Boat Tours in Maryland at a glance
- Our pick: Sailboat Cruise Chesapeake Bay: Wind-Powered 2.5-Hour Sail, US$ 116 per person (2h 30m, 4.81★ · 42).
- Best value: Assateague Island Cruise from Ocean Pines: Wild Ponies, US$ 40 per person (2h, 4.83★ · 46).
- Private option: 2-Hour Chesapeake Bay Sail from St. Michaels: Historic Lady Patty, US$ 160 per person (2h, 4.96★ · 28).
Price per person across the 5 options priced per person: US$ 40–US$ 160 (median US$ 116).
Of the 6 options: 6 with live guides in English, 6 with free cancellation, 4 with instant confirmation, 3 kid-friendly, 2 private and 2 bookable last-minute.
How we rank: quality, number of reviews, availability, booking conditions and relevance to the topic. In the comparison table, our top 3 comes first. Prices are per person, except options priced per group: that price is for the whole group, and the per-person figure assumes the group is full.
Boat Tours in Maryland
Based on each operator's calendar. Confirmed when you book.
6 options
Sailboat Cruise Chesapeake Bay: Wind-Powered 2.5-Hour Sail Sail the Chesapeake Bay aboard the 42-foot Eternal Hope, powered by wind alone, with chances to spot dolphins and ospreys. Snacks and water included. Next departure: 12 May 2027 ★ 4.81 (42 reviews) Duration: 2h 30m Live guide: EN ✓ Free cancellation. from US$ 116 per person
2-Hour Chesapeake Bay Sail from St. Michaels: Historic Lady Patty Two-hour sail on the historic Lady Patty from St. Michaels harbor, gliding past the Hooper Strait Lighthouse with chances to spot osprey and dolphins. Next departure: 6 Jul 2027 · All ages ★ 4.96 (28 reviews) Duration: 2h Live guide: EN ✓ Free cancellation. from US$ 160 per person
Assateague Island Cruise from Ocean Pines: Wild Ponies Boat cruise from Ocean Pines Yacht Club down Assawoman Bay to Assateague Island to see wild ponies and dolphins up close. 2 hours round trip with live English-speaking guide. Next departure: 28 Sep 2027 ★ 4.83 (46 reviews) Duration: 2h Live guide: EN ✓ Free cancellation. from US$ 40 per person
Sunset Cruise Chesapeake Bay: 42-ft Sailing Yacht Sail the Chesapeake Bay at sunset aboard the 42-foot Eternal Hope, watching Western Shores and Cliffs of Calvert while enjoying snacks and water over 2.5 hours. Next departure: 12 May 2027 ★ 4.42 (12 reviews) Duration: 2h 30m Live guide: EN ✓ Free cancellation. from US$ 139 per person
Assateague Island Cruise with Orange Crush & Lunch Cruise Assawoman Bay behind Assateague Island for two hours with a certified guide, food from Harborside Grill. Next departure: 1 May 2027 ★ 5.00 (5 reviews) Duration: 2h Live guide: EN ✓ Free cancellation. from US$ 45 per person
Private Sunset Cruise Chesapeake Bay: Sparkling Cider & Snacks Two-and-a-half-hour private sunset cruise on Chesapeake Bay from Maryland with sparkling cider, snacks and live guide. No group crowds, just your party on the water. Next departure: 12 May 2027 Duration: 2h 30m Live guide: EN ✓ Free cancellation. from US$ 797 per group
All 6 options, side by side
✓ 2026-11-14| Option | Price | Duration | Rating | Days and times | Guide languages |
|---|---|---|---|---|---|
| Sailboat Cruise Chesapeake Bay: Wind-Powered 2.5-Hour SailOur pickGroup of up to 6 | US$ 116 per person | 2h 30m | 4.81★ · 42 | Next departure: 12 May 2027 | English |
| Assateague Island Cruise from Ocean Pines: Wild PoniesBest valueGroup of up to 10 | US$ 40 per person | 2h | 4.83★ · 46 | Next departure: 28 Sep 2027 | English |
| 2-Hour Chesapeake Bay Sail from St. Michaels: Historic Lady PattyPrivate optionPrivate | US$ 160 per person | 2h | 4.96★ · 28 | Next departure: 6 Jul 2027 | English |
| Sunset Cruise Chesapeake Bay: 42-ft Sailing YachtGroup of up to 6 | US$ 139 per person | 2h 30m | 4.42★ · 12 | Next departure: 12 May 2027 | English |
| Assateague Island Cruise with Orange Crush & LunchGroup of up to 6 | US$ 45 per person | 2h | 5.00★ only 5 reviews | Next departure: 1 May 2027 | English |
| Private Sunset Cruise Chesapeake Bay: Sparkling Cider & SnacksPrivate | US$ 797 per group up to 6 people · ≈ US$ 133 per person if 6 go | 2h 30m | — | Next departure: 12 May 2027 | English |
By what you need
- Private (2): 2-Hour Chesapeake Bay Sail from St. Michaels: Historic Lady Patty (US$ 160 per person) · Private Sunset Cruise Chesapeake Bay: Sparkling Cider & Snacks (US$ 797 per group)