the mainland. There is a lighthouse at the north end and a huge lagoon and sandspit at the south end. The lagoon is home to many waterfowl and unusual birds and plant life. Pull in to the sandspit for a lunch on the way to or from Stockton Island.
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Madeline Island
"The Island" has a marina with showers and full facilities. The town of LaPointe has restaurants, bars, a golf course, shops, etc. and is fun to spend a night in. La Pointe has a long history, with the Anishinabe (Ojibway) Nation settling there long ago and the a fur trading post established there over 400 years ago. There is a museum on the Island and lots of other attractions. A night on Madeline can be included in any of the trips or if the weather gets bad, can be an alternate overnight destination.
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Cornucopia
"Corni" is on the far side of the Islands and has a quaint harbor with showers, shops and the town has a fine restaurant and two bars. Corni also has one of the world’s greatest public beaches with a volleyball game most evenings and great sunsets. A sail to Corni is a great way to split up a several day trip and can be reached in a day from Raspberry, Sand, Rocky or Oak Islands.
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